3172:
1026:
6029:
406:
255:
40:
1025:
948:
30:
1913:
943:
2602:
60:
938:
2175:
70:
7258:
1021:
6011:
7222:
6020:
2184:
3009:(Antabuse) inhibits acetaldehyde dehydrogenase, an enzyme that oxidizes the compound into acetic acid. Metabolism of ethanol forms acetaldehyde before acetaldehyde dehydrogenase forms acetic acid, but with the enzyme inhibited, acetaldehyde accumulates. If one consumes ethanol while taking disulfiram, the hangover effect of ethanol is felt more rapidly and intensely (
2281:
7246:
7234:
1215:
3066:
The use of acetaldehyde is widespread in different industries, and it may be released into waste water or the air during production, use, transportation and storage. Sources of acetaldehyde include fuel combustion emissions from stationary internal combustion engines and power plants that burn fossil
3057:
with respect to their health effects. It has been pointed that in renovated or completely new buildings, the VOCs concentration levels are often several orders of magnitude higher. The main sources of acetaldehydes in homes include building materials, laminate, PVC flooring, varnished wood flooring,
3139:
food and many alcoholic beverages can also contain significant amounts of acetaldehyde. Acetaldehyde, derived from mucosal or microbial oxidation of ethanol, tobacco smoke, and diet, appears to act as a cumulative carcinogen in the upper digestive tract of humans. According to
European Commission's
2813:
may grow slightly at 1.6% per year through 2018. Western Europe is the second-largest consumer of acetaldehyde worldwide, accounting for 20% of world consumption in 2012. As with China, the
Western European acetaldehyde market is expected to increase only very slightly at 1% per year during
2955:
patients. This repair pathway results in increased mutation frequency and altered mutational spectrum. The second repair pathway requires replication fork convergence, breakage of the acetaldehyde crosslink, translesion synthesis by a Y-family DNA polymerase and homologous recombination.
5296:
Clements, A. L.; Jia, Y.; Denbleyker, A.; McDonald-Buller, E.; Fraser, M. P.; Allen, D. T.; Collins, D. R.; Michel, E.; Pudota, J.; Sullivan, D.; Zhu, Y. (2009). "Air pollutant concentrations near three Texas roadways, part II: Chemical characterization and transformation of pollutants".
1024:
1049:
4881:
Secretan B, Straif K, Baan R, Grosse Y, El
Ghissassi F, Bouvard V, Benbrahim-Tallaa L, Guha N, Freeman C, Galichet L, Cogliano V (November 2009). "A review of human carcinogens—Part E: tobacco, areca nut, alcohol, coal smoke, and salted fish".
3058:
and varnished cork/pine flooring (found in the varnish, not the wood). It is also found in plastics, oil-based and water-based paints, in composite wood ceilings, particle-board, plywood, treated pine wood, and laminated chipboard furniture.
2950:
Acetaldehyde induces DNA interstrand crosslinks, a form of DNA damage. These can be repaired by either of two replication-coupled DNA repair pathways. The first is referred to as the FA pathway, because it employs gene products defective in
2252:
The German chemist
Valentin Hermann Weidenbusch (1821–1893) synthesized paraldehyde in 1848 by treating acetaldehyde with acid (either sulfuric or nitric acid) and cooling to 0 °C. He found it quite remarkable that when paraldehyde was
3026:
Acetaldehyde is a potential contaminant in workplace, indoors, and ambient environments. Moreover, the majority of humans spend more than 90% of their time in indoor environments, increasing any exposure and the risk to human health.
1878:
In this endothermic process, ethanol vapor is passed at 260–290 °C over a copper-based catalyst. The process was once attractive because of the value of the hydrogen coproduct, but in modern times is not economically viable.
1042:
918:
1281:, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of
1737:
1597:
3135:
produce acetaldehyde from ethanol, but they have a lower capacity to eliminate the acetaldehyde, which can lead to the accumulation of acetaldehyde in saliva, stomach acid, and intestinal contents.
1472:
2809:
and pentaerythritol are expected to grow faster than acetic acid, but the volumes are not large enough to offset the decline in acetic acid. As a consequence, overall acetaldehyde consumption in
3733:
Dabit, a pharmacist in Nantes, France, performed a series of experiments and concluded that acetaldehyde was formed when hydrogen in ethanol combined with oxygen in sulfuric acid to form water:
2519:
mutation which makes them significantly less efficient at oxidizing acetaldehyde. On consuming alcohol, their bodies tend to accumulate excessive amounts of acetaldehyde, causing the so-called
1873:
5793:
5114:
Homann, N.; Stickel, F.; König, I. R.; Jacobs, A.; Junghanns, K.; Benesova, M.; Schuppan, D.; Himsel, S.; Zuber-Jerger, I.; Hellerbrand, C.; Ludwig, D.; Caselmann, W. H.; Seitz, H. K. (2006).
2871:
Acetaldehyde is an irritant of the skin, eyes, mucous membranes, throat, and respiratory tract. This occurs at concentrations as low as 1000 ppm. Symptoms of exposure to this compound include
2597:, once produced from acetaldehyde, is made predominantly by the lower-cost methanol carbonylation process. The impact on demand has led to increase in prices and thus slowdown in the market.
3804:
1000:
1895:
with catalysts like cobalt, nickel, or iron salts also produces acetaldehyde, although this process is of no industrial importance. Similarly noncompetitive, acetaldehyde arises from
4763:
Tsukamoto, S; Muto, T; Nagoya, T; Shimamura, M; Saito, M; Tainaka, H (1989). "Determinations of ethanol, acetaldehyde and acetate in blood and urine during alcohol oxidation in man".
2805:
is the largest consumer of acetaldehyde in the world, accounting for almost half of global consumption in 2012. Major use has been the production of acetic acid. Other uses such as
5766:
3782:
4127:
Heazlewood, B. R.; MacCarone, A. T.; Andrews, D. U.; Osborn, D. L.; Harding, L. B.; Klippenstein, S. J.; Jordan, M. J. T.; Kable, S. H. (2011). "Near-threshold H/D exchange in CD
3362:
2234:. Paraldehyde can be produced in good yields, using a sulfuric acid catalyst. Metaldehyde is only obtained in a few percent yield and with cooling, often using HBr rather than
1143:
3182:
of around 20–40 ppb and can cause an off-taste in bottled water. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity.
1228:
2539:
Traditionally, acetaldehyde was mainly used as a precursor to acetic acid. This application has declined because acetic acid is produced more efficiently from methanol by the
5632:
5014:
Hodskinson MR, Bolner A, Sato K, Kamimae-Lanning AN, Rooijers K, Witte M, Mahesh M, Silhan J, Petek M, Williams DM, Kind J, Chin JW, Patel KJ, Knipscheer P (March 2020).
5465:
Singh, R (2009). "Evaluation of the DNA Damaging
Potential of Cannabis Cigarette Smoke by the Determination of Acetaldehyde Derived N2-Ethyl-2'-deoxyguanosine Adducts".
5555:
Day, M.; Wiles, D. M. (January 1972). "Photochemical degradation of poly(ethylene terephthalate). III. Determination of decomposition products and reaction mechanism".
4678:
2508:, followed by the conversion of acetaldehyde into ethanol. The latter reaction is again catalyzed by an alcohol dehydrogenase, now operating in the opposite direction.
7042:
6962:
6778:
6713:
6653:
6581:
6487:
6381:
6251:
5802:
1027:
5786:
7308:
2846:
is observed. When taken up by the organism, acetaldehyde is metabolized rapidly in the liver to acetic acid. Only a small proportion is exhaled unchanged. After
1750:
to acetaldehyde. The reaction is conducted at 90–95 °C, and the acetaldehyde formed is separated from water and mercury and cooled to 25–30 °C. In the
4174:
Andrews, D. U.; Heazlewood, B. R.; MacCarone, A. T.; Conroy, T.; Payne, R. J.; Jordan, M. J. T.; Kable, S. H. (2012). "Photo-Tautomerization of
Acetaldehyde to
3067:
fuels, wood, or trash, oil and gas extraction, refineries, cement kilns, lumber and wood mills and paper mills. Acetaldehyde is also present in automobile and
1777:
can catalyze an analogous reaction without involving any compounds of mercury. However, it has thus far not been brought to any large-scale or commercial use.
455:
3123:. This finding emerged through the use of new chemical techniques that demonstrated the acetaldehyde present was causing DNA damage in laboratory settings.
3034:, the mean indoor concentration of acetaldehydes measured in 16 homes was approximately seven times higher than the outside acetaldehyde concentration. The
4856:
2927:
2915:
2839:
is 25ppm (STEL/ceiling value) and the MAK (Maximum
Workplace Concentration) is 50 ppm. At 50 ppm acetaldehyde, no irritation or local tissue damage in the
1308:
4091:
Keeffe, J. R.; Kresge, A. J.; Schepp, N. P. (1990). "Keto-enol equilibrium constants of simple monofunctional aldehydes and ketones in aqueous solution".
2582:
The global market for acetaldehyde is declining. Demand has been impacted by changes in the production of plasticizer alcohols, which has shifted because
5779:
4818:
4631:
Lee H, Kim SS, You KS, Park W, Yang JH, Kim M, Hayman LL (2014). "Asian flushing: genetic and sociocultural factors of alcoholism among East asians".
2021:
or stratospheric conditions. This photo-tautomerization is relevant to the Earth's atmosphere, because vinyl alcohol is thought to be a precursor to
3516:"Quantitative Determination of Acetaldehyde in Foods Using Automated Digestion with Simulated Gastric Fluid Followed by Headspace Gas Chromatography"
2822:. The supply of butadiene has been volatile in Japan and the rest of Asia. This should provide the much needed boost to the flat market, as of 2013.
1994:
10 at room temperature, thus that the relative amount of the enol form in a sample of acetaldehyde is very small. At room temperature, acetaldehyde (
2898:
irritations have been observed after a 15-minute exposure to concentrations of 25 and 50 ppm, but transient conjunctivitis and irritation of the
2523:. They develop a characteristic flush on the face and body, along with "nausea, headache and general physical discomfort". Ingestion of the drug
7313:
1328:
5728:
988:
5745:
5180:
4864:
3442:
3391:
3377:
3310:
3271:
809:
3171:
3193:
in patients with potentially carcinogenic oral diseases has been shown to produce acetaldehyde in quantities sufficient to cause problems.
2989:
A study of 818 heavy drinkers found that those exposed to more acetaldehyde than normal through a genetic variant of the gene encoding for
39:
5239:
Shrestha, Krishna Prasad; Giri, Binod Raj; Adil, Mohammad; Seidel, Lars; Zeuch, Thomas; Farooq, Aamir; Mauss, Fabian (16 September 2021).
2335:
rather than referring to this specific compound — in fact, 1,1-diethoxyethane is also described as the diethyl acetal of acetaldehyde.
7303:
7165:
5204:
Dafni A. Missia; E. Demetriou; N. Michael; E.I. Tolis; J.G. Bartzis (2010). "Indoor exposure from building materials: A field study".
5452:
3689:
Scheele, C. W. (1774) "Om
Brunsten eller Magnesia nigra och dess egenskaper" (On brown-stone or black magnesia and its properties),
7293:
7065:
3882:
3333:
420:
2323:
but is commonly referred to as "acetal". This can cause confusion as "acetal" is more commonly used to describe compounds with the
5625:
5436:
2230:", a cyclic trimer containing C-O single bonds. Similarly condensation of four molecules of acetaldehyde give the cyclic molecule
3616:
1637:
1490:
7190:
4812:"Opinion of the Scientific Committee on Cosmetic Products and Non-Food Products Intended for Consumers Concerning Acetaldehyde"
3071:. As a result, acetaldehyde is "one of the most frequently found air toxics with cancer risk greater than one in a million".
899:
291:
1484:
of ethanol in an exothermic reaction. This process typically is conducted over a silver catalyst at about 500–650 °C.
29:
1185:
7115:
5657:
Gainza-Cirauqui, M.L.; Nieminen, M.T.; Novak Frazer, L.; Aguirre-Urizar, J.M.; Moragues, M.D.; Rautemaa, R. (March 2013).
5582:
Nawrocki, J; Dąbrowska, A; Borcz, A (November 2002). "Investigation of carbonyl compounds in bottled waters from Poland".
2104:
1384:
1336:
7150:
5713:
5063:
Ohta, S; Ohsawa I; Kamino K; Ando F; Shimokata H. (April 2004). "Mitochondrial ALDH2 Deficiency as an
Oxidative Stress".
2818:
could emerge as a potential consumer for acetaldehyde in next five years due to newfound use in commercial production of
1235:
4596:
Hipolito, L.; Sanchez, M. J.; Polache, A.; Granero, L. (2007). "Brain metabolism of ethanol and alcoholism: An update".
2994:
982:
363:
5542:
1795:
1297:
consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of
947:
6346:
3595:
3157:
3010:
384:
5761:
4970:"Acetaldehyde-Induced Cardiac Contractile Dysfunction May Be Alleviated by Vitamin B1 but Not by Vitamins B6 or B12"
4674:
1477:
In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process exceeded 2 million tonnes annually.
1035:
942:
5500:
Salaspuro, M. (2009). "Acetaldehyde as a common denominator and cumulative carcinogen in digestive tract cancers".
3294:
3161:
2863:
Many serious cases of acute intoxication have been recorded. Acetaldehyde naturally breaks down in the human body.
2469:
1302:
1154:
649:
59:
7105:
7100:
6913:
6281:
5332:
Talhout, R; Opperhuizen, A; van
Amsterdam, JG (October 2007). "Role of acetaldehyde in tobacco smoke addiction".
4917:
Lambert, B; He, S. M. (1988). "DNA and chromosome damage induced by acetaldehyde in human lymphocytes in vitro".
4852:
3100:
3046:
262:
2245:
as the catalyst. At −40 °C in the presence of acid catalysts, polyacetaldehyde is produced. There are two
1315:. Acetaldehyde is "one of the most frequently found air toxins with cancer risk greater than one in a million".
7145:
6571:
6341:
6301:
3834:
In this paper, Döbereiner made acetaldehyde by exposing ethanol vapor to air in the presence of platinum black.
2158:
1197:
1072:
69:
4002:
6502:
6477:
6467:
4811:
937:
7225:
5626:"Do Acetaldehyde and Formaldehyde from Pet Bottles Result in Unacceptable Flavor or Aroma in Bottled Water?"
5375:
Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011).
1774:
1332:
678:
5740:. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Vol. 71. 1999. pp. 319–334.
3415:
250:
7080:
6873:
6201:
6142:
6050:
6045:
5955:
5832:
5827:
2974:
2520:
2505:
2352:
2150:
785:
6206:
5877:
3847:
3721:(ethanol treated with nitric acid). Later investigators realized that Scheele had produced acetaldehyde.
3594:. Office of Pollution Prevention and Toxics, United States Environmental Protection Agency. August 1994.
2887:
threshold for acetaldehyde in air is in the range between 0.07 and 0.25 ppm. At such concentrations, the
1305:, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.
212:
7298:
7135:
7110:
6748:
6507:
6366:
6351:
6321:
5913:
4381:
3566:
3202:
2836:
2485:
2457:
2066:
2062:
1375:
1286:
956:
930:
626:
101:
6437:
6417:
6090:
5116:"Alcohol dehydrogenase 1C*1 allele is a genetic marker for alcohol-associated cancer in heavy drinkers"
4501:
4471:
Frank, R. L.; Pilgrim, F. J.; Riener, E. F. (1950). "5-Ethyl-2-Methylpyridine (2-Picoline, 5-ethyl-)".
6462:
4737:
7196:
7180:
6805:
6176:
6147:
6028:
5852:
5591:
5453:
Nicotine's addictive hold increases when combined with other tobacco smoke chemicals, UCI study finds
5306:
5213:
5072:
4926:
4187:
4140:
4018:
3751:
Fourcroy and Vauquelin stated that sulfuric acid was not consumed in the production of acetaldehyde:
3644:
3207:
2568:
2344:
1987:
1324:
1277:
CHO. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important
89:
6100:
2969:
People with a genetic deficiency for the enzyme responsible for the conversion of acetaldehyde into
7140:
7120:
6933:
6623:
6457:
6111:
5975:
5950:
5918:
5837:
4695:
Omran, Z (15 May 2021). "Development of new disulfiram analogues as ALDH1a1-selective inhibitors".
4523:
3291:
Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
2952:
2923:
2847:
2489:
1770:
401:
131:
6127:
4046:"Acetylene hydratase: A non-redox enzyme with tungsten and iron–sulfur centers at the active site"
3178:
Although the levels produced by this process are minute acetaldehyde has an exceedingly low taste/
7238:
7160:
7130:
7075:
6952:
6928:
6673:
6427:
6361:
6226:
6186:
6070:
6037:
6000:
5960:
5939:
5882:
5857:
5525:
5357:
5278:
5145:
5096:
4950:
4750:
4720:
4656:
4211:
4073:
2935:
2899:
2320:
2285:
2014:) by 42.7 kJ/mol: Overall the keto-enol tautomerization occurs slowly but is catalyzed by acids.
1620:
992:
726:
6221:
3251:
3087:, have been shown to be the primary precursors making acetaldehyde a significant constituent of
2143:
6132:
3633:"Carcinogenic Air Toxics Exposure and Their Cancer-Related Health Impacts in the United States"
3107:. Acetaldehyde is also the most abundant carcinogen in tobacco smoke; it is dissolved into the
2930:
updated the classification of acetaldehyde stating that acetaldehyde included in and generated
7283:
7185:
6768:
6668:
6638:
6556:
6296:
6181:
6137:
6085:
5892:
5887:
5819:
5741:
5682:
5607:
5517:
5482:
5416:
5398:
5349:
5270:
5186:
5176:
5172:
5137:
5088:
5045:
4991:
4942:
4899:
4860:
4780:
4712:
4648:
4613:
4532:
4473:
4437:
4394:
4347:
4307:
4267:
4203:
4156:
4065:
4045:
3941:]. Vol. 2 (3rd ed.). Braunschweig, Germany: Friedrich Vieweg und Sohn. pp.
3899:
3878:
3821:
3754:
3736:
3698:
3672:
3547:
3448:
3438:
3397:
3387:
3306:
3267:
3013:). As such, disulfiram is sometimes used as a deterrent for alcoholics wishing to stay sober.
2576:
2512:
2269:
2078:
2038:
2034:
1921:
1755:
1628:
1340:
1179:
996:
836:
6316:
3874:
7288:
7262:
7250:
7170:
7070:
7000:
6975:
6923:
6356:
6231:
6196:
6117:
6105:
6065:
5970:
5903:
5674:
5658:
5599:
5564:
5509:
5474:
5406:
5388:
5341:
5314:
5260:
5252:
5221:
5164:
5127:
5080:
5035:
5027:
4981:
4934:
4891:
4772:
4704:
4640:
4605:
4575:
4541:
4482:
4446:
4403:
4356:
4316:
4276:
4237:
4195:
4148:
4100:
4057:
4026:
3985:
3942:
3662:
3652:
3537:
3527:
3298:
3259:
3165:
3120:
2601:
2564:
2540:
2348:
2324:
1912:
1888:
1759:
1259:
1255:
691:
573:
483:
1343:(1835). In 1835, Liebig named it "aldehyde"; the name was later altered to "acetaldehyde".
372:
6858:
6833:
6532:
6371:
6311:
6291:
6211:
6095:
5995:
5980:
5965:
5872:
5862:
5440:
4776:
3474:
3337:
3080:
2843:
2552:
2135:
2082:
2022:
1786:
1085:
874:
5702:
3328:
2589:
is less often produced from acetaldehyde, instead being generated by hydroformylation of
2257:
with a trace of the same acid, the reaction went the other way, recreating acetaldehyde.
232:
172:
165:
5595:
5310:
5241:"Detailed Chemical Kinetic Study of Acetaldehyde Oxidation and Its Interaction with NOx"
5217:
5076:
4930:
4191:
4144:
4022:
3648:
1602:
This method is one of the oldest routes for the industrial preparation of acetaldehyde.
192:
141:
7095:
7060:
6843:
6733:
6698:
6683:
6618:
6613:
6512:
6412:
6331:
6306:
6271:
6216:
6191:
6060:
5908:
5433:
5411:
5376:
5040:
5015:
4938:
4579:
4010:
3667:
3632:
3542:
3515:
3179:
3068:
2556:
2544:
2501:
2058:
1616:
1371:
1294:
1206:
886:
639:
405:
254:
5603:
4895:
4845:
3258:. Cancer Growth and Progression. Vol. 16. Springer. pp. 177–210 See p. 190.
3140:
Scientific Committee on Consumer Safety's (SCCS) "Opinion on Acetaldehyde" (2012) the
3042:
was 18.2±16.9 μg m, whereas the outdoor air had a mean concentration of 2.3±2.6 μg m.
2922:
evidence for the carcinogenicity of acetaldehyde (the major metabolite of ethanol) in
2174:
2146:. These imines can be used to direct subsequent reactions like an aldol condensation.
7277:
7125:
6980:
6863:
6838:
6819:
6763:
6643:
6601:
6596:
6336:
6326:
6286:
6161:
6055:
6010:
5985:
5867:
5847:
5678:
5282:
5165:
4724:
4660:
4175:
3470:
3240:
SciFinderScholar (accessed 4 November 2009). Acetaldehyde (75-07-0) Substance Detail.
3088:
2583:
2572:
2261:
2003:
1933:
1896:
1751:
1743:
962:
766:
594:
562:
552:
243:
5771:
5529:
5361:
5345:
5256:
5149:
5100:
4954:
4566:
Lavinia, M.; Gheorghe, I. (2010). "Poly(vinylphosphonic acid) and its derivatives".
4504:[On some products of the reaction of alkalies and acids with acetaldehyde].
4215:
4077:
3631:
Zhou, Ying; Li, Chaoyang; Huijbregts, Mark A. J.; Mumtaz, M. Moiz (7 October 2015).
7201:
7055:
6908:
6848:
6828:
6800:
6728:
6608:
6546:
6497:
6402:
6122:
6075:
5923:
5318:
5225:
4428:
4254:
4233:
3212:
3136:
2911:
2840:
2074:
2070:
1360:
870:
5240:
4433:"Directed Aldol Condensations: β-Phenylcinnamaldehyde (2-Propenal, 3,3-diphenyl-)"
3989:
3144:
products special risk limit is 5 mg/L and acetaldehyde should not be used in
2280:
4644:
3657:
7175:
7085:
7050:
7017:
6943:
6918:
6758:
6663:
6633:
6517:
6432:
6422:
6152:
6080:
5755:
4843:
International Agency for Rescarch on Cancer, World Health Organization. (1988).
4527:
4432:
4385:
4342:
4302:
4258:
3302:
3263:
3217:
3035:
2970:
2902:
tract have been reported after exposure to 200 ppm acetaldehyde for 15 minutes.
2895:
2594:
2465:
2231:
2227:
2213:
2205:
1763:
1127:
1109:
1061:
970:
336:
5568:
4810:
Scientific Committee on Cosmetic Products and Non-Food Products (25 May 2004).
4708:
4609:
7090:
7032:
6995:
6970:
6868:
6678:
6541:
5707:
5513:
5031:
4502:"Ueber einige Producte der Einwirkung von Alkalien und Säuren auf den Aldehyd"
4061:
3452:
3358:
3222:
3006:
2931:
2884:
2524:
2120:
2116:
2018:
1312:
1298:
619:
610:
584:
508:
281:
223:
5762:
United States Food and Drug Administration (FDA) information for acetaldehyde
5402:
5274:
4545:
4486:
4450:
4407:
4360:
4320:
4280:
3401:
1758:
is used to reoxidize the mercury back to the mercury(II) salt. The resulting
1359:
were the major sources of acetaldehyde. Since then, ethylene is the dominant
966:
7022:
6887:
6723:
6527:
6407:
6261:
6236:
5190:
5084:
4986:
4969:
4199:
3822:"Bildung des Sauerstoff-Aethers durch atmosphärische Oxidation des Alkohols"
3492:
3383:
3145:
3141:
3104:
3084:
3054:
2819:
2612:(* Included in others -glyoxal/glyoxalic acid, crotonaldehyde, lactic acid,
2590:
2246:
2042:
1624:
1481:
1356:
710:
5686:
5611:
5521:
5486:
5420:
5353:
5141:
5092:
5049:
4995:
4903:
4797:
4716:
4652:
4617:
4207:
4160:
4069:
3676:
3587:
3551:
974:
5393:
4946:
4784:
3532:
6990:
6902:
6703:
6566:
6551:
6522:
6391:
6166:
5990:
5934:
5928:
5897:
5842:
5810:
3132:
3096:
2880:
2876:
2806:
2548:
2497:
2481:
2193:
1925:
1892:
1747:
1619:
and the availability of cheap ethylene, acetaldehyde was produced by the
1290:
1278:
1048:
1041:
1034:
1007:
864:
5737:
Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide
5265:
5016:"Alcohol-derived DNA crosslinks are repaired by two distinct mechanisms"
4104:
2938:
is a Group I human carcinogen. In addition, acetaldehyde is damaging to
2183:
7155:
6985:
6938:
6897:
6853:
6795:
6790:
6753:
6743:
6738:
6693:
6688:
6628:
6561:
6452:
6447:
6397:
6276:
6266:
6019:
5767:
Acetaldehyde production process flow sheet by ethylene oxidation method
4241:
4152:
4030:
3931:
The name change occurred at least as early as 1868. See, for example:
3250:
Shackelford, R.E.; Abdelbaqi, M.Q.; Almhanna, K.; Meredith, K. (2014).
3092:
3039:
2461:
2297:
2154:
2123:
2112:
2108:
2097:
2054:
1352:
1282:
614:
602:
598:
590:
539:
323:
263:
5478:
5132:
5115:
3824:[Formation of oxy-ether by atmospheric oxidation of alcohol].
3807:[Döbereiner's apparatus for the preparation of oxygen-ether].
7206:
7027:
7009:
6472:
6442:
5944:
4117:
Johnson, R.D. III "CCCBDB NIST Standard Reference Database". nist.gov
3108:
3050:
3031:
2872:
2454:
2293:
1367:
1351:
In 2003, global production was about 1 million tonnes. Before 1962,
1274:
1270:
1263:
746:
606:
203:
5543:
Scientific Committee on Consumer Safety SCCS OPINION ON Acetaldehyde
3935:
Lehrbuch der organischen Chemie für den Unterricht auf Universitäten
2484:
is primarily responsible for oxidizing ethanol to acetaldehyde, and
1205:
Except where otherwise noted, data are given for materials in their
5758:, Indiana University Research and Creative Activity, Vol. 17 no. 3.
4263:-Benzyl-2,3-Azetidinedione (2,3-Azetidinedione, 1-(phenylmethyl)-)"
2850:
injection, the half-life in the blood is approximately 90 seconds.
311:
6241:
6171:
5735:
2990:
2978:
2888:
2815:
2810:
2802:
2600:
2560:
2516:
2493:
2472:. These two oxidation reactions are coupled with the reduction of
2450:
2279:
2131:
2127:
1911:
1323:
Acetaldehyde was first observed by the Swedish pharmacist/chemist
753:
664:
347:
183:
171:
164:
154:
5381:
International Journal of Environmental Research and Public Health
5163:
Spengler, John D.; McCarthy, John F.; Samet, Jonathan M. (2000).
3939:
Textbook of Organic Chemistry for Instruction at Universities ...
2527:, which inhibits ALDH2, leads to a similar reaction. See section
5663:
from patients with potentially malignant oral mucosal disorders"
4677:. Dartmouth Undergraduate Journal of Science. 21 November 2009.
3252:"Molecular Pathology and Diagnostics in Esophago-gastric Cancer"
2942:
and causes abnormal muscle development as it binds to proteins.
2891:
2477:
2464:
into acetaldehyde, which is then further oxidized into harmless
2073:
derivatives. In one of the more spectacular addition reactions,
1929:
1167:
529:
302:
5775:
2351:
membranes. The synthesis sequence begins with a reaction with
3588:"Chemicals in the Environment: Acetaldehyde (CAS NO. 75-07-0)"
2939:
1916:
Tautomeric equilibrium between acetaldehyde and vinyl alcohol.
3757:[On the ether prepared in the way of citizen Dabit].
3805:"Döbereiner's Apparat zur Darstellung des Sauerstoffaethers"
3170:
2993:, ADH1C*1, are at greater risk of developing cancers of the
1732:{\displaystyle {\ce {C2H2 + Hg^2+ + H2O -> CH3CHO + Hg}}}
1592:{\displaystyle {\ce {CH3CH2OH + 1/2 O2 -> CH3CHO + H2O}}}
389:
68:
58:
38:
28:
3739:[Extract of the memoir by citizen Dabit on ether].
715:
0.21 mPa-s at 20 °C (0.253 mPa-s at 9.5 °C)
3049:
such as benzene, formaldehyde, acetaldehyde, toluene, and
3701:, Scheele mentions that refluxing ("digesting") ethanol (
3567:"How Hangovers Work: Biology of a Hangover: Acetaldehyde"
1861:
1842:
1823:
1810:
1716:
1697:
1665:
1652:
1582:
1563:
1547:
1518:
1505:
1457:
1437:
1421:
1403:
1019:
4303:"1-(α-Pyridyl)-2-Propanol (2-(β-Hydroxypropyl)pyridine)"
3693:(Proceedings of the Royal Swedish Academy of Sciences),
3520:
Journal of Automated Methods and Management in Chemistry
2017:
Photo-induced keto-enol tautomerization is viable under
1785:
Traditionally, acetaldehyde was produced by the partial
1327:(1774); it was then investigated by the French chemists
3902:[On the products of the oxidation of alcohol].
3514:
Uebelacker, Michael; Lachenmeier, Dirk (13 June 2011).
1223:
4228:
Sowin, T. J.; Melcher, L. M. (2004) "Acetaldehyde" in
2300:
under conditions that favor dehydration. The product,
1527:
5756:
Genetic Influences on Alcohol Drinking and Alcoholism
3363:
National Institute for Occupational Safety and Health
2265:
1798:
1640:
1493:
1467:{\displaystyle {\ce {2 CH2=CH2 + O2 -> 2 CH3CHO}}}
1387:
4968:
Aberle, N. S.; Burd, L; Zhao, B. H.; Ren, J (2004).
4591:
4589:
3850:[On the products of oxidation of alcohol ].
3433:
Rumble, J.R.; Lide, D.R.; Bruno, T.J., eds. (2018).
3376:
Haynes, W.M.; Lide, D.R.; Bruno, T.J., eds. (2016).
7041:
6961:
6886:
6777:
6712:
6652:
6580:
6486:
6380:
6250:
6036:
5818:
5809:
5434:"NIDA — Publications — NIDA Notes — Vol. 20, No. 3"
2153:. In one example, it converts, upon treatment with
290:
4844:
4001:Dmitry A. Ponomarev; Sergey M. Shevchenko (2007).
2559:. Urea and acetaldehyde combine to give a useful
2226:Three molecules of acetaldehyde condense to form "
1868:{\displaystyle {\ce {CH3CH2OH -> CH3CHO + H2}}}
1867:
1731:
1591:
1480:Smaller quantities can be prepared by the partial
1466:
1366:The main method of production is the oxidation of
5009:
5007:
5005:
4751:"Acetaldehyde — Global Business Strategic Report"
2883:. These symptoms may not happen immediately. The
557:−123.37 °C (−190.07 °F; 149.78 K)
3755:"Sur l'éther préparé à la manière du cit. Dabit"
3691:Kungliga Svenska vetenskapsakademiens handlingar
2488:plays a minor role. The last steps of alcoholic
2149:It is also a building block in the synthesis of
1773:discovered in the strictly anaerobic bacterium
335:
3848:"Ueber die Producte der Oxydation des Alkohols"
1309:The International Agency for Research on Cancer
1023:
140:
4230:Encyclopedia of Reagents for Organic Synthesis
3982:Ullmann's Encyclopedia of Industrial Chemistry
3737:"Extrait du mémoire du cit. Dabit sur l'éther"
3330:Stoffdaten Acetaldehyd bei Celanese Chemicals.
1080:175.00 °C; 347.00 °F; 448.15 K
1066:−39.00 °C; −38.20 °F; 234.15 K
5787:
5723:(4th ed.). 15 March 2003. pp. 1–10.
4003:"Hydration of Acetylene: A 125th Anniversary"
3900:"Sur les produits de l'oxidation de l'alcool"
3256:Molecular Pathology and Diagnostics of Cancer
1374:, which involves oxidation of ethene using a
8:
5659:"Production of carcinogenic acetaldehyde by
4697:Bioorganic & Medicinal Chemistry Letters
4690:
4688:
4178:: A Potential Route to Tropospheric Acids".
2547:. Acetaldehyde is an important precursor to
1311:(IARC) has listed acetaldehyde as a Group 1
4857:International Agency for Research on Cancer
3912:Je le décrirai dans ce mémoire sous le nom
3871:Justus von Liebig: The Chemical Gatekeeper
3285:
3283:
2981:deficiency is a risk factor for LOAD ..."
2928:International Agency for Research on Cancer
2916:International Agency for Research on Cancer
2045:. It is used primarily as a source of the "
1742:The mechanism involves the intermediacy of
5815:
5794:
5780:
5772:
5065:Annals of the New York Academy of Sciences
4919:Annals of the New York Academy of Sciences
3437:(99th ed.). CRC Press. pp. 5–3.
3324:
3322:
2610:Consumption of acetaldehyde (10 t) in 2003
567:20.2 °C (68.4 °F; 293.3 K)
404:
253:
231:
17:
5721:NIOSH Manual of Analytical Methods (NMAM)
5410:
5392:
5264:
5131:
5039:
4985:
4050:Journal of Biological Inorganic Chemistry
3933:von Gorup-Besanez, Eugen F., ed. (1868).
3666:
3656:
3541:
3531:
2033:Acetaldehyde is a common electrophile in
1860:
1855:
1841:
1836:
1822:
1817:
1809:
1804:
1799:
1797:
1715:
1710:
1696:
1691:
1675:
1664:
1659:
1651:
1646:
1641:
1639:
1581:
1576:
1562:
1557:
1546:
1541:
1517:
1512:
1504:
1499:
1494:
1492:
1456:
1451:
1446:
1436:
1431:
1420:
1415:
1406:
1402:
1397:
1392:
1388:
1386:
371:
5545:. European Commission. 18 September 2012
5502:Scandinavian Journal of Gastroenterology
4675:"Esophageal Cancer and the 'Asian Glow'"
4093:Journal of the American Chemical Society
3357:NIOSH Pocket Guide to Chemical Hazards.
2608:
2528:
2436:
2432:
2428:
2424:
2415:
2411:
2407:
2403:
2399:
2386:
2369:
2365:
2361:
2315:
2311:
2307:
2303:
2249:of paraldehyde and four of metaldehyde.
2241:
2237:
2199:
2092:
2088:
2048:
2009:
1997:
1946:
1942:
1265:
666:
5703:International Chemical Safety Card 0009
3972:
3873:. Cambridge University Press. pp.
3582:
3580:
3487:
3485:
3483:
3466:
3464:
3462:
3352:
3350:
3348:
3346:
3233:
2266:§ Tautomerization to vinyl alcohol
1762:is oxidized in a separate reactor with
460:
425:
400:
5708:NIOSH Pocket Guide to Chemical Hazards
5667:Journal of Oral Pathology and Medicine
5455:. University of California. 2004-10-28
5377:"Hazardous Compounds in Tobacco Smoke"
3970:
3968:
3966:
3964:
3962:
3960:
3958:
3956:
3954:
3952:
2347:, which is used to make adhesives and
2272:cannot be produced from acetaldehyde.
244:
7309:Organic compounds with 2 carbon atoms
4777:10.1093/oxfordjournals.alcalc.a044872
4681:from the original on 12 January 2016.
3626:
3624:
3435:CRC Handbook of Chemistry and Physics
3379:CRC Handbook of Chemistry and Physics
3091:. It has been demonstrated to have a
3038:had a mean of 18.1±17.5 μg m and the
2264:is a polymeric form of acetaldehyde (
432:Key: IKHGUXGNUITLKF-UHFFFAOYSA-N
211:
191:
7:
4800:, US Environmental Protection Agency
3156:Acetaldehyde can be produced by the
5638:from the original on 9 October 2022
4824:from the original on 9 October 2022
3598:from the original on 17 August 2002
2977:. "These results indicate that the
2069:compounds react with MeCHO to give
2029:Addition and condensation reactions
1329:Antoine François, comte de Fourcroy
442:Key: IKHGUXGNUITLKF-UHFFFAOYAB
326:
310:
7166:Nexus for Exoplanet System Science
5714:"ALIPHATIC ALDEHYDES: METHOD 2018"
5557:Journal of Applied Polymer Science
4939:10.1111/j.1749-6632.1988.tb30124.x
4580:10.1016/j.progpolymsci.2010.04.001
4236:), J. Wiley & Sons, New York.
1378:palladium/copper catalyst system:
913:potential occupational carcinogen
43:Skeletal structure of acetaldehyde
14:
7066:Atomic and molecular astrophysics
5803:Molecules detected in outer space
4798:Chemical Summary For Acetaldehyde
3795:Döbereiner named the new "ether"
2567:reacts with acetaldehyde to give
2339:Precursor to vinylphosphonic acid
2126:. Acetaldehyde can condense with
7256:
7244:
7232:
7221:
7220:
6027:
6018:
6009:
5679:10.1111/j.1600-0714.2012.01203.x
3904:Annales de Chimie et de Physique
3709:) and either hydrochloric acid (
3617:List of IARC Group 1 carcinogens
3047:volatile organic compounds (VOC)
2182:
2173:
1908:Tautomerization to vinyl alcohol
1627:. This reaction is catalyzed by
1335:(1800), and the German chemists
1213:
946:
941:
936:
546:0.7904–0.7928 g·cm (10 °C)
495:
7191:Polycyclic aromatic hydrocarbon
5346:10.1016/j.euroneuro.2007.02.013
5257:10.1021/acs.energyfuels.1c01948
5120:International Journal of Cancer
3119:Acetaldehyde has been found in
3053:have to be considered priority
2343:Acetaldehyde is a precursor to
1289:and is a contributing cause of
1209:(at 25 °C , 100 kPa).
33:Lewis structure of acetaldehyde
5319:10.1016/j.atmosenv.2009.06.044
5226:10.1016/j.atmosenv.2010.07.049
3697: : 89–116; 177–194. On
3565:Lacy Perry (12 October 2004).
3295:The Royal Society of Chemistry
2284:Conversion of acetaldehyde to
2107:, acetaldehyde condenses with
1829:
1703:
1550:
1440:
900:Occupational safety and health
501:
489:
1:
7314:Recreational drug metabolites
7116:Extraterrestrial liquid water
5604:10.1016/S0043-1354(02)00201-4
4896:10.1016/s1470-2045(09)70326-2
4044:Kroneck, Peter M. H. (2016).
3990:10.1002/14356007.a01_031.pub2
3826:Journal für Chemie und Physik
3809:Journal für Chemie und Physik
3787:Journal für Chemie und Physik
2894:of acetaldehyde is apparent.
1148:(US health exposure limits):
429:InChI=1S/C2H4O/c1-2-3/h2H,1H3
4645:10.1097/SGA.0000000000000062
3753:Fourcroy; Vauquelin (1800).
3658:10.1371/journal.pone.0140013
2995:upper gastrointestinal tract
2641:Acetic Acid/Acetic anhydride
2292:Acetaldehyde forms a stable
1883:Hydroformylation of methanol
439:InChI=1/C2H4O/c1-2-3/h2H,1H3
6347:Protonated hydrogen cyanide
5167:Indoor Air Quality Handbook
4568:Progress in Polymer Science
4341:Schurink, H. B. J. (1925).
3303:10.1039/9781849733069-00648
3264:10.1007/978-94-007-7192-5_6
3045:It has been concluded that
3011:disulfiram-alcohol reaction
2973:may have a greater risk of
2701:Pyridine and pyridine bases
2575:, which is used to produce
2480:. In the brain, the enzyme
1273:, sometimes abbreviated as
1098:or concentration (LD, LC):
54:
24:
7332:
5569:10.1002/app.1972.070160118
4749:Research and Markets ltd.
4709:10.1016/j.bmcl.2021.127958
4610:10.2174/138920007782109797
4459:, vol. 6, p. 901
4384:; McKenzie, B. F. (1929).
4369:, vol. 1, p. 425
4329:, vol. 3, p. 757
4289:, vol. 10, p. 41
3869:Brock, William H. (1997).
3705:) with manganese dioxide (
3477:. Retrieved on 2022-02-15.
3162:polyethylene terephthalate
2616:-butanol, 2-ethylhexanol)
2605:Production of Acetaldehyde
2496:involve the conversion of
2470:acetaldehyde dehydrogenase
1781:Dehydrogenation of ethanol
1337:Johann Wolfgang Döbereiner
1303:acetaldehyde dehydrogenase
7304:IARC Group 2B carcinogens
7215:
7106:Earliest known life forms
7101:Diffuse interstellar band
6572:Protonated cyanoacetylene
6342:Protonated carbon dioxide
6302:Hydromagnesium isocyanide
6007:
5631:. PET Resin Association.
5514:10.1080/00365520902912563
5032:10.1038/s41586-020-2059-5
4853:World Health Organization
4512:: 152–165, see pp. 155–8.
4416:, vol. 1, p. 21
4062:10.1007/s00775-015-1330-y
3980:(2007) "Acetaldehyde" in
3820:Döbereiner, J.W. (1832).
3803:Döbereiner, J.W. (1822).
3781:Döbereiner, J.W. (1821).
2492:in bacteria, plants, and
2144:ethylidenecyclohexylamine
1899:with modest selectivity.
1256:organic chemical compound
1203:
1196:
1191:
1142:
1094:
917:
897:
892:
856:
759:
732:trigonal planar (sp) at C
719:
524:Colourless gas or liquid
476:
451:
416:
124:
112:
100:
88:
83:
53:
23:
7294:Hazardous air pollutants
7151:Iron–sulfur world theory
7146:Photodissociation region
6849:Methyl-cyano-diacetylene
5334:Eur Neuropsychopharmacol
4633:Gastroenterology Nursing
4554:, vol. 1, p. 1
4546:10.15227/orgsyn.003.0001
4526:; Nissen, B. H. (1923).
4500:Weidenbusch, H. (1848).
4487:10.15227/orgsyn.030.0041
4451:10.15227/orgsyn.050.0066
4408:10.15227/orgsyn.009.0004
4361:10.15227/orgsyn.004.0053
4321:10.15227/orgsyn.023.0083
4281:10.15227/orgsyn.075.0106
4131:CHO photodissociation".
3717:) produces a smell like
3571:health.howstuffworks.com
3495:. NIOSH. 4 December 2014
3254:. In Coppola, D. (ed.).
3166:Type II Norrish reaction
2161:("aldehyde-collidine").
2159:5-ethyl-2-methylpyridine
2065:. Grignard reagents and
1936:; IUPAC name: ethenol):
1198:Acetaldehyde (data page)
1192:Supplementary data page
983:Precautionary statements
544:0.784 g·cm (20 °C)
7226:Category:Astrochemistry
6816:, fullerene, buckyball)
6503:Cyanobutadiynyl radical
6478:Silicon-carbide cluster
6468:Protonated formaldehyde
5299:Atmospheric Environment
5206:Atmospheric Environment
5171:. McGraw-Hill. p.
5085:10.1196/annals.1293.004
4200:10.1126/science.1220712
3846:Liebig, Justus (1835).
3785:[A new ether].
3420:Acetaldehyde (Compound)
2964:
2926:." In October 2009 the
2914:in humans. In 1988 the
1775:Pelobacter acetylenicus
1339:(1821, 1822, 1832) and
1333:Louis Nicolas Vauquelin
1250:(IUPAC systematic name
1116:1930 mg/kg (rat, oral)
679:Magnetic susceptibility
7239:Outer space portal
7081:Circumstellar envelope
6046:Aluminium(I) hydroxide
5956:Phosphorus mononitride
5833:Aluminium monofluoride
5828:Aluminium monochloride
5439:25 August 2009 at the
4974:Alcohol and Alcoholism
4765:Alcohol and Alcoholism
4301:Walter, L. A. (1943).
3984:, Wiley-VCH, Weinheim
3916:; ce nom est formé de
3910:: 289–327 See p. 290.
3175:
2606:
2521:alcohol flush reaction
2506:pyruvate decarboxylase
2500:into acetaldehyde and
2353:phosphorus trichloride
2289:
2151:heterocyclic compounds
2081:adds to MeCHO to give
2063:condensation reactions
2002:) is more stable than
1917:
1869:
1733:
1611:Hydration of acetylene
1593:
1468:
1030:
644:740 mmHg (20 °C)
74:
64:
44:
34:
7136:Interplanetary medium
7111:Extraterrestrial life
6749:Octatetraynyl radical
6367:Tricarbon monosulfide
5914:Magnesium monohydride
5394:10.3390/ijerph8020613
4987:10.1093/alcalc/agh085
3918:alcool dehydrogenatus
3297:. 2014. p. 908.
3203:Alcohol dehydrogenase
3174:
2837:threshold limit value
2604:
2486:alcohol dehydrogenase
2458:alcohol dehydrogenase
2283:
1915:
1870:
1734:
1594:
1469:
1287:alcohol dehydrogenase
1136:17,000 ppm (hamster),
1029:
737:tetrahedral (sp) at C
102:Systematic IUPAC name
72:
62:
42:
32:
7263:Chemistry portal
7251:Astronomy portal
7197:RNA world hypothesis
7181:PAH world hypothesis
6874:Heptatrienyl radical
6806:Buckminsterfullerene
6694:Methylcyanoacetylene
6202:Silicon carbonitride
6177:Methylidynephosphane
6143:Magnesium isocyanide
6051:Aluminium isocyanide
5853:Carbon monophosphide
4431:; Hesse, A. (1970).
3713:) or sulfuric acid (
3340:as of December 1999.
3208:Disulfiram-like drug
2924:experimental animals
2814:2012–2018. However,
2569:ethylidene diacetate
2529:#Aggravating factors
2345:vinylphosphonic acid
2319:, is formally named
2134:; for example, with
1988:equilibrium constant
1796:
1638:
1491:
1385:
1325:Carl Wilhelm Scheele
1285:by the liver enzyme
1128:median concentration
1012:(fire diamond)
618:slightly soluble in
90:Preferred IUPAC name
63:Ball-and-stick model
7141:Interstellar medium
7121:Forbidden mechanism
6934:Hydrogen isocyanide
6624:Hexatriynyl radical
6207:c-Silicon dicarbide
6112:Hydrogen isocyanide
5976:Silicon monosulfide
5951:Phosphorus monoxide
5919:Methylidyne radical
5878:Fluoromethylidynium
5838:Aluminium(II) oxide
5596:2002WatRe..36.4893N
5311:2009AtmEn..43.4523C
5218:2010AtmEn..44.4388M
5077:2004NYASA1011...36O
4931:1988NYASA.534..369L
4192:2012Sci...337.1203A
4145:2011NatCh...3..443H
4105:10.1021/ja00168a035
4023:2007JChEd..84.1725P
3898:Liebig, J. (1835).
3649:2015PLoSO..1040013Z
3533:10.1155/2011/907317
3336:17 May 2008 at the
3127:Alcohol consumption
3017:Sources of exposure
2975:Alzheimer's disease
2965:Alzheimer's disease
2960:Aggravating factors
2936:alcoholic beverages
2741:1,3-Butylene glycol
2617:
2296:upon reaction with
2077:in the presence of
2025:in the atmosphere.
1863:
1844:
1825:
1812:
1771:Acetylene hydratase
1718:
1699:
1667:
1654:
1584:
1565:
1549:
1520:
1507:
1459:
1439:
1423:
1405:
1161:200 ppm (360 mg/m)
830:−192.2 kJ·mol
803:160.2 J·mol·K
662:13.57 (25 °C,
574:Solubility in water
516: g·mol
73:Space-filling model
20:
7161:Molecules in stars
7131:Intergalactic dust
7076:Circumstellar dust
7018:Naphthalene cation
6953:Trihydrogen cation
6929:Hydrogen deuteride
6854:Methyltriacetylene
6689:Hexapentaenylidene
6508:E-Cyanomethanimine
6428:Cyclopropenylidene
6362:Tricarbon monoxide
6352:Silicon tricarbide
6322:Methylene amidogen
6312:Isothiocyanic acid
6227:Thioxoethenylidene
6187:Trihydrogen cation
6001:Titanium(II) oxide
5961:Potassium chloride
5940:Sulfur mononitride
5883:Helium hydride ion
5858:Carbon monosulfide
5467:Chem. Res. Toxicol
5245:Energy & Fuels
4506:Annalen der Chemie
4242:10.1002/047084289X
4153:10.1038/nchem.1052
4031:10.1021/ed084p1725
3852:Annalen der Chemie
3416:"3.2.17 Viscosity"
3186:Candida overgrowth
3176:
2985:Genetic conditions
2918:stated, "There is
2609:
2607:
2321:1,1-diethoxyethane
2290:
2286:1,1-diethoxyethane
2276:Acetal derivatives
2039:addition reactions
1922:carbonyl compounds
1918:
1865:
1851:
1832:
1813:
1800:
1729:
1706:
1687:
1655:
1642:
1589:
1572:
1553:
1537:
1536:
1508:
1495:
1464:
1447:
1427:
1411:
1393:
1236:Infobox references
1170:(Immediate danger)
1031:
857:Related compounds
75:
65:
45:
35:
18:
7271:
7270:
7186:Pseudo-panspermia
6882:
6881:
6829:Cyanodecapentayne
6769:N-Methylformamide
6744:Methyldiacetylene
6669:Aminoacetonitrile
6639:Methyl isocyanate
6557:Methyl isocyanide
6438:Isocyanoacetylene
6418:Cyanoformaldehyde
6297:Hydrogen peroxide
6182:Potassium cyanide
6138:Magnesium cyanide
6091:Disilicon carbide
6086:Dicarbon monoxide
5893:Hydrogen fluoride
5888:Hydrogen chloride
5747:978-92-832-1271-3
5590:(19): 4893–4901.
5479:10.1021/tx900106y
5182:978-0-07-445549-4
5133:10.1002/ijc.21583
4866:978-92-832-1244-7
4552:Collected Volumes
4533:Organic Syntheses
4474:Organic Syntheses
4457:Collected Volumes
4438:Organic Syntheses
4414:Collected Volumes
4395:Organic Syntheses
4367:Collected Volumes
4348:Organic Syntheses
4343:"Pentaerythritol"
4327:Collected Volumes
4308:Organic Syntheses
4287:Collected Volumes
4268:Organic Syntheses
3797:"Sauerstoffäther"
3759:Annales de Chimie
3741:Annales de Chimie
3715:Spiritus Vitrioli
3471:Sigma-Aldrich Co.
3444:978-1-138-56163-2
3393:978-1-4987-5429-3
3386:. pp. 5–88.
3382:(97th ed.).
3312:978-0-85404-182-4
3273:978-94-007-7192-5
2800:
2799:
2577:polyvinyl acetate
2571:, a precursor to
2513:East Asian people
2325:functional groups
2270:polyvinyl alcohol
2196:of acetaldehyde (
2105:Strecker reaction
2079:calcium hydroxide
2035:organic synthesis
1854:
1847:
1835:
1828:
1816:
1803:
1756:iron(III) sulfate
1727:
1721:
1709:
1702:
1690:
1674:
1658:
1645:
1587:
1575:
1568:
1556:
1540:
1535:
1523:
1511:
1498:
1462:
1450:
1430:
1414:
1396:
1341:Justus von Liebig
1244:Chemical compound
1242:
1241:
1180:Safety data sheet
1138:20,000 ppm (rat)
1134:13,000 ppm (rat),
957:Hazard statements
882:Related compounds
837:Gibbs free energy
385:CompTox Dashboard
173:Interactive image
166:Interactive image
79:
78:
49:
48:
7321:
7261:
7260:
7259:
7249:
7248:
7247:
7237:
7236:
7235:
7224:
7223:
7171:Organic compound
7071:Chemical formula
6976:Dihydroxyacetone
6924:Hydrogen cyanide
6609:Cyanodiacetylene
6463:Propadienylidene
6357:Thioformaldehyde
6232:Titanium dioxide
6197:Sodium hydroxide
6118:Hydrogen sulfide
6106:Hydrogen cyanide
6066:Carbonyl sulfide
6031:
6022:
6013:
5971:Silicon monoxide
5904:Hydroxyl radical
5816:
5796:
5789:
5782:
5773:
5751:
5733:
5724:
5718:
5691:
5690:
5661:Candida albicans
5654:
5648:
5647:
5645:
5643:
5637:
5630:
5622:
5616:
5615:
5579:
5573:
5572:
5552:
5546:
5540:
5534:
5533:
5497:
5491:
5490:
5462:
5456:
5450:
5444:
5443:. drugabuse.gov.
5431:
5425:
5424:
5414:
5396:
5372:
5366:
5365:
5329:
5323:
5322:
5293:
5287:
5286:
5268:
5251:(18): 14963–83.
5236:
5230:
5229:
5201:
5195:
5194:
5170:
5160:
5154:
5153:
5135:
5126:(8): 1998–2002.
5111:
5105:
5104:
5060:
5054:
5053:
5043:
5011:
5000:
4999:
4989:
4965:
4959:
4958:
4914:
4908:
4907:
4878:
4872:
4870:
4850:
4847:Alcohol drinking
4840:
4834:
4833:
4831:
4829:
4823:
4816:
4807:
4801:
4795:
4789:
4788:
4760:
4754:
4747:
4741:
4735:
4729:
4728:
4692:
4683:
4682:
4671:
4665:
4664:
4628:
4622:
4621:
4598:Curr. Drug Metab
4593:
4584:
4583:
4563:
4557:
4555:
4548:
4520:
4514:
4513:
4497:
4491:
4489:
4468:
4462:
4460:
4453:
4425:
4419:
4417:
4410:
4378:
4372:
4370:
4363:
4338:
4332:
4330:
4323:
4298:
4292:
4290:
4283:
4250:
4244:
4226:
4220:
4219:
4186:(6099): 1203–6.
4171:
4165:
4164:
4133:Nature Chemistry
4124:
4118:
4115:
4109:
4108:
4088:
4082:
4081:
4041:
4035:
4034:
4007:
3998:
3992:
3974:
3947:
3946:
3929:
3923:
3922:
3895:
3889:
3888:
3866:
3860:
3859:
3843:
3837:
3833:
3816:
3794:
3775:
3769:
3766:
3748:
3728:
3722:
3687:
3681:
3680:
3670:
3660:
3643:(10): e0140013.
3628:
3619:
3614:
3608:
3607:
3605:
3603:
3584:
3575:
3574:
3562:
3556:
3555:
3545:
3535:
3511:
3505:
3504:
3502:
3500:
3489:
3478:
3468:
3457:
3456:
3430:
3424:
3423:
3412:
3406:
3405:
3373:
3367:
3366:
3354:
3341:
3326:
3317:
3316:
3287:
3278:
3277:
3247:
3241:
3238:
3191:Candida albicans
3079:Natural tobacco
2953:Fanconi's anemia
2910:Acetaldehyde is
2618:
2565:Acetic anhydride
2545:Cativa processes
2475:
2440:
2419:
2397:
2396:
2393:
2381:
2380:
2379:
2376:
2318:
2244:
2203:
2186:
2177:
2095:
2052:
2041:acetaldehyde is
2023:carboxylic acids
2013:
2001:
1993:
1974:
1971:
1968:
1965:
1962:
1959:
1956:
1953:
1950:
1920:Like many other
1889:hydroformylation
1874:
1872:
1871:
1866:
1864:
1862:
1859:
1852:
1845:
1843:
1840:
1833:
1826:
1824:
1821:
1814:
1811:
1808:
1801:
1760:iron(II) sulfate
1738:
1736:
1735:
1730:
1728:
1725:
1719:
1717:
1714:
1707:
1700:
1698:
1695:
1688:
1683:
1682:
1672:
1666:
1663:
1656:
1653:
1650:
1643:
1598:
1596:
1595:
1590:
1588:
1585:
1583:
1580:
1573:
1566:
1564:
1561:
1554:
1548:
1545:
1538:
1528:
1521:
1519:
1516:
1509:
1506:
1503:
1496:
1473:
1471:
1470:
1465:
1463:
1460:
1458:
1455:
1448:
1438:
1435:
1428:
1422:
1419:
1412:
1410:
1404:
1401:
1394:
1269:
1226:
1220:
1217:
1216:
1086:Explosive limits
1051:
1044:
1037:
1022:
1002:
998:
994:
990:
976:
972:
968:
964:
950:
945:
940:
848:
826:
799:
779:89 J·mol·K
775:
760:Thermochemistry
692:Refractive index
671:
515:
503:
497:
491:
484:Chemical formula
409:
408:
393:
391:
375:
339:
328:
314:
294:
265:
257:
246:
235:
215:
195:
175:
168:
144:
55:
25:
21:
7331:
7330:
7324:
7323:
7322:
7320:
7319:
7318:
7274:
7273:
7272:
7267:
7257:
7255:
7245:
7243:
7233:
7231:
7211:
7037:
7013:
7004:
6957:
6947:
6890:
6878:
6859:Propionaldehyde
6834:Ethylene glycol
6823:
6815:
6811:
6782:
6780:
6773:
6729:Cyanohexatriyne
6715:
6708:
6655:
6648:
6583:
6576:
6536:
6489:
6482:
6453:Methoxy radical
6383:
6376:
6372:Thiocyanic acid
6253:
6246:
6156:
6096:Ethynyl radical
6032:
6026:
6025:
6024:
6023:
6017:
6016:
6015:
6014:
6005:
5996:Sulfur monoxide
5981:Sodium chloride
5966:Silicon carbide
5873:Diatomic carbon
5863:Carbon monoxide
5805:
5800:
5748:
5731:
5727:
5716:
5712:
5699:
5694:
5656:
5655:
5651:
5641:
5639:
5635:
5628:
5624:
5623:
5619:
5581:
5580:
5576:
5554:
5553:
5549:
5541:
5537:
5499:
5498:
5494:
5464:
5463:
5459:
5451:
5447:
5441:Wayback Machine
5432:
5428:
5387:(12): 613–628.
5374:
5373:
5369:
5331:
5330:
5326:
5305:(30): 4523–34.
5295:
5294:
5290:
5238:
5237:
5233:
5212:(35): 4388–95.
5203:
5202:
5198:
5183:
5162:
5161:
5157:
5113:
5112:
5108:
5062:
5061:
5057:
5026:(7800): 603–8.
5013:
5012:
5003:
4967:
4966:
4962:
4916:
4915:
4911:
4880:
4879:
4875:
4867:
4842:
4841:
4837:
4827:
4825:
4821:
4814:
4809:
4808:
4804:
4796:
4792:
4762:
4761:
4757:
4748:
4744:
4736:
4732:
4694:
4693:
4686:
4673:
4672:
4668:
4630:
4629:
4625:
4595:
4594:
4587:
4565:
4564:
4560:
4550:
4522:
4521:
4517:
4499:
4498:
4494:
4470:
4469:
4465:
4455:
4427:
4426:
4422:
4412:
4380:
4379:
4375:
4365:
4340:
4339:
4335:
4325:
4300:
4299:
4295:
4285:
4255:Paquette, L. A.
4252:
4251:
4247:
4227:
4223:
4173:
4172:
4168:
4130:
4126:
4125:
4121:
4116:
4112:
4090:
4089:
4085:
4043:
4042:
4038:
4005:
4000:
3999:
3995:
3975:
3950:
3932:
3930:
3926:
3897:
3896:
3892:
3885:
3868:
3867:
3863:
3845:
3844:
3840:
3819:
3802:
3799:(oxygen-ether).
3780:
3776:
3772:
3752:
3734:
3729:
3725:
3688:
3684:
3630:
3629:
3622:
3615:
3611:
3601:
3599:
3586:
3585:
3578:
3564:
3563:
3559:
3513:
3512:
3508:
3498:
3496:
3491:
3490:
3481:
3469:
3460:
3445:
3432:
3431:
3427:
3414:
3413:
3409:
3394:
3375:
3374:
3370:
3356:
3355:
3344:
3338:Wayback Machine
3327:
3320:
3313:
3289:
3288:
3281:
3274:
3249:
3248:
3244:
3239:
3235:
3231:
3199:
3188:
3158:photo-oxidation
3154:
3129:
3117:
3111:while smoking.
3081:polysaccharides
3077:
3064:
3024:
3019:
3003:
2987:
2967:
2962:
2948:
2908:
2906:Carcinogenicity
2869:
2861:
2856:
2833:
2831:Exposure limits
2828:
2681:Pentaerythritol
2611:
2598:
2553:pentaerythritol
2537:
2473:
2447:
2438:
2434:
2430:
2426:
2422:
2417:
2413:
2409:
2405:
2401:
2394:
2391:
2390:
2388:
2384:
2377:
2374:
2373:
2371:
2367:
2363:
2359:
2341:
2334:
2330:
2317:
2313:
2309:
2305:
2301:
2278:
2243:
2239:
2235:
2224:
2223:
2222:
2221:
2212:= 3, left) and
2201:
2197:
2189:
2188:
2187:
2179:
2178:
2167:
2165:Polymeric forms
2136:cyclohexylamine
2115:to give, after
2094:
2090:
2086:
2083:pentaerythritol
2059:aldol reactions
2050:
2046:
2031:
2011:
2007:
1999:
1995:
1991:
1981:
1972:
1969:
1966:
1963:
1960:
1957:
1954:
1951:
1948:
1944:
1940:
1924:, acetaldehyde
1910:
1905:
1885:
1794:
1793:
1787:dehydrogenation
1783:
1671:
1636:
1635:
1613:
1608:
1489:
1488:
1383:
1382:
1349:
1321:
1267:
1262:
1245:
1238:
1233:
1232:
1231: ?)
1222:
1218:
1214:
1210:
1171:
1158:
1137:
1135:
1131:
1125:
1113:
1107:
1077:
1074:
1056:
1055:
1054:
1053:
1046:
1039:
1032:
1028:
1020:
985:
959:
933:
910:
883:
875:Propionaldehyde
873:
867:
849:
843:
839:
827:
824:
818:
814:
811:
810:Std enthalpy of
800:
797:
790:
787:
776:
769:
749:
740:
736:
735:
729:
727:Molecular shape
702:
700:
682:
668:
663:
658:
617:
576:
513:
500:
494:
486:
472:
469:
464:
459:
458:
447:
444:
443:
440:
434:
433:
430:
424:
423:
412:
394:
387:
378:
358:
342:
329:
317:
297:
284:
275:
238:
218:
198:
178:
158:
147:
134:
120:
118:
116:
115:Acetic aldehyde
108:
107:
96:
95:
12:
11:
5:
7329:
7328:
7325:
7317:
7316:
7311:
7306:
7301:
7296:
7291:
7286:
7276:
7275:
7269:
7268:
7266:
7265:
7253:
7241:
7229:
7216:
7213:
7212:
7210:
7209:
7204:
7199:
7194:
7188:
7183:
7178:
7173:
7168:
7163:
7158:
7153:
7148:
7143:
7138:
7133:
7128:
7123:
7118:
7113:
7108:
7103:
7098:
7096:Cosmochemistry
7093:
7088:
7083:
7078:
7073:
7068:
7063:
7061:Astrochemistry
7058:
7053:
7047:
7045:
7039:
7038:
7036:
7035:
7030:
7025:
7020:
7015:
7011:
7007:
7002:
6998:
6993:
6988:
6983:
6978:
6973:
6967:
6965:
6959:
6958:
6956:
6955:
6950:
6945:
6941:
6936:
6931:
6926:
6921:
6916:
6914:Formyl radical
6911:
6906:
6900:
6894:
6892:
6884:
6883:
6880:
6879:
6877:
6876:
6871:
6866:
6861:
6856:
6851:
6846:
6844:Methyl acetate
6841:
6836:
6831:
6826:
6821:
6817:
6813:
6809:
6803:
6798:
6793:
6787:
6785:
6775:
6774:
6772:
6771:
6766:
6761:
6756:
6751:
6746:
6741:
6736:
6734:Dimethyl ether
6731:
6726:
6720:
6718:
6710:
6709:
6707:
6706:
6701:
6699:Methyl formate
6696:
6691:
6686:
6684:Glycolaldehyde
6681:
6676:
6671:
6666:
6660:
6658:
6650:
6649:
6647:
6646:
6641:
6636:
6631:
6626:
6621:
6619:Glycolonitrile
6616:
6614:Ethylene oxide
6611:
6606:
6605:
6604:
6594:
6588:
6586:
6578:
6577:
6575:
6574:
6569:
6564:
6559:
6554:
6549:
6544:
6539:
6534:
6530:
6525:
6520:
6515:
6513:Cyclopropenone
6510:
6505:
6500:
6494:
6492:
6484:
6483:
6481:
6480:
6475:
6470:
6465:
6460:
6455:
6450:
6445:
6440:
6435:
6430:
6425:
6420:
6415:
6413:Cyanoacetylene
6410:
6405:
6400:
6395:
6388:
6386:
6378:
6377:
6375:
6374:
6369:
6364:
6359:
6354:
6349:
6344:
6339:
6334:
6332:Methyl radical
6329:
6324:
6319:
6314:
6309:
6307:Isocyanic acid
6304:
6299:
6294:
6289:
6284:
6279:
6274:
6272:Isocyanic acid
6269:
6264:
6258:
6256:
6248:
6247:
6245:
6244:
6239:
6234:
6229:
6224:
6219:
6217:Sulfur dioxide
6214:
6209:
6204:
6199:
6194:
6192:Sodium cyanide
6189:
6184:
6179:
6174:
6169:
6164:
6159:
6154:
6150:
6145:
6140:
6135:
6130:
6125:
6120:
6115:
6109:
6103:
6101:Formyl radical
6098:
6093:
6088:
6083:
6078:
6073:
6068:
6063:
6061:Carbon dioxide
6058:
6053:
6048:
6042:
6040:
6034:
6033:
6008:
6006:
6004:
6003:
5998:
5993:
5988:
5983:
5978:
5973:
5968:
5963:
5958:
5953:
5948:
5942:
5937:
5932:
5926:
5921:
5916:
5911:
5909:Iron(II) oxide
5906:
5901:
5895:
5890:
5885:
5880:
5875:
5870:
5865:
5860:
5855:
5850:
5845:
5840:
5835:
5830:
5824:
5822:
5813:
5807:
5806:
5801:
5799:
5798:
5791:
5784:
5776:
5770:
5769:
5764:
5759:
5752:
5746:
5729:"ACETALDEHYDE"
5725:
5710:
5705:
5698:
5697:External links
5695:
5693:
5692:
5649:
5617:
5584:Water Research
5574:
5563:(1): 203–215.
5547:
5535:
5508:(8): 912–925.
5492:
5457:
5445:
5426:
5367:
5340:(10): 627–36.
5324:
5288:
5231:
5196:
5181:
5155:
5106:
5055:
5001:
4960:
4909:
4890:(11): 1033–4.
4873:
4865:
4835:
4817:. p. 11.
4802:
4790:
4755:
4742:
4738:"Acetaldehyde"
4730:
4684:
4666:
4623:
4604:(7): 716–727.
4585:
4574:(8): 1078–92.
4558:
4515:
4492:
4463:
4420:
4382:Kendall, E. C.
4373:
4333:
4293:
4245:
4221:
4166:
4128:
4119:
4110:
4099:(12): 4862–8.
4083:
4036:
4011:J. Chem. Educ.
3993:
3948:
3924:
3890:
3883:
3861:
3838:
3836:
3835:
3817:
3800:
3770:
3768:
3767:
3749:
3735:Dabit (1800).
3723:
3719:"Aether nitri"
3682:
3620:
3609:
3576:
3557:
3506:
3493:"Acetaldehyde"
3479:
3458:
3443:
3425:
3407:
3392:
3368:
3342:
3318:
3311:
3279:
3272:
3242:
3232:
3230:
3227:
3226:
3225:
3220:
3215:
3210:
3205:
3198:
3195:
3187:
3184:
3180:odor threshold
3153:
3150:
3128:
3125:
3121:cannabis smoke
3116:
3115:Cannabis smoke
3113:
3101:rodent studies
3076:
3073:
3069:diesel exhaust
3063:
3060:
3030:In a study in
3023:
3020:
3018:
3015:
3002:
2999:
2986:
2983:
2966:
2963:
2961:
2958:
2947:
2946:DNA crosslinks
2944:
2907:
2904:
2868:
2865:
2860:
2857:
2855:
2852:
2832:
2829:
2827:
2824:
2798:
2797:
2794:
2791:
2788:
2785:
2782:
2778:
2777:
2774:
2771:
2768:
2765:
2762:
2758:
2757:
2754:
2751:
2748:
2745:
2742:
2738:
2737:
2734:
2731:
2728:
2725:
2722:
2721:Peracetic acid
2718:
2717:
2714:
2711:
2708:
2705:
2702:
2698:
2697:
2694:
2691:
2688:
2685:
2682:
2678:
2677:
2674:
2671:
2668:
2665:
2662:
2661:Acetate esters
2658:
2657:
2654:
2651:
2648:
2645:
2642:
2638:
2637:
2634:
2631:
2628:
2625:
2622:
2587:-butyraldehyde
2557:crotonaldehyde
2536:
2533:
2504:by the enzyme
2502:carbon dioxide
2446:
2443:
2442:
2441:
2420:
2382:
2349:ion conductive
2340:
2337:
2332:
2328:
2277:
2274:
2191:
2190:
2181:
2180:
2172:
2171:
2170:
2169:
2168:
2166:
2163:
2030:
2027:
1984:
1983:
1982:= +42.7 kJ/mol
1979:
1909:
1906:
1904:
1901:
1884:
1881:
1876:
1875:
1858:
1850:
1839:
1831:
1820:
1807:
1782:
1779:
1740:
1739:
1724:
1713:
1705:
1694:
1686:
1681:
1678:
1670:
1662:
1649:
1617:Wacker process
1612:
1609:
1607:
1604:
1600:
1599:
1579:
1571:
1560:
1552:
1544:
1534:
1531:
1526:
1515:
1502:
1475:
1474:
1454:
1445:
1442:
1434:
1426:
1418:
1409:
1400:
1391:
1372:Wacker process
1348:
1345:
1320:
1317:
1243:
1240:
1239:
1234:
1212:
1211:
1207:standard state
1204:
1201:
1200:
1194:
1193:
1189:
1188:
1183:
1176:
1175:
1172:
1166:
1163:
1162:
1159:
1153:
1150:
1149:
1140:
1139:
1132:
1123:
1121:
1118:
1117:
1114:
1105:
1103:
1100:
1099:
1092:
1091:
1088:
1082:
1081:
1078:
1071:
1068:
1067:
1064:
1058:
1057:
1047:
1040:
1033:
1018:
1017:
1016:
1015:
1013:
1004:
1003:
1001:P305+P351+P338
986:
981:
978:
977:
960:
955:
952:
951:
934:
929:
926:
925:
915:
914:
911:
908:
905:
904:
895:
894:
890:
889:
887:Ethylene oxide
884:
881:
878:
877:
868:
862:
859:
858:
854:
853:
852:-127.6 kJ·mol
850:
841:
835:
832:
831:
828:
822:
816:
808:
805:
804:
801:
795:
784:
781:
780:
777:
765:
762:
761:
757:
756:
750:
745:
742:
741:
738:
733:
730:
725:
722:
721:
717:
716:
713:
707:
706:
703:
698:
690:
687:
686:
683:
677:
674:
673:
660:
656:
646:
645:
642:
640:Vapor pressure
636:
635:
632:
623:
622:
589:miscible with
587:
581:
580:
577:
572:
569:
568:
565:
559:
558:
555:
549:
548:
542:
536:
535:
532:
526:
525:
522:
518:
517:
511:
505:
504:
498:
492:
487:
482:
479:
478:
474:
473:
471:
470:
467:
465:
462:
454:
453:
452:
449:
448:
446:
445:
441:
438:
437:
435:
431:
428:
427:
419:
418:
417:
414:
413:
411:
410:
397:
395:
383:
380:
379:
377:
376:
368:
366:
360:
359:
357:
356:
352:
350:
344:
343:
341:
340:
332:
330:
322:
319:
318:
316:
315:
307:
305:
299:
298:
296:
295:
287:
285:
280:
277:
276:
274:
273:
269:
267:
259:
258:
248:
240:
239:
237:
236:
228:
226:
220:
219:
217:
216:
208:
206:
200:
199:
197:
196:
188:
186:
180:
179:
177:
176:
169:
161:
159:
152:
149:
148:
146:
145:
137:
135:
130:
127:
126:
122:
121:
119:Acetylaldehyde
117:Ethyl aldehyde
114:
110:
109:
105:
104:
98:
97:
93:
92:
86:
85:
81:
80:
77:
76:
66:
51:
50:
47:
46:
36:
13:
10:
9:
6:
4:
3:
2:
7327:
7326:
7315:
7312:
7310:
7307:
7305:
7302:
7300:
7297:
7295:
7292:
7290:
7287:
7285:
7282:
7281:
7279:
7264:
7254:
7252:
7242:
7240:
7230:
7228:
7227:
7218:
7217:
7214:
7208:
7205:
7203:
7200:
7198:
7195:
7192:
7189:
7187:
7184:
7182:
7179:
7177:
7174:
7172:
7169:
7167:
7164:
7162:
7159:
7157:
7154:
7152:
7149:
7147:
7144:
7142:
7139:
7137:
7134:
7132:
7129:
7127:
7126:Homochirality
7124:
7122:
7119:
7117:
7114:
7112:
7109:
7107:
7104:
7102:
7099:
7097:
7094:
7092:
7089:
7087:
7084:
7082:
7079:
7077:
7074:
7072:
7069:
7067:
7064:
7062:
7059:
7057:
7054:
7052:
7049:
7048:
7046:
7044:
7040:
7034:
7031:
7029:
7026:
7024:
7021:
7019:
7016:
7014:
7008:
7006:
6999:
6997:
6994:
6992:
6989:
6987:
6984:
6982:
6981:Methoxyethane
6979:
6977:
6974:
6972:
6969:
6968:
6966:
6964:
6960:
6954:
6951:
6949:
6942:
6940:
6937:
6935:
6932:
6930:
6927:
6925:
6922:
6920:
6917:
6915:
6912:
6910:
6907:
6904:
6901:
6899:
6896:
6895:
6893:
6889:
6885:
6875:
6872:
6870:
6867:
6865:
6864:Butyronitrile
6862:
6860:
6857:
6855:
6852:
6850:
6847:
6845:
6842:
6840:
6839:Ethyl formate
6837:
6835:
6832:
6830:
6827:
6825:
6818:
6807:
6804:
6802:
6799:
6797:
6794:
6792:
6789:
6788:
6786:
6784:
6776:
6770:
6767:
6765:
6764:Propionitrile
6762:
6760:
6757:
6755:
6752:
6750:
6747:
6745:
6742:
6740:
6737:
6735:
6732:
6730:
6727:
6725:
6722:
6721:
6719:
6717:
6711:
6705:
6702:
6700:
6697:
6695:
6692:
6690:
6687:
6685:
6682:
6680:
6677:
6675:
6672:
6670:
6667:
6665:
6662:
6661:
6659:
6657:
6651:
6645:
6644:Vinyl alcohol
6642:
6640:
6637:
6635:
6632:
6630:
6627:
6625:
6622:
6620:
6617:
6615:
6612:
6610:
6607:
6603:
6602:Vinyl cyanide
6600:
6599:
6598:
6597:Acrylonitrile
6595:
6593:
6590:
6589:
6587:
6585:
6579:
6573:
6570:
6568:
6565:
6563:
6562:Pentynylidyne
6560:
6558:
6555:
6553:
6550:
6548:
6545:
6543:
6540:
6538:
6531:
6529:
6526:
6524:
6521:
6519:
6516:
6514:
6511:
6509:
6506:
6504:
6501:
6499:
6496:
6495:
6493:
6491:
6485:
6479:
6476:
6474:
6471:
6469:
6466:
6464:
6461:
6459:
6458:Methylenimine
6456:
6454:
6451:
6449:
6446:
6444:
6441:
6439:
6436:
6434:
6431:
6429:
6426:
6424:
6421:
6419:
6416:
6414:
6411:
6409:
6406:
6404:
6401:
6399:
6396:
6393:
6390:
6389:
6387:
6385:
6379:
6373:
6370:
6368:
6365:
6363:
6360:
6358:
6355:
6353:
6350:
6348:
6345:
6343:
6340:
6338:
6337:Propynylidyne
6335:
6333:
6330:
6328:
6327:Methyl cation
6325:
6323:
6320:
6318:
6315:
6313:
6310:
6308:
6305:
6303:
6300:
6298:
6295:
6293:
6290:
6288:
6287:Fulminic acid
6285:
6283:
6280:
6278:
6275:
6273:
6270:
6268:
6265:
6263:
6260:
6259:
6257:
6255:
6249:
6243:
6240:
6238:
6235:
6233:
6230:
6228:
6225:
6223:
6220:
6218:
6215:
6213:
6210:
6208:
6205:
6203:
6200:
6198:
6195:
6193:
6190:
6188:
6185:
6183:
6180:
6178:
6175:
6173:
6170:
6168:
6165:
6163:
6162:Nitrous oxide
6160:
6158:
6151:
6149:
6146:
6144:
6141:
6139:
6136:
6134:
6131:
6129:
6126:
6124:
6121:
6119:
6116:
6113:
6110:
6107:
6104:
6102:
6099:
6097:
6094:
6092:
6089:
6087:
6084:
6082:
6079:
6077:
6074:
6072:
6069:
6067:
6064:
6062:
6059:
6057:
6056:Amino radical
6054:
6052:
6049:
6047:
6044:
6043:
6041:
6039:
6035:
6030:
6021:
6012:
6002:
5999:
5997:
5994:
5992:
5989:
5987:
5986:Sodium iodide
5984:
5982:
5979:
5977:
5974:
5972:
5969:
5967:
5964:
5962:
5959:
5957:
5954:
5952:
5949:
5946:
5943:
5941:
5938:
5936:
5933:
5930:
5927:
5925:
5922:
5920:
5917:
5915:
5912:
5910:
5907:
5905:
5902:
5899:
5896:
5894:
5891:
5889:
5886:
5884:
5881:
5879:
5876:
5874:
5871:
5869:
5868:Cyano radical
5866:
5864:
5861:
5859:
5856:
5854:
5851:
5849:
5848:Carbon cation
5846:
5844:
5841:
5839:
5836:
5834:
5831:
5829:
5826:
5825:
5823:
5821:
5817:
5814:
5812:
5808:
5804:
5797:
5792:
5790:
5785:
5783:
5778:
5777:
5774:
5768:
5765:
5763:
5760:
5757:
5753:
5749:
5743:
5739:
5738:
5730:
5726:
5722:
5715:
5711:
5709:
5706:
5704:
5701:
5700:
5696:
5688:
5684:
5680:
5676:
5672:
5668:
5664:
5662:
5653:
5650:
5634:
5627:
5621:
5618:
5613:
5609:
5605:
5601:
5597:
5593:
5589:
5585:
5578:
5575:
5570:
5566:
5562:
5558:
5551:
5548:
5544:
5539:
5536:
5531:
5527:
5523:
5519:
5515:
5511:
5507:
5503:
5496:
5493:
5488:
5484:
5480:
5476:
5473:(6): 1181–8.
5472:
5468:
5461:
5458:
5454:
5449:
5446:
5442:
5438:
5435:
5430:
5427:
5422:
5418:
5413:
5408:
5404:
5400:
5395:
5390:
5386:
5382:
5378:
5371:
5368:
5363:
5359:
5355:
5351:
5347:
5343:
5339:
5335:
5328:
5325:
5320:
5316:
5312:
5308:
5304:
5300:
5292:
5289:
5284:
5280:
5276:
5272:
5267:
5262:
5258:
5254:
5250:
5246:
5242:
5235:
5232:
5227:
5223:
5219:
5215:
5211:
5207:
5200:
5197:
5192:
5188:
5184:
5178:
5174:
5169:
5168:
5159:
5156:
5151:
5147:
5143:
5139:
5134:
5129:
5125:
5121:
5117:
5110:
5107:
5102:
5098:
5094:
5090:
5086:
5082:
5078:
5074:
5070:
5066:
5059:
5056:
5051:
5047:
5042:
5037:
5033:
5029:
5025:
5021:
5017:
5010:
5008:
5006:
5002:
4997:
4993:
4988:
4983:
4979:
4975:
4971:
4964:
4961:
4956:
4952:
4948:
4944:
4940:
4936:
4932:
4928:
4925:(1): 369–76.
4924:
4920:
4913:
4910:
4905:
4901:
4897:
4893:
4889:
4885:
4877:
4874:
4868:
4862:
4858:
4854:
4849:
4848:
4839:
4836:
4820:
4813:
4806:
4803:
4799:
4794:
4791:
4786:
4782:
4778:
4774:
4770:
4766:
4759:
4756:
4752:
4746:
4743:
4739:
4734:
4731:
4726:
4722:
4718:
4714:
4710:
4706:
4702:
4698:
4691:
4689:
4685:
4680:
4676:
4670:
4667:
4662:
4658:
4654:
4650:
4646:
4642:
4639:(5): 327–36.
4638:
4634:
4627:
4624:
4619:
4615:
4611:
4607:
4603:
4599:
4592:
4590:
4586:
4581:
4577:
4573:
4569:
4562:
4559:
4553:
4547:
4543:
4539:
4535:
4534:
4529:
4525:
4519:
4516:
4511:
4507:
4503:
4496:
4493:
4488:
4484:
4480:
4476:
4475:
4467:
4464:
4458:
4452:
4448:
4444:
4440:
4439:
4434:
4430:
4424:
4421:
4415:
4409:
4405:
4401:
4397:
4396:
4391:
4389:
4383:
4377:
4374:
4368:
4362:
4358:
4354:
4350:
4349:
4344:
4337:
4334:
4328:
4322:
4318:
4314:
4310:
4309:
4304:
4297:
4294:
4288:
4282:
4278:
4274:
4270:
4269:
4264:
4262:
4256:
4253:Behrens, C.;
4249:
4246:
4243:
4239:
4235:
4231:
4225:
4222:
4217:
4213:
4209:
4205:
4201:
4197:
4193:
4189:
4185:
4181:
4177:
4176:Vinyl Alcohol
4170:
4167:
4162:
4158:
4154:
4150:
4146:
4142:
4138:
4134:
4123:
4120:
4114:
4111:
4106:
4102:
4098:
4094:
4087:
4084:
4079:
4075:
4071:
4067:
4063:
4059:
4055:
4051:
4047:
4040:
4037:
4032:
4028:
4024:
4020:
4016:
4013:
4012:
4004:
3997:
3994:
3991:
3987:
3983:
3979:
3976:Eckert, Marc
3973:
3971:
3969:
3967:
3965:
3963:
3961:
3959:
3957:
3955:
3953:
3949:
3944:
3940:
3936:
3928:
3925:
3921:
3919:
3915:
3909:
3905:
3901:
3894:
3891:
3886:
3884:0-521-52473-3
3880:
3876:
3872:
3865:
3862:
3857:
3853:
3849:
3842:
3839:
3831:
3827:
3823:
3818:
3814:
3810:
3806:
3801:
3798:
3792:
3788:
3784:
3783:"Neue Aether"
3779:
3778:
3774:
3771:
3764:
3760:
3756:
3750:
3746:
3742:
3738:
3732:
3731:
3727:
3724:
3720:
3716:
3712:
3711:Spirtus salis
3708:
3704:
3700:
3699:pages 109–110
3696:
3692:
3686:
3683:
3678:
3674:
3669:
3664:
3659:
3654:
3650:
3646:
3642:
3638:
3634:
3627:
3625:
3621:
3618:
3613:
3610:
3597:
3593:
3589:
3583:
3581:
3577:
3572:
3568:
3561:
3558:
3553:
3549:
3544:
3539:
3534:
3529:
3525:
3521:
3517:
3510:
3507:
3494:
3488:
3486:
3484:
3480:
3476:
3472:
3467:
3465:
3463:
3459:
3454:
3450:
3446:
3440:
3436:
3429:
3426:
3421:
3417:
3411:
3408:
3403:
3399:
3395:
3389:
3385:
3381:
3380:
3372:
3369:
3364:
3360:
3353:
3351:
3349:
3347:
3343:
3339:
3335:
3332:
3331:
3325:
3323:
3319:
3314:
3308:
3304:
3300:
3296:
3293:. Cambridge:
3292:
3286:
3284:
3280:
3275:
3269:
3265:
3261:
3257:
3253:
3246:
3243:
3237:
3234:
3228:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3200:
3196:
3194:
3192:
3185:
3183:
3181:
3173:
3169:
3167:
3164:(PET), via a
3163:
3159:
3151:
3149:
3147:
3146:mouth-washing
3143:
3138:
3134:
3126:
3124:
3122:
3114:
3112:
3110:
3106:
3102:
3098:
3094:
3090:
3089:tobacco smoke
3086:
3082:
3075:Tobacco smoke
3074:
3072:
3070:
3061:
3059:
3056:
3052:
3048:
3043:
3041:
3037:
3033:
3028:
3021:
3016:
3014:
3012:
3008:
3000:
2998:
2996:
2992:
2984:
2982:
2980:
2976:
2972:
2959:
2957:
2954:
2945:
2943:
2941:
2937:
2933:
2929:
2925:
2921:
2917:
2913:
2905:
2903:
2901:
2897:
2893:
2890:
2886:
2882:
2878:
2874:
2866:
2864:
2858:
2853:
2851:
2849:
2845:
2842:
2838:
2830:
2825:
2823:
2821:
2817:
2812:
2808:
2804:
2795:
2792:
2789:
2786:
2783:
2780:
2779:
2775:
2772:
2769:
2766:
2763:
2760:
2759:
2755:
2752:
2749:
2746:
2743:
2740:
2739:
2735:
2732:
2729:
2726:
2723:
2720:
2719:
2715:
2712:
2709:
2706:
2703:
2700:
2699:
2695:
2692:
2689:
2686:
2683:
2680:
2679:
2675:
2672:
2669:
2666:
2663:
2660:
2659:
2655:
2652:
2649:
2646:
2643:
2640:
2639:
2635:
2632:
2629:
2626:
2623:
2620:
2619:
2615:
2603:
2599:
2596:
2593:. Likewise,
2592:
2588:
2586:
2580:
2578:
2574:
2573:vinyl acetate
2570:
2566:
2562:
2558:
2554:
2551:derivatives,
2550:
2546:
2542:
2534:
2532:
2530:
2526:
2522:
2518:
2514:
2509:
2507:
2503:
2499:
2495:
2491:
2487:
2483:
2479:
2471:
2467:
2463:
2459:
2456:
2452:
2444:
2421:
2383:
2358:
2357:
2356:
2354:
2350:
2346:
2338:
2336:
2331:or RR'C(OR'')
2326:
2322:
2299:
2295:
2287:
2282:
2275:
2273:
2271:
2267:
2263:
2262:vinyl alcohol
2258:
2256:
2250:
2248:
2233:
2229:
2219:
2215:
2211:
2207:
2195:
2185:
2176:
2164:
2162:
2160:
2156:
2152:
2147:
2145:
2141:
2137:
2133:
2129:
2125:
2122:
2118:
2114:
2110:
2106:
2101:
2099:
2084:
2080:
2076:
2072:
2068:
2067:organolithium
2064:
2060:
2056:
2044:
2040:
2036:
2028:
2026:
2024:
2020:
2015:
2005:
2004:vinyl alcohol
1989:
1978:
1945:CH=O ⇌ CH
1939:
1938:
1937:
1935:
1934:vinyl alcohol
1931:
1927:
1923:
1914:
1907:
1902:
1900:
1898:
1897:synthesis gas
1894:
1890:
1882:
1880:
1856:
1848:
1837:
1818:
1805:
1792:
1791:
1790:
1788:
1780:
1778:
1776:
1772:
1767:
1765:
1761:
1757:
1753:
1752:wet oxidation
1749:
1745:
1744:vinyl alcohol
1722:
1711:
1692:
1684:
1679:
1676:
1668:
1660:
1647:
1634:
1633:
1632:
1630:
1626:
1622:
1618:
1615:Prior to the
1610:
1606:Other methods
1605:
1603:
1577:
1569:
1558:
1542:
1532:
1529:
1524:
1513:
1500:
1487:
1486:
1485:
1483:
1478:
1452:
1443:
1432:
1424:
1416:
1407:
1398:
1389:
1381:
1380:
1379:
1377:
1373:
1369:
1364:
1362:
1358:
1354:
1346:
1344:
1342:
1338:
1334:
1330:
1326:
1318:
1316:
1314:
1310:
1306:
1304:
1300:
1296:
1292:
1288:
1284:
1280:
1276:
1272:
1268:
1261:
1257:
1253:
1249:
1237:
1230:
1225:
1208:
1202:
1199:
1195:
1190:
1187:
1184:
1181:
1178:
1177:
1173:
1169:
1165:
1164:
1160:
1157:(Permissible)
1156:
1152:
1151:
1147:
1146:
1141:
1133:
1129:
1120:
1119:
1115:
1111:
1102:
1101:
1097:
1093:
1089:
1087:
1084:
1083:
1079:
1076:
1070:
1069:
1065:
1063:
1060:
1059:
1052:
1045:
1038:
1014:
1011:
1010:
1006:
1005:
987:
984:
980:
979:
961:
958:
954:
953:
949:
944:
939:
935:
932:
928:
927:
923:
921:
916:
912:
907:
906:
902:
901:
896:
891:
888:
885:
880:
879:
876:
872:
869:
866:
861:
860:
855:
851:
846:
838:
834:
833:
829:
821:
813:
807:
806:
802:
794:
789:
783:
782:
778:
773:
768:
767:Heat capacity
764:
763:
758:
755:
751:
748:
747:Dipole moment
744:
743:
731:
728:
724:
723:
718:
714:
712:
709:
708:
704:
697:
693:
689:
688:
684:
680:
676:
675:
670:
661:
655:
651:
648:
647:
643:
641:
638:
637:
633:
631:
630:
625:
624:
621:
616:
612:
608:
604:
600:
596:
592:
588:
586:
583:
582:
578:
575:
571:
570:
566:
564:
563:Boiling point
561:
560:
556:
554:
553:Melting point
551:
550:
547:
543:
541:
538:
537:
533:
531:
528:
527:
523:
520:
519:
512:
510:
507:
506:
488:
485:
481:
480:
475:
466:
461:
457:
450:
436:
426:
422:
415:
407:
403:
402:DTXSID5039224
399:
398:
396:
386:
382:
381:
374:
370:
369:
367:
365:
362:
361:
354:
353:
351:
349:
346:
345:
338:
334:
333:
331:
325:
321:
320:
313:
309:
308:
306:
304:
301:
300:
293:
289:
288:
286:
283:
279:
278:
271:
270:
268:
266:
261:
260:
256:
252:
249:
247:
245:ECHA InfoCard
242:
241:
234:
230:
229:
227:
225:
222:
221:
214:
210:
209:
207:
205:
202:
201:
194:
190:
189:
187:
185:
182:
181:
174:
170:
167:
163:
162:
160:
156:
151:
150:
143:
139:
138:
136:
133:
129:
128:
123:
111:
103:
99:
91:
87:
82:
71:
67:
61:
57:
56:
52:
41:
37:
31:
27:
26:
22:
19:Acetaldehyde
16:
7299:Hepatotoxins
7219:
7202:Spectroscopy
7056:Astrobiology
6909:Formaldehyde
6801:Benzonitrile
6592:Acetaldehyde
6591:
6547:Methanethiol
6498:Acetonitrile
6403:Carbodiimide
6282:Formaldehyde
6277:Cyanoethynyl
6128:Iron cyanide
6123:Hydroperoxyl
5924:Nitric oxide
5754:Hal Kibbey,
5736:
5720:
5673:(3): 243–9.
5670:
5666:
5660:
5652:
5640:. Retrieved
5620:
5587:
5583:
5577:
5560:
5556:
5550:
5538:
5505:
5501:
5495:
5470:
5466:
5460:
5448:
5429:
5384:
5380:
5370:
5337:
5333:
5327:
5302:
5298:
5291:
5266:10754/670859
5248:
5244:
5234:
5209:
5205:
5199:
5166:
5158:
5123:
5119:
5109:
5071:(1): 36–44.
5068:
5064:
5058:
5023:
5019:
4980:(5): 450–4.
4977:
4973:
4963:
4922:
4918:
4912:
4887:
4884:Lancet Oncol
4883:
4876:
4846:
4838:
4828:28 September
4826:. Retrieved
4805:
4793:
4771:(2): 101–8.
4768:
4764:
4758:
4745:
4733:
4700:
4696:
4669:
4636:
4632:
4626:
4601:
4597:
4571:
4567:
4561:
4551:
4537:
4531:
4518:
4509:
4505:
4495:
4478:
4472:
4466:
4456:
4442:
4436:
4423:
4413:
4399:
4393:
4387:
4376:
4366:
4352:
4346:
4336:
4326:
4312:
4306:
4296:
4286:
4272:
4266:
4260:
4248:
4229:
4224:
4183:
4179:
4169:
4139:(6): 443–8.
4136:
4132:
4122:
4113:
4096:
4092:
4086:
4056:(1): 29–38.
4053:
4049:
4039:
4017:(10): 1725.
4014:
4009:
3996:
3981:
3977:
3938:
3934:
3927:
3917:
3913:
3911:
3907:
3903:
3893:
3870:
3864:
3855:
3851:
3841:
3829:
3825:
3812:
3808:
3796:
3790:
3786:
3773:
3762:
3758:
3744:
3740:
3726:
3718:
3714:
3710:
3706:
3703:Alkohol vini
3702:
3694:
3690:
3685:
3640:
3636:
3612:
3600:. Retrieved
3591:
3570:
3560:
3523:
3519:
3509:
3497:. Retrieved
3475:Acetaldehyde
3434:
3428:
3419:
3410:
3378:
3371:
3329:
3290:
3255:
3245:
3236:
3213:Formaldehyde
3190:
3189:
3177:
3155:
3130:
3118:
3095:effect with
3083:, including
3078:
3065:
3044:
3029:
3025:
3004:
2988:
2968:
2949:
2932:endogenously
2919:
2912:carcinogenic
2909:
2896:Conjunctival
2870:
2862:
2834:
2801:
2613:
2584:
2581:
2538:
2510:
2490:fermentation
2448:
2445:Biochemistry
2427:CH(Cl)PO(OH)
2410:CH(Cl)PO(OH)
2406:H → CH
2368:CHO → CH
2342:
2291:
2259:
2254:
2251:
2225:
2217:
2209:
2148:
2139:
2102:
2075:formaldehyde
2071:hydroxyethyl
2061:and related
2032:
2016:
1985:
1976:
1926:tautomerizes
1919:
1886:
1877:
1789:of ethanol:
1784:
1768:
1748:tautomerizes
1741:
1614:
1601:
1479:
1476:
1365:
1350:
1322:
1307:
1251:
1248:Acetaldehyde
1247:
1246:
1144:
1095:
1073:Autoignition
1008:
919:
909:Main hazards
898:
871:Formaldehyde
844:
819:
792:
771:
695:
685:-.5153 cm/g
653:
628:
545:
348:RTECS number
213:ChEMBL170365
125:Identifiers
113:Other names
94:Acetaldehyde
15:
7176:Outer space
7086:Cosmic dust
7051:Abiogenesis
6963:Unconfirmed
6919:Heavy water
6759:Ethanethiol
6674:Cyanoallene
6664:Acetic acid
6634:Methylamine
6518:Diacetylene
6433:Formic acid
6423:Cyanomethyl
6081:Diazenylium
6071:CCP radical
5947:(molecular)
5931:(molecular)
5900:(molecular)
5642:26 February
4234:L. Paquette
3499:12 February
3218:Paraldehyde
3093:synergistic
3062:Outdoor air
3036:living room
2997:and liver.
2971:acetic acid
2900:respiratory
2848:intravenous
2595:acetic acid
2466:acetic acid
2232:metaldehyde
2228:paraldehyde
2220:= 4, right)
2214:metaldehyde
2206:paraldehyde
2019:atmospheric
1928:to give an
1769:The enzyme
1764:nitric acid
1629:mercury(II)
1376:homogeneous
1110:median dose
1096:Lethal dose
1075:temperature
1062:Flash point
903:(OHS/OSH):
521:Appearance
477:Properties
251:100.000.761
193:CHEBI:15343
7278:Categories
7091:Cosmic ray
7033:Silylidyne
6996:Hemolithin
6971:Anthracene
6888:Deuterated
6869:Pyrimidine
6679:Ethanimine
6542:Ketenimine
6398:Butadiynyl
6222:Thioformyl
6076:Chloronium
4740:. ihs.com.
4703:: 127958.
4524:Adkins, H.
4429:Wittig, G.
3914:d'aldehyde
3858:: 133–167.
3793:: 269–270.
3765:: 318–332.
3747:: 289–305.
3602:22 January
3526:: 907317.
3453:1043763515
3422:. PubChem.
3229:References
3223:Wine fault
3148:products.
3055:pollutants
3022:Indoor air
3007:disulfiram
3001:Disulfiram
2920:sufficient
2885:perception
2867:Irritation
2525:disulfiram
2247:stereomers
2121:amino acid
2117:hydrolysis
1347:Production
1313:carcinogen
1299:disulfiram
931:Pictograms
720:Structure
620:chloroform
611:turpentine
585:Solubility
509:Molar mass
373:GO1N1ZPR3B
282:IUPHAR/BPS
224:ChemSpider
153:3D model (
132:CAS Number
7023:Phosphine
6891:molecules
6824:fullerene
6724:Acetamide
6528:Formamide
6408:Cyanamide
6262:Acetylene
6237:Tricarbon
6148:Methylene
6133:Isoformyl
6038:Triatomic
5811:Molecules
5403:1660-4601
5283:239683740
5275:0887-0624
4725:232311209
4661:206059192
4390:-Alanine"
3875:pp. 83–84
3402:957751024
3384:CRC Press
3137:Fermented
3105:addiction
3085:cellulose
3005:The drug
2820:butadiene
2807:pyridines
2630:W. Europe
2591:propylene
2460:oxidizes
2435:=CHPO(OH)
2260:Although
2194:oligomers
2130:to yield
2043:prochiral
1903:Reactions
1830:⟶
1754:process,
1704:⟶
1625:acetylene
1621:hydration
1551:⟶
1482:oxidation
1441:⟶
1361:feedstock
1357:acetylene
1301:inhibits
1279:aldehydes
1258:with the
1174:2000 ppm
922:labelling
865:aldehydes
812:formation
786:Std molar
711:Viscosity
579:miscible
534:Ethereal
355:AB1925000
272:200-836-8
264:EC Number
7284:Alkanals
7010:Linear C
6991:Graphene
6903:Ammonium
6704:Acrolein
6567:Propynal
6552:Methanol
6523:Ethylene
6392:Ammonium
6167:Nitroxyl
5991:Sulfanyl
5935:Imidogen
5929:Nitrogen
5898:Hydrogen
5843:Argonium
5820:Diatomic
5687:22909057
5633:Archived
5612:12448533
5530:23291758
5522:19396661
5487:19449825
5437:Archived
5421:21556207
5362:25866206
5354:17382522
5191:50566621
5150:11716548
5142:16287084
5101:28571902
5093:15126281
5050:32132710
4996:15304379
4955:22732731
4904:19891056
4851:. Lyon:
4819:Archived
4717:33744437
4679:Archived
4653:25271825
4618:17979660
4528:"Acetal"
4257:(1998).
4216:42079807
4208:22903524
4161:21602858
4078:17179063
4070:26790879
3832:: 466–8.
3815:: 124–5.
3707:Brunsten
3677:26444872
3637:PLOS ONE
3596:Archived
3552:21747735
3365:(NIOSH).
3334:Archived
3197:See also
3152:Plastics
3142:cosmetic
3133:microbes
3097:nicotine
2881:headache
2877:vomiting
2859:Toxicity
2549:pyridine
2541:Monsanto
2515:have an
2498:pyruvate
2482:catalase
2389:CH(O)PCl
2372:CH(O)PCl
2327:RCH(OR')
2138:to give
1893:methanol
1746:, which
1291:hangover
1254:) is an
1090:4.0–60%
1009:NFPA 704
893:Hazards
863:Related
681:(χ)
7289:Flavors
7156:Kerogen
7043:Related
6986:Glycine
6939:Propyne
6898:Ammonia
6796:Benzene
6791:Acetone
6783:or more
6754:Propene
6739:Ethanol
6629:Propyne
6448:Methane
6317:Ketenyl
6267:Ammonia
5592:Bibcode
5412:3084482
5307:Bibcode
5214:Bibcode
5073:Bibcode
5041:7116288
4947:3389666
4927:Bibcode
4785:2719768
4275:: 106.
4188:Bibcode
4180:Science
4141:Bibcode
4019:Bibcode
3668:4596837
3645:Bibcode
3592:epa.gov
3543:3124883
3359:"#0001"
3051:xylenes
3040:bedroom
2854:Dangers
2621:Product
2531:below.
2462:ethanol
2449:In the
2431:→ CH
2414:+ 2 CH
2398:+ 2 CH
2298:ethanol
2202:CHO)_{n
2192:Cyclic
2155:ammonia
2124:alanine
2113:ammonia
2109:cyanide
2098:formate
2055:synthon
1631:salts:
1370:by the
1353:ethanol
1319:History
1295:alcohol
1283:ethanol
1260:formula
1252:ethanal
1229:what is
1227: (
840:(Δ
788:entropy
705:1.3316
650:Acidity
615:acetone
603:toluene
599:benzene
591:ethanol
540:Density
324:PubChem
142:75-07-0
106:Ethanal
7207:Tholin
7028:Pyrene
6473:Silane
6443:Ketene
5945:Oxygen
5744:
5685:
5610:
5528:
5520:
5485:
5419:
5409:
5401:
5360:
5352:
5281:
5273:
5189:
5179:
5148:
5140:
5099:
5091:
5048:
5038:
5020:Nature
4994:
4953:
4945:
4902:
4863:
4783:
4723:
4715:
4659:
4651:
4616:
4481:: 41.
4445:: 66.
4355:: 53.
4315:: 83.
4214:
4206:
4159:
4076:
4068:
3978:et al.
3881:
3730:Note:
3675:
3665:
3550:
3540:
3451:
3441:
3400:
3390:
3309:
3270:
3109:saliva
3032:France
2889:fruity
2879:, and
2873:nausea
2844:mucosa
2826:Safety
2761:Others
2636:Total
2627:Mexico
2555:, and
2455:enzyme
2453:, the
2439:+ HCl
2306:CH(OCH
2294:acetal
2255:heated
2132:imines
2128:amines
2119:, the
2051:CH(OH)
1973:
1970:
1967:
1964:
1961:
1958:
1955:
1952:
1368:ethene
1293:after
1224:verify
1221:
1182:(SDS)
634:-0.34
607:xylene
514:44.053
456:SMILES
312:C00084
204:ChEMBL
84:Names
7193:(PAH)
6781:atoms
6716:atoms
6656:atoms
6654:Eight
6584:atoms
6582:Seven
6490:atoms
6384:atoms
6254:atoms
6242:Water
6172:Ozone
6114:(HNC)
6108:(HCN)
5732:(PDF)
5717:(PDF)
5636:(PDF)
5629:(PDF)
5526:S2CID
5358:S2CID
5279:S2CID
5146:S2CID
5097:S2CID
4951:S2CID
4822:(PDF)
4815:(PDF)
4721:S2CID
4657:S2CID
4540:: 1.
4402:: 4.
4232:(Ed:
4212:S2CID
4074:S2CID
4006:(PDF)
3937:[
3777:See:
3131:Many
2991:ADH1C
2979:ALDH2
2934:from
2841:nasal
2816:Japan
2811:China
2803:China
2781:Total
2633:Japan
2561:resin
2517:ALDH2
2511:Many
2494:yeast
2451:liver
2364:+ CH
2157:, to
2103:In a
2037:. In
2012:=CHOH
1980:298,g
1949:=CHOH
1145:NIOSH
595:ether
421:InChI
184:ChEBI
155:JSmol
6714:Nine
6382:Five
6292:HCCN
6252:Four
6212:SiNC
5742:ISBN
5683:PMID
5644:2015
5608:PMID
5518:PMID
5483:PMID
5417:PMID
5399:ISSN
5350:PMID
5271:ISSN
5187:OCLC
5177:ISBN
5138:PMID
5089:PMID
5069:1011
5046:PMID
4992:PMID
4943:PMID
4900:PMID
4861:ISBN
4830:2011
4781:PMID
4713:PMID
4649:PMID
4614:PMID
4204:PMID
4157:PMID
4066:PMID
3879:ISBN
3673:PMID
3604:2011
3548:PMID
3524:2011
3501:2015
3449:OCLC
3439:ISBN
3398:OCLC
3388:ISBN
3307:ISBN
3268:ISBN
2892:odor
2835:The
2796:766
2676:321
2656:147
2543:and
2535:Uses
2478:NADH
2418:COCl
2111:and
2096:and
2087:C(CH
2000:CH=O
1990:is 6
1986:The
1930:enol
1887:The
1355:and
1331:and
1186:HMDB
1168:IDLH
997:P281
993:P261
989:P210
975:H351
971:H335
967:H319
963:H224
752:2.7
627:log
530:Odor
468:CC=O
463:O=CC
364:UNII
303:KEGG
292:6277
7005:NCO
6905:ion
6812:, C
6779:Ten
6488:Six
6394:ion
5675:doi
5600:doi
5565:doi
5510:doi
5475:doi
5407:PMC
5389:doi
5342:doi
5315:doi
5261:hdl
5253:doi
5222:doi
5173:761
5128:doi
5124:118
5081:doi
5036:PMC
5028:doi
5024:579
4982:doi
4935:doi
4923:534
4892:doi
4773:doi
4705:doi
4641:doi
4606:doi
4576:doi
4542:doi
4483:doi
4447:doi
4404:doi
4357:doi
4317:doi
4277:doi
4238:doi
4196:doi
4184:337
4149:doi
4101:doi
4097:112
4058:doi
4027:doi
3986:doi
3663:PMC
3653:doi
3538:PMC
3528:doi
3299:doi
3260:doi
3160:of
3103:of
3099:in
2940:DNA
2793:362
2790:206
2784:176
2776:98
2756:14
2736:23
2716:83
2696:80
2673:224
2624:USA
2563:.
2476:to
2474:NAD
2468:by
2360:PCl
2268:),
2204:}:
2091:OH)
2057:in
1891:of
1846:CHO
1720:CHO
1623:of
1567:CHO
1461:CHO
1271:CHO
1155:PEL
920:GHS
823:298
796:298
390:EPA
337:177
327:CID
233:172
7280::
6822:70
6814:60
6810:60
6808:(C
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5681:.
5671:42
5669:.
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1275:Me
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1124:50
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613:,
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1998:3
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