2117:. Prolonged and excessive exposure can affect many areas in the human body; blood, brain, eye, heart, kidney, lung, nose and throat have all been shown to react to the presence of excessive 1,3-butadiene. Animal data suggest that women have a higher sensitivity to possible carcinogenic effects of butadiene over men when exposed to the chemical. This may be due to estrogen receptor impacts. While these data reveal important implications to the risks of human exposure to butadiene, more data are necessary to draw conclusive risk assessments. There is also a lack of human data for the effects of butadiene on reproductive and development shown to occur in mice, but animal studies have shown breathing butadiene during pregnancy can increase the number of birth defects, and humans have the same hormone systems as animals.
2014:
425:
272:
1898:
876:
67:
77:
768:
877:
773:
763:
47:
1631:
872:
37:
1983:
2053:
1192:
1555:
1421:. When mixed with steam and briefly heated to very high temperatures (often over 900 °C), aliphatic hydrocarbons give up hydrogen to produce a complex mixture of unsaturated hydrocarbons, including butadiene. The quantity of butadiene produced depends on the hydrocarbons used as feed. Light feeds, such as
2099:('carcinogenic to humans'), and the Agency for Toxic Substances Disease Registry and the US EPA also list the chemical as a carcinogen. The American Conference of Governmental Industrial Hygienists (ACGIH) lists the chemical as a suspected carcinogen. The Natural Resource Defense Council (NRDC) lists some
1959:
conformer. Overall, there is a barrier of 24.8 kJ/mol (5.9 kcal/mol) for isomerization between the two conformers. This increased rotational barrier and strong overall preference for a near-planar geometry is evidence for a delocalized Ï system and a small degree of partial double bond character in
1664:
This process was one of the three used in the United States to produce "government rubber" during World War II, although it is less economical than the butane or butene routes for the large volumes. Still, three plants with a total capacity of 200,000 tons per year were constructed in the U.S.
1602:'s synthetic rubber industry during and after World War II, and it remained in limited use in Russia and other parts of eastern Europe until the end of the 1970s. At the same time this type of manufacture was canceled in Brazil. As of 2017, no butadiene was produced industrially from ethanol.
2000:
1,3-Butadiene is also thermodynamically stabilized. While a monosubstituted double bond releases about 30.3 kcal/mol of heat upon hydrogenation, 1,3-butadiene releases slightly less (57.1 kcal/mol) than twice this energy (60.6 kcal/mol), expected for two isolated double bonds. That implies a
1921:
conformation, in which the molecule is planar, with the two pairs of double bonds facing opposite directions. This conformation is most stable because orbital overlap between double bonds is maximized, allowing for maximum conjugation, while steric effects are minimized. Conventionally, the
875:
1825:(SBR). These copolymers are tough and/or elastic depending on the ratio of the monomers used in their preparation. SBR is the material most commonly used for the production of automobile tyres. Precursors to still other synthetic rubbers are prepared from butadiene. One is
2024:
The industrial uses illustrate the tendency of butadiene to polymerize. Its susceptibility to 1,4-addition reactions is illustrated by its hydrocyanation. Like many dienes, it undergoes Pd-catalyzed reactions that proceed via allyl complexes. It is a partner in
1942:
conformation, in which the dihedral angle is 0°, with the pair of double bonds facing the same direction is approximately 16.5 kJ/mol (3.9 kcal/mol) higher in energy, due to steric hindrance. This geometry is a local energy maximum, so in contrast to the
2490:
3214:
Grosse, Yann; Baan, Robert; Straif, Kurt; Secretan, BĂ©atrice; El
Ghissassi, Fatiha; Bouvard, VĂ©ronique; Altieri, Andrea; Cogliano, Vincent (2008). "Carcinogenicity of 1,3-butadiene, ethylene oxide, vinyl chloride, vinyl fluoride, and vinyl bromide".
2005:)-1,3-pentadiene releases only 26.5 kcal/mol, implying a very similar value of 3.6 kcal/mol for the stabilization energy. The ~3.5 kcal/mol difference in these heats of hydrogenation can be taken to be the resonance energy of a conjugated diene.
1978:
butadiene has a length of 133.8 pm, while that for ethylene has a length of 133.0 pm. This was taken as evidence of a Ï-bond weakened and lengthened by delocalization, as depicted by the resonance structures shown below.
3133:
Nyström, J. E.; Rein, T.; BÀckvall, J. E. (1989). "1,4-Functionalization of 1,3-Dienes via
Palladium-Catalyzed Chloroacetoxylation and Allylic Amination: 1-Acetoxy-4-diethylamino-2-butene and 1-Acetoxy-4-benzylamino-2-butene".
893:
781:
743:
1866:. The most widely used such reactions involve reactions of butadiene with one or two other molecules of butadiene, i.e., dimerization and trimerization respectively. Via dimerization butadiene is converted to
2001:
stabilization energy of 3.5 kcal/mol. Similarly, the hydrogenation of the terminal double bond of 1,4-pentadiene releases 30.1 kcal/mol of heat, while hydrogenation of the terminal double bond of conjugated (
1542:. While not competitive with steam cracking for producing large volumes of butadiene, lower capital costs make production from ethanol a viable option for smaller-capacity plants. Two processes were in use.
900:
1677:) with start-ups completed in 1943, the Louisville plant initially created butadiene from acetylene generated by an associated calcium carbide plant. The process remains in use today in China and India.
1361:
The butadiene industry originated in the years before World War II. Many of the belligerent nations realized that in the event of war, they could be cut off from rubber plantations controlled by the
1358:
polymerized butadiene and obtained a material with rubber-like properties. This polymer was, however, found to be too soft to replace natural rubber in many applications, notably automobile tires.
1762:
1,3-Butadiene is inconvenient for laboratory use because it is gas. Laboratory procedures have been optimized for its generation from nongaseous precursors. It can be produced by the retro-
1967:
conformation, 1,3-butadiene needs to assume this conformation (or one very similar) before it can participate as the four-electron component in concerted cycloaddition reactions like the
2959:
Craig, Norman C.; Groner, Peter; McKean, Donald C. (1 June 2006). "Equilibrium
Structures for Butadiene and Ethylene: Compelling Evidence for Î -Electron Delocalization in Butadiene".
2451:
2408:
1066:
1205:
2093:
2086:
Long-term exposure has been associated with cardiovascular disease. There is a consistent association with leukemia, as well as a significant association with other cancers.
2763:
878:
1511:, to produce synthetic rubber for the war effort as part of the United States Synthetic Rubber Program. Total capacity was 68 KMTA (Kilo Metric Tons per Annum).
474:
1786:
Most butadiene(75% of the manufactured 1,3-butadiene) is used to make synthetic rubbers for the manufacture of tyres and components of many consumer items.
2089:
1955:
geometry are twisted to give a dihedral angle of around 38°, is a second conformer that is around 12.0 kJ/mol (2.9 kcal/mol) higher in energy than the
2129:
3476:
3188:
5054:
3579:
831:
3420:
2378:
2351:
3266:
2645:
3552:
1874:. In fact, vinylcyclohexene is a common impurity that accumulates when butadiene is stored. Via trimerization, butadiene is converted to
66:
3052:
3019:
2908:
Feller, David; Craig, Norman C. (26 February 2009). "High Level ab Initio
Energies and Structures for the Rotamers of 1,3-Butadiene".
2780:
1793:, a process by which small molecules (monomers) are linked to make large ones (polymers). The mere polymerization of butadiene gives
5049:
5039:
2885:
2740:
2311:
439:
76:
1299:
quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant
4504:
2181:
1814:
395:
2617:"The decomposition and genesis of hydrocarbons at high temperatures. I. The products of the manufacture of gas from petroleum"
1381:
and butadiene that could be used in automobile tires. Worldwide production quickly ensued, with butadiene being produced from
3502:
721:
36:
2103:
that are suspected to be associated with this chemical. Some researchers have concluded it is the most potent carcinogen in
1549:, ethanol is converted to butadiene, hydrogen, and water at 400â450 °C over any of a variety of metal oxide catalysts:
46:
2586:"Ueber eine mit dem zweifach-gebromten Brombutylen isomere Verbindung und ĂŒber die bromhaltigen Derivate des Brombutylens"
1697:
835:
2502:
1212:
827:
5059:
2030:
1538:
In other parts of the world, including South
America, Eastern Europe, China, and India, butadiene is also produced from
821:
370:
843:
767:
2018:
403:
886:
5069:
3572:
2335:
1546:
1355:
1098:
1077:
772:
2486:
2121:
279:
2026:
1968:
2036:
Like other dienes, butadiene is a ligand for low-valent metal complexes, e.g. the derivatives Fe(butadiene)(CO)
1910:
1666:
923:
3540:
1280:. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to
762:
5064:
3964:
1717:
839:
267:
4914:
4312:
3894:
3833:
3728:
2013:
1897:
1713:
1508:
1496:
1449:
1351:
3480:
3313:"Application of toxicological risk assessment principles to the chemical constituents of cigarette smoke"
229:
4975:
4909:
4302:
3565:
3524:
1441:
795:
755:
4297:
3818:
4284:
3805:
1366:
4493:
4292:
3876:
3089:
2968:
2917:
1863:
1774:
is a convenient solid storable source for 1,3-butadiene in the laboratory. It releases the diene and
1763:
1733:
1674:
1670:
1430:
1296:
96:
5034:
4821:
4324:
3845:
3409:
2332:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
2136:
2065:
1606:
1527:
847:
420:
143:
4370:
1836:, a precursor to some nylons. The conversion of butadiene to adiponitrile entails the addition of
805:
5008:
4965:
4385:
4380:
4365:
3950:
3823:
3813:
3192:
2684:
2422:
1867:
1729:
1709:
189:
4454:
4423:
4202:
4192:
4077:
2663:"Industrially applied and relevant transformations of 1,3-butadiene using homogeneous catalysts"
4459:
4438:
4433:
4217:
4212:
4207:
4197:
4092:
4087:
4082:
4072:
3738:
2872:
5044:
4899:
4871:
4714:
4474:
4469:
4307:
3828:
3458:
3391:
3342:
3240:
3232:
3115:
3058:
3048:
3025:
3015:
2992:
2984:
2941:
2933:
2881:
2776:
2736:
2374:
2347:
1990:
1875:
1822:
1705:
1460:
1127:
1974:
Similarly, a combined experimental and computational study has found that the double bond of
1754:
After World War II, the production from butenes became the major type of production in USSR.
1409:
In the United States, western Europe, and Japan, butadiene is produced as a byproduct of the
177:
4863:
3450:
3381:
3373:
3362:"Critical assessment of epidemiologic studies on the human carcinogenicity of 1,3-butadiene"
3332:
3324:
3224:
3170:
3143:
3105:
3097:
2976:
2925:
2854:
2768:
2674:
2628:
2597:
2339:
1994:
1837:
1704:. The process was much more economical than the alcohol or n-butane route but competed with
1289:
1281:
1269:
1230:
678:
603:
497:
379:
5013:
4970:
4879:
4753:
3718:
3708:
2133:
2104:
2100:
1751:
using a proprietary catalyst. It is unclear if this technology is practiced commercially.
1748:
1689:
1480:
936:
298:
249:
1354:
isolated it from among the pyrolysis products of petroleum. In 1910, the
Russian chemist
1133:
153:
3093:
2972:
2921:
1630:
424:
271:
209:
4944:
4939:
4904:
4855:
4761:
3733:
3723:
3386:
3361:
3337:
3312:
3110:
3077:
2301:
2203:
1886:
1871:
1841:
1818:
1790:
1775:
1725:
1429:
when cracked, but heavier feeds favor the formation of heavier olefins, butadiene, and
1410:
1362:
1183:
659:
3228:
2482:
2465:
5028:
4621:
4428:
4418:
3914:
2815:
2688:
2306:
2271:
2233:
2108:
1810:
1794:
1500:
1315:
1304:
645:
592:
582:
260:
1889:
with methanol. This reaction produces 1-methoxy- 2,7-octadiene as an intermediate.
4727:
4691:
4587:
4360:
4350:
4259:
4249:
4239:
3780:
3770:
3760:
3161:
Cope, Arthur C.; Herrick, Elbert C. (1950). "cis-Î4-Tetrahydrophthalic
Anhydride".
2661:
Yang, Ji; Wang, Peng; Neumann, Helfried; Jackstell, Ralf; Beller, Matthias (2023).
2164:
1982:
1859:
1855:
1833:
1701:
1614:
1599:
1504:
1464:
1445:
1347:
707:
3510:
2772:
2559:
2534:
2368:
1743:
company known as "Petro-Tex" patented a process to produce butadiene from normal
851:
343:
4775:
4732:
4705:
4639:
4602:
4521:
4375:
4355:
4342:
4274:
4269:
4264:
4254:
4244:
4231:
4062:
3795:
3790:
3785:
3775:
3765:
3752:
3588:
3283:
2803:. Vol. 4 (3rd ed.). New York: John Wiley & Sons. pp. 313â337.
2343:
2061:
1993:
of 1,3-butadiene is readily obtained by applying HĂŒckel theory. (The article on
1826:
1797:, which is a very soft, almost liquid material. The polymerization of butadiene
1767:
1437:
1370:
1300:
1285:
1162:
1046:
982:
960:
912:
3258:
4834:
4722:
4526:
4413:
4403:
4332:
4067:
3889:
3884:
3859:
3713:
3703:
3546:
3454:
3297:
3101:
2506:
2404:
2190:
2173:
2096:
736:
630:
525:
240:
3236:
3174:
3147:
2988:
2937:
2858:
2601:
2443:
1522:, which was developed during World War II. This entails treating butane over
4839:
4577:
4546:
4536:
4531:
4136:
3924:
3919:
3698:
3298:"Disease Clusters Spotlight the Need to Protect People from Toxic Chemicals"
3062:
3029:
2114:
2073:
1848:
1802:
1771:
1686:
1610:
1386:
1374:
1343:
697:
390:
3346:
3244:
3119:
2996:
2945:
1878:. Some of these processes employ nickel- or titanium-containing catalysts.
3462:
3395:
2052:
5003:
4998:
4808:
4800:
4792:
4672:
4664:
4656:
4607:
4592:
4582:
4572:
4567:
4541:
4464:
4176:
4156:
4006:
3934:
3929:
3909:
2632:
2057:
1882:
1618:
1587:
1456:
1426:
1414:
1158:
899:
892:
885:
858:
809:
17:
3377:
3328:
1605:
In the other, two-step process, developed by the
Russian emigre chemist
1499:, a part of the United States government, constructed several plants in
4960:
4934:
4784:
4629:
4562:
4161:
4151:
4141:
4031:
4021:
4011:
3899:
3865:
3853:
3667:
3657:
3647:
3637:
2679:
2662:
2284:
2069:
1806:
1740:
1721:
1559:
1539:
1523:
1492:
1382:
1378:
1147:
801:
649:
639:
555:
330:
280:
2980:
2929:
2814:
Welch, L. Marshall; Croce, Louis; Christmann, Harold (November 1978).
2701:
Sun, H.P. Wristers, J.P. (1992). Butadiene. In J.I. Kroschwitz (Ed.),
1981:
4829:
4748:
4648:
4597:
4171:
4166:
4146:
4106:
4046:
4041:
4036:
4026:
4016:
3977:
3904:
3682:
3677:
3672:
3662:
3652:
3642:
3607:
2563:
1744:
1693:
1622:
1487:-butane). The first such post-war commercial plant, producing 65,000
1422:
1418:
1331:
1311:
1174:
220:
3439:"Mechanistic data indicate that 1,3-butadiene is a human carcinogen"
3438:
2616:
2585:
1365:, and sought to reduce their dependence on natural rubber. In 1929,
1182:
Except where otherwise noted, data are given for materials in their
1554:
318:
4513:
4479:
4395:
2125:
2051:
2012:
1896:
1862:, as it reacts with double and triple carbon-carbon bonds through
1629:
1579:
1553:
1319:
1152:
354:
200:
176:
166:
2128:, and as such, emissions of the chemical are highly regulated by
1708:
for available butene molecules (butenes were plentiful thanks to
1397:
In 2020, 14.2 million tons were estimated to have been produced.
1385:
in the Soviet Union and the United States, and from coal-derived
2714:
Beychok, M.R. and Brack, W.J., "First
Postwar Butadiene Plant",
2080:
1840:
to each of the double bonds in butadiene. The process is called
1342:
In 1863, French chemist E. Caventou isolated butadiene from the
1111:
1007:
813:
545:
309:
3561:
3557:
3078:"Redetermination of (η-s-cis-1,3-butadiene)tricarbonyliron(0)"
1488:
1440:
produced in steam cracking by extractive distillation using a
1350:. This hydrocarbon was identified as butadiene in 1886, after
1257:
2448:
Immediately Dangerous to Life or Health Concentrations (IDLH)
1805:, which are more valued. The polymerization of butadiene and
3265:. Agency for Toxic Substances and Disease Registry (ATSDR).
1239:
408:
75:
65:
45:
35:
2845:
Hershberg, E. B.; Ruhoff, John R. (1937). "1,3-Butadiene".
2799:
Kirshenbaum, I. (1978). "Butadiene". In Grayson, M. (ed.).
1789:
The conversion of butadiene to synthetic rubbers is called
1436:
Butadiene is typically isolated from the other four-carbon
1254:
1245:
2503:"BUTADIENE | Meaning & Definition for UK English"
917:â85 °C (â121 °F; 188 K) liquid flash point
870:
2705:, vol. 4, pp. 663â690. New York: John Wiley & Sons.
1200:
2373:(97th ed.). Boca Raton: CRC Press. p. 3-76.
1960:
the CâC single bond, in accord with resonance theory.
2452:
National Institute for Occupational Safety and Health
2409:
National Institute for Occupational Safety and Health
1260:
1233:
2472:. International Programme on Chemical Safety (IPCS).
1251:
1242:
1236:
4991:
4953:
4927:
4892:
4848:
4820:
4783:
4774:
4741:
4713:
4704:
4684:
4647:
4638:
4620:
4555:
4512:
4503:
4492:
4447:
4394:
4341:
4323:
4283:
4230:
4185:
4129:
4105:
4055:
3999:
3976:
3963:
3943:
3875:
3844:
3804:
3751:
3691:
3630:
3606:
3595:
2083:is 12.5â11.5 vol% for inhalation by rats and mice.
1491:per year of butadiene, began operations in 1957 in
1248:
3543:â Agency for Toxic Substances and Disease Registry
3286:. Occupational Safety & Health Administration.
3010:Vollhardt, K. Peter C.; Schore, Neil Eric (2007).
2120:1,3-Butadiene is recognized as a highly reactive
1284:. The molecule can be viewed as the union of two
587:â108.91 °C (â164.04 °F; 164.24 K)
1997:gives a derivation for the butadiene orbitals.)
1625:catalyst at 325â350 °C to yield butadiene:
1479:Butadiene can also be produced by the catalytic
342:
3507:Technology Transfer Network Air Toxics Web Site
3317:Institute of Environmental Science and Research
2733:Synthetic Rubber: A Project That Had to Succeed
874:
152:
3549:â CDC - NIOSH Pocket Guide to Chemical Hazards
2764:Ullmann's Encyclopedia of Industrial Chemistry
1832:Smaller amounts of butadiene are used to make
1617:, which reacts with additional ethanol over a
3573:
3437:Melnick, Ronald L.; Kohn, Michael C. (1995).
1854:Butadiene is also useful in the synthesis of
597:â4.41 °C (24.06 °F; 268.74 K)
8:
3553:National Pollutant Inventory â 1,3-Butadiene
3527:. Texas Commission on Environmental Quality.
2703:Encyclopedia of Chemical Technology, 4th ed.
2491:Institute for Occupational Safety and Health
16:"Divinyl" redirects here. For the band, see
3311:Fowles, J.; Dybing, E. (4 September 2003).
3278:
3276:
2794:
2792:
1951:geometry, in which the double bonds of the
1712:). The USSRP constructed several plants in
1518:-butane is commercially produced using the
4780:
4710:
4644:
4635:
4509:
4500:
4126:
3996:
3973:
3627:
3603:
3580:
3566:
3558:
2756:
2754:
2752:
2726:
2724:
2146:
2124:(HRVOC) for its potential to readily form
423:
270:
248:
24:
3385:
3336:
3109:
3012:Organic chemistry: structure and function
2816:"BUTADIENE VIA OXIDATIVE DEHYDROGENATION"
2761:Grub, J.; Löser, E. (2012). "Butadiene".
2678:
2656:
2654:
1934:dihedral angle of 180°. In contrast, the
1495:, Texas. Prior to that, in the 1940s the
1310:The name butadiene can also refer to the
378:
3014:(5th ed.). New York: W.H. Freeman.
2615:Armstrong, H. E.; Miller, A. K. (1886).
2403:NIOSH Pocket Guide to Chemical Hazards.
2113:1,3-Butadiene is also a suspected human
1736:. Total annual production was 275 KMTA.
1545:In the single-step process developed by
40:Full structural formula of 1,3-butadiene
2322:
2068:information including a diamond-shaped
479:
444:
419:
2438:
2436:
2398:
2396:
2394:
2392:
2390:
1926:conformation is considered to have a C
1893:Structure, conformation, and stability
1847:Butadiene is used to make the solvent
1685:1,3-Butadiene can also be produced by
931:414 °C (777 °F; 687 K)
261:
3047:(5th ed.). London: McGraw-Hill.
2562:. US Environmental Protection Agency
2370:CRC Handbook of Chemistry and Physics
2029:, e.g. with maleic anhydride to give
1947:geometry, it is not a conformer. The
451:Key: KAKZBPTYRLMSJV-UHFFFAOYSA-N
228:
208:
70:Ball-and-stick model of 1,3-butadiene
7:
3477:"Environment Agency - 1,3-Butadiene"
2667:Industrial Chemistry & Materials
2528:
2526:
2524:
2079:Butadiene is of low acute toxicity.
1463:, from which it is then stripped by
80:Space-filling model of 1,3-butadiene
2961:The Journal of Physical Chemistry A
2910:The Journal of Physical Chemistry A
2801:Encyclopedia of Chemical Technology
2107:, twice as potent as the runner up
1696:. This method was also used by the
1598:This process was the basis for the
461:Key: KAKZBPTYRLMSJV-UHFFFAOYAZ
333:
317:
2646:Simple Things Won't Save the Earth
2092:has designated 1,3-butadiene as a
1105:Potential occupational carcinogen
448:InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2
14:
3366:Environmental Health Perspectives
3269:from the original on 9 June 2012.
2590:Justus Liebigs Annalen der Chemie
2312:Hydroxyl-terminated polybutadiene
1881:Butadiene is also a precursor to
550:Mildly aromatic or gasoline-like
458:InChI=1/C4H6/c1-3-4-2/h3-4H,1-2H2
50:Skeletal formula of 1,3-butadiene
3426:from the original on 8 May 2009.
3410:"1,3-Butadiene CAS No. 106-99-0"
3082:Acta Crystallographica Section E
1377:in Germany, made a copolymer of
1334:has no industrial significance.
1229:
1190:
771:
766:
761:
3284:"1,3-Butadiene: Health Effects"
2048:Environmental health and safety
1963:Despite the high energy of the
1815:acrylonitrile butadiene styrene
1186:(at 25 °C , 100 kPa).
2336:The Royal Society of Chemistry
722:Occupational safety and health
567:g/cm at 25 °C, p>1 atm
1:
5055:U.S. Synthetic Rubber Program
3525:"Controlling HRVOC Emissions"
3229:10.1016/S1470-2045(07)70235-8
2773:10.1002/14356007.a04_431.pub2
1989:A qualitative picture of the
1698:U.S. Synthetic Rubber Program
1071:(US health exposure limits):
2505:. Lexico.com. Archived from
2031:tetrahydrophthalic anhydride
2367:Haynes, William M. (2016).
2344:10.1039/9781849733069-FP001
2019:(butadiene)iron tricarbonyl
949:or concentration (LD, LC):
530:54.0916 g/mol
61:
31:
5086:
3043:Carey, Francis A. (2002).
2134:Houston-Brazoria-Galveston
574:g/cm at â6 °C, liquid
15:
3360:Landrigan, P. J. (1990).
3102:10.1107/S1600536810039218
2834:– via ResearchGate.
2487:GESTIS Substance Database
2245:
2215:
2197:
2158:
2151:
2137:Ozone Non-Attainment Area
2122:volatile organic compound
2060:carrying a butadiene and
1901:Comparison of butadiene (
1180:
1139:
1065:
945:
742:
719:
714:
490:
470:
435:
136:
107:
95:
90:
60:
30:
5050:IARC Group 1 carcinogens
5040:Hazardous air pollutants
3175:10.15227/orgsyn.030.0093
3148:10.15227/orgsyn.067.0105
3076:Reiss, Guido J. (2010).
2859:10.15227/orgsyn.017.0025
2731:Herbert, Vernon (1985).
2602:10.1002/jlac.18631270112
2539:pubchem.ncbi.nlm.nih.gov
2169:164.2 K (-109.0 °C)
1913:of 1,3-butadiene is the
1885:via palladium catalyzed
1667:Institute, West Virginia
1520:Houdry Catadiene process
1471:From dehydrogenation of
1413:process used to produce
822:Precautionary statements
3455:10.1093/carcin/16.2.157
3263:Toxic Substances Portal
2767:. Weinheim: Wiley-VCH.
1905:conformer) and ethylene
1718:Lake Charles, Louisiana
735:Flammable, irritative,
540:or refrigerated liquid
4915:1,3,5-Triheptylbenzene
2820:Hydrocarbon Processing
2427:NIST Chemistry WebBook
2076:
2021:
1986:
1906:
1659:
1593:
1530:at high temperatures.
1514:Today, butadiene from
1509:El Segundo, California
1497:Rubber Reserve Company
1352:Henry Edward Armstrong
881:
81:
71:
51:
41:
4910:1,3,5-Triethylbenzene
3509:. EPA. Archived from
3417:Report on Carcinogens
2584:Caventou, E. (1863).
2338:. 2014. p. 374.
2055:
2027:DielsâAlder reactions
2016:
1985:
1900:
1864:Diels-Alder reactions
1801:other monomers gives
1633:
1557:
1453:-methyl-2-pyrrolidone
1442:polar aprotic solvent
1431:aromatic hydrocarbons
1288:. It is the simplest
880:
79:
69:
49:
39:
4313:Isopropylcyclohexene
3895:Perhydrophenanthrene
3834:Isopropylcyclohexane
3300:. NRDC. 10 May 2011.
2633:10.1039/CT8864900074
2064:mixture, displaying
1969:Diels-Alder reaction
1764:Diels-Alder reaction
1734:Torrance, California
1675:Kobuta, Pennsylvania
1671:Louisville, Kentucky
983:median concentration
863:(fire diamond)
97:Preferred IUPAC name
5060:Commodity chemicals
5009:Alicyclic compounds
4822:Tetramethylbenzenes
3378:10.1289/ehp.9086143
3329:10.1136/tc.12.4.424
3217:The Lancet Oncology
3195:on 22 December 2003
3094:2010AcCrE..66m1369R
2973:2006JPCA..110.7461C
2922:2009JPCA..113.1601F
2735:. Greenwood Press.
2186:425 K (152 °C)
2148:
2066:hazardous materials
1607:Ivan Ostromislensky
1295:Although butadiene
1272:with the formula CH
604:Solubility in water
190:Beilstein Reference
27:
4966:Cyclopropenylidene
4303:Methylcyclopentene
4293:Methylcyclopropene
3824:Methylcyclopentane
3814:Methylcyclopropane
3483:on 3 February 2011
2874:4-Vinylcyclohexene
2680:10.1039/D3IM00009E
2648:, J. Robert Hunter
2246:Liquid properties
2147:
2077:
2022:
1991:molecular orbitals
1987:
1907:
1868:4-vinylcyclohexene
1758:For laboratory use
1730:Port Neches, Texas
1710:catalytic cracking
1660:
1594:
1483:of normal butane (
1213:Infobox references
1140:Related compounds
1114:(Immediate danger)
971:mg/kg (rat, oral)
882:
82:
72:
52:
42:
25:
5070:Conjugated dienes
5022:
5021:
4987:
4986:
4923:
4922:
4900:Hexamethylbenzene
4888:
4887:
4770:
4769:
4715:Trimethylbenzenes
4700:
4699:
4616:
4615:
4488:
4487:
4475:Cyclododecatriene
4470:Cyclooctatetraene
4308:Methylcyclohexene
4298:Methylcyclobutene
4285:Alkylcycloalkenes
4226:
4225:
4101:
4100:
3959:
3958:
3829:Methylcyclohexane
3819:Methylcyclobutane
3806:Alkylcycloalkanes
3747:
3746:
3419:(11th ed.).
3045:Organic chemistry
2981:10.1021/jp060695b
2967:(23): 7461â7469.
2930:10.1021/jp8095709
2716:Petroleum Refiner
2509:on 20 August 2020
2380:978-1-4987-5429-3
2353:978-0-85404-182-4
2293:
2292:
2040:and Mo(butadiene)
2017:The structure of
1876:cyclododecatriene
1823:styrene-butadiene
1819:nitrile-butadiene
1706:aviation gasoline
1621:-promoted porous
1461:dimethylformamide
1425:, give primarily
1401:Extraction from C
1221:Chemical compound
1219:
1218:
1170:Related compounds
1128:Safety data sheet
796:Hazard statements
404:CompTox Dashboard
178:Interactive image
86:
85:
56:
55:
5077:
4979:-Propenylbenzene
4781:
4711:
4645:
4636:
4510:
4501:
4186:Branched alkynes
4127:
4056:Branched alkenes
3997:
3974:
3877:Polycycloalkanes
3862:(bicycloheptane)
3856:(bicyclopentane)
3692:Branched alkanes
3628:
3604:
3582:
3575:
3568:
3559:
3529:
3528:
3521:
3515:
3514:
3499:
3493:
3492:
3490:
3488:
3479:. Archived from
3473:
3467:
3466:
3434:
3428:
3427:
3425:
3414:
3406:
3400:
3399:
3389:
3357:
3351:
3350:
3340:
3308:
3302:
3301:
3294:
3288:
3287:
3280:
3271:
3270:
3255:
3249:
3248:
3211:
3205:
3204:
3202:
3200:
3191:. Archived from
3185:
3179:
3178:
3158:
3152:
3151:
3130:
3124:
3123:
3113:
3073:
3067:
3066:
3040:
3034:
3033:
3007:
3001:
3000:
2956:
2950:
2949:
2916:(8): 1601â1607.
2905:
2899:
2898:
2896:
2894:
2879:
2869:
2863:
2862:
2842:
2836:
2835:
2833:
2831:
2811:
2805:
2804:
2796:
2787:
2786:
2758:
2747:
2746:
2728:
2719:
2712:
2706:
2699:
2693:
2692:
2682:
2658:
2649:
2643:
2637:
2636:
2612:
2606:
2605:
2581:
2575:
2574:
2572:
2570:
2556:
2550:
2549:
2547:
2545:
2530:
2519:
2518:
2516:
2514:
2499:
2493:
2480:
2474:
2473:
2462:
2456:
2455:
2440:
2431:
2430:
2419:
2413:
2412:
2400:
2385:
2384:
2364:
2358:
2357:
2330:"Front Matter".
2327:
2154:
2149:
2132:in parts of the
2101:disease clusters
2070:U.S. DOT placard
1909:The most stable
1838:hydrogen cyanide
1739:In the 1960s, a
1367:Eduard Tschunker
1322:with structure H
1290:conjugated diene
1282:synthetic rubber
1270:organic compound
1267:
1266:
1263:
1262:
1259:
1256:
1253:
1250:
1247:
1244:
1241:
1238:
1235:
1203:
1197:
1194:
1193:
1121:
1091:
1087:
1060:
1056:
1047:lowest published
1031:
1027:
1020:
1016:
1006:
1002:
995:
970:
937:Explosive limits
902:
895:
888:
873:
853:
849:
845:
841:
837:
833:
829:
815:
811:
807:
803:
775:
770:
765:
705:
679:Refractive index
671:
667:
638:Very soluble in
624:
620:
616:
612:
573:
566:
498:Chemical formula
428:
427:
412:
410:
382:
346:
335:
321:
299:Gmelin Reference
282:
274:
263:
252:
232:
212:
180:
156:
62:
32:
28:
5085:
5084:
5080:
5079:
5078:
5076:
5075:
5074:
5025:
5024:
5023:
5018:
5014:Petroleum jelly
4983:
4971:Phenylacetylene
4949:
4919:
4884:
4880:Isobutylbenzene
4844:
4816:
4766:
4737:
4696:
4680:
4634:
4612:
4551:
4495:
4484:
4443:
4390:
4337:
4319:
4279:
4222:
4181:
4123:
4115:
4109:
4097:
4051:
3993:
3986:
3980:
3969:
3967:
3955:
3939:
3871:
3868:(bicyclodecane)
3840:
3800:
3743:
3709:3-Methylpentane
3687:
3624:
3616:
3610:
3599:
3597:
3591:
3586:
3537:
3532:
3523:
3522:
3518:
3513:on 11 May 2012.
3503:"1,3-Butadiene"
3501:
3500:
3496:
3486:
3484:
3475:
3474:
3470:
3436:
3435:
3431:
3423:
3412:
3408:
3407:
3403:
3359:
3358:
3354:
3310:
3309:
3305:
3296:
3295:
3291:
3282:
3281:
3274:
3259:"1,3-Butadiene"
3257:
3256:
3252:
3213:
3212:
3208:
3198:
3196:
3187:
3186:
3182:
3160:
3159:
3155:
3132:
3131:
3127:
3075:
3074:
3070:
3055:
3042:
3041:
3037:
3022:
3009:
3008:
3004:
2958:
2957:
2953:
2907:
2906:
2902:
2892:
2890:
2888:
2877:
2871:
2870:
2866:
2844:
2843:
2839:
2829:
2827:
2813:
2812:
2808:
2798:
2797:
2790:
2783:
2760:
2759:
2750:
2743:
2730:
2729:
2722:
2713:
2709:
2700:
2696:
2660:
2659:
2652:
2644:
2640:
2614:
2613:
2609:
2583:
2582:
2578:
2568:
2566:
2560:"1,3-Butadiene"
2558:
2557:
2553:
2543:
2541:
2535:"1,3-Butadiene"
2532:
2531:
2522:
2512:
2510:
2501:
2500:
2496:
2481:
2477:
2466:"1,3-Butadiene"
2464:
2463:
2459:
2444:"1,3-Butadiene"
2442:
2441:
2434:
2423:"1,3-Butadiene"
2421:
2420:
2416:
2402:
2401:
2388:
2381:
2366:
2365:
2361:
2354:
2329:
2328:
2324:
2320:
2298:
2275:
2254:
2237:
2224:
2216:Gas properties
2211:
2187:
2170:
2159:Phase behavior
2152:
2145:
2105:cigarette smoke
2050:
2043:
2039:
2011:
1933:
1929:
1895:
1784:
1760:
1749:dehydrogenation
1700:(USSRP) during
1690:dehydrogenation
1683:
1657:
1653:
1649:
1645:
1641:
1637:
1591:
1583:
1577:
1573:
1567:
1563:
1536:
1481:dehydrogenation
1477:
1407:
1404:
1395:
1340:
1329:
1325:
1320:cumulated diene
1279:
1275:
1232:
1228:
1222:
1215:
1210:
1209:
1208: ?)
1199:
1195:
1191:
1187:
1171:
1161:
1155:
1150:
1119:
1115:
1102:
1089:
1085:
1081:
1058:
1057:ppm (rabbit, 30
1054:
1050:
1044:
1035:
1029:
1025:
1018:
1014:
1004:
1000:
993:
986:
980:
968:
964:
958:
928:
925:
907:
906:
905:
904:
897:
890:
883:
879:
871:
824:
798:
784:
758:
732:
703:
689:
687:
669:
665:
654:
622:
618:
614:
610:
606:
577:
571:
564:
539:
519:
515:
511:
510:
506:
500:
486:
483:
478:
477:
466:
463:
462:
459:
453:
452:
449:
443:
442:
431:
413:
406:
385:
365:
349:
336:
324:
301:
292:
255:
235:
215:
192:
183:
170:
159:
146:
132:
131:
103:
102:
21:
12:
11:
5:
5083:
5081:
5073:
5072:
5067:
5065:Petrochemicals
5062:
5057:
5052:
5047:
5042:
5037:
5027:
5026:
5020:
5019:
5017:
5016:
5011:
5006:
5001:
4995:
4993:
4989:
4988:
4985:
4984:
4982:
4981:
4973:
4968:
4963:
4957:
4955:
4951:
4950:
4948:
4947:
4945:4-Vinyltoluene
4942:
4940:Divinylbenzene
4937:
4931:
4929:
4925:
4924:
4921:
4920:
4918:
4917:
4912:
4907:
4905:2-Phenylhexane
4902:
4896:
4894:
4890:
4889:
4886:
4885:
4883:
4882:
4877:
4869:
4861:
4852:
4850:
4846:
4845:
4843:
4842:
4837:
4832:
4826:
4824:
4818:
4817:
4815:
4814:
4806:
4798:
4789:
4787:
4778:
4772:
4771:
4768:
4767:
4765:
4764:
4762:4-Ethyltoluene
4759:
4757:-Propylbenzene
4751:
4745:
4743:
4739:
4738:
4736:
4735:
4730:
4725:
4719:
4717:
4708:
4702:
4701:
4698:
4697:
4695:
4694:
4688:
4686:
4682:
4681:
4679:
4678:
4670:
4662:
4653:
4651:
4642:
4633:
4632:
4626:
4624:
4618:
4617:
4614:
4613:
4611:
4610:
4605:
4600:
4595:
4590:
4585:
4580:
4575:
4570:
4565:
4559:
4557:
4553:
4552:
4550:
4549:
4544:
4539:
4534:
4529:
4524:
4518:
4516:
4507:
4498:
4490:
4489:
4486:
4485:
4483:
4482:
4477:
4472:
4467:
4462:
4457:
4451:
4449:
4445:
4444:
4442:
4441:
4436:
4431:
4426:
4421:
4416:
4411:
4406:
4400:
4398:
4392:
4391:
4389:
4388:
4383:
4378:
4373:
4368:
4363:
4358:
4353:
4347:
4345:
4339:
4338:
4336:
4335:
4329:
4327:
4325:Bicycloalkenes
4321:
4320:
4318:
4317:
4315:
4310:
4305:
4300:
4295:
4289:
4287:
4281:
4280:
4278:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4236:
4234:
4228:
4227:
4224:
4223:
4221:
4220:
4215:
4210:
4205:
4200:
4195:
4189:
4187:
4183:
4182:
4180:
4179:
4174:
4169:
4164:
4159:
4154:
4149:
4144:
4139:
4133:
4131:
4130:Linear alkynes
4124:
4117:
4111:
4103:
4102:
4099:
4098:
4096:
4095:
4090:
4085:
4080:
4075:
4070:
4065:
4059:
4057:
4053:
4052:
4050:
4049:
4044:
4039:
4034:
4029:
4024:
4019:
4014:
4009:
4003:
4001:
4000:Linear alkenes
3994:
3988:
3982:
3971:
3961:
3960:
3957:
3956:
3954:
3953:
3947:
3945:
3941:
3940:
3938:
3937:
3932:
3927:
3922:
3917:
3912:
3907:
3902:
3897:
3892:
3887:
3881:
3879:
3873:
3872:
3870:
3869:
3863:
3857:
3850:
3848:
3846:Bicycloalkanes
3842:
3841:
3839:
3838:
3836:
3831:
3826:
3821:
3816:
3810:
3808:
3802:
3801:
3799:
3798:
3793:
3788:
3783:
3778:
3773:
3768:
3763:
3757:
3755:
3749:
3748:
3745:
3744:
3742:
3741:
3736:
3731:
3726:
3721:
3716:
3711:
3706:
3701:
3695:
3693:
3689:
3688:
3686:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3634:
3632:
3631:Linear alkanes
3625:
3618:
3612:
3601:
3593:
3592:
3587:
3585:
3584:
3577:
3570:
3562:
3556:
3555:
3550:
3544:
3536:
3535:External links
3533:
3531:
3530:
3516:
3494:
3468:
3449:(2): 157â163.
3443:Carcinogenesis
3429:
3401:
3352:
3323:(4): 424â430.
3303:
3289:
3272:
3250:
3223:(8): 679â680.
3206:
3180:
3153:
3125:
3068:
3054:978-0071151498
3053:
3035:
3021:978-0716799498
3020:
3002:
2951:
2900:
2886:
2864:
2837:
2806:
2788:
2782:978-3527306732
2781:
2748:
2741:
2720:
2707:
2694:
2673:(2): 155â174.
2650:
2638:
2607:
2576:
2551:
2520:
2494:
2475:
2457:
2432:
2414:
2386:
2379:
2359:
2352:
2321:
2319:
2316:
2315:
2314:
2309:
2304:
2302:Cyclobutadiene
2297:
2294:
2291:
2290:
2289:0.64 Ă10 kg/m
2287:
2285:Liquid density
2281:
2280:
2279:123.6 J/mol·K
2277:
2273:
2268:
2267:
2266:199.0 J/mol·K
2264:
2260:
2259:
2256:
2252:
2248:
2247:
2243:
2242:
2239:
2235:
2230:
2229:
2226:
2222:
2218:
2217:
2213:
2212:
2209:
2206:
2204:Symmetry group
2200:
2199:
2195:
2194:
2184:
2182:Critical point
2178:
2177:
2167:
2161:
2160:
2156:
2155:
2144:
2141:
2049:
2046:
2041:
2037:
2010:
2007:
1931:
1927:
1894:
1891:
1887:telomerization
1872:cyclooctadiene
1842:hydrocyanation
1791:polymerization
1783:
1780:
1778:upon heating.
1776:sulfur dioxide
1759:
1756:
1682:
1679:
1662:
1661:
1655:
1651:
1647:
1643:
1639:
1635:
1596:
1595:
1589:
1581:
1575:
1571:
1565:
1561:
1547:Sergei Lebedev
1535:
1532:
1476:
1469:
1411:steam cracking
1406:
1402:
1399:
1394:
1391:
1373:, working for
1363:British Empire
1356:Sergei Lebedev
1339:
1336:
1327:
1323:
1305:motor vehicles
1277:
1273:
1220:
1217:
1216:
1211:
1189:
1188:
1184:standard state
1181:
1178:
1177:
1172:
1169:
1166:
1165:
1156:
1145:
1142:
1141:
1137:
1136:
1131:
1124:
1123:
1116:
1110:
1107:
1106:
1103:
1097:
1094:
1093:
1082:
1076:
1073:
1072:
1063:
1062:
1051:
1042:
1040:
1037:
1036:
1034:
1033:
1022:
1011:
997:
989:
987:
978:
976:
973:
972:
965:
956:
954:
951:
950:
943:
942:
939:
933:
932:
929:
922:
919:
918:
915:
909:
908:
898:
891:
884:
869:
868:
867:
866:
864:
855:
854:
825:
820:
817:
816:
799:
794:
791:
790:
785:
780:
777:
776:
759:
754:
751:
750:
740:
739:
733:
730:
727:
726:
717:
716:
712:
711:
700:
694:
693:
690:
685:
677:
674:
673:
662:
660:Vapor pressure
656:
655:
653:
652:
642:
635:
633:
627:
626:
607:
602:
599:
598:
595:
589:
588:
585:
579:
578:
576:
575:
568:
560:
558:
552:
551:
548:
542:
541:
538:Colourless gas
536:
532:
531:
528:
522:
521:
517:
513:
508:
504:
501:
496:
493:
492:
488:
487:
485:
484:
481:
473:
472:
471:
468:
467:
465:
464:
460:
457:
456:
454:
450:
447:
446:
438:
437:
436:
433:
432:
430:
429:
416:
414:
402:
399:
398:
393:
387:
386:
384:
383:
375:
373:
367:
366:
364:
363:
359:
357:
351:
350:
348:
347:
339:
337:
329:
326:
325:
323:
322:
314:
312:
306:
305:
302:
297:
294:
293:
291:
290:
286:
284:
276:
275:
265:
257:
256:
254:
253:
245:
243:
237:
236:
234:
233:
225:
223:
217:
216:
214:
213:
205:
203:
197:
196:
193:
188:
185:
184:
182:
181:
173:
171:
164:
161:
160:
158:
157:
149:
147:
142:
139:
138:
134:
133:
130:
129:
126:
123:
120:
117:
114:
110:
109:
105:
104:
101:Buta-1,3-diene
100:
99:
93:
92:
88:
87:
84:
83:
73:
58:
57:
54:
53:
43:
26:1,3-Butadiene
13:
10:
9:
6:
4:
3:
2:
5082:
5071:
5068:
5066:
5063:
5061:
5058:
5056:
5053:
5051:
5048:
5046:
5043:
5041:
5038:
5036:
5033:
5032:
5030:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4996:
4994:
4990:
4980:
4978:
4974:
4972:
4969:
4967:
4964:
4962:
4959:
4958:
4956:
4952:
4946:
4943:
4941:
4938:
4936:
4933:
4932:
4930:
4928:Vinylbenzenes
4926:
4916:
4913:
4911:
4908:
4906:
4903:
4901:
4898:
4897:
4895:
4891:
4881:
4878:
4876:
4875:-Butylbenzene
4874:
4870:
4868:
4867:-Butylbenzene
4866:
4862:
4860:
4859:-Butylbenzene
4858:
4854:
4853:
4851:
4847:
4841:
4838:
4836:
4833:
4831:
4828:
4827:
4825:
4823:
4819:
4813:
4811:
4807:
4805:
4803:
4799:
4797:
4795:
4791:
4790:
4788:
4786:
4782:
4779:
4777:
4773:
4763:
4760:
4758:
4756:
4752:
4750:
4747:
4746:
4744:
4740:
4734:
4731:
4729:
4726:
4724:
4721:
4720:
4718:
4716:
4712:
4709:
4707:
4703:
4693:
4690:
4689:
4687:
4683:
4677:
4675:
4671:
4669:
4667:
4663:
4661:
4659:
4655:
4654:
4652:
4650:
4646:
4643:
4641:
4637:
4631:
4628:
4627:
4625:
4623:
4622:Alkylbenzenes
4619:
4609:
4606:
4604:
4601:
4599:
4596:
4594:
4591:
4589:
4586:
4584:
4581:
4579:
4576:
4574:
4571:
4569:
4566:
4564:
4561:
4560:
4558:
4554:
4548:
4545:
4543:
4540:
4538:
4535:
4533:
4530:
4528:
4525:
4523:
4520:
4519:
4517:
4515:
4511:
4508:
4506:
4502:
4499:
4497:
4491:
4481:
4478:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4453:
4452:
4450:
4446:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4401:
4399:
4397:
4393:
4387:
4384:
4382:
4379:
4377:
4374:
4372:
4369:
4367:
4364:
4362:
4359:
4357:
4354:
4352:
4349:
4348:
4346:
4344:
4340:
4334:
4331:
4330:
4328:
4326:
4322:
4316:
4314:
4311:
4309:
4306:
4304:
4301:
4299:
4296:
4294:
4291:
4290:
4288:
4286:
4282:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4237:
4235:
4233:
4229:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4190:
4188:
4184:
4178:
4175:
4173:
4170:
4168:
4165:
4163:
4160:
4158:
4155:
4153:
4150:
4148:
4145:
4143:
4140:
4138:
4135:
4134:
4132:
4128:
4125:
4121:
4114:
4108:
4104:
4094:
4091:
4089:
4086:
4084:
4081:
4079:
4076:
4074:
4071:
4069:
4066:
4064:
4061:
4060:
4058:
4054:
4048:
4045:
4043:
4040:
4038:
4035:
4033:
4030:
4028:
4025:
4023:
4020:
4018:
4015:
4013:
4010:
4008:
4005:
4004:
4002:
3998:
3995:
3992:
3985:
3979:
3975:
3972:
3966:
3962:
3952:
3949:
3948:
3946:
3942:
3936:
3933:
3931:
3928:
3926:
3923:
3921:
3918:
3916:
3915:Dodecahedrane
3913:
3911:
3908:
3906:
3903:
3901:
3898:
3896:
3893:
3891:
3888:
3886:
3883:
3882:
3880:
3878:
3874:
3867:
3864:
3861:
3858:
3855:
3852:
3851:
3849:
3847:
3843:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3811:
3809:
3807:
3803:
3797:
3794:
3792:
3789:
3787:
3784:
3782:
3779:
3777:
3774:
3772:
3769:
3767:
3764:
3762:
3759:
3758:
3756:
3754:
3750:
3740:
3737:
3735:
3732:
3730:
3727:
3725:
3722:
3720:
3717:
3715:
3712:
3710:
3707:
3705:
3702:
3700:
3697:
3696:
3694:
3690:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3635:
3633:
3629:
3626:
3622:
3615:
3609:
3605:
3602:
3594:
3590:
3583:
3578:
3576:
3571:
3569:
3564:
3563:
3560:
3554:
3551:
3548:
3547:1,3-Butadiene
3545:
3542:
3541:1,3-Butadiene
3539:
3538:
3534:
3526:
3520:
3517:
3512:
3508:
3504:
3498:
3495:
3482:
3478:
3472:
3469:
3464:
3460:
3456:
3452:
3448:
3444:
3440:
3433:
3430:
3422:
3418:
3411:
3405:
3402:
3397:
3393:
3388:
3383:
3379:
3375:
3371:
3367:
3363:
3356:
3353:
3348:
3344:
3339:
3334:
3330:
3326:
3322:
3318:
3314:
3307:
3304:
3299:
3293:
3290:
3285:
3279:
3277:
3273:
3268:
3264:
3260:
3254:
3251:
3246:
3242:
3238:
3234:
3230:
3226:
3222:
3218:
3210:
3207:
3194:
3190:
3184:
3181:
3176:
3172:
3168:
3164:
3157:
3154:
3149:
3145:
3141:
3137:
3129:
3126:
3121:
3117:
3112:
3107:
3103:
3099:
3095:
3091:
3088:(11): m1369.
3087:
3083:
3079:
3072:
3069:
3064:
3060:
3056:
3050:
3046:
3039:
3036:
3031:
3027:
3023:
3017:
3013:
3006:
3003:
2998:
2994:
2990:
2986:
2982:
2978:
2974:
2970:
2966:
2962:
2955:
2952:
2947:
2943:
2939:
2935:
2931:
2927:
2923:
2919:
2915:
2911:
2904:
2901:
2889:
2887:9789283212607
2883:
2876:
2875:
2868:
2865:
2860:
2856:
2852:
2848:
2841:
2838:
2826:(11): 131â136
2825:
2821:
2817:
2810:
2807:
2802:
2795:
2793:
2789:
2784:
2778:
2774:
2770:
2766:
2765:
2757:
2755:
2753:
2749:
2744:
2742:0-313-24634-3
2738:
2734:
2727:
2725:
2721:
2717:
2711:
2708:
2704:
2698:
2695:
2690:
2686:
2681:
2676:
2672:
2668:
2664:
2657:
2655:
2651:
2647:
2642:
2639:
2634:
2630:
2626:
2622:
2618:
2611:
2608:
2603:
2599:
2595:
2591:
2587:
2580:
2577:
2565:
2561:
2555:
2552:
2540:
2536:
2529:
2527:
2525:
2521:
2508:
2504:
2498:
2495:
2492:
2488:
2484:
2479:
2476:
2471:
2467:
2461:
2458:
2453:
2449:
2445:
2439:
2437:
2433:
2428:
2424:
2418:
2415:
2410:
2406:
2399:
2397:
2395:
2393:
2391:
2387:
2382:
2376:
2372:
2371:
2363:
2360:
2355:
2349:
2345:
2341:
2337:
2334:. Cambridge:
2333:
2326:
2323:
2317:
2313:
2310:
2308:
2307:Polybutadiene
2305:
2303:
2300:
2299:
2295:
2288:
2286:
2283:
2282:
2278:
2276:
2270:
2269:
2265:
2262:
2261:
2257:
2250:
2249:
2244:
2241:79.5 J/mol·K
2240:
2238:
2232:
2231:
2228:110.2 kJ/mol
2227:
2220:
2219:
2214:
2207:
2205:
2202:
2201:
2196:
2193:
2192:
2185:
2183:
2180:
2179:
2176:
2175:
2168:
2166:
2163:
2162:
2157:
2150:
2142:
2140:
2138:
2135:
2131:
2127:
2123:
2118:
2116:
2111:
2110:
2109:acrylonitrile
2106:
2102:
2098:
2095:
2091:
2087:
2084:
2082:
2075:
2071:
2067:
2063:
2059:
2054:
2047:
2045:
2034:
2032:
2028:
2020:
2015:
2008:
2006:
2004:
1998:
1996:
1995:HĂŒckel theory
1992:
1984:
1980:
1977:
1972:
1970:
1966:
1961:
1958:
1954:
1950:
1946:
1941:
1937:
1925:
1920:
1916:
1912:
1904:
1899:
1892:
1890:
1888:
1884:
1879:
1877:
1873:
1869:
1865:
1861:
1857:
1852:
1850:
1845:
1843:
1839:
1835:
1830:
1828:
1824:
1820:
1816:
1812:
1811:acrylonitrile
1808:
1804:
1800:
1796:
1795:polybutadiene
1792:
1787:
1781:
1779:
1777:
1773:
1769:
1765:
1757:
1755:
1752:
1750:
1747:by oxidative
1746:
1742:
1737:
1735:
1731:
1727:
1723:
1719:
1715:
1711:
1707:
1703:
1699:
1695:
1691:
1688:
1680:
1678:
1676:
1672:
1668:
1632:
1628:
1627:
1626:
1624:
1620:
1616:
1612:
1609:, ethanol is
1608:
1603:
1601:
1592:
1585:
1569:
1556:
1552:
1551:
1550:
1548:
1543:
1541:
1533:
1531:
1529:
1525:
1521:
1517:
1512:
1510:
1506:
1502:
1501:Borger, Texas
1498:
1494:
1490:
1486:
1482:
1474:
1470:
1468:
1466:
1462:
1458:
1454:
1452:
1447:
1443:
1439:
1434:
1432:
1428:
1424:
1420:
1416:
1412:
1400:
1398:
1392:
1390:
1388:
1384:
1383:grain alcohol
1380:
1376:
1372:
1368:
1364:
1359:
1357:
1353:
1349:
1345:
1337:
1335:
1333:
1321:
1318:, which is a
1317:
1316:1,2-butadiene
1313:
1308:
1306:
1302:
1298:
1293:
1291:
1287:
1283:
1271:
1265:
1226:
1225:1,3-Butadiene
1214:
1207:
1202:
1185:
1179:
1176:
1173:
1168:
1167:
1164:
1160:
1157:
1154:
1149:
1144:
1143:
1138:
1135:
1132:
1129:
1126:
1125:
1117:
1113:
1109:
1108:
1104:
1101:(Recommended)
1100:
1096:
1095:
1083:
1080:(Permissible)
1079:
1075:
1074:
1070:
1069:
1064:
1052:
1048:
1039:
1038:
1023:
1012:
1009:
1003:ppm (mouse, 2
998:
991:
990:
988:
984:
975:
974:
966:
962:
953:
952:
948:
944:
940:
938:
935:
934:
930:
927:
921:
920:
916:
914:
911:
910:
903:
896:
889:
865:
862:
861:
857:
856:
826:
823:
819:
818:
800:
797:
793:
792:
789:
786:
783:
779:
778:
774:
769:
764:
760:
757:
753:
752:
748:
746:
741:
738:
734:
729:
728:
724:
723:
718:
713:
710:at 0 °C
709:
701:
699:
696:
695:
691:
684:
680:
676:
675:
663:
661:
658:
657:
651:
647:
643:
641:
637:
636:
634:
632:
629:
628:
608:
605:
601:
600:
596:
594:
593:Boiling point
591:
590:
586:
584:
583:Melting point
581:
580:
569:
562:
561:
559:
557:
554:
553:
549:
547:
544:
543:
537:
534:
533:
529:
527:
524:
523:
502:
499:
495:
494:
489:
480:
476:
469:
455:
445:
441:
434:
426:
422:
421:DTXSID3020203
418:
417:
415:
405:
401:
400:
397:
394:
392:
389:
388:
381:
377:
376:
374:
372:
369:
368:
361:
360:
358:
356:
353:
352:
345:
341:
340:
338:
332:
328:
327:
320:
316:
315:
313:
311:
308:
307:
303:
300:
296:
295:
288:
287:
285:
283:
278:
277:
273:
269:
266:
264:
262:ECHA InfoCard
259:
258:
251:
247:
246:
244:
242:
239:
238:
231:
227:
226:
224:
222:
219:
218:
211:
207:
206:
204:
202:
199:
198:
194:
191:
187:
186:
179:
175:
174:
172:
168:
163:
162:
155:
151:
150:
148:
145:
141:
140:
135:
127:
124:
122:Vinylethylene
121:
118:
115:
112:
111:
106:
98:
94:
89:
78:
74:
68:
64:
63:
59:
48:
44:
38:
34:
33:
29:
23:
19:
4976:
4872:
4864:
4856:
4809:
4801:
4793:
4754:
4728:Pseudocumene
4692:Ethylbenzene
4673:
4665:
4657:
4588:Phenanthrene
4496:hydrocarbons
4408:
4371:Cycloheptyne
4361:Cyclopentyne
4351:Cyclopropyne
4343:Cycloalkynes
4260:Cycloheptene
4250:Cyclopentene
4240:Cyclopropene
4232:Cycloalkenes
4119:
4112:
3990:
3983:
3970:hydrocarbons
3951:Spiroalkanes
3781:Cycloheptane
3771:Cyclopentane
3761:Cyclopropane
3753:Cycloalkanes
3620:
3613:
3600:hydrocarbons
3589:Hydrocarbons
3519:
3511:the original
3506:
3497:
3485:. Retrieved
3481:the original
3471:
3446:
3442:
3432:
3416:
3404:
3369:
3365:
3355:
3320:
3316:
3306:
3292:
3262:
3253:
3220:
3216:
3209:
3197:. Retrieved
3193:the original
3183:
3166:
3162:
3156:
3139:
3135:
3128:
3085:
3081:
3071:
3044:
3038:
3011:
3005:
2964:
2960:
2954:
2913:
2909:
2903:
2891:. Retrieved
2873:
2867:
2850:
2846:
2840:
2828:. Retrieved
2823:
2819:
2809:
2800:
2762:
2732:
2718:, June 1957.
2715:
2710:
2702:
2697:
2670:
2666:
2641:
2624:
2621:J. Chem. Soc
2620:
2610:
2593:
2589:
2579:
2567:. Retrieved
2554:
2542:. Retrieved
2538:
2511:. Retrieved
2507:the original
2497:
2478:
2469:
2460:
2447:
2426:
2417:
2369:
2362:
2331:
2325:
2258:90.5 kJ/mol
2188:
2171:
2165:Triple point
2119:
2112:
2088:
2085:
2078:
2035:
2023:
2002:
1999:
1988:
1975:
1973:
1964:
1962:
1956:
1952:
1948:
1944:
1939:
1935:
1923:
1918:
1914:
1908:
1902:
1880:
1860:cycloalkenes
1856:cycloalkanes
1853:
1846:
1834:adiponitrile
1831:
1798:
1788:
1785:
1761:
1753:
1738:
1702:World War II
1684:
1681:From butenes
1663:
1615:acetaldehyde
1604:
1600:Soviet Union
1597:
1544:
1537:
1534:From ethanol
1519:
1515:
1513:
1505:Toledo, Ohio
1484:
1478:
1472:
1465:distillation
1450:
1446:acetonitrile
1438:hydrocarbons
1435:
1408:
1405:hydrocarbons
1396:
1389:in Germany.
1360:
1348:amyl alcohol
1341:
1309:
1294:
1286:vinyl groups
1224:
1223:
1067:
946:
924:Autoignition
859:
787:
744:
731:Main hazards
720:
682:
355:RTECS number
230:ChEMBL537970
137:Identifiers
108:Other names
22:
4776:C4-Benzenes
4733:Hemellitene
4706:C3-Benzenes
4640:C2-Benzenes
4603:Corannulene
4522:Naphthalene
4386:Cyclodecyne
4381:Cyclononyne
4376:Cyclooctyne
4366:Cyclohexyne
4356:Cyclobutyne
4275:Cyclodecene
4270:Cyclononene
4265:Cyclooctene
4255:Cyclohexene
4245:Cyclobutene
3965:Unsaturated
3796:Cyclodecane
3791:Cyclononane
3786:Cyclooctane
3776:Cyclohexane
3766:Cyclobutane
3372:: 143â147.
3189:"NPI sheet"
2569:2 September
2062:hydrocarbon
1827:chloroprene
1821:(NBR), and
1768:cyclohexene
1714:Baton Rouge
1371:Walter Bock
1297:breaks down
1163:Chloroprene
1028:ppm (rat, 4
1017:ppm (rat, 4
996:ppm (mouse)
961:median dose
947:Lethal dose
926:temperature
913:Flash point
782:Signal word
725:(OHS/OSH):
644:Soluble in
535:Appearance
491:Properties
268:100.003.138
210:CHEBI:39478
5035:Alkadienes
5029:Categories
4835:Prehnitene
4723:Mesitylene
4578:Circulenes
4527:Anthracene
4455:Alkatriene
4424:Heptadiene
4414:Pentadiene
4404:Propadiene
4333:Norbornene
4203:Isoheptyne
4193:Isopentyne
4078:Isoheptene
4068:Isopentene
3890:Diamondoid
3885:Adamantane
3860:Norbornane
3724:Isoheptane
3714:Neopentane
3704:Isopentane
3199:10 January
3163:Org. Synth
3136:Org. Synth
2847:Org. Synth
2318:References
2198:Structure
2153:Properties
2143:Data sheet
2097:carcinogen
2072:showing a
2056:A railway
1813:, such as
1803:copolymers
1692:of normal
1417:and other
1393:Production
756:Pictograms
737:carcinogen
631:Solubility
621:mg/L at 20
526:Molar mass
380:JSD5FGP5VD
241:ChemSpider
165:3D model (
144:CAS Number
113:Biethylene
5004:Annulynes
4999:Annulenes
4840:Isodurene
4573:Helicenes
4547:Heptacene
4537:Pentacene
4532:Tetracene
4460:Alkadiyne
4439:Decadiene
4434:Nonadiene
4429:Octadiene
4419:Hexadiene
4409:Butadiene
4218:Isodecyne
4213:Isononyne
4208:Isooctyne
4198:Isohexyne
4093:Isodecene
4088:Isononene
4083:Isooctene
4073:Isohexene
4063:Isobutene
3968:aliphatic
3925:Churchane
3920:Basketane
3739:Isodecane
3734:Isononane
3729:Isooctane
3719:Isohexane
3699:Isobutane
3598:aliphatic
3596:Saturated
3487:20 August
3237:1470-2045
2989:1089-5639
2938:1089-5639
2689:258122761
2627:: 74â93.
2596:: 93â97.
2533:PubChem.
2513:24 August
2115:teratogen
2074:UN number
2009:Reactions
1911:conformer
1849:sulfolane
1772:Sulfolene
1687:catalytic
1650:=CHâCH=CH
1574:=CHâCH=CH
1387:acetylene
1375:IG Farben
1344:pyrolysis
1326:C=C=CHâCH
1276:=CH-CH=CH
1268:) is the
1134:ECSC 0017
840:P308+P313
747:labelling
698:Viscosity
516:=CH-CH=CH
391:UN number
362:EI9275000
289:271-039-0
281:EC Number
128:Butadiene
116:Erythrene
5045:Monomers
4608:Kekulene
4593:Chrysene
4583:Butalene
4568:Fluorene
4542:Hexacene
4494:Aromatic
4465:Cumulene
3935:Twistane
3930:Pagodane
3910:Prismane
3421:Archived
3347:14660781
3267:Archived
3245:17726789
3120:21588810
3063:49907089
3030:61448218
2997:16759136
2946:19199679
2893:19 April
2880:. IARC.
2454:(NIOSH).
2411:(NIOSH).
2296:See also
2058:tank car
1976:s-trans-
1883:1-octene
1646:CHO â CH
1619:tantalum
1611:oxidized
1457:furfural
1444:such as
1427:ethylene
1415:ethylene
1301:emission
1159:Isoprene
1146:Related
1088:ppm ST 5
860:NFPA 704
715:Hazards
613:g/L at 5
154:106-99-0
18:Divinyls
4961:Benzene
4935:Styrene
4812:-Cymene
4804:-Cymene
4796:-Cymene
4785:Cymenes
4676:-Xylene
4668:-Xylene
4660:-Xylene
4649:Xylenes
4630:Toluene
4563:Azulene
4162:Heptyne
4152:Pentyne
4142:Propyne
4107:Alkynes
4032:Heptene
4022:Pentene
4012:Propene
3978:Alkenes
3900:Sterane
3866:Decalin
3854:Housane
3668:Heptane
3658:Pentane
3648:Propane
3638:Methane
3608:Alkanes
3463:7859343
3396:2205484
3387:1567758
3338:1747794
3142:: 105.
3111:3009352
3090:Bibcode
2969:Bibcode
2918:Bibcode
2489:of the
2485:in the
2483:Record
2405:"#0067"
2094:Group 1
1957:s-trans
1945:s-trans
1924:s-trans
1903:s-trans
1817:(ABS),
1809:and/or
1807:styrene
1745:butenes
1741:Houston
1726:Baytown
1722:Houston
1694:butenes
1642:OH + CH
1540:ethanol
1528:chromia
1524:alumina
1493:Houston
1475:-butane
1419:alkenes
1379:styrene
1338:History
1330:. This
1206:what is
1204: (
1148:Alkenes
1053:250,000
1024:130,000
1013:126,667
999:122,000
992:115,111
692:1.4292
668:atm (20
650:ethanol
640:acetone
617:°C, 735
556:Density
520:
331:PubChem
195:605258
125:Bivinyl
119:Divinyl
4830:Durene
4749:Cumene
4598:Pyrene
4514:Acenes
4396:Dienes
4177:Decyne
4172:Nonyne
4167:Octyne
4157:Hexyne
4147:Butyne
4137:Ethyne
4047:Decene
4042:Nonene
4037:Octene
4027:Hexene
4017:Butene
4007:Ethene
3905:Cubane
3683:Decane
3678:Nonane
3673:Octane
3663:Hexane
3653:Butane
3643:Ethane
3461:
3394:
3384:
3345:
3335:
3243:
3235:
3169:: 93.
3118:
3108:
3061:
3051:
3028:
3018:
2995:
2987:
2944:
2936:
2884:
2853:: 25.
2830:1 June
2779:
2739:
2687:
2564:US EPA
2470:INCHEM
2377:
2350:
1949:gauche
1732:; and
1728:, and
1673:, and
1623:silica
1507:, and
1423:ethane
1332:allene
1312:isomer
1201:verify
1198:
1175:Butane
1153:dienes
1130:(SDS)
1120:
1090:
1086:
1059:
1055:
1030:
1026:
1019:
1015:
1005:
1001:
994:
969:
941:2â12%
788:Danger
704:
670:
666:
623:
619:
615:
611:
572:
565:
563:0.6149
482:C=CC=C
475:SMILES
319:C16450
304:25198
221:ChEMBL
91:Names
4992:Other
4977:trans
4954:Other
4893:Other
4849:Other
4742:Other
4685:Other
4556:Other
4480:Enyne
4448:Other
3944:Other
3424:(PDF)
3413:(PDF)
2878:(PDF)
2685:S2CID
2544:8 May
2189:43.2
2126:ozone
1965:s-cis
1953:s-cis
1919:trans
1654:+ 2 H
1459:, or
1303:from
1084:TWA 1
1068:NIOSH
1061:min)
646:ether
440:InChI
201:ChEBI
167:JSmol
4873:tert
4505:PAHs
3489:2010
3459:PMID
3392:PMID
3343:PMID
3241:PMID
3233:ISSN
3201:2006
3116:PMID
3059:OCLC
3049:ISBN
3026:OCLC
3016:ISBN
2993:PMID
2985:ISSN
2942:PMID
2934:ISSN
2895:2009
2882:ISBN
2832:2019
2777:ISBN
2737:ISBN
2571:2014
2546:2024
2515:2022
2375:ISBN
2348:ISBN
2130:TCEQ
2090:IARC
2081:LC50
1870:and
1858:and
1782:Uses
1716:and
1578:+ 2
1570:â CH
1526:and
1489:tons
1369:and
1151:and
1122:ppm
1118:2000
1112:IDLH
1092:ppm
852:P403
848:P381
844:P377
836:P280
832:P210
828:P202
814:H350
810:H340
806:H280
802:H220
702:0.25
672:°C)
570:0.64
546:Odor
396:1010
371:UNII
344:7845
310:KEGG
250:7557
4865:sec
4122:â 2
3623:+ 2
3451:doi
3382:PMC
3374:doi
3333:PMC
3325:doi
3225:doi
3171:doi
3144:doi
3106:PMC
3098:doi
2977:doi
2965:110
2926:doi
2914:113
2855:doi
2769:doi
2675:doi
2629:doi
2598:doi
2594:127
2340:doi
2191:bar
2174:bar
1940:cis
1799:and
1766:of
1613:to
1346:of
1240:juË
1099:REL
1078:PEL
967:548
745:GHS
664:2.4
625:°C
609:1.3
409:EPA
334:CID
5031::
3505:.
3457:.
3447:16
3445:.
3441:.
3415:.
3390:.
3380:.
3370:86
3368:.
3364:.
3341:.
3331:.
3321:12
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3261:.
3239:.
3231:.
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3165:.
3140:67
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3086:66
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3057:.
3024:.
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2822:.
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2669:.
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2619:.
2592:.
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2537:.
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2468:.
2450:.
2446:.
2435:^
2425:.
2407:.
2389:^
2346:.
2210:2h
2172:?
2139:.
2044:.
2033:.
1971:.
1930:-C
1851:.
1844:.
1829:.
1770:.
1724:,
1720:;
1669:,
1658:O
1638:CH
1634:CH
1586:+
1568:OH
1564:CH
1560:CH
1558:2
1503:,
1467:.
1455:,
1448:,
1433:.
1314:,
1307:.
1292:.
1258:iË
1255:aÉȘ
1043:Lo
1041:LC
1032:h)
1021:h)
979:50
977:LC
957:50
955:LD
850:,
846:,
842:,
838:,
834:,
830:,
812:,
808:,
804:,
749::
648:,
512:CH
4857:n
4810:p
4802:m
4794:o
4755:n
4674:p
4666:m
4658:o
4120:n
4118:2
4116:H
4113:n
4110:C
3991:n
3989:2
3987:H
3984:n
3981:C
3621:n
3619:2
3617:H
3614:n
3611:C
3581:e
3574:t
3567:v
3491:.
3465:.
3453::
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3173::
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3065:.
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2604:.
2600::
2573:.
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2274:p
2272:C
2263:S
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2251:Î
2236:p
2234:C
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2223:f
2221:Î
2208:C
2042:3
2038:3
2003:E
1938:-
1936:s
1932:3
1928:2
1917:-
1915:s
1665:(
1656:2
1652:2
1648:2
1644:3
1640:2
1636:3
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1588:H
1584:O
1582:2
1580:H
1576:2
1572:2
1566:2
1562:3
1516:n
1485:n
1473:n
1451:N
1403:4
1328:3
1324:2
1278:2
1274:2
1264:/
1261:n
1252:d
1249:Ë
1246:É
1243:t
1237:b
1234:Ë
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887:3
708:P
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514:2
509:6
507:H
505:4
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407:(
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