40:
31:
252:
177:
713:
779:, meaning dimethyl carbonate can dissolve most common coating resins except perhaps rubber based resins. Hildebrand solubility parameter is 20.3 MPa and Hansen solubility parameters are: dispersion = 15.5, polar = 3.9, H bonding = 9.7. Dimethyl carbonate is partially soluble in water up to 13%, however it is hydrolyzed in water-based systems over time to methanol and CO
461:
762:
until it too was exempted. Dimethyl carbonate has an ester- or alcohol-like odor, which is more favorable to users than most hydrocarbon solvents it replaces. Dimethyl carbonate has an evaporation rate of 3.22 (butyl acetate = 1.0), which slightly slower than MEK (3.8) and
1500:
Aurbach, D.; Markovsky, B.; Shechter, A.; EinâEli, Y.; Cohen, H. (December 1996). "A Comparative Study of
Synthetic Graphite and Li Electrodes in Electrolyte Solutions Based on Ethylene CarbonateâDimethyl Carbonate Mixtures".
835:. However, the film in dry DMC solutions is not as effective in passivating the negative electrode as the film in wet solutions. For this reason dimethyl carbonate is rarely used in lithium batteries without a co-solvent.
1264:
Shieh, Wen-Chung; Dell, Steven; RepiÄ, Oljan (2001). "1,8-Diazabicycloundec-7-ene (DBU) and
Microwave-Accelerated Green Chemistry in Methylation of Phenols, Indoles, and Benzimidazoles with Dimethyl Carbonate".
807:-polycarbonate in a melt polycondensation process, the resulting product being recyclable by reversing the process and transesterifying the polycarbonate with phenol to yield diphenyl carbonate and bisphenol A.
863:, methyl ethyl ketone). Workers should wear protective organic vapor respirators when using DMC indoors or in other conditions where concentrations exceed the REL. DMC is metabolized by the body to
899:
KĂśntje, M.; Memm, M.; Axmann, P.; Wohlfahrt-Mehrens, M. (December 2014). "Substituted transition metal phospho olivines LiMMâ˛PO4 (M = Mn, MⲠ= Fe, Co, Mg): Optimisation routes for LiMnPO4".
1309:
Information about the EPA's action on exempting dimethyl carbonate as a VOC and petitioner's background information, public comments and other references are available electronically at
1228:
Shieh, Wen-Chung; Dell, Stephen; RepiÄ, Oljan (2002). "Nucleophilic
Catalysis with 1,8-Diazabicycloundec-7-ene (DBU) for the Esterification of Carboxylic Acids with Dimethyl Carbonate".
783:
unless properly buffered. Dimethyl carbonate can freeze at same temperatures as water, it can be thawed out with no loss of properties to itself or coatings based on dimethyl carbonate.
474:
1432:
1121:
39:
1465:
Aurbach, Doron; EinâEli, Yair (June 1995). "The Study of LiâGraphite
Intercalation Processes in Several Electrolyte Systems Using In Situ XâRay Diffraction".
859:
recommends limiting exposure by inhalation to less than 100 ppm over an 8-hour work day, which is similar to that of a number of common industrial solvents (
712:
301:
552:
World production in 1997 was estimated at 1000 barrels a day. Production of dimethyl carbonate worldwide is limited to Asia, the Middle East, and Europe.
856:
1051:
Pacheco, Michael A.; Marshall, Christopher L. (1997). "Review of
Dimethyl Carbonate (DMC) Manufacture and Its Characteristics as a Fuel Additive".
30:
1449:
1138:
1414:
1381:
954:
747:
in 2009. Due to its classification as VOC exempt, dimethyl carbonate has grown in popularity and applications as a replacement for
266:
1302:
1313:, EPA's electronic public docket and comment system. The docket number for this action is Docket ID No. EPA-HQ-OAR-2006-0948. See
1536:
Durbin, Thomas D.; Karavalakis, Georgios; Johnson, Kent C.; Cocker, David; Yang, Jiacheng; Jiang, Yu; Kumar, Sachin (June 2017).
925:
421:
481:
209:
1558:
1317:
230:
1156:"Novel eco-efficient reactive distillation process for dimethyl carbonate production by indirect alcoholysis of urea"
752:
1563:
740:
541:
1342:
1019:
847:
of 17 °C (63 °F), which limits its use in consumer and indoor applications. DMC is still safer than
1406:
816:
675:
611:
172:
1568:
525:
1510:
1474:
880:
832:
564:
52:
1299:
1193:
Lee, Youngmin; Shimizu, Isao (1998). "Convenient O-Methylation of
Phenols with Dimethyl Carbonate".
1539:
Evaluating the viability of dimethyl carbonate as an alternative fuel for the transportation sector
796:
748:
659:
651:
247:
80:
1373:
114:
1210:
946:
868:
828:
792:
756:
655:
727:
is its low toxicity. Additionally, it is biodegradable. Unfortunately, it is a relatively weak
1445:
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1101:
1053:
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728:
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942:
926:
https://www.fsc.go.jp/fsciis/attachedFile/download?retrievalId=kya20180111146&fileId=202
908:
724:
667:
505:
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404:
324:
17:
218:
154:
1321:
1306:
1085:
972:"Toxicity assessment of dimethyl carbonate following 28 days repeated inhalation exposure"
912:
696:
615:
537:
517:
1366:
90:
1514:
1478:
251:
176:
134:
996:
971:
852:
831:, dimethyl carbonate forms an electronically-insulating Li-conducting film at negative
452:
1552:
1230:
1214:
764:
393:
383:
165:
867:
and carbon dioxide, so accidental ingestion should be treated in the same manner as
776:
198:
1083:
Pietro Tundo & Maurizio Selva (2002). "The
Chemistry of Dimethyl Carbonate".
844:
804:
772:
720:
440:
1171:
533:
352:
145:
1441:
1179:
1130:
1155:
704:
671:
1537:
1368:
Handbook for
Critical Cleaning: Cleaning Agents and Systems, Second Edition
1314:
1286:
1250:
1105:
1005:
719:
Dimethyl carbonate's main benefit over other methylating reagents such as
987:
864:
744:
703:, albeit usually slowly. Sometimes these reactions require the use of an
663:
560:
556:
1206:
803:. Diphenyl carbonate is a widely used raw material for the synthesis of
860:
848:
768:
700:
692:
373:
185:
1522:
1486:
1278:
1242:
1097:
1066:
800:
1334:
1027:
775:(1.7). Dimethyl carbonate has solubility profile similar to common
451:
Except where otherwise noted, data are given for materials in their
791:
A large captive use of dimethyl carbonate is for the production of
739:
In the US, dimethyl carbonate was exempted under the definition of
1154:
PatraĹcu, Iulian; BĂŽldea, Costin S.; Kiss, Anton A. (2022-02-01).
937:
Kreutzberger, Charles B. (2001). "Chloroformates and
Carbonates".
125:
113:
103:
1300:
http://www.epa.gov/ttn/oarpg/t1/fact_sheets/voc_exemp01011309.pdf
855:
and methyl ethyl ketone from a flammability point of view. The
555:
Dimethyl carbonate is traditionally prepared by the reaction of
516:. It is a colourless, flammable liquid. It is classified as a
1310:
235:
536:. Instead, dimethyl carbonate is often considered to be a
540:, and it is exempt from the restrictions placed on most
469:
1364:
Kanegsberg, Barbara; Kanegsberg, Edward (2011-04-04).
666:, which also affords respectively ethylene glycol or
388:
2 to 4 °C (36 to 39 °F; 275 to 277 K)
1335:"Update: U.S. EPA Exempt Volatile Organic Compounds"
1020:"Update: U.S. EPA Exempt Volatile Organic Compounds"
815:There is also interest in using this compound as a
610:This synthesis route has been largely replaced by
1324:and scroll down to Jan 13, 2009 pdf for the rule.
670:. This route is complicated by the methanol-DMC
197:
939:Kirk-Othmer Encyclopedia of Chemical Technology
618:and an oxidizer provide the equivalent of CO:
89:
1433:Ullmann's Encyclopedia of Industrial Chemistry
1430:Buysch, Hans-Josef (2000). "Carbonic Esters".
1122:Ullmann's Encyclopedia of Industrial Chemistry
857:National Center for Sustainable Transportation
1403:- Industrialization of Green Chemical Process
1160:Frontiers of Chemical Science and Engineering
976:Environmental Analysis, Health and Toxicology
8:
947:10.1002/0471238961.0301180204011312.a01.pub2
1046:
1044:
823:In lithium-ion and lithium-metal batteries
650:It can also be produced industrially by a
250:
175:
153:
22:
995:
217:
1315:http://www.epa.gov/ttn/oarpg/t1pfpr.html
731:compared to these traditional reagents.
528:. Notably, dimethyl carbonate is a weak
1078:
1076:
891:
787:Intermediate in polycarbonate synthesis
306:
271:
246:
1503:Journal of the Electrochemical Society
1467:Journal of the Electrochemical Society
1372:(Second ed.). CRC Press. p.
1119:Hans-Josef Buysch. "Carbonic Esters".
166:
913:10.1016/j.progsolidstchem.2014.04.005
398:90 °C (194 °F; 363 K)
278:Key: IEJIGPNLZYLLBP-UHFFFAOYSA-N
133:
7:
682:Reactions and potential applications
445:17 °C (63 °F; 290 K)
520:. This compound has found use as a
288:Key: IEJIGPNLZYLLBP-UHFFFAOYAC
275:InChI=1S/C3H6O3/c1-5-3(4)6-2/h1-2H3
188:
1399:Non-Phosgene Polycarbonate from CO
285:InChI=1/C3H6O3/c1-5-3(4)6-2/h1-2H3
14:
901:Progress in Solid State Chemistry
843:DMC is a flammable liquid with a
711:
567:is produced as an intermediate:
459:
336:
38:
29:
1345:from the original on 2019-03-20
455:(at 25 °C , 100 kPa).
970:Seo, Dongseok (16 June 2021).
691:Dimethyl carbonate methylates
544:(VOCs) in the United States.
422:Occupational safety and health
342:
330:
1:
1339:American Coatings Association
1024:American Coatings Association
532:, and is not considered as a
1026:. 2018-01-30. Archived from
1585:
1397:Fukuoka, Shinsuke (2012).
1311:http://www.regulations.gov
753:parachlorobenzotrifluoride
741:volatile organic compounds
542:volatile organic compounds
15:
1172:10.1007/s11705-021-2047-9
811:Alternative fuel additive
449:
419:
414:
317:
297:
262:
73:
63:
51:
46:
37:
28:
1442:10.1002/14356007.a05_197
1131:10.1002/14356007.a05_197
941:. New York: John Wiley.
16:Not to be confused with
1436:. Weinheim: Wiley-VCH.
1407:Nova Science Publishers
1125:. Weinheim: Wiley-VCH.
817:fuel oxygenate additive
767:(4.1), and faster than
676:azeotropic distillation
612:oxidative carbonylation
524:and as a co-solvent in
678:or other techniques.
526:lithium-ion batteries
68:Methyl carbonate, di-
988:10.5620/eaht.2021012
881:Dimethyl dicarbonate
833:electrode potentials
565:Methyl chloroformate
53:Preferred IUPAC name
1515:1996JElS..143.3809A
1479:1995JElS..142.1746A
1207:10.1055/s-1998-1893
797:transesterification
749:methyl ethyl ketone
660:propylene carbonate
652:transesterification
614:. In this process,
405:Solubility in water
360: g¡mol
25:
24:Dimethyl carbonate
1559:Methylating agents
1320:2012-01-07 at the
1305:2021-02-08 at the
1054:Energy & Fuels
869:methanol poisoning
829:ethylene carbonate
793:diphenyl carbonate
656:ethylene carbonate
494:Dimethyl carbonate
482:Infobox references
57:Dimethyl carbonate
23:
1523:10.1149/1.1837300
1509:(12): 3809â3820.
1487:10.1149/1.2044188
1279:10.1021/ol016949n
1243:10.1021/jo011036s
1201:(10): 1063â1064.
1098:10.1021/ar010076f
1067:10.1021/ef9600974
982:(2): e2021012-0.
729:methylating agent
687:Methylating agent
674:, which requires
530:methylating agent
522:methylating agent
490:Chemical compound
488:
487:
378:1.069-1.073 g/mL
368:colorless liquid
231:CompTox Dashboard
115:Interactive image
1576:
1564:Carbonate esters
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1237:(7): 2188â2191.
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725:dimethyl sulfate
715:
697:carboxylic acids
668:propylene glycol
502:organic compound
472:
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463:
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359:
344:
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325:Chemical formula
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117:
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42:
33:
26:
18:dimethyl carbate
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1322:Wayback Machine
1307:Wayback Machine
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1273:(26): 4279â81.
1267:Organic Letters
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1086:Acc. Chem. Res.
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518:carbonate ester
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1341:. 2018-01-30.
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1166:(2): 316â331.
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1140:978-3527306732
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907:(4): 106â117.
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853:methyl acetate
840:
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760:-butyl acetate
743:(VOCs) by the
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410:13.9 g/100 mL
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1569:Methyl esters
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1092:(9): 706â16.
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1030:on 2021-02-08
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765:ethyl acetate
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624:CO + 1/2 O
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431:Main hazards
420:
74:Identifiers
64:Other names
845:flash point
805:bisphenol-A
773:isopropanol
721:iodomethane
583:OCOCl + HCl
441:Flash point
425:(OHS/OSH):
365:Appearance
318:Properties
173:100.009.527
135:CHEBI:36596
1553:Categories
1034:2019-03-20
887:References
771:(2.0) and
751:(MEK) and
590:OCOCl + CH
548:Production
534:carcinogen
435:Flammable
353:Molar mass
219:KE9J097SPN
146:ChemSpider
102:3D model (
81:CAS Number
1215:196807122
1180:2095-0187
705:autoclave
672:azeotrope
504:with the
309:COC(=O)OC
1349:June 23,
1343:Archived
1318:Archived
1303:Archived
1287:11784197
1251:11925227
1106:12234200
1061:: 2â29.
1006:34130377
875:See also
865:methanol
795:through
745:U.S. EPA
693:anilines
664:methanol
632:OH â (CH
561:methanol
557:phosgene
500:) is an
415:Hazards
91:616-38-6
1511:Bibcode
1475:Bibcode
1195:Synlett
997:8421751
861:toluene
849:acetone
769:toluene
735:Solvent
701:phenols
594:OH â CH
579:OH â CH
506:formula
475:what is
473: (
374:Density
186:PubChem
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839:Safety
801:phenol
699:, and
640:CO + H
628:+ 2 CH
508:OC(OCH
470:verify
467:
358:90.078
302:SMILES
47:Names
1211:S2CID
799:with
606:+ HCl
267:InChI
199:12021
155:11526
126:ChEBI
104:JSmol
1446:ISBN
1411:ISBN
1378:ISBN
1351:2020
1283:PMID
1247:PMID
1199:1998
1176:ISSN
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1002:PMID
951:ISBN
758:tert
723:and
662:and
575:+ CH
571:COCl
563:.
559:and
210:UNII
1519:doi
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992:PMC
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236:EPA
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