| 词条 | Vinyl acetate |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 439823992 | Name = Vinyl acetate | ImageFile = Vinylacetaat.png | ImageSize = 150px | ImageName = Skeletal formula | ImageFile1 = Vinyl-acetate-3D-balls.png | ImageSize1 = 170px | ImageName1 = Ball-and-stick model | PIN = Ethenyl acetate | SystematicName = Ethenyl ethanoate | OtherNames = {{bulletedlist|Acetic acid vinyl ester|Vinyl ethanoate|Acetoxyethene|VyAc|VAM|Vinyl acetate monomer|Acetic acid ethenyl ester|1-Acetoxyethylene}} |Section1={{Chembox Identifiers | SMILES = C=COC(C)=O | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 108-05-4 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = L9MK238N77 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C19309 | EINECS = 203-545-4 | PubChem = 7904 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 7616 | InChI = 1/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3 | InChIKey = XTXRWKRVRITETP-UHFFFAOYAB | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = XTXRWKRVRITETP-UHFFFAOYSA-N | RTECS = | MeSHName = C011566 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 46916 }} |Section2={{Chembox Properties | C=4|H=6|O=2 | Appearance = Colorless liquid | Odor = Sweet, pleasant, fruity; may be sharp and irritating[1] | Density = 0.934 g/cm3 | MeltingPtC = -93.5 | BoilingPtC = 72.7 | MagSus = -46.4·10−6 cm3/mol |Section7={{Chembox Hazards | ExternalSDS = ICSC 0347 | NFPA-H = 2 | NFPA-R = 2 | NFPA-F = 3 | RPhrases = {{R11}} | SPhrases = {{S16}}, {{S23}}, {{S29}}, {{S33}} | FlashPtC = −8 | AutoignitionPtC = 427 | ExploLimits = 2.6–13.40% | PEL = none[2] }}Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, an important industrial polymer.[3] ProductionThe worldwide production capacity of vinyl acetate was estimated at 6,154,000 tonnes/year in 2007, with most capacity concentrated in the United States (1,585,000 all in Texas), China (1,261,000), Japan (725,000) and Taiwan (650,000).[3] The average list price for 2008 was $1600/tonne. Celanese is the largest producer (ca 25% of the worldwide capacity), while other significant producers include China Petrochemical Corporation (7%), Chang Chun Group (6%), and LyondellBasell (5%).[3] It is a key ingredient in furniture glue.[4] PreparationVinyl acetate is the acetate ester of vinyl alcohol. Since vinyl alcohol is highly unstable (with respect to acetaldehyde), the preparation of vinyl acetate is more complex than the synthesis of other acetate esters. The major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst.[5] The main side reaction is the combustion of organic precursors. MechanismIsotope labeling and kinetics experiments suggest that the mechanism involves PdCH2CH2OAc-containing intermediates. Beta-hydride elimination would generate vinyl acetate and a palladium hydride, which would be oxidized to give hydroxide.[6] Alternative routesVinyl acetate was once prepared by hydroesterification. This method involves the gas-phase addition of acetic acid to acetylene in the presence of metal catalysts. By this route, using mercury(II) catalysts, vinyl acetate was first prepared by Fritz Klatte in 1912.[7] Another route to vinyl acetate involves thermal decomposition of ethylidene diacetate: PolymerizationIt can be polymerized to give polyvinyl acetate (PVA). With other monomers it can be used to prepare various copolymers such as ethylene-vinyl acetate (EVA), vinyl acetate-acrylic acid (VA/AA), polyvinyl chloride acetate (PVCA), and polyvinylpyrrolidone (Vp/Va Copolymer, used in hair gels).[8] Due to the instability of the radical, attempts to control the polymerization via most 'living/controlled' radical processes have proved problematic. However, RAFT (or more specifically MADIX) polymerization offers a convenient method of controlling the synthesis of PVA by the addition of a xanthate or a dithiocarbamate chain transfer agent. Other reactionsVinyl acetate undergoes many of the reactions anticipated for an alkene and an ester. Bromine adds to give the dibromide. Hydrogen halides add to give 1-haloethyl acetates, which cannot be generated by other methods because of the non-availability of the corresponding halo-alcohols. Acetic acid adds in the presence of palladium catalysts to give ethylidene diacetate, CH3CH(OAc)2. It undergoes transesterification with a variety of carboxylic acids.[9] The alkene also undergoes Diels-Alder and 2+2 cycloadditions. Vinyl acetate undergoes transesterification, giving access to vinyl ethers:[10][11] ROH + CH2=CHOAc → ROCH=CH2 + HOAc Toxicity evaluationTests suggest that vinyl acetate is of low toxicity. For rats (oral) LD50 is 2920 mg/kg.[7] On January 31, 2009, the Government of Canada's final assessment concluded that exposure to vinyl acetate is not harmful to human health.[12] This decision under the Canadian Environmental Protection Act (CEPA) was based on new information received during the public comment period, as well as more recent information from the risk assessment conducted by the European Union. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[13] See also
References1. ^{{cite web| publisher = Agency for Toxic Substances and Disease Registry, Centers for Disease Control | title = Public Health Statement for Vinyl Acetate | url = https://www.atsdr.cdc.gov/phs/phs.asp?id=669&tid=124 | quote = It has a sweet, pleasant, fruity smell, but the odor may be sharp and irritating to some people.}} 2. ^{{PGCH|0656}} 3. ^1 {{cite web|url=http://www.sriconsulting.com/CEH/Private/Reports/696.5000/|title=CEH Marketing Research Report: Vinyl Acetate|author=H. Chinn|date=September 2008|work=Chemical Economics Handbook|publisher=SRI consulting|accessdate=July 2011}} 4. ^{{cite web|title=Madhukar Parekh's Pidilite Industries Earns His Family $1.36 Billion|url=https://www.forbes.com/sites/forbesasia/2012/10/24/madhukar-parekhs-pidilite-industries-earns-his-family-1-36-billion/print/|publisher=Forbes.com|accessdate=27 January 2013|author=Karl Shmavonian|date=2012-10-24|quote=though Pidilite has had to contend with the rising price of vinyl acetate monomer, its key raw material}} 5. ^{{cite journal|author1=Y.-F. Han |author2=D. Kumar |author3=C. Sivadinarayana |author4=D.W. Goodman|last-author-amp=yes | title = Kinetics of ethylene combustion in the synthesis of vinyl acetate over a Pd/SiO2 catalyst | journal = Journal of Catalysis | volume = 224 |year = 2004 |pages = 60–68 | url = http://www.chem.tamu.edu/rgroup/goodman/pdf%20files/442_joc-224-04-60.pdf| doi=10.1016/j.jcat.2004.02.028}} 6. ^{{cite journal|authors=Stacchiola, D.; Calaza, F.; Burkholder, L.; Schwabacher Alan, W.; Neurock, M.; Tysoe Wilfred, T., |title=Elucidation of the Reaction Mechanism for the Palladium‐Catalyzed Synthesis of Vinyl Acetate|journal=Angewandte Chemie International Edition|year=2005|volume=44|pages=4572-4574|doi=10.1002/anie.200500782}} 7. ^1 2 {{cite encyclopedia|author=G. Roscher|title=Vinyl Esters|encyclopedia=Ullmann's Encyclopedia of Chemical Technology|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a27_419}} 8. ^{{cite web|title=VP/VA Copolymer|url=http://www.cosmeticsinfo.org/ingredient_details.php?ingredient_id=1064|publisher=Personal Care Products Council|accessdate=13 December 2012}} 9. ^{{cite journal |author1=D. Swern |author2=E. F. Jordan, Jr. |lastauthoramp=yes |title=Vinyl Laurate and Other Vinyl Esters |journal=Organic Syntheses, Collected Volume 4 |pages=977 |year=1963 |url=http://www.orgsyn.org/orgsyn/pdfs/CV4P0977.pdf |access-date=2007-11-11 |archive-url=https://web.archive.org/web/20110605225303/http://www.orgsyn.org/orgsyn/pdfs/CV4P0977.pdf |archive-date=2011-06-05 |dead-url=yes |df= }} 10. ^{{cite journal|title=Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate|authors=Tomotaka Hirabayashi, Satoshi Sakaguchi, Yasutaka Ishii|journal=Org. Synth.|year=2005|volume=82|pages=55|doi=10.15227/orgsyn.082.0055}} 11. ^{{cite journal|title=Discussion Addendum: Iridium-catalyzed Synthesis of Vinyl Ethers from Alcohols and Vinyl Acetate|authors=Yasushi Obora, Yasutaka Ishii|journal=Org. Synth.|year=2012|volume=89|page=307|doi=10.15227/orgsyn.089.0307}} 12. ^http://www.ec.gc.ca/ese-ees/59EC93F6-2C5D-42B4-BB09-EB198C44788D/batch2_108-05-4_pc_en.pdf 13. ^{{Cite journal|last=|first=|date=December 2017|title=40 C.F.R: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities|url=https://www.gpo.gov/fdsys/pkg/CFR-2017-title40-vol30/pdf/CFR-2017-title40-vol30-part355-appA.pdf|journal=Code of Federal Regulations|edition=December 2017|publisher=Government Printing Office|volume=title 40, vol 30, part 355, app A (EPA)|pages=474|accessdate=7 March 2018|postscript=.|via=US GPO}} External links
6 : Hazardous air pollutants|Monomers|IARC Group 2B carcinogens|Acetate esters|Commodity chemicals|Vinyl compounds |
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