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Revision as of 11:11, 11 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 04:52, 13 May 2024 edit undoOAbot (talk | contribs)Bots440,440 editsm Open access bot: doi updated in citation with #oabot.
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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 402877568		| verifiedrevid = 444245601
⚫	|ImageFile=Vinylacetylene-2D.png
	|ImageFile1=Vinylacetylene-2D-skeletal.png		| ImageFile =Vinylacetylene-2D.png
	|ImageFile2=Vinylacetylene-3D-vdW.png		| ImageFile1 =Vinylacetylene-2D-skeletal.png
		⚫	| ImageFile2 =Vinylacetylene-3D-vdW.png
	|ImageSize=		| ImageSize =
	|IUPACName=but-1-en-3-yne
	|OtherNames= butenyne, 3-butene-1-yne		| PIN = But-1-en-3-yne
			| OtherNames = Butenyne, normal isomer<br />3-Butene-1-yne, Vinyl acetylene
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 12197		| ChemSpiderID = 12197
	| InChI = 1/C4H4/c1-3-4-2/h1,4H,2H2		| InChI = 1/C4H4/c1-3-4-2/h1,4H,2H2
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	| StdInChIKey = WFYPICNXBKQZGB-UHFFFAOYSA-N		| StdInChIKey = WFYPICNXBKQZGB-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo= 689-97-4		| CASNo = 689-97-4
			| UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem=12720
	| ChEBI = 48088		| UNII = VW72FM10OQ
			| PubChem =12720
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 48088
	| SMILES = C#CC=C		| SMILES = C#CC=C
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>4</sub>H<sub>4</sub>		| Formula =C<sub>4</sub>H<sub>4</sub>
	| MolarMass=52.07456 g/mol		| MolarMass =52.07456 g/mol
	| Appearance= colourless gas		| Appearance = colourless gas
	| Density=		| Density =
	| MeltingPt=		| MeltingPt =
			| BoilingPtC = 0 to 6
	| BoilingPt= 0–6 °C
			| BoilingPt_notes =
	| Solubility= low
			| Solubility = low
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards= flammable		| MainHazards = flammable
			| NFPA-H = 2
	| FlashPt= < -5 °C
			| NFPA-F = 4
	| Autoignition=
			| NFPA-R = 3
	}}
			| NFPA-S = W
			| FlashPt = <
			| FlashPtC = -5
			| AutoignitionPt =
			}}<ref>{{cite web | url=http://www.newenv.com/resources/nfpa_chemicals | title=New Environment Inc. - NFPA Chemicals }}</ref>
	}}		}}
	'''Vinylacetylene''' is the ] with the formula C<sub>4</sub>H<sub>4</sub>. The colourless gas was once used in the polymer industry. It is composed of both ] and ] groups.		'''Vinylacetylene''' is the ] with the formula C<sub>4</sub>H<sub>4</sub>. The colourless gas was once used in the polymer industry. It is composed of both ] and ] groups and is the simplest ].
			Vinylacetylene is extremely dangerous because in high enough concentrations (typically > 30 mole percent, but pressure dependent) it can auto-detonate (explode without air being present) especially at elevated pressures, such as those seen in chemical plants processing C4 hydrocarbons.<ref>Ritzert and Berthol, Chem Ing Tech 45(3), 131-136, Feb 1973, reproduced in Viduari, J Chem Eng Data 20(3), 328-333, 1975.</ref> An example of such an explosion occurred at a ] plant in ] in 1969.<ref>Carver, Chemical Process Hazards V, Paper F</ref>
	== Synthesis ==		== Synthesis ==
	Vinylacetylene was first prepared by ] of the related quaternary ammonium salt:<ref>Richard Willstätter, Theodor Wirth "Über Vinyl-acetylen" Ber., volume 46, p. 535 (1913). {{DOI|10.1002/cber.19130460172}}</ref>		Vinylacetylene was first synthesized by ] of the related quaternary ammonium salt:<ref>{{cite journal|doi=10.1002/cber.19130460172 |title=Über Vinyl-acetylen |date=1913 |last1=Willstätter |first1=Richard |last2=Wirth |first2=Theodor |journal=Berichte der Deutschen Chemischen Gesellschaft |volume=46 |pages=535–538 |url=https://zenodo.org/record/1426499 }}</ref>
	:I<sub>2</sub> → 2 I + HC≡C-CH=CH<sub>2</sub>		:I<sub>2</sub> → 2 I + HC≡C-CH=CH<sub>2</sub>
	It is usually synthesized by ] of 1,3-dichloro-2-butene.<ref name=OS>{{OrgSynth | author = G. F. Hennion, Charles C. Price, and Thomas F. McKeon, Jr. | title = Monovinylacetylene | collvol = 4 | collvolpages = 683 | year = 1963 | prep = cv4p0683}}</ref> It also arises via the dimerization of acetylene.		It is usually synthesized by ] of 1,3-dichloro-2-butene.<ref name=OS>{{cite journal | author = G. F. Hennion, Charles C. Price, Thomas F. McKeon, Jr. | title = Monovinylacetylene | journal = Organic Syntheses | volume = 38 | page = 70 | year = 1958 | doi = 10.15227/orgsyn.038.0070}}</ref>
			It also arises via the ] of ], which is catalyzed by ].<ref>{{cite journal |doi=10.1021/cr400357r |title=Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited |date=2014 |last1=Trotuş |first1=Ioan-Teodor |last2=Zimmermann |first2=Tobias |last3=Schüth |first3=Ferdi |journal=Chemical Reviews |volume=114 |issue=3 |pages=1761–1782 |pmid=24228942 |doi-access=free }}</ref>
			] of ] is yet another route.{{cn|date=May 2024}}
	== Application ==		== Application ==
	At one time, ] (2-chloro-1,3-butadiene), an industrially important ], was produced via the intermediacy of vinyl acetylene.<ref>{{cite journal | author = ], Ira Williams, Arnold M. Collins, and James E. Kirby | title = Acetylene Polymers and their Derivatives. II. A New Synthetic Rubber: Chloroprene and its Polymers | journal = ] | year = 1937 | volume = 53 | pages = 4203–4225 | doi = 10.1021/ja01362a042}}</ref> In this process, ] is dimerized to give vinyl acetylene, which is then combined with ] to give 4-chloro-1,2-butadiene, which, in the presence of ], rearranges to 2-chloro-1,3-butadiene.<ref name=Ross>Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry, 2006 John Wiley-VCH: Weinheim.{{DOI| 10.1002/14356007.a06_233.pub2}}</ref>		At one time, ] (2-chloro-1,3-butadiene), an industrially important ], was produced via the intermediacy of vinyl acetylene.<ref>{{cite journal | author = ], ], ], and James E. Kirby | title = Acetylene Polymers and their Derivatives. II. A New Synthetic Rubber: Chloroprene and its Polymers | journal = ] | year = 1937 | volume = 53 | pages = 4203–4225 | doi = 10.1021/ja01362a042 | issue = 11}}</ref> In this process, ] is dimerized to give vinyl acetylene, which is then combined with ] to give 4-chloro-1,2-butadiene via 1,4-addition. This allene derivative which, in the presence of ], rearranges to 2-chloro-1,3-butadiene:<ref name=Ross>Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, 2006 John Wiley-VCH: Weinheim.{{doi| 10.1002/14356007.a06_233.pub2}}</ref>
			:H<sub>2</sub>C=CH-C≡CH + HCl → H<sub>2</sub>ClC-CH=C=CH<sub>2</sub>
			:H<sub>2</sub>ClC-CH=C=CH<sub>2</sub> → H<sub>2</sub>C=CH-CCl=CH<sub>2</sub>
	== References ==		== References ==
			{{reflist}}
	<references/>
	{{hydrocarbon-stub}}
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