Divinyl sulfide
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| Other names vinyl sulfide, DVS | |
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| Properties | |
Chemical formula | C4H6S |
Molar mass | 86.15 g·mol−1 |
| Appearance | colorless liquid |
Density | 0.9098 g/cm3 (20 °C) |
Melting point | 20 °C (68 °F; 293 K) |
Boiling point | 84 °C (183 °F; 357 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Divinyl sulfide is the organosulfur compound with the formula S(CH=CH2)2. It is a colorless liquid with a faint odor. It is notable as the product from hydrogen sulfide and acetylene, a combination that arises when acetylene is generated by hydrolysis of technical grade calcium carbide, which contains impurities of calcium sulfide.[1]
Divinylsulfide was first prepared in 1920 by the reaction of sulfur mustard with sodium ethoxide:[1]
- (ClCH2CH2)2S + 2 NaOEt → (CH2=CH)2S + 2 EtOH + 2 NaCl
A variety of monovinyl sulfides are known, often arising from the reactions of thiols and acetylenes.[2]
References
^ ab Boris A. Trofimov, S. V. Amosova (1984). "Divinyl Sulfide: Synthesis, Properties, and Applications". Sulfur Reports. 3: 323–393. doi:10.1080/01961778408082463.CS1 maint: Uses authors parameter (link) .mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ Nina A. Nedolya, Boris A. Trofimov (1994). "Sulfur-containing vinyl ethers". Sulfur Reports. 15: 237–316. doi:10.1080/01961779408048961.CS1 maint: Uses authors parameter (link)
