Names | |
---|---|
Preferred IUPAC name But-1-en-3-yne | |
Other names Butenyne, normal isomer 3-Butene-1-yne, Vinyl acetylene | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.010.650 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C4H4 | |
Molar mass | 52.07456 g/mol |
Appearance | colourless gas |
Boiling point | 0 to 6 °C (32 to 43 °F; 273 to 279 K) |
low | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | flammable |
NFPA 704 (fire diamond) | |
Flash point | <−5 °C (23 °F; 268 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Vinylacetylene is the organic compound with the formula C4H4. The colourless gas was once used in the polymer industry. It is composed of both alkyne and alkene groups and is the simplest enyne.
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. [2] An example of such an explosion occurred at a Union Carbide plant in Texas City in 1969. [3]
Vinylacetylene was first synthesized by Hofmann elimination of the related quaternary ammonium salt: [4]
It is usually synthesized by dehydrohalogenation of 1,3-dichloro-2-butene. [5]
It also arises via the dimerization of acetylene, which is catalyzed by copper(I) chloride. [6]
Dehydrogenation of 1,3-butadiene is yet another route.[ citation needed ]
At one time, chloroprene (2-chloro-1,3-butadiene), an industrially important monomer, was produced via the intermediacy of vinyl acetylene. [7] In this process, acetylene is dimerized to give vinyl acetylene, which is then combined with hydrogen chloride to give 4-chloro-1,2-butadiene via 1,4-addition. This allene derivative which, in the presence of cuprous chloride, rearranges to 2-chloro-1,3-butadiene: [8]
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.
In organic chemistry, a diene ; also diolefin, dy-OH-lə-fin) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alkene units, with the standard prefix di of systematic nomenclature. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in organic synthesis. Conjugated dienes are widely used as monomers in the polymer industry. Polyunsaturated fats are of interest to nutrition.
In organic chemistry, a vinyl group is a functional group with the formula −CH=CH2. It is the ethylene molecule with one fewer hydrogen atom. The name is also used for any compound containing that group, namely R−CH=CH2 where R is any other group of atoms.
A Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, is a catalyst used in the synthesis of polymers of 1-alkenes (alpha-olefins). Two broad classes of Ziegler–Natta catalysts are employed, distinguished by their solubility:
1,3-Butadiene is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.
In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.
In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas MC≡CH and MC≡CM, where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure RC≡CM. Acetylides are reagents in organic synthesis. The calcium acetylide commonly called calcium carbide is a major compound of commerce.
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone. Multiple carbon–carbon bond are replaced by carbonyl groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.
Chloroprene (IUPAC name 2-chlorobuta-1,3-diene) is a chemical compound with the molecular formula CH2=CCl−CH=CH2. Chloroprene is a colorless volatile liquid, almost exclusively used as a monomer for the production of the polymer polychloroprene, better known as neoprene, a type of synthetic rubber.
A dendralene is a discrete acyclic cross-conjugated polyene. The simplest dendralene is buta-1,3-diene (1) or [2]dendralene followed by [3]dendralene (2), [4]dendralene (3) and [5]dendralene (4) and so forth. [2]dendralene (butadiene) is the only one not cross-conjugated.
In organic chemistry, pentadiene is any hydrocarbon with an open chain of five carbons, connected by two single bonds and two double bonds. All those compounds have the same molecular formula C5H8. The inventory of pentadienes include:
Trimethylsilylacetylene is the organosilicon compound with the formula (CH3)3SiC2H. A colorless liquid, "tms acetylene", as it is also called, is used as a source of "HC2−" in organic synthesis.
1,4-Dichlorobut-2-ene are organochlorine compounds with the formula ClCH2CH=CHCH2L. Cis and trans isomers exist. These compounds are intermediates in the industrial production of chloroprene. They are main impurity in technical grade chloroprene.
Dimethylbutadiene, formally referred to as 2,3-dimethyl-1,3-butadiene, is an organic compound with the formula (CH3)2C4H4. It is colorless liquid which served an important role in the early history of synthetic rubber. It is now a specialty reagent.
Group 14 hydrides are chemical compounds composed of hydrogen atoms and group 14 atoms.
In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols
Arnold Miller Collins (1899-1982) was a chemist at DuPont who, working under Elmer Bolton and Wallace Carothers with Ira Williams, first isolated polychloroprene and 2-chloro-1, 3-butadiene in 1930.
In organic chemistry, hydrovinylation is the formal insertion of an alkene into the C-H bond of ethylene. The more general reaction, hydroalkenylation, is the formal insertion of an alkene into the C-H bond of any terminal alkene. The reaction is catalyzed by metal complexes. A representative reaction is the conversion of styrene and ethylene to 3-phenybutene:
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