4-Vinylcyclohexene
Encyclopedia
4-Vinylcyclohexene is an organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 formed when 1,3-butadiene
1,3-Butadiene
1,3-Butadiene is a simple conjugated diene with the formula C4H6. It is an important industrial chemical used as a monomer in the production of synthetic rubber. When the word butadiene is used, most of the time it refers to 1,3-butadiene....

 dimerizes in a Diels-Alder reaction
Diels-Alder reaction
The Diels–Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly formed ring are not carbon...

. It is found in industrial processes involving 1,3-butadiene, including the manufacture of lauric acid
Lauric acid
Lauric acid , the saturated fatty acid with a 12-carbon atom chain, is a white, powdery solid with a faint odor of bay oil or soap.-Occurrence:...

. The 4-vinylcyclohexene formed may be sold as-is or converted to 4-vinylcyclohexene diepoxide.

Reactions

Industrially, 4-vinylcyclohexene is manufactured by dimerizing 1,3-butadiene at 110 - 425°C at pressures of 1.3 - 100 MPa over silicon carbide
Silicon carbide
Silicon carbide , also known as carborundum, is a compound of silicon and carbon with chemical formula SiC. It occurs in nature as the extremely rare mineral moissanite. Silicon carbide powder has been mass-produced since 1893 for use as an abrasive...

 and salts of copper
Copper
Copper is a chemical element with the symbol Cu and atomic number 29. It is a ductile metal with very high thermal and electrical conductivity. Pure copper is soft and malleable; an exposed surface has a reddish-orange tarnish...

 or chromium
Chromium
Chromium is a chemical element which has the symbol Cr and atomic number 24. It is the first element in Group 6. It is a steely-gray, lustrous, hard metal that takes a high polish and has a high melting point. It is also odorless, tasteless, and malleable...

.

Safety

4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC
.
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