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Chloroprene

 

 
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Chloroprene
 
 
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Chloroprene is the common name for the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 2-chloro-1,3-butadiene, which has the chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 CH2=CCl-CH=CH2. This colorless liquid is the monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
 for the production of the polymer
Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
 polychloroprene, a type of synthetic rubber
Synthetic rubber

Synthetic rubber is any type of artificially made polymer material, which acts as an elastomer. An elastomer is a material with the mechanical property that it can undergo much more Elasticity deformation under stress, than most materials and still return to its previous size without permanent deformation....
. Polychloroprene is better known to the public as Neoprene
Neoprene

Neoprene or polychloroprene is a family of synthetic rubbers that are produced by polymerization of chloroprene. It is used in a wide variety of applications, such as in wetsuits, laptop sleeves, orthopedic braces , electricity electrical insulation, and automobile fan belt s....
, the trade name DuPont
DuPont

E. I. du Pont de Nemours and Company is an United States chemical industry that was founded in July 1802 as a gunpowder mill by Eleuth?re Ir?n?e du Pont....
 gave it when the company first developed it and currently used by DuPont Performance Elastomers.

roprene is produced in three steps from 1,3-butadiene: (i) chlorination
Chlorination

Chlorination is the process of adding the element chlorine to water as a method of water purification to make it fit for human consumption as drinking water....
, (ii) isomerization of part of the product stream, and (iii) dehydrochlorination
Dehydrohalogenation

Dehydrohalogenation is an organic chemistry reaction from which an alkene is obtained from an alkyl halide. It is also called the ?-Elimination reaction....
 of 3,4-dichloro-1-butene.

Chlorine
Chlorine

Chlorine...
 adds to 1,3-butadiene to afford a mixture of 3,4-dichloro-1-butene and 2,3-dichloro-2-butene.






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Encyclopedia


Chloroprene is the common name for the organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 2-chloro-1,3-butadiene, which has the chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 CH2=CCl-CH=CH2. This colorless liquid is the monomer
Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
 for the production of the polymer
Polymer

A polymer is a large molecule composed of repeating structural units typically connected by covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large class of natural and synthetic materials with a variety of properties....
 polychloroprene, a type of synthetic rubber
Synthetic rubber

Synthetic rubber is any type of artificially made polymer material, which acts as an elastomer. An elastomer is a material with the mechanical property that it can undergo much more Elasticity deformation under stress, than most materials and still return to its previous size without permanent deformation....
. Polychloroprene is better known to the public as Neoprene
Neoprene

Neoprene or polychloroprene is a family of synthetic rubbers that are produced by polymerization of chloroprene. It is used in a wide variety of applications, such as in wetsuits, laptop sleeves, orthopedic braces , electricity electrical insulation, and automobile fan belt s....
, the trade name DuPont
DuPont

E. I. du Pont de Nemours and Company is an United States chemical industry that was founded in July 1802 as a gunpowder mill by Eleuth?re Ir?n?e du Pont....
 gave it when the company first developed it and currently used by DuPont Performance Elastomers.

Production of chloroprene

Chloroprene is produced in three steps from 1,3-butadiene: (i) chlorination
Chlorination

Chlorination is the process of adding the element chlorine to water as a method of water purification to make it fit for human consumption as drinking water....
, (ii) isomerization of part of the product stream, and (iii) dehydrochlorination
Dehydrohalogenation

Dehydrohalogenation is an organic chemistry reaction from which an alkene is obtained from an alkyl halide. It is also called the ?-Elimination reaction....
 of 3,4-dichloro-1-butene.

Chlorine
Chlorine

Chlorine...
 adds to 1,3-butadiene to afford a mixture of 3,4-dichloro-1-butene and 2,3-dichloro-2-butene. The 2,3-chloro isomer is subsequently isomerized to 3,4 isomer, which in turn is treated with base to induce dehydrochlorination to 2-chloro-1,3-butadiene. This dehydrohalogenation entails loss of a hydrogen atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
 in the 3 position and the chlorine atom in the #4 position thereby forming a double bond between carbons #3 and #4. In 1983, approximately 2,000,000 kg were produced in this manner. The chief impurity in chloroprene prepared in this way is 1-chloro-1,3-butadiene, which is usually separated by distillation
Distillation

Distillation is a method of separation process mixtures based on differences in their Volatility in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....
.

Acetylene process

Until the 1960s, chloroprene production was dominated by the “acetylene process,” which was modeled after the original synthesis of vinylacetylene
Vinylacetylene

Vinylacetylene or butenyne is the organic compound with the formula C4H4. This easily condensed, colorless gas was discovered by workers at duPont....
. In this process, acetylene
Acetylene

Acetylene is the chemical compound with the symbol carbonhydrogen. It is the simplest alkyne.As an alkyne, acetylene is Saturation because its two carbon atoms are Chemical bond together in a triple bond....
 is dimerized to give vinyl acetylene, which is then combined with hydrogen chloride
Hydrogen chloride

The Chemical compound hydrogen chloride has the chemical formula HydrogenChlorine. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity....
 to afford in succession vinyl acetylene, 3-chloro-1,2-butadiene, which, finally in the presence of cuprous chloride, rearranges to the targeted 2-chloro-1,3-butadiene. The conversion is shown here:

Chloroprene Synthesis
This process had disadvantages in that it is very energy-intensive and has high investment costs. Furthermore, the intermediate vinyl acetylene is unstable.

External links

    • IARC
      IARC

      IARC may refer to:* International Aerial Robotics Competition* International Agency for Research on Cancer* International Arctic Research Center...
       Monograph ""