| Chloroprene | |
|---|---|
|
|
|
| IUPAC name | 2-Chloro-1,3-butadiene |
| Other names | Chloroprene |
| Identifiers | |
| CAS number | [126-99-8] |
| RTECS number | EL9625000 |
| SMILES | C=C(Cl)C=C |
| Properties | |
| Molecular formula | C4H5Cl |
| Molar mass | 88. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference 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 Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 5365 g/mol |
| Appearance | Colorless liquid. |
| Density | 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 9598 g/cm3, liquid. |
| Melting point |
-130 °C, 143 K, -202 °F |
| Boiling point |
59. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 4 °C, 333 K, 139 °F |
| Solubility in water | 0. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 026 g/100 mL, liquid. |
| Hazards | |
| Main hazards | Highly flammable, toxic. Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in |
| NFPA 704 |
3
2
0
|
| R-phrases | R45, R11, R20/22, R36/37/38, R48/20 |
| S-phrases | S53, S45 |
| Flash point | -15. Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air 6°C |
| Related compounds | |
| Related Dienes | Butadiene Isoprene |
| Related compounds | Vinyl chloride |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Chloroprene is the common name for the organic compound 2-chloro-1,3-butadiene, which has the chemical formula CH2=CCl-CH=CH2. Dienes or diolefins are Hydrocarbons which contain two double bonds. Isoprene is a common synonym for the chemical compound 2-methylbuta-13-diene Vinyl chloride is the Organic compound with the formula CH2CHCl In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. 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 This colorless liquid is the monomer for the production of the polymer polychloroprene, a type of synthetic rubber. A monomer (from Greek mono "one" and meros "part" is a small Molecule that may become chemically bonded to other A polymer is a large Molecule ( Macromolecule) composed of repeating Structural units typically connected by Covalent Chemical bonds Elastomer Synthetic rubber is any type of artificially made Polymer material which acts as an Elastomer. Polychloroprene is better known to the public as Neoprene, the trade name DuPont gave it when the company first developed it and currently used by DuPont Performance Elastomers. Neoprene or polychloroprene is a family of synthetic Rubbers that are produced by Polymerization of Chloroprene. E I du Pont de Nemours and Company (,) is an American chemical company that was founded in July 1802 as a Gunpowder mill by Eleuthère Irénée
Contents |
Chloroprene is produced in three steps from 1,3-butadiene: (i) chlorination, (ii) isomerization of part of the product stream, and (iii) dehydrochlorination of 3,4-dichloro-1-butene. 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 Dehydrohalogenation is an Organic chemistry reaction from which an Alkene is obtained from an Alkyl halide.
Chlorine adds to 1,3-butadiene to afford a mixture of 3,4-dichloro-1-butene and 2,3-dichloro-2-butene. Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and 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 in the 3 position and the chlorine atom in the #4 position thereby forming a double bond between carbons #3 and #4. History See also Atomic theory, Atomism The concept that matter is composed of discrete units and cannot be divided into arbitrarily tiny In 1983, approximately 2,000,000 kg were produced in this manner. [1] The chief impurity in chloroprene prepared in this way is 1-chloro-1,3-butadiene, which is usually separated by distillation. Distillation is a method of separating Mixtures based on differences in their volatilities in a boiling liquid mixture
Until the 1960s, chloroprene production was dominated by the “acetylene process,” which was modeled after the original synthesis of vinyl acetylene. Vinylacetylene or butenyne is the Organic compound with the formula C4H4 [2] In this process, acetylene is dimerized to give vinyl acetylene, which is then combine with hydrogen chloride 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. Acetylene ( IUPAC name ethyne), C2H2 is a Hydrocarbon belonging to the group of Alkynes It is the simplest of all alkynes Copper(I chloride, commonly called cuprous chloride is the lower Chloride of Copper, with the formula CuCl [1] The conversion is shown here:
![]()
This process had disadvantages in that it is very energy-intensive and has high investment costs. Furthermore, the intermediate vinyl acetylene is unstable.