9010-98-4

Basic information

• Product Name: Polychloroprene
• Synonyms: CHLOROPRENE RESIN;POLYCHLOROPRENE;POLY(2-CHLORO-1,3-BUTADIENE);NEOPRENE GNA;NEOPRENE GRT;NEOPRENE GW;NEOPRENE(R);NEOPRENE TRT
• CAS NO: 9010-98-4
• Molecular Formula: C4H5Cl
• Molecular Weight: 88.5355
• EINECS: 204-818-0
• Product Categories: Polychloroprene;Polymers;Dienes;Hydrophobic Polymers;Polymer Science;Hydrophobic Polymers;Materials Science;Polymer Science
• Mol File: 9010-98-4.mol

Chemical Properties

• Melting Point: >260 °C
• Appearance: White to beige/chunks
• Density: 1.23 g/mL at 25 °C(lit.)
• Storage Temp.: -196°C
• CAS DataBase Reference: Polychloroprene(CAS DataBase Reference)
• NIST Chemistry Reference: Polychloroprene(9010-98-4)
• EPA Substance Registry System: Polychloroprene(9010-98-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: EI9640000
• Hazardous Substances Data: 9010-98-4(Hazardous Substances Data)

Usage

Uses

Used in Mechanical Rubber Products Industry:
Polychloroprene is used as a solid mechanical rubber product for its exceptional resistance to oil, heat, and weathering. This makes it ideal for manufacturing durable and reliable mechanical rubber products.
Used in Chemical Industry:
Polychloroprene serves as a lining for oil-loading hoses and reaction equipment due to its outstanding resistance to chemicals and ability to withstand high temperatures.
Used in Construction Industry:
As an adhesive cement, polychloroprene provides strong bonding properties and durability in various construction applications.
Used in Aerospace Industry:
Polychloroprene acts as a binder for rocket fuels, offering a stable and reliable component in space exploration and rocket propulsion systems.
Used in Electrical Industry:
Polychloroprene is utilized as a coating for electric wiring, providing insulation and protection against environmental factors and wear.
Used in Automotive and Industrial Seals:
Polychloroprene is employed in the production of gaskets and seals, ensuring tight and durable sealing in various automotive and industrial applications.
Used in Specialty Items Industry:
In the form of liquid, polychloroprene is used to create specialty items through dipping or electrophoresis from the latex, offering unique properties and applications.
Used in Automotive Accessories and Furniture Industry:
Polychloroprene foam serves as an adhesive tape to replace metal fasteners in automotive accessories, providing a lightweight and efficient alternative.
Used in Upholstery and Flooring Industry:
Polychloroprene foam is also used in seat cushions and carpet backing, offering comfort, durability, and adherence to various surfaces.
Used in Sealant Industry:
Polychloroprene foam is utilized as a sealant, providing a reliable and long-lasting solution for sealing and bonding applications.

History

Polychloroprene was discovered in 1930 at E. I. DuPont de Nemours & Co. inWilmington Delaware. The discovery grew out of a need to develop a synthetic substitute for natural rubber. DuPont first marketed this first commercially successful synthetic elastomer as DuPrene in 1933. In response to new technology development that significantly improved the product and manufacturing process, the name was changed to Neoprene in 1936. The current commercially acceptable generic name for this class of chlorinated elastomers is CR or chloroprene rubber. polychloroprene structure

Production Methods

Commercial polychloroprene rubber is manufactured by aqueous free-radical emulsion polymerization followed by isolation of the solid polymer by one of several processes: freeze roll isolation, drum drying , extruder isolation, precipitation and drying or spray drying. Isolation of powdered polychloroprene has been reviewed. Of the methods cited, freeze roll and drum drying isolation are commercially important. The large-scale commercial manufacture of polychloroprene consists of eight or nine unit operations: (1) Monomer solution makeup Water solution makeup (2) Emulsification (3) Polymerization (4) Stripping of residual monomer (5) Peptization for chloroprene–sulfur copolymers (6) Freeze roll isolation Drum drying (7) Drying of freeze-rolled film (8) Roping (9) Cutting and packaging (25kg)

Preparation

Polychloroprene is made from one of two starting materials, acetylene or butadiene. Acetylene can be dimerized and then chloronated to form chloroprene. Alternatively, when adequate butadiene is available, this can be directly halogenated (eqs. 7 and 8). In either case, the chloroprene product can then be polymerized to polychloroprene. Essentially a butadiene elastomer with chlorine present in the backbone,the polymer exhibits excellent tensile strength and low hysteresis, much like natural rubber. Tensile strength properties up to 28 MPa are possible with the proper reinforcing system (see FILLERS). The polarity imparted by the chlorine atom improves the oil and solvent resistance approaching those of nitrile polymers. The polymer can be protected with para-phenylenediamine antiozonants to give ozone resistance, and heat aging is also good. As a result, chloroprene elastomers are used in a wide variety of applications needing a balance of such properties.

Hazard

Questionable carcinogen.

Upstream product

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• 64-17-5 ethanol 
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Relevant articles and documents

Addition of Chloroprene Grignards to Aromatic Aldehydes: Synthesis of Homoallenyl Alcohols

A general procedure for the one-pot synthesis of racemic homoallenyl alcohols from the corresponding aldehyde and chloroprene-derived Grignards is described. Employing bis[2-dimethylaminoethyl]ether (BDMAEE) as an additive at low temperatures shifts the selectivity of the chloroprene Grignard addition to aldehydes such that it is almost exclusive toward allene formation. In a set of follow-up experiments, simple and more elaborate methods for further derivatization have been demonstrated, allowing quick access to more complex structures.

Strontium chloride modified Nieuwland catalyst in the dimerization of acetylene to monovinylacetylene

SrCl2 was used as a co-catalyst of CuCl in Nieuwland catalyst and CuCl as the main catalyst, NH4Cl as the solubilizer, water as the solvent and a certain amount of hydrochloric acid, thereby forming Sr-Cu bimetallic cooperative catalysis reaction systems for C2H2 dimerization. Under the optimum condition, the acetylene conversion is 13 % and monovinylacetylene selectivity can reach to 94 %.

Thermal ring opening of 1,1-dibromo and 1-bromo-2- chloromethylcyclopropanes: Observation of a formal debromochlorination

When the title compounds are thermolyzed in the gas phase under vacuum or in hot quinoline, several products are formed. A predominant product in all cases is a chlorine-free buta-1,3-diene which has been formed by formal debromochlorination, a reaction n

Synthesis of the potent anticancer agents ottelione A and ottelione B in both racemic and natural optically pure forms

(Chemical Equation Presented) The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an α-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access by the same method to the trans ring fused isomer (-)-ottelione B.

Gas phase surface-catalyzed HCl addition to vinylacetylene: motion along a catalytic surface. Experiment and theory

Gaseous mixtures of HCl and vinylacetylene were permitted to react in Pyrex IR cells (NaCl windows). Gaseous 4-chloro-1,2-butadiene and 2-chloro-1,3-butadiene (chloroprene) were the major products. Kinetic data (FTIR) generated a rate expression in concert with surface catalysis. Computational studies involving surface associated water provide a view that accounts for the experimentally determined orders and a bifurcated pathway producing both products. The results are in accord with wall-adsorbed reactant(s) as well as previously reported computational studies on the reactants.

In vitro metabolism of chloroprene: Species differences, epoxide stereochemistry and a de-chlorination pathway

Chloroprene (1) was metabolized by liver microsomes from Sprague-Dawley rats, Fischer 344 rats, B6C3F1 mice, and humans to the monoepoxides, (1-chloro-ethenyl)oxirane (5a/5b), and 2-chloro-2-ethenyloxirane (4a/4b). The formation of 4a/4b was inferred from the identification of their degradation products. With male Sprague-Dawley and Fischer 344 rat liver microsomes, there was a ca. 3:2 preference for the formation of (R)-(1-chloroethenyl)oxirane (5a) compared to the (S)-enantiomer (5b). A smaller but distinct enantioselectivity in the formation of (S)-(1-chloro-ethenyl)oxirane occurred with liver microsomes from male mouse (R:S, 0.90:1) or male human (R:S, 0.86:1). 2-Chloro-2-ethenyloxirane was very unstable in the presence of the microsomal mixture and was rapidly converted to 1-hydroxybut-3-en-2-one (11) and 1-chlorobut-3-en-2-one (12). An additional rearrangement pathway of 2-chloro-2-ethenyloxirane gave rise to 2-chlorobut-3-en-1-al (14) and 2-chlorobut-2-en-1-al (15). Further reductive metabolism of these metabolites occurred to form 1-hydroxybutan-2-one (17) and 1-chlorobutan-2-one (18). In the absence of an epoxide hydrolase inhibitor, the microsomal incubations converted (1-chloroethenyl)oxirane to 3-chlorobut-3-ene-1,2-diol (21a/21b). When microsomal incubations were supplemented with glutathione, 1-hydroxybut-3-en-2-one was not detected because of its rapid conjugation with this thiol scavenger.

Process for preparing chloroprene

Process for preparing chloroprene by dehydrochlorinating 3,4-dichloro-1-butene in the presence of lime and a polyol, such as a glycol selected from (poly)ethylene glycol and (poly)propylene glycol or sugars, with ethylene glycol being preferred.

Phenylselenium Trichloride in Organic Synthesis. Reaction with Unsaturated Compounds. Preparation of Vinylic Chlorides via Selenoxide Elimination

Phenylselenium trichloride, PhSeCl3, was reacted with a number olefinic compounds to produce (β-chloroalkyl)phenylselenium dichlorides.The addition was anti stereospecific and irreversible.The presence of an oxygen substituent (acyloxy or aryloxy group) in the allylic position of the olefin directed the attack of PhSeCl3 to occur regiospecifically anti-Markovnikov to give a (β-acyloxy/aryloxy-β'-chloroalkyl)phenylselenium dichloride.When the (β-chloroalkyl)phenylselenium dichlorides were treated in methylene chloride with aqueous sodium hydrogen carbonate, the selenium dichloride moiety was readily hydrolyzed to a selenoxide, which underwent the usual selenoxide elimination reaction to produce an allylic or a vinylic chloride.Symmetrical olefins containing no allylic hydrogens were converted to vinylic chlorides with retention of olefin geometry.Olefins containing a directing oxygen substituent in the allylic position afforded vinylic chlorides where the vinylic halogen atom was oriented 1,3 to the oxygen substituent (E/Z mixture).Other olefins afforded mixtures of allylic and vinylic halides in varying proportions.The reaction of phenyselenium tribromide, PhSeBr3, with some olefinic compounds was also investigated.This material showed the same stereo- and regiochemical behavior as PhSeCl3 in its addition reactions.However, the adducts were not useful for the preparation of vinylic or allylic bromides by using the hydrolytic selenoxide elimination reaction.

Process for preparing 1,4-dihydroxy, 5,8-dihydronaphthalene and related compounds

1,4-dihydroxy, 5,8-dihydronaphthalene and related compounds are provided from benzoquinone, and 1,3-butadiene which may be substituted with halogen, acyl, and alkyl, in a one step reaction in the presence of a ferric salt catalyst.