Vinyl chloride, industrial preparation

Vinyl chloride (H2C=CHC1), the starting material used in the industrial preparation of poly(vinyl chloride), is prepared by a two-step process that begins with the reaction of Cl2 with ethylene to yield 1,2-dichloroethane ... 

Vinyl chloride is an industrial chemical produced in large amounts (10 ° Ib/year in the United States) and is used in the preparation of poly(vmyl chloride) Poly(vinyl chio ride) often called simply vinyl has many applications including siding for houses wall coverings and PVC piping... 

ETHYLENE We discussed ethylene production in an earlier boxed essay (Section 5 1) where it was pointed out that the output of the U S petrochemi cal industry exceeds 5 x 10 ° Ib/year Approximately 90% of this material is used for the preparation of four compounds (polyethylene ethylene oxide vinyl chloride and styrene) with polymerization to poly ethylene accounting for half the total Both vinyl chloride and styrene are polymerized to give poly(vinyl chloride) and polystyrene respectively (see Table 6 5) Ethylene oxide is a starting material for the preparation of ethylene glycol for use as an an tifreeze in automobile radiators and in the produc tion of polyester fibers (see the boxed essay Condensation Polymers Polyamides and Polyesters in Chapter 20)... 

Alkenyl halides such as vinyl chloride (H2C=CHC1) do not form carbocations on treatment with aluminum chloride and so cannot be used m Friedel-Crafts reactions Thus the industrial preparation of styrene from benzene and ethylene does not involve vinyl chloride but proceeds by way of ethylbenzene... 

The polymer may be prepared readily in bulk, emulsion and suspension, the latter technique apparently being preferred on an industrial scale. The monomer must be free from oxygen and metallic impurities. Peroxide such as benzoyl peroxide are used in suspension polymerisations which may be carried out at room temperature or at slightly elevated temperatures. Persulphate initiators and the conventional emulsifying soaps may be used in emulsion polymerisation. The polymerisation rate for vinylidene chloride-vinyl chloride copolymers is markedly less than for either monomer polymerised alone. 

An alkyne is a hydrocarbon that contains a carbon-carbon triple bond. Acetylene.. H—C= C—H, the simplest alkyne, was once widely used in industry as the starting material for the preparation of acetaldehyde, acetic acid, vinyl chloride, and other high-volume chemicals, but more efficient routes to these substances using ethylene as starting material are now available. Acetylene is still used in the preparation of acrylic polymers but is probably best known as the gas burned in high-temperature oxy-acetylene welding torches. 

Ethynes are industrially used as a starting material for polymers, e.g. vinyl flooring, plastic piping. Teflon and acrylics. Polymers are large molecules, which are prepared hy linking many small monomers. Polyvinyl chloride, also commonly known as PVC, is a polymer produced from the polymerization of vinyl chloride. 

Tetrahydroindole (1) was isolated by extraction of the reaction mixture with organic solvents (Et20, benzene) and purified by distillation or recrystallization. This process for preparing 4,5,6,7-tetrahydroindole is simple enough, industrially feasible, safe, and based on the cheap and accessible raw materials. Cyclohexanone oxime is an inexpensive large-scale commercial product (caprolactam synthesis intermediate), vinyl chloride being one of the cheapest commercial vinyl compounds. 

Sodium hydroxide has many different uses in the chemical industry. Considerable amounts are used in the manufacture of paper and to make sodium hypochlorite for use in disinfectants and bleaches. Chlorine is also used to produce vinyl chloride, the starting material for the manufacture of polyvinyl chloride (PVC), and in water purification. Hydrochloric acid may be prepared by the direct reaction of chlorine and hydrogen gas or by the reaction of sodium chloride and sulfuric acid. It is used as a chlorinating agent for metals and organic compounds. 

Poly(vinyl chloride), also known as PVC, is prepared by radical polymerization to produce material composed of an average of 10,000 to 24,000 monomer units. It is atactic and therefore amorphous, but it has a relatively high Tg because of the large size of its molecules and its polar carbon-chlorine bonds. It is a rigid material and is used to make pipe, panels, and molded objects. About 68% of PVC is used in the building and construction industry. A more flexible form of PVC is produced by adding a plasticizer such as dioctyl phthalate. This is used to prepare electric wire coatings, film, and simulated leather or vinyl. ... 

This is one of the largest electrochemical industries in the world. It consists in the electrolysis of sodium chloride as brine to give chlorine and caustic soda. Chlorine is used in the preparation of vinyl chloride for PVC, as a bleaching agent for paper and paper pulp, as a disinfectant, besides other chloration applications. Caustic soda is important in mineral processing, and in the paper, textile, and glass industries. Table 15.2 shows recent data for industrial consumption of chlorine and caustic soda in the USA. 

More industrial polyethylene copolymers were modeled using the same method of ADMET polymerization followed by hydrogenation using catalyst residue. Copolymers of ethylene-styrene, ethylene-vinyl chloride, and ethylene-acrylate were prepared to examine the effect of incorporation of available vinyl monomer feed stocks into polyethylene [81]. Previously prepared ADMET model copolymers include ethylene-co-carbon monoxide, ethylene-co-carbon dioxide, and ethylene-co-vinyl alcohol [82,83]. In most cases,these copolymers are unattainable by traditional chain polymerization chemistry, but a recent report has revealed a highly active Ni catalyst that can successfully copolymerize ethylene with some functionalized monomers [84]. Although catalyst advances are proving more and more useful in novel polymer synthesis, poor structure control and reactivity ratio considerations are still problematic in chain polymerization chemistry. 

The most important industrial applications of radical reaction to date are used for the manufacture of polymers. Around 108 tonnes (or 75%) of all polymers are prepared using radical processes. These are chain reactions in which an initial radical adds to the double bond of an alkene monomer and the resulting radical adds to another alkene monomer and so on. This addition polymerisation is used to make a number of important polymers, including poly(vinyl chloride) (PVC), polystyrene, polyethylene and poly(methyl methacrylate). Copolymers can also be easily prepared starting from a mixture of two or more monomers. These polymers have found widespread use as they possess a range of chemical and mechanical properties (such as strength and toughness). 

The most common method for industrial preparation of 1,1,1-trichloroethane is the reaction of hydrochloric acid with vinyl chloride (obtained from 1,2-dichloroethane) to obtain 1,1-dichloroethane, followed by either thermal or photochemical chlorination. Other methods include the catalyzed addition of hydrogen chloride to 1.1-dichloroethylene, and the direct chlorination of ethane itself, followed by separation from the other products produced (Archer 1979). Commercial grades of... 

Thus, the industrial preparation of styrene from benzene and ethylene does not involve vinyl chloride but proceeds by way of ethylbenzene. 

Figure 16.2a summarizes the major uses of chlorine. Chlorinated organic compounds, including 1,2-dichloro-ethene and vinyl chloride for the polymer industry, are hugely important. Dichlorine was widely used as a bleach in the paper and pulp industry, but environmental legislations have resulted in changes (Figure 16.2b). Chlorine dioxide, CIO2 (an elemental chlorine-free bleaching agent), is prepared from NaC103 and is favoured over CI2 because it does not produce toxic effluents. ...

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