And vinyl chloride

Vinylidene chloride and vinyl chloride lead to the copolymer known as Saran. Other commercial copolymers are produced from vinyl chloride and acrylonitrile (Dynel), and from maleic anhydride and styrene. 

Use Learning By Modeling to compare the calculated dipole moments of ethylene propene vinyl chloride and trans 1 chloropropene Unlike measured dipole moments the calculated ones do show the direction of the dipole moment How do the directions of the calculated dipole moments compare with those deduced by experimenf ... 

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)... 

Polyolefin Polyester Block copolymers of styrene and butadiene or styrene and isoprene Block copolymers of styrene and ethylene or styrene and butylene Poly(vinyl chloride) and poly(vinyl acetate) ... 

This route has been completely displaced, first by chlorination and dehydro-chlorination of ethylene or vinyl chloride, and more recendy by oxychlorination of two-carbon raw materials (2) (see Chlorocarbonsandchlorohydrocarbons). 

In early work, vinyl chloride had been heated with stoichiometric amounts of alkaU alkoxides in excess alcohol as solvent, giving vinyl ethers as products (210). Supposedly this involved a Williamson ether synthesis, where alkaU alkoxide and organic haUde gave an ether and alkaU haUde. However, it was observed that small amounts of acetylene were formed by dehydrohalogenation of vinyl chloride, and that this acetylene was consumed as the reaction proceeded. Hence acetylene was substituted for vinyl chloride and only catalytic amounts of alkaU were used. Vinylation proceeded readily with high yields (211). 

Automated analyzers may be used for continuous monitoring of ambient poUutants and EPA has developed continuous procedures (23) as alternatives to the referenced methods. Eor source sampling, EPA has specified extractive sampling trains and analytical methods for poUutants such as SO2 and SO [7446-11-9] sulfuric acid [7664-93-9] mists, NO, mercury [7439-97-6], beryUium [7440-41-7], vinyl chloride, and VOCs (volatile organic compounds). Some EPA New Source Performance Standards requite continuous monitors on specified sources. 

Akzo Process. Akzo Zout Chemie has developed a route to vinyl chloride and soda ash from salt usiag an amine—solvent system catalyzed by a copper—iodide mixture (13). This procedure theoretically requires half the energy of the conventional Solvay processes. 

BiaxiaHy oriented films have excellent tensile strength properties and good tear and impact properties. They are especially well regarded for their brilliance and clarity. Essentially all poly(ethylene terephthalate) film is biaxiaHy oriented, and more than 80% of polypropylene film is biaxiaHy oriented. Polystyrene film is oriented, and a lesser amount of polyethylene, polyamide, poly(vinyl chloride), and other polymers are so processed. Some of the specialty films, like polyimides (qv), are also oriented. 

Alumina trihydtate is also used as a secondary flame retardant and smoke suppressant for flexible poly(vinyl chloride) and polyolefin formulations in which antimony and a halogen ate used. The addition of minor amounts of either zinc borate or phosphoms results in the formation of glasses which insulate the unbumed polymer from the flame (21). 

The combination of stmctural strength and flotation has stimulated the design of pleasure boats using a foamed-in-place polyurethane between thin skins of high tensUe strength (231). Other ceUular polymers that have been used in considerable quantities for buoyancy appHcations are those produced from polyethylene, poly(vinyl chloride), and certain types of mbber. The susceptibUity of polystyrene foams to attack by certain petroleum products that are likely to come in contact with boats led to the development of foams from copolymers of styrene and acrylonitrUe which are resistant to these materials... 

Types of internal enamel for food containers include oleoresins, vinyl, acryflc, phenoHc, and epoxy—phenoHc. Historically can lacquers were based on oleoresinous products. PhenoHc resins have limited flexibiHty and high bake requirements, but are used on three-piece cans where flexibiHty is not required. Vinyl coatings are based on copolymers of vinyl chloride and vinyl acetate dissolved in ketonic solvents. These can be blended with alkyd, epoxy, and phenoHc resins to enhance performance. FlexibiHty allows them to be used for caps and closures as weU as drawn cans. Their principal disadvantage is high sensitivity to heat and retorting processes this restricts their appHcation to cans which are hot filled, and to beer and beverage products. 

The alcohols, proprietary denatured ethyl alcohol and isopropyl alcohol, are commonly used for E-type inks. Many E-type inks benefit from the addition of small amounts of ethyl acetate, MEK, or normal propyl acetate to the solvent blends. Aromatic hydrocarbon solvents are used for M-type inks. Polystyrene resins are used to reduce the cost of top lacquers. T-type inks are also reduced with aromatic hydrocarbons. Acryflc resins are used to achieve specific properties for V-type inks. Vehicles containing vinyl chloride and vinyl acetate copolymer resins make up the vinyl ink category. Ketones are commonly used solvents for these inks. 

Catalysts. Mercury is or has been used in the catalysis (qv) of various plastics, including polyurethane [26778-67-6] poly(vinyl chloride) [9002-86-2] and poly(vinyl acetate) [9003-20-7]. Most poly(vinyl chloride) and poly(vinyl acetate) is manufactured by processes that do not use mercury (3). 

Until about 1980, mercuric chloride was used extensively as a catalyst for the preparation of vinyl chloride from acetjiene (7). Since the early 1980s, vinyl chloride and vinyl acetate have been prepared from ethylene instead of acetjiene, and the use of mercuric chloride as a catalyst has practically disappeared. 

Vinyl resins ie, copolymers of vinyl chloride and vinyl acetate which contain hydroxyl groups from the partial hydrolysis of vinyl acetate and/or carboxyl groups, eg, from copolymerized maleic anhydride, may be formulated with alkyd resins to improve their appHcation properties and adhesion. The blends are primarily used in making marine top-coat paints. 

Shipment ndStora.ge. The crystalline material is shipped as a nonha2ardous material, in polyethylene-lined fiber dmms. The solution can be shipped in dmms or bulk. Suitable materials of constmction for handling ammonium thiocyanate are aluminum, 316 stainless steel, mbber, poly(vinyl chloride), and glass-reinforced epoxy. Steel, 304 stainless steel, and copper alloys should be avoided (375,376). 

The physical properties of vinyl chloride are Hsted in Table 1 (12). Vinyl chloride and water [7732-18-5] are nearly immiscible. The equiUbrium concentration of vinyl chloride at 1 atm partial pressure in water is 0.276 wt % at 25°C, whereas the solubiUty of water in vinyl chloride is 0.0983 wt % at 25°C and saturated pressure (13). Vinyl chloride is soluble in hydrocarbons, oil, alcohol, chlorinated solvents, and most common organic Hquids. 

Vinyl chloride can be hydrogenated over a 0.5% platinum [7440-06-4], Pt, on alumina catalyst to ethyl chloride and ethane [74-84-0]. This reaction is 2ero order in vinyl chloride and first order in hydrogen. 

Ethylene Dichloride Pyrolysis to Vinyl Chloride. Thermal pyrolysis or cracking of EDC to vinyl chloride and HCl occurs as a homogenous, first-order, free-radical chain reaction. The accepted general mechanism involves the four steps shown in equations 10—13 ... 

Vinyhdene chloride is hepatotoxic, but does not appear to be a carcinogen (13—18). Pharmacokinetic studies indicate that the behavior of vinyl chloride and vinyhdene chloride in rats and mice is substantially different (19). No unusual health problems have been observed in workers exposed to vinyhdene chloride monomer over varying periods (20). Because vinyhdene chloride degrades rapidly in the atmosphere, air pollution is not likely to be a problem (21). Worker exposure is the main concern. Sampling techniques for monitoring worker exposure to vinyhdene chloride vapor are being developed (22). 

Heterogeneous polymerization is characteristic of a number of monomers, including vinyl chloride and acrylonitrile. A completely satisfactory mechanism for these reactions has not been deterrnined. This is tme for VDC also. Earlier studies have not been broad enough to elucidate the mechanism (26,30,31). Morphologies of as-polymerized poly(vinyl chloride) (PVC) and polyacrylonitrile (PAN) are similar, suggesting a similar mechanism. 

A primary use of vinyhdene chloride copolymer lacquers is the coating of films made from regenerated ceUulose or of board or paper coated with polyamide, polyester, polypropylene, poly(vinyl chloride), and polyethylene. The lacquer imparts resistance to fats, oils, oxygen, and water vapor (165). 

Polymerization. Spills of chemicals that are monomers or low-order polymers can be polymerized by adding a catalyst. Compounds that may be treated by polymerization include aromatics, aHphatics, and other oxygenated monomers such as vinyl chloride and acrylonitrile [107-13-1]. 

Another important use of BCl is as a Ftiedel-Crafts catalyst ia various polymerisation, alkylation, and acylation reactions, and ia other organic syntheses (see Friedel-Crafts reaction). Examples include conversion of cyclophosphasenes to polymers (81,82) polymerisation of olefins such as ethylene (75,83—88) graft polymerisation of vinyl chloride and isobutylene (89) stereospecific polymerisation of propylene (90) copolymerisation of isobutylene and styrene (91,92), and other unsaturated aromatics with maleic anhydride (93) polymerisation of norhornene (94), butadiene (95) preparation of electrically conducting epoxy resins (96), and polymers containing B and N (97) and selective demethylation of methoxy groups ortho to OH groups (98). 

Tile is based mainly on vinyl chloride and vinyl acetate copolymers. Some polypropylene tile systems have recendy been iatroduced. A petroleum resia is usually employed as an extender and processiag aid conventional vinyl plasticizers and stabilizers also are iacorporated. Reinforcing fibers and limestone constitute the remainder of the tile composition the fibers contribute hot strength for processiag and dimensional stabiHty ia the finished tile, limestone suppHes bulk at an economical cost. Stable pigments are also iacorporated. Siace tile is iastalled oa and below grade level, it is important that the finished product be resistant to the effects of moisture and alkaH. 

A significant use of butylene oxide [26249-20-7] is as an acid scavenger for chlorine-containing materials such as trichloroethylene. Inclusion of about 0.25—0.5% of butylene oxide, based on the solvent weight, during preparation of vinyl chloride and copolymer resin solutions minimizes container corrosion which may be detrimental to resin color and properties. 

Oxychlorination of ethylene to dichloroethane is the first reaction performed in an integrated vinyl chloride plant. In the second stage, dichloroethane is cracked thermally over alumina to give vinyl chloride and hydrogen chloride. The hydrogen chloride produced is recycled back to the oxychlorination reactor. 

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