JPS6324492B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to stabilized allyl chloride compositions. Specifically, the present invention relates to a stabilized allyl chloride composition obtained by adding an organic tin compound to an allyl chloride compound. Allyl chloride is used as a variety of raw materials, and is particularly important as a raw material for epichlorohydrin. It is also a raw material for the synthesis of allyl compounds such as glycerin, allyl alcohol, allyl amine, allyl glycidyl ether, diallyl phthalate, and even homopolymers or acrylonitrile. , vinyl cyanide copolymer raw materials, pharmaceutical manufacturing raw materials, herbicides,
It is useful as a raw material for agricultural chemicals such as insecticides, a raw material for pharmaceuticals such as sedatives and anesthetics, and a raw material for fragrances. However, allyl chloride compounds easily decompose under the action of heat and light, turning yellow to black, and in severe cases turning into tar-like substances, which significantly impairs commercial value. In view of the current situation, the present inventors have conducted research for many years, and as a result, have succeeded in stabilizing allyl chloride compounds and have arrived at the present invention. That is, the present invention provides a stabilized allyl chloride composition obtained by adding an organotin compound to allyl chloride. The allyl chloride composition of the present invention will be explained in detail below. Examples of the organic tin compound to be added to allyl chloride of the present invention include methylstanoitsuccinic acid, butylstanoitsuccinic acid, octylstanoitsuccinic acid, dimethyltin oxide, dibutyltin oxide, dioctyltin oxide, dimethyltin sulfide,
Dibutyltin sulfide, dioctyltin sulfide, dicyclohexyltin sulfide, monobutyltin oxide sulfide, methylthiostanoitsuccinic acid, butylthiostanoitsuccinic acid, octylthiostanoitsuccinic acid, dibutyltin laurate, dibutyltin stearate, dioctyltin diolate , dibutyltin basic laurate, dibutyltin diclonate, dibutyltin bis(butoxydiethylene glycol malate), dibutyltin methyl octyl neobentyl glycol malate, dibutyltin isooctyl 1,4-butanediol malate, dibutyltin dichlorate methacrylate,
Dibutyltin disinnamate, dioctyltin bis(oleyl maleate), dibutyltin bis(stearyl maleate), dibutyltin itaconate, dioctyltin maleate, diamyltin bis(cyclohexyl maleate), dimethyltin diclonate, diethyltin bis(isooctylcytophyl) dipropyltin bis(benzyl maleate), diisobutyltin bis(propyl maleate), dicyclohexyltin maleate, dioctyltin bis(butyl maleate), dibutyltin dimethoxide, dibutyltin dilauroxide, dioctyltin ethylene glycoxide, pentaerythritol. Dibutyltin oxide condensate, dibutyltin bis(lauryl mercaptite), dimethyltin bis(stearyl mercaptite), monobutyltin tris(lauryl mercaptide), dibutyltin-β-mercaptopropionate, dioctyltin-β -Mercaptopropionate, dibutyltin mercaptoacetate, monobutyltin tris(isooctylmercaptoacetate), monooctyltin tris(2-ethylhexylmercaptoacetate), dibutyltin bis(isooctylmercaptoacetate), dioctyltin bis(isooctylmercaptoacetate) acetate),
Dioctyltin bis(2-ethylhexylmercaptoacetate), dimethyltin bis(isooctylmercaptoacetate), dimethyltin bis(isooctylmercaptopropionate), monobutyltin tris(isooctylmercaptopropionate), bis[monobutyldi(isooctylmercaptopropionate) octoxycarbonylmethylenethio)tin] sulfide, bis[dibutylmono(isooctoxycarbonylmethylenethio)tin]sulfide, monobutylmonochlorotinbis(isooctylmercaptopropionate), monobutylmonochlorotinbis(isooctylmercaptoacetate) , monobutyl monochlorotin bis(lauryl mercaptide), dibutyltin bis(ethylcellulobutyl malate), bis(dioctyltin laurate) maleate, bis(dioctyltin butyl maleate) malate, bis(methyltin diisooctylthioglycolate) ) disulfide, bis(methyl/dimethyltin mono/diisooctylthioglycolate) disulfide,
Bis(methyltin diisooctylthioglycolate) trisulfide, bis(butyltin diisooctylthioglycolate) trisulfide, 2
-Butoxycarbonylethyltin tris (butylthioglycolate), 2-methoxycarbonylethyltin tris (isooctylthiopropionate),
2-Butoxycarbonylethyltin tris (stearylthiopropionate), 2-methoxycarbonylethyltin tris (isooctyl glycolate), 2-methoxycarbonylpropyltin tris (octylthioglycolate), 2-methoxycarbonylethyltin tris (2-ethylhexylthiopropionate), 2-methoxycarbonylethyltin sulfide polymer, 2-ethoxycarbonylpropyltin sulfide polymer, 2-butoxycarbonylethyltin sulfide polymer,
2-isopropoxycarbonylethyltin sulfide polymer, bis(2-methoxycarbonylethyl)tin bis(isooctylthioglycolate),
Bis(2-butoxycarbonylethyl)tin bis(2-ethylhexylthioglycolate), bis(methoxycarbonylethyl)tin bis(2-ethylhexylthiopropionate), bis(2-butoxycarbonylethyl)tin bis(butylthio) glycolate), bis(2-methoxycarbonylethyl)tin bis(stearinorthioglycolate),
Bis(2-ethoxycarbonylpropyl)tin bis(laurylthioglycolate), bis(2-isopropoxycarbonylethyl)tin bis(isooctylthiopropionate), bis(2-methoxycarbonylethyl)tin sulfide polymer, Bis(2-methoxycarbonylpropyltin sulfide polymer, bis(2-propoxycarbonylethyl)tin sulfide polymer, bis(2-methoxycarbonylethyl)tin sulfide polymer, bis(2-methoxycarbonylethyl)tin maleate polymer , bis(2-ethoxycarbonylethyl)tin dilaurate, bis(2-methoxycarbonylisopropoxy)tin dilaurate, bis(2-methoxycarbonylethyl)tin bis(isooctylmalate), etc. , the amount of the organic tin compound added is 0.01 to 5% by weight, preferably 0.01 to 5% by weight based on the allyl chloride compound.
It is 0.1 to 3% by weight. Incidentally, an epoxy compound, alcohol or phenols can be used in combination with the composition of the present invention to improve its performance. Examples of the epoxy compounds include epoxidized animal and vegetable oils such as epoxidized soybean oil, epoxidized linseed oil, and epoxidized fish oil, or epoxidized products of fatty acid esters of these animal and vegetable oils, methyl epoxy stearate, butyl epoxy stearate, and octyl epoxy stearate. Epoxidized fatty acid esters such as ethyl glycidyl ether, diethylene glycol diglycidyl ether, bisphenol A diglycidyl ether, phenyl glycidyl ether, phenyl glycidyl ester, glycidyl compounds such as glycerin triglycidyl ether, vinyl cyclohexene diepoxide, Cyclic epoxy compounds such as dicyclopentadiene diepoxide, alkylene oxides such as epichlorohydrin and propylene oxide, epoxidized polybutadiene,
Tris (epoxypropyl) isocyanurate and the like can be used. Examples of the alcohols that can be used include monohydric alcohols such as methanol, ethanol, and octanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, glycerin, trimethylolpropane, pentaerythritol, and sorbitol. Examples of the phenols include phenol, Cresol, nonylphenol, hydroquinone, resorcinol, etc. can be used. The composition of the present invention also includes triphenyl phosphite, trisnonylphenyl phosphite, diphenyl decyl phosphite, tridecyl phosphite, diphenyl acid phosphite, tetra(mixed alkyl)-4,4'- Phosphites such as isopropylidene diphenyl diphosphite and amines such as triethanolamine and ethylenediamine can be used in combination to improve the performance. Furthermore, since adding an antioxidant to the composition of the present invention can increase the anti-oxidative deterioration properties of the composition, it can be used as appropriate depending on the purpose of use. These antioxidants include phenolic antioxidants, sulfur-containing compounds, and the like. Furthermore, if an ultraviolet absorber is added to the composition of the present invention, the photostability can be improved, so it is possible to appropriately select and use these depending on the purpose of use. These include benzophenones,
Included are benzotriazole series, salicylates, substituted acrylonitrile series, various metal salts or metal chelates, especially nickel or chromium salts or chelates, triazine series, piperidine series, and the like. Next, examples of compositions of the present invention will be shown. However, the present invention is not limited to these examples. Example 1 100 g of allyl chloride and 0.5 g (0.5% by weight) of the organic tin compound shown in Table 1 were placed in a flask, a cooling tube was attached, and the flask was placed in an oil bath set at 40°C to prepare the composition of the present invention. Accelerated thermal stability tests were conducted. The results obtained are shown in Table 1.

【table】

[Table] In the table, - indicates no coloring, + indicates pale yellow, yellow indicates yellow, ++++++ indicates brown, and the number of + indicates the degree of promotion of coloring.
Example 2 100g of allyl chloride and organic tin compound shown in Table 2
0.3g (0.3% by weight) was added and left at room temperature for 180 days to examine changes in color tone. The results are shown in Table 2.

【table】

【table】

Claims (1)

[Claims] 1. A stabilized allyl chloride composition obtained by adding an organic tin compound to allyl chloride.