Azelaic anhydride

Polyester synthesis was carried out hy insertion-dehydration of glycols into polyanhydrides using lipase CA as catalyst (Scheme 6). The insertion of 1,8-octanediol into poly(azelaic anhydride) took place at 30-60°C to give the corresponding polyester with molecular weight of several thousands. Effects of the reaction parameters on the polymer yield and molecular weight were systematically investigated. The dehydration reachon also proceeded in water. The reaction behaviors depended on the monomer structure and reaction media. 

Most cyclic a-diazoketones are oxidized by peracids to a-diketones in good yield, but low yields were obtained for oxidation of a-diazocyclo-octanone and a-diazo-cyclononanone because of further oxidation to suberic and azelaic anhydrides, respectively. Since the rate of oxidation is only slightly dependent upon ring size, the conformation of the transition state must be similar to that of the ground state a concerted nitrogen extrusion-oxygen addition mechanism has been proposed. 

Polyanhydrides were effective as diacid substrate for enzjunatic synthesis of polyesters (136). The reaction of poly(azelaic anhydride) and 1,8-octanediol took place by lipase CA catalyst to give the corresponding polyester with molecular weight of several thousands. In the reaction of poly(azelaic anhydride) and glycerol, a highly branched polyester was obtained. 

Figure 12.12 THM GC/MS curves of a Winsor Newton lemon alkyd paint (a) and of an alkyd sample taken from Fontana s work Concetto spaziale (1961) (b). Peak assignments 1, 1,3 dimethoxy 2 propanol 2, 1,2,3 trimethoxy propane 3, 3 methoxy 1,2 propandiol 4, 4 chloro benzenamine 5, 3 methoxy 2,2 bis(methoxymethyl) 1 propanol 6, 3 chloro N methyl benzenamine 7, 3 methoxy 2 methoxymethyl 1 propanol 8, 4 chloro N methyl benzenamine 9, phthalic anhydride 10, 3 chloro 4 methoxy benzenamine 11, suberic acid dimethyl ester 12, dimethyl phthalate 13, azelaic acid dimethyl ester 14, sebacic acid dimethyl ester 15, palmitic acid methyl ester 16, oleic acid methyl ester 17, stearic acid methyl ester 18, 12 hydroxy stearic acid methyl ester 19, 12 methoxy stearic acid methyl ester 20, styrene 21, 2 (2 methoxyethoxy) ethanol 22, 1,1 oxybis(2 methoxy ethane) 23, benzoic acid methyl ester 24, adipic acid dimethyl ester 25, hexadecenoic acid methyl ester 26, dihydroisopimaric acid methyl ester 27, dehydroabietic acid methyl ester 28, 4 epidehydroabietol...

On an industrial scale, the traditional method for cleavage of carbon-carbon double bonds is ozonolysis, used for the manufacture of azelaic acid and nonanoic acids from oleic acid, and of butane tetracarboxylic acid from tetrahydrophthalic anhydride. The process is effectively a quantitative and mild process.178 However, it is capital and energy intensive. The intermediate ozonide is worked up either reductively or oxidatively to produce the aldehyde, ketone or carboxylic acid. Hydrogen peroxide is the common oxidizing agent used in the second step.179-181 Oxygen can also be used either alone182 or in combination with zeolites.183 Reviews on ozonolysis are available and the reader is directed to reference 184 for further information. 

The selenophene ring may be acylated by acyl chlorides under Friedel-Crafts conditions7 63 by acid anhydrides in the presence of 85% phosphoric acid64 and by organic silicoanhydrides (tetraacyloxy-silanes) in the presence of stannic chloride.65-67 When acylated by silicoanhydrides of dibasic organic acids (succinic, adipic, azelaic, or... 

Azelaic acid (1,9-nonanedioic acid, heptane-l,7-dicarboxylic acid) [123-99-9] M 188.2, m 105-106 , b 225 /10mm, 256 /50mm, pK 4.53, pK 5.33. Reciystallise it from H2O (charcoal) or thiophene-free benzene. The acid can be dried by azeotropic distillation with toluene, the residual toluene solution is then cooled and filtered, and the precipitate is dried in a vacuum oven. It has been purified by zone refining or by sublimation onto a cold finger at 10 torr. It distils above 360 with partial formation of the anhydride. The dimethyl ester has in -3.9° and b 140°/8mm. [Hill McEwen Org Synth Coll Vol II 53 1943, Beilstein 2 IV 2055.]... 

Aluminum acetate Aluminum caprylate Aluminum distearate Aluminum myristates/palmitates Aluminum stearate Aluminum tristearate N-2-Aminoethyl-3-aminopropyl trimethoxysilane Aminoethylethanolamine Aminomethyl propanol Aminopropyltriethoxysilane Aminopropyltrimethoxysilane Ammonium benzoate Ammonium borate Ammonium citrate dibasic Ammonium laureth sulfate Ammonium laureth-5 sulfate Ammonium laureth-7 sulfate Ammonium laureth-12 sulfate Ammonium laureth-30 sulfate Ammonium lauryl sulfate Ammonium maleic anhydride/diisobutylene copolymer Ammonium oleate Ammonium persulfate Ammonium polyacrylate Ammonium potassium hydrogen phosphate Ammonium stearate Ammonium sulfamate Ammonium thiocyanate Ammonium thiosulfate Amyl acetate Antimony trioxide Asbestos Asphalt Azelaic acid 2,2 -Azobisisobutyronitrile Barium acetate Barium peroxide Barium sulfatej Bentonite Benzalkonium chloride Benzene Benzethonium chloride Benzothiazyl disulfide Benzoyl peroxide Benzyl alcohol Benzyl benzoate 1,3-Bis (2-benzothiazolylmercaptomethyl) urea 1,2-Bis (3,5-di-t-butyl-4-hydroxyhydrocinnamoyl) hydrazine 4,4 -Bis (a,a-dimethylbenzyl) diphenylamine Bisphenol A Bis (trichloromethyl) sulfone Boric acid 2-Bromo-2-nitropropane-1,3-diol 1,4-Butanediol Butoxydiglycol Butoxyethanol Butoxyethanol acetate n-Butyl acetate Butyl acetyl ricinoleate Butyl alcohol Butyl benzoate Butyl benzyl phthalate Butyidecyl phthalate Butylene glycol t-Butyl hydroperoxide... 

Polyester, saturated n. Any polyester in which the polyester backbone has no double bonds. The class includes low-molecular-weight liquids used as plasticizers and as reactants in forming urethane polymers and linear, high-molecular-weight thermoplastics such as polyethylene terephthalate. Usual reactants for the saturated polyesters are (1) a glycol such as ethylene-, propylene-, diethylene-, dipropylene-, or butylene glycol (2) An acid or anhydride such as adipic, azelaic, or terephthalic acid or phthalic anhydride. Some saturated, branched polyesters are used in high-temperature varnishes and adhesives. 

Trivial name Acetaldehyde Acetamide Acetic acid Acetic anhydride Acetoacetic acid Acetone Acetonitrile Acetophenone Acetyl chloride Acetylene Acrolein Acrylamide Acrylic acid Acrylonitrile Adipic acid Amyl acetate Amyl alcohol tert-Amy alcohol Aniline Azelaic acid Benzoic acid Benzoyl peroxide Benzyl alcohol Bisphenol A... 

Includes trimellitic anhydride, chlorendic anhydride, short-chain aliphatic dibasic acids, and dimerized fatty acids. Typical short-chain aliphatic dibasic acids include adipic acid, azelaic acid, sebacic acid, and succinic acid. 

The most common alkyd raw materials are polybasic acids (phthalic anhydride, isophthalic acid, maleic anhydride, fumaric, azelaic, succinic, adipic, and sebacic acids), oils (linseed, soya, dehydrated castor, tung, fish, safflower, oiticica, cotton seed, and coconut), polyhydric alcohols (glycerol, pentaerythritol, dipen-taerythritol, trimethylolethane, sorbitol, trimethylolpropane, ethyleneglycol, propylene glycol, neopentyleneglycol, and dipropylene glycol), and monobasic acids (tail-oil fatty acids and synthetic saturated fatty acids). 

Other dibasic acids used in alkyds to impart special properties are adipic acid, azelaic acid, sebacic acid, tetrachlorophthalic anhydride, chlorendic anhydride, dimerized fatty acids, and trimellitic anhydride. Adipic, azelaic, and sebacic acids impart flexibility in the alkyd structure and are primarily used in alkyds designed for application as plasticizers. Tetrachlorophthalic anhydride and chlorendic anhydride are used to impart fire-retardant properties to the resin system. 

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