Hydrogen peroxide Azelaic acid

Hydrogen peroxide, Sulfuric acid See Hydrogen peroxide Azelaic acid, Sulfuric acid... 

A U.S. patent describes the reaction of commercial oleic acid with hydrogen peroxide in acetic acid foUowed by air oxidation using a heavy metal compound and an inorganic bromine or chlorine compound to catalyze the oxidation. ExceUent yields of dibasic acids are obtained (up to 99%) containing up to 72% azelaic acid (55). 

The mechanism of inhibition by the salts of the long chain fatty acids has been examined . It was concluded that, in the case of the lead salts, metallic lead was first deposited at certain points and that at these points oxygen reduction proceeded more easily, consequently the current density was kept sufficiently high to maintain ferric film formation in addition, any hydrogen peroxide present may assist in keeping the iron ions in the oxide film in the ferric condition, consequently the air-formed film is thickened until it becomes impervious to iron ions. The zinc, calcium and sodium salts are not as efficient inhibitors as the lead salts and recent work has indicated that inhibition is due to the formation of ferric azelate, which repairs weak spots in the air-formed film. This conclusion has been confirmed by the use of C labelled azelaic acid, which was found to be distributed over the surface of the mild steel in a very heterogeneous manner. ... 

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. 

Ozone, when combined with hydrogen peroxide [101] or peroxyacetic acid [268], cleaves the triple bond to yield carboxylic acids. Stearolic acid is converted into a mixture of pelargonic acid and azelaic acid [268] (equation 474). 9-Octadecynedioic acid, on treatment with ozone in acetic acid at room temperature followed by oxidation with hydrogen peroxide, gives azelaic acid in 81% yield [101]. 

The trend is toward oxidants that are relatively harmless and that generate no noxious by-products. Oxygen, and materials derived from it, are examples. Ozone is quite toxic itself, but produces no harmful by-products. It is used commercially for the cleavage of oleic acid to azelaic and pelargonic acids.158 Hydrogen peroxide is made from oxygen (4.23).159... 

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... 

Acrylic/styrene/acrylonitrile terpolymer Allyl isocyanate Azelaic acid t-Butyl cumyl peroxide 4-t-Butyl-o-thiocresol Dimer acid, hydrogenated Dipentene-styrene resin t-Hexadecanethiol 1-Hexene n-Hexyl acrylate... 

---