Phosphorus acid anhydrides esters

Phenyl cinnamate and other phenolic esters have been prepared by heating the acid and phenol in the presence of phosphorus oxychloride,1 and by heating the acid anhydride and phenol together in the presence of a dehydrating agent such as fused zinc chloride or anhydrous sodium acetate.2 Phenyl cinnamate has also been prepared by the careful distillation of phenyl fumarate.3... 

Chlorinated Fatty Acids. Chlorination of carboxylic acids is much more difficult because the contribution or the carbonyl group toward proton removal is offset by the electron donation effect from the hydroxyl group. This hindrance is obviated by reaction with the acid chloride or anhydride. Chlorination is normally accomplished hy use of n catalyst, such as phosphorus trichloride. Monochloroacelic acid is an important industrial chemical. Dichloro- and trichloroacetic acids can he produced by further chlorination, although the latter can be produced convenienlly by nitric acid oxidation of chloral. Higher chlorinalcd tally acids can be produced by treatment or the hydroxy carboxylic acid or ester with HCI ur PCL ... 

This compound will be referred to again in connection with the synthesis of salicylic acid (p. 717). The acid ester of phenol and sulphuric acid, phenyl sulphuric acid, CeHs—O—SO2OH, is a constituent of animal urine. The esters of phenols and organic acids are not readily formed by the direct action of the acids, in which respect the phenols again resemble tertiary alcohols. They may be prepared from phenols by the action of acid chlorides acid anhydrides or a mixture of the acid and phosphorus oxychloride. 

Starch esters of either mono-, di-, or trichloroacetic acid can be pre-pared by heating starch with the appropriate acid or by treatment with the acid anhydride and sulfuric acid. Starch triacetates can be chlorinated by phosphorus pentachloride at 135-140 to produce a starch trichloroacetic ester. ... 

Starches have been chemically modified to improve their solution and gelling characteristics for food applications. Common modifications involve the cross linking of the starch chains, formation of esters and ethers, and partial depolymerization. Chemical modifications that have been approved in the United States for food use, involve esterification with acetic anhydride, succinic anhydride, mixed acid anhydrides of acetic and adipic acids, and 1-octenylsuccinic anhydride to give low degrees of substitution (d.s.), such as 0.09 [31]. Phosphate starch esters have been prepared by reaction with phosphorus oxychloride, sodium trimetaphosphate, and sodium tripolyphosphate the maximum phosphate d.s. permitted in the US is 0.002. Starch ethers, approved for food use, have been prepared by reaction with propylene oxide to give hydroxypropyl derivatives [31]. 

Cramer, R, Preparation of esters, amides, and phosphoric acid anhydrides, Angew. Chem.. 72. 236, 1960. Allen, J.E, and Johnson, O.H.. The synthesis of monovinyl esters of phosphorus(V) acids. J. Am. Chem. Soc., 77, 2871, 1955. 

The reaction of N-arylsulfonylsuinmides with a range of trivalent phosphorus compounds gave near quantitative yields of the phosphinimides and the sulfide. I Addition of protic solvents led to reduction products, which contain, besides the original sulfides, an alkyl-exchanged sulfide in which the alkyl group derived from the alcohol. 126.127 other derivatives, (acid anhydride, amide, ester or thioester) were formed in the presence of carboxylic acid derivatives. 128,129 xhese reactions were favoured by the dipolar nature of the intermediately formed sulfurane. 127... 

DIPHOSPHORIC ACID, TETRAETHYL ESTER (107-49-3) Reacts with water, forming phosphoric acid and flammable ethylene gas. Alkalis or elevated temperatures above 300°F/150°C can cause decomposition, forming flammable ethylene gas and phosphorus oxides. Aqueous solution is incompatible with sulfuric acid, alkalis, ammonia, aliphatic amines, alkanolamines, alkylene oxides, amides, epichlorohydrin, nitromethane, organic anhydrides, isocyanates, vinyl acetate. Attacks some plastics, rubber, and coatings. Corrosive to metals in the presence of moisture. 

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