Ester-acids => succinate esters

Corrosion inhibitors partial esters of succinic acid, fatty acids, sulfonates, phenates, amine phosphates. 

Methyl, ethyl, n-propyl, isopropyl, n-hutyl, benzyl, cyclohexyl esters of formic, acetic, oxalic, succinic, tartaric, citric, benzoic, salicylic (and other substituted benzoic acids), phthalic and cinnamic acids phenyl esters of acetic, benzoic and salicylic acids. 

The condensation of aldehydes and ketones with succinic esters in the presence of sodium ethoxide is known as the Stobbe condensation. The reaction with sodium ethoxide is comparatively slow and a httlo reduction of the ketonic compound to the carbinol usually occurs a shorter reaction time and a better yield is generally obtained with the more powerful condensing agent potassium ieri.-butoxide or with sodium hydride. Thus benzophenone condenses with diethyl succinate in the presence of potassium [Pg.919]

Butanediol. 1,4-Butanediol [110-63-4] tetramethylene glycol, 1,4-butylene glycol, was first prepared in 1890 by acid hydrolysis of N,]S3-dinitro-l,4-butanediamine (117). Other early preparations were by reduction of succinaldehyde (118) or succinic esters (119) and by saponification of the diacetate prepared from 1,4-dihalobutanes (120). Catalytic hydrogenation of butynediol, now the principal commercial route, was first described in 1910 (121). Other processes used for commercial manufacture are described in the section on Manufacture. Physical properties of butanediol are Hsted in Table 2. 

Condensation with Aldehydes and Ketones. Succinic anhydride and succinic esters in the presence of different catalysts react in the gas phase with formaldehyde to give citraconic acid or anhydride and itaconic acid (94—96). Dialkyl acyl succinates are obtained by reaction of dialkyl succinates with C 4 aldehydes over peroxide catalysts (97). 

Succinic esters condense with aldehydes and ketones in the presence of bases, eg, sodium alkoxide or piperidine, to form monoesters of alkybdenesuccinic acids, eg, condensation of diethyl succinate with acetone yields ethyl 2-isopropyhdenesuccinate (eq. 3). This reaction, known as Stobbe condensation, is specific for succinic esters and substituted succinic esters (98,99). 

Cellulose esters of aromatic acids, aUphatic acids containing more than four carbon atoms and aUphatic diacids are difficult and expensive to prepare because of the poor reactivity of the corresponding anhydrides with cellulose Httle commercial interest has been shown in these esters. Of notable exception, however, is the recent interest in the mixed esters of cellulose succinates, prepared by the sodium acetate catalyzed reaction of cellulose with succinic anhydride. The additional expense incurred in manufacturing succinate esters is compensated by the improved film properties observed in waterborne coatings (5). 

B. a-Ketoglularic acid. The ester obtained by the foregoing procedure is mixed with 600 ml. of concentrated hydrochloric acid and left overnight. The mixture is concentrated by distillation (Note 5) until the temperature of the liquid reaches 140°. It is poured into an evaporating dish and allowed to cool. The solid mass, weighing 11(3-112 g., is then pulverized. The yield of a-ketoglutaric acid is 92-93% of the theoretical for the last step, or 75-77% based upon diethyl succinate. The light tan product, obtained as described above, is suitable for most purposes, but a purer add, m.p. 109-110° (corr.) may be obtained by recrystallization from an acetone-benzene mixture. 

Methylindole and acetylenedicarboxylic acid is reported to give two unidentified products, but with the dimethyl ester the crs and trans (61) adducts were obtained. It was suggested that the major product had the trans configuration but this was not proved. Hydrogenation of both adducts gave the corresponding succinic ester, which was also obtained from 2-methylindole and maleic anhydride, followed by esterification. 

Succinaldehyde, 7, 41 Succinic acid, 5, 10, 8, 13 Succinic ester (ethyl), 5, 10 Sulfonation, with chlorosulfomc acid, 5, 3... 

The possibility exists that the acid used in hydrolysis could catalyze the hydrolysis of the succinic ester group in the middle of the telechelomer itself. Even though NMR ( H and C) cannot easily eliminate this possibility, we have evidence that such a hydrolysis did not take place. For instance, hydrolysis should result in the formation of poly(pivalolactone) which is insoluble both in methylene chloride and water, but no insolubles were evident. Also, the Gel Permeation Chromatograms do not show impurities in the product. 

Another class of PSA-fatty acid-based copolymers has been synthesized from the ricinoleic acid and ricinoleic half-esters with maleic and succinic anhydride, poly(sebacic-co-ricinoleic acid maleate), poly(sebacic-co-ricinoleic acid succinate), and poly(sebacic-co-12-hydroxystearic acid succinate) (P(SA-RAM), P(SA-RAS), and P(SA-HSAS)) (Krasko et al., 2003 Teomim et al., 1999). These syntheses result in poly(anhydride-co-esters). 

Esters of succinic acid condense to esters of succinylsuccinic acid (1 4-diketohexamethylene-2 5-dicarboxylic esters). Study Baeyer s work on the hydrogenated derivatives of benzene, based on this synthesis. 

EM for cyclization of succinamic acid assumed equal to that for cyclization of succinic esters (Table A.2 see text). Direct rate comparisons give EM s for substituted succinamic acids at 25°. No corrections for pX,... 

These syntlieses give no indication as to the structure of aspartic acid, the constitutional formula of which is based upon Kolbe s work, that it is amino-succinic acid the only synthesis of aspartic acid which confirms this constitution appears to be that by Piutti in 1887. Sodium oxalacetic ester, prepared from oxalic ester and acetic ester in the presence of sodium ethylate —... 

Succinic acid. Succinic add is also available via fermentation of glucose, and has the potential to become a large-scale industrial chemical in the future. However, there are only a few reports on dehydration reactions involving succinic acids in the literature, and most of these are concerned with esterification to produce dialkyl esters. The synthesis of various dialkyl esters was reported using metal exchanged montmorillonite clays (Na, Mn ", ... 

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