Succinic acid diester

Succinic acid diesters are also obtained by one-step hydrogenation (over Pd on charcoal) and esterification of maleic anhydride dissolved in alcohols (40) carbonylation of acrylates in the presence of alcohols and Co complex catalysts (41—43) carbonylation of ethylene in alcohol in the presence of Pd or Pd—Cu catalysts (44—50) hydroformylation of acetylene with Mo and W complexes in the presence of butanol (51) and a biochemical process from dextrose/com steep Hquor, using Jinaerobiumspirillum succiniciproducens as a bacterium (52). 

The reductive coupling of a-bromo acetate to succinic acid diesters mediated by Sml2 in the presence of HMPA has been reported [76] (Scheme 32). 

Esterification. Succinic anhydride reacts readily with alcohols to give monoesters of succinic acid, which are readily esterified to diesters by the usual methods (34—37). 

Diesters and even triesters have been converted to bis- and tris(cyclopropanol)s, respectively. Dimethyl succinate gave the bis (cyclopropanol) derivative 17 in 80% yield, while triethyl trans-cyclopropanetricarboxylate (18) yields the tris (cyclopropanol) 19 (90%) (Scheme 11.4 selected examples in Table 11.2) [77,78], Higher homologous dicarboxylic acid diesters are likewise smoothly converted with ethylmagnesium bromide in the presence of Ti(OiPr)4 to provide the corresponding bis (cyclopropanol) s [71,78]. 

The synthesis of succinic acid derivatives, /3-alkoxy esters, and a,j3-unsaturated esters from olefins by palladium catalyzed carbonylation reactions in alcohol have been reported (24, 25, 26, 27), but full experimental details of the syntheses are incomplete and in most cases the yields of yS-alkoxy ester and diester products are low. A similar reaction employing stoichiometric amounts of palladium (II) has also been reported (28). In order to explore the scope of this reaction for the syntheses of yS-alkoxy esters and succinic acid derivatives, representative cyclic and acyclic olefins were carbonylated under these same conditions (Table I). The reactions were carried out in methanol at room temperature using catalytic amounts of palladium (II) chloride and stoichiometric amounts of copper (II) chloride under 2 atm of carbon monoxide. The methoxypalladation reaction of 1-pentene affords a good conversion (55% ) of olefin to methyl 3-methoxyhexanoate, the product of Markov-nikov addition. In the carbonylation of other 1-olefins, f3-methoxy methyl esters were obtained in high yields however, substitution of a methyl group on the double bond reduced the yield of ester markedly. For example, the carbonylation of 2-methyl-l-butene afforded < 10% yield of methyl 3-methyl-3-methoxypentanoate. This suggests that unsubstituted 1-olefins may be preferentially carbonylated in the presence of substituted 1-olefins or internal olefins. The reactivities of the olefins fall in the order RCH =CHo ]> ci -RCH=CHR > trans-RCH =CHR >... 

Malonic, succinic, maleic diesters Perfluorinated dicarboxylic acids (10-15 m) I 0 j)... 

It is possible to make either the diester or the monoester of butanedioic acid (succinic acid) from the cyclic anhydride as shown. Why does the one method give the monoester and the other the diester ... 

A variation on this reaction is when the anion is formed from the diester derivative of 4-butandioic acid (succinic acid). In this case, the reaction proceeds via an intermediate that is a cyclic ester (i.e. a lactone). Write down the mechanism for the reaction between a general ketone, R CK), and the... 

In Group 9 various organic acids like lactic acid (Flavis 08.004, FEMA 2611), pyruvic acid (Flavis 08.019, FEMA 2970) and succinic acid (Flavis 08.024, registered in Food Chemical Codex) together with various diesters are found. Beside some diols, numerous lactones such as y-decalactone (Flavis 10.017, FEMA 2360) with peach-like notes and 8-decalactone (Flavis 10.007, FEMA 2361) with a sweet coconut-like profile are represented. 

An efficient enzyme-catalyzed reaction for the large-scale preparation of (R)-2-iso-butyl succinic acid 4-ethyl ester (R)-2a, a key intermediate in the synthesis of collagenase inhibitor R00319790 (1), is described (Fig. 1). The corresponding racemic diethyl ester substrate 9 is applied at 20% concentration and hydrolyzed re-gio- and enantioselectively ( >100) at the sterically more hindered secondary ester group using a cheap commercial subtilisin preparation. The desired (R)-monoacid is separated from the remaining antipodal diester (S)-9 by means of extraction and obtained in > 99% ee and > 43% yield. The development of the reaction from process research to the pilot-scale is described. 

An anhydride reacts with an alcohol to produce an ester and a carboxylic acid. So when succinic anhydride is heated in methanol it produces the monomethyl ester of succinic acid. This Is apparent from the presence of an OH band and two carbonyl bands in the IR spectrum and the signal at 10.25 5 in the NMR spectrum of the product. However, in the presence of a catalytic amount of sulfuric acid, the carboxylic acid group of the initial product reacts with methanol to form a diester. This is consistent with the IR spectrum of this product and the fact that it shows only three absorptions in its C-NMR spectrum. 

U n itex http //www. unitexchemical. com] Dicyclohexyl sodium sulfosuccinate CAS 23386-52-9 EINECS/ELINCS 245-629-3 Synonyms Sodium 1,4-dicyclohexyl sulfobutanedioic acid Sodium 1,4-dicyclohexyl sulfonatosuccinate Sodium dicyclohexyl sulfosuccinate Sodium 1,4-dicyclohexyl sulfosuccinate Succinic acid, sulfo-, 1,4-dicyclohexyl ester, sodium salt Definition Sodium salt of the diester of cyclohexyl alcohol and sulfosuccinic acid Empiricai C16H26O7S Na Properties Anionic Toxicoiogy TSCA listed Uses Dispersant, surfactant, emulsifier for modified S/B post additive to stabilize latex and promote adhesion pigment dispersant surfactant, foaming agent, hydrotrope in cosmetics emulsifier in food pkg. 

Trade Name Synonyms Diplast E t[Lonza SpA] Diheptyl sodium sulfosuccinate CAS 4680-44-8 EINECS/ELINCS 225-131-2 Synonyms Butanedioic acid, sulfo-, 1,4-diheptyl ester, sodium salt Sodium 1,4-diheptyl sulfobutanedioate Sodium 1,4-diheptyl sulfonatosuccinate Succinic acid, sulfo-, diheptyl ester, sodium salt Sulfosuccinic acid, diheptyl ester, sodium salt Definition Sodium salt of the diester of heptyl alcohol and sulfosuccinic acid Empiricai C18H34O7S Na Uses Surfactant in cosmetics... 

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