Succinic acid modification

Succinic anhydride is dimerised to 1,6-dioxaspiro [4.4] nonane-2,7-dione by heating with sodium hydroxide. Modification of an existing procedure by adding further sodium hydroxide after the initial reaction led to a severe exothermic reaction after heating for some 30 h which fused the glass flask to the heating mantle, probably at a temperature approaching 550°C. The reason for this was not known [1], At elevated temperatures and under influence of alkali, succinic acid condenses decarboxylatively beyond the dimeric spiroacetal, sometimes explosively. Contamination of the anhydride with base is to be avoided [2],... 

Davey, R.J., Whiting, M.J.L., (1982). Habit modification of succinic acid crystals grown from different solvents. Journal of Crystal Growth., 58, 304-312. 

The above procedure is a modification of that described by Rasinski.2 Diphenyl succinate has also been prepared by the reaction of phenol and succinic acid in the presence of phosphorus pentoxide in toluene8 and by the treatment of phenol with succinyl chloride.4... 

Certain microorganisms have a modification of this cycle in which isocitric acid is cleaved to succinic acid and glyoxylic acid. The latter acid is condensed with acetyl-CoA to form malic acid. In this modification (the glvoxvlic acid cvcle), oxalsuccinic acid and alpha-ketoglularic acid are not involved. This is sometimes referred to as the glyoxylate shunt pathway. 

J.W. Rhim, C.K. Yeom, S.W. Kim, Modification of poly (vinyl alcohol) membranes using sulfur-succinic acid and its application to pervaporation separation of water/alcohol mixtures, J. Appl. Polym. 

The mechanisms of modification are different and depend on the chemical molecules used for the reactions. The anhydride of succinic acid reacts with lysine residues, a-amino groups of proteins and free thiol groups. During succinylation, proteins lose their globular structure and undergo aggregation by disulfide cross-binding with other whey proteins. Acetyl anhydride can modify tyrosine residues. 

Ludlam-Brown, 1. and York, P. (1993). The crystalline modification of succinic acid by variations in crystallization conditions. / Phys. D Appl. Phys., 26, B60-B65. [92] MacDonald, J. C. (1993). Hydrogen-bonded aggregates imidazole as a hydrogen-bond director with applications toward the design of solid-state materials. Ph.D. Thesis, University of Minnesota, Minneapolis, Minnesota. [58]... 

A detailed study on solvent effects relating to the growth of succinic acid crystals from water and isopropanol solutions was reported by Davey, Mullin and Whiting (1982). The faster growth of the (010) and (001) faces in water than in isopropanol resulted in a succinic acid habit modification from platelets to needles, as shown in Figure 6.36. Calculated a-factors for the two faces were found to be similar for both solvents, so the change of habit was considered to result from chemical interaction with the solvent. Succinic acid interacts, pre-... 

Myriant (United States) received a grant Irom the US Department of Energy for their activities on the production of bio-succinic acid. These activities include building of a 20 000 litre reactor in Louisiana, modification of a leased facility of 15 000 ton/year and the construction of a greenfield plant also with a capacity of 15 000 ton/year. The Myriant process uses E. coli and unrefined sugar as feedstock. 

As shown in Table III, the BDSA process offers significant advantages in two primary areas. First, the process has a significantly lower estimated production cost for BDO, succinic acid, and several other commodity chemicals, as well as lower energy consumption during production. Current com production could easily supply the 100 to 200 hundred million pounds of com sugar required for each major chemical plant, and use of this feedstock would decrease petroleum consumption and imports. Further analysis by ACC and New Horizon of the production cost for succinic acid in our fermentation process has included several process modifications to further decrease costs. The estimated costs in 1998 were 0.20/lb sodium succinate. However, the petrochemical routes to BDO have also had further improvements, increased capacity and presumably lowered the target price. 

A related method also involved an a-bromo-ketone. Succinic acid derivative ij.151) was brominated and then converted to the phthalimidoyl derivative 1.152). Acid hydrolysis gave ethyl S-amino-4-oxopentanoate, 1.153. Alkyl substituents can be incorporated into the backbone of oxo-amino acids by simple modification of the method just described. 

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