Succinic acid physical properties

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. 

Physical properties of the acid and its anhydride are summarized in Table 1. Other references for more data on specific physical properties of succinic acid are as follows solubiUty in water at 278.15—338.15 K (12) water-enhanced solubiUty in organic solvents (13) dissociation constants in water—acetone (10 vol %) at 30—60°C (14), water—methanol mixtures (10—50 vol %) at 25°C (15,16), water—dioxane mixtures (10—50 vol %) at 25°C (15), and water—dioxane—methanol mixtures at 25°C (17) nucleation and crystal growth (18—20) calculation of the enthalpy of formation using semiempitical methods (21) enthalpy of solution (22,23) and enthalpy of dilution (23). For succinic anhydride, the enthalpies of combustion and sublimation have been reported (24). 

Table 1. Physical Properties of Succinic Acid and Succinic Anhydride...

The pronounced influence of the phenyl group on optical activity led Fredga and Palm" to initiate an investigation on the optical activity of thiophene derivatives, in order to use this physical property for the elucidation of the aromatic character of thiophene. 2-(27) and 3-Thenylsuccinic acid (28), 2- (29) and 3-thienyl-succinic acid (30), 2- (31) and 3-thienylglycolic acid (32), 2-(33) and 3-a-methoxythienylacetie acid (34), -phenyl 2-thienyl-glycolic acid (35), -(2-thienyl)-y5-phenylpropionic acid (36), a-phenyl- -(2-thienyl) propionic acid (37), a,/ -di (2-thienyl)propionic acid (38) have been resolved into antipodes with the help of optically active bases. 

As part of a more extensive study of cocrystals formed by isonicotinamide with carboxylic acids, 1 1 products containing the dicarboxylic fumaric or succinic acids [59]. In the structures of these particular cocrystals, the typical discrete dimeric synthon was not observed, but instead effectively infinite assemblies of one-dimensional chains were found instead. In a subsequent work, cocrystals of isonicotinamide containing mixed fumaric/succinic acids were prepared using both solid-state grinding and solution crystallization [60]. A full physical characterization of the products demonstrated that the products consisted of a single cocrystal phase, and were not simple physical mixtures of two cocrystal components. Such solid solutions were proposed as yet another method whereby one might obtain even finer control over the physical properties of cocrystal systems proposed as drug substances. 

One way of improving the physical and mechanical properties of the polymeric materials produced was to copolymerize the original monomers with stiffer comonomers, whose corresponding homopolymers are endowed with high thermal and mechanical properties. Therefore, 1,4-cyclohexanedimetha-nol was copolymerized with 1,3-propanediol and succinic acid. Segmented copolymers between oligofpropylene succinate)s and PEG were also produced in order to modify their hydrophilic/hydrophobic properties. 

Common Names of Dicarboxylic Acids A dicarboxylic acid (also called a diacid) is a compound with two carboxyl groups. The common names of simple dicarboxylic acids are used more frequently than their systematic names. A common mnemonic for these names is Oh my, such good apple pie, standing for oxalic, malonic, succinic, glutaric, adipic, and pimelic acids. The names and physical properties of some dicarboxylic acids are given in Table 20-2. 

Two acids are known to which these formulas are assigned. The cis form (formula 1) is given to maleic acid, and the trans form (formula 2) to fumaric acid. The two acids differ markedly in physical properties. Fumaric acid, which occurs somewhat widely distributed in plants, does not melt, but sublimes at about 200°. It is difficultly soluble in water. Maleic acid melts at 130°, is readily soluble in water and is a much stronger acid than fumaric acid (344). Both acids can be prepared by heating malic acid, which is a hydroxyl derivative of succinic acid. If the temperature is kept at between 130° and 150° fumaric acid is obtained when the acid is distilled, the chief product is the anhydride of maleic acid, which is readily converted into the acid by water. The reaction by which fumaric acid is obtained is represented by the equation,—... 

Reference materials for combustion calorimetry have been recommended by the lUPAC Commission Physicochemical Measurements and Standards [130-132] and by the ICTAC Thermochemistry Working Group [133]. They are classified as primary, secondary and tertiary reference materials and when their properties are certified by a national or international organization, agency or laboratory authorized they are called certified reference materials . For combustion calorimetry, the recommended reference materials must be selected according to the atoms in the molecule and its physical state [133] benzoic acid (C,H,0, cr, primary), succinic acid (C,H,0, cr, secondary), hippuric acid (C,H,0,N, cr, tertiary), acetanilide (C,H,0,N, cr, secondary), nicotinic acid (C,H,0,N, cr, tertiary), 1,2,4-triazole (C,H,0,N, cr, secondary)[134], urea (C,H,0,N, cr, tertiary), thiantrene (C,H,0,S, cr, secodary), 4-fluorobenzoic acid (C,H,0,F, cr, secondary), pentafluorobenzoic acid (C,H,0,F1, cr, tertiary), 4-chorobenzoic acid (C,H,0,C1, cr, secondary), 4-bromobenzoic acid (C,H,0,Br, cr, tertiary), 4-iodobenzoic acid (C,H,0,I, cr, tertiary), triphenylphosphine oxide... 

Papers concerning the physical properties of polymers as the guest components in urea inclusion compounds and polymerization reactions of guest monomer molecules within the urea tunnel structure have been reviewed elsewhere. The polymers studied included poly (ethylene), poly (acrylonitrile), poly (1,3-butadiene), poly(eth-ylene oxide), poly(tetrahydrofiiran), poly(acrolein), poly(vinyl chloride), poly(ethyl acrylate), poly(lactide), poIy(lactic acid), poly(ethylene adipate). poly(ethylene succinate), acrylonitrile-ethyl acrylate copolymer, and poly(hexanediol di acrylate). 

At the downstream side, the method of THF extraction is unlikely to be applicable on a large scale due to the low solubility of FDCA in this solvent. Well-established methods for the purification of, e.g., bio-based citric, glutamic, and succinic acid may serve as a starting point for optimization, although the specific physical properties of FDCA will eventually require a tailor-made purification process. 

In 2006, Yoon et al. studied the effect of additives such as glycerol, succinic acid, malic acid, and tartaric acid on the physical properties of starch/PVA blend films the results showed that the flexibility and strength of the films could be improved with alcohol and carboxylic acid functionalities. 

TABLE 9.2 Physical Properties of Succinic Acid (Lin et al., 2005a,b). Chemical Abstracts Service (CAS) number 110-15-6... 

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