Succinic acid, manufacture

Succinic acid is one of the high-volume specialty chemicals. It is produced by the catalytic hydrogenation of petrochemical maleic acid or anhydride. However, due to cost reductions delivered via the production of succinic acid from the bacterial fermentation of carbohydrates, a large-volume commodity market could be realized. Presently, the bacterial strain used for succinic acid manufacturing is Escherichia coli. However, the requirement for lower costs is moving companies toward other microorganisms, such as Coryne-type bacteria and yeast. Succinic acid can be converted to 1,4-butanediol (EDO) and other products. It also serves as a raw material for diverse important chemicals, including polymers, polybutylene terephthalate, and polybutylene succinate. 

Colourless prisms m.p. 130 C. Manufactured by treating maleic anhydride with water. It is converted to the anhydride by heating at By prolonged heating at 150 "C or by heating with water under pressure at 200 C, it is converted to the isomeric (trans) fumaric acid. Reduced by hydrogen to succinic acid. Oxidized by alkaline solutions of potassium permanganate to mesotartaric acid. When heated with solutions of sodium hydroxide at 100 C, sodium( )-malate is formed. Used in the preparation of ( )-malic acid and in some polymer formulations. 

Although many variations of the cyclohexane oxidation step have been developed or evaluated, technology for conversion of the intermediate ketone—alcohol mixture to adipic acid is fundamentally the same as originally developed by Du Pont in the early 1940s (98,99). This step is accomplished by oxidation with 40—60% nitric acid in the presence of copper and vanadium catalysts. The reaction proceeds at high rate, and is quite exothermic. Yield of adipic acid is 92—96%, the major by-products being the shorter chain dicarboxytic acids, glutaric and succinic acids,and CO2. Nitric acid is reduced to a combination of NO2, NO, N2O, and N2. Since essentially all commercial adipic acid production arises from nitric acid oxidation, the trace impurities patterns ate similar in the products of most manufacturers. 

Pyrrohdinone (2-pyrrohdone, butyrolactam or 2-Pyrol) (27) was first reported in 1889 as a product of the dehydration of 4-aminobutanoic acid (49). The synthesis used for commercial manufacture, ie, condensation of butyrolactone with ammonia at high temperatures, was first described in 1936 (50). Other synthetic routes include carbon monoxide insertion into allylamine (51,52), hydrolytic hydrogenation of succinonitnle (53,54), and hydrogenation of ammoniacal solutions of maleic or succinic acids (55—57). Properties of 2-pyrrohdinone are Hsted in Table 2. 2-Pyrrohdinone is completely miscible with water, lower alcohols, lower ketones, ether, ethyl acetate, chloroform, and benzene. It is soluble to ca 1 wt % in aUphatic hydrocarbons. 

Succinic anhydride [108-30-5] (3,4-dihydro-2,5-furandione butanedioic anhydride tetrahydro-2,5-dioxofuran 2,5-diketotetrahydrofuran succinyl oxide), C H O, was first obtained by dehydration of succinic acid. In the 1990s anhydride is produced by hydrogenation of maleic anhydride and the acid by hydration of the anhydride, by hydrogenation of aqueous solutions of maleic acid, or as a by-product in the manufacture of adipic acid (qv) (see Maleic ANHYDRIDE, MALEIC ACID, AND FUMARIC ACID). 

Succinic acid reacts with urea in aqeous solution to give a 2 1 compound having mp 141°C (116,117), which has low solubiUty in water. A method for the recovery of succinic acid from the wastes from adipic acid manufacture is based on this reaction (118,119). The monoamide succinamic acid [638-32-4] NH2COCH2CH2COOH, is obtained from ammonia and the anhydride or by partial hydrolysis of succinknide. The diamide succinamide [110-14-3], (CH2C0NH2)2, nip 268—270°C, is obtained from succinyl chloride and ammonia or by partial hydrolysis of succinonitrile. Heating succinknide with a primary amine gives A/-alkylsucckiknides (eq. 9). 

One-Step manufacture of 2-pyiiolidinone can be effected by reaction of succinic acid or anhydride with NH and in the presence of Pd—AI2O2 catalyst in water or ether (120). 

Mixed esters containing the dicarboxylate moiety, eg, cellulose acetate phthalate, are usually prepared from the partially hydroly2ed lower aUphatic acid ester of cellulose in acetic acid solvent by using the corresponding dicarboxyhc acid anhydride and a basic catalyst such as sodium acetate (41,42). Cellulose acetate succinate and cellulose acetate butyrate succinate are manufactured by similar methods as described in reference 43. 

The manufacturing path of major monomers, succinic acid and 1,4-butanediol is shown in Fig. 15. Both monomers are manufactured from petroleum at the moment. There are several paths for the production of 1,4-butanediol. 

Twenty-five sorbents were screened for uptake of succinic acid. Table 1 lists the initial capacity for each of the sorbents as well as the type and manufacturer of the sorbents. 

Manufacturers also commonly convert the phenol form of the vitamins (with a free hydroxyl group) to esters, using acetic or succinic acid. The fortification of foods and feeds with oc-tocopherol esters is common because they are more stable and provide vitamin E activity when consumed. 

Hypromellose acetate succinate should be stored in a well-closed container, in a cool, dry place. In such storage conditions, hypromellose acetate succinate is a stable material. It is stable for four years after manufacturing. Hypromellose acetate succinate is hygroscopic. It is hydrolyzed to acetic acid and succinic acid, and the hypromellose polymer starts to form if dissolved in 1 mol/L sodium hydroxide for more than two hours. The hydrolysis is the main degradation pathway that is responsible for increasing amounts of free acids in storage, especially upon exposure to moisture. 

Succinic acid is currently manufactured by the hydrogenation of maleic anhydride to succinic anhydride, followed by hydration to succinic acid. A fermentation process for succinic acid production is desirable because in such processes, renewable resources such as starchy crops and other agricultural products can be used as feedstock for the biological production of succinic acid. It addition, a high purity product, which is required as raw material for polymer manufacture, can be obtained. 

About 5 billion pounds per year of adipic acid are manufactured worldwide by the nitric acid oxidation of cyclohexanone and/or cyclohexanol (KA). The KA to adipic acid yields are near 94% of theory. Glutaric and succinic acids are the major byproducts and account for most of the yield loss. Monsanto and some other adipic acid producers recover or upgrade these to salable b products resulting in an overall KA utilization efiflciency that approaches 99%. However, the nitric acid efficiency is lower because approximately 1 mole N2O is produced per mole of adipic acid, in addition to the easily recyclable NOx that is generated as a result of nitric acid reduction. 

Succinic acid, which has the structure HOOC— CH2—CH2—COOH and on a C-mole basis is represented by CH3/2O, is useful as a starting material in the manufacture of solvents and polymers. It is typically made by the catalytic oxidation of butane. However, by that route only about 40 percent of the carbon initially present in the butane is converted to succinic acid. It has been suggested instead to use glucose as a starling material and a biochemical pathway with the following proposed reaction stoichiometry ... 

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