Succinic acid, anhydride preparation

Dihydroanthracene-9,10-a,p-succinic Acid Anhydride Preparation Using a Monomode Microwave Apparatus... 

The dispersants prepared by the reaction of hydrocarbon substituted succinic acid anhydrides with polyamines to give linear mono- and bis-succinimides, are well known lubricating oil additives commercially available (Gutierrez and Brois, 1980 Le Suer and Norman, 1965 and 1966 Song et al., 1993, 1994 and 1995). 

Oxadiazole has been prepared by heating glyoxal dioxime with succinic acid anhydride at 150-170°C. For the synthesis of substituted compounds, mere heating is sufficient in some cases, whereas the action of thionyl chloride in 1,2-dichloroethane gives good results in others. 

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. 

Succinic anhydride can be prepared from succinic acid by dehydration it operates in high boiling solvent (31), in the presence of clays as a catalyst (32), or at room temperature with triphosgene (33). 

The total consumption of succinic acid and succinic anhydride in 1990 was 1,500 t in the United States, 2,500 t in Europe, 7,500 t in Japan, and 1,500 t in other countries. Production was 500 t in the United States, 2,500 t in Europe, and 11,000 t in Japan. The total installed capacity is in the 18,000—20,000-t/yr range. The total consumption decreased slightly between 1990 and 1994 mainly because of the replacement of succinic acid by fumaric acid in bath preparations, which is one of the main uses of succinic acid in Japan. The principal producers are Buffalo Color in the United States, Lon2a SpA and Chemie Tin 2 in Europe, Kawasaki Kasei, Nippon Shokubai, Takeda Chemical, Kyowa Hakko, and New Japan Chemical in Japan. 

Friedel-Crafts Acylation. The Friedel-Crafts acylation procedure is the most important method for preparing aromatic ketones and thein derivatives. Acetyl chloride (acetic anhydride) reacts with benzene ia the presence of aluminum chloride or acid catalysts to produce acetophenone [98-86-2], CgHgO (1-phenylethanone). Benzene can also be condensed with dicarboxyHc acid anhydrides to yield benzoyl derivatives of carboxyHc acids. These benzoyl derivatives are often used for constmcting polycycHc molecules (Haworth reaction). For example, benzene reacts with succinic anhydride ia the presence of aluminum chloride to produce P-benzoylpropionic acid [2051-95-8] which is converted iato a-tetralone [529-34-0] (30). 

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. 

FIGURE 8 Cumulative release of methylene blue (o), [1,4 - 14c] succinic acid (a), and polymer weight loss ( ) from polymer discs prepared from 3,9-bis(ethylidene-2,4,8,10-tetraoxaspiro[5,5Jundecane) and a 50 50 mole ratio of trans - cyclohexane dimethanol and 1,6-hexanediol at pH 7.4 and 37°C. Polymer contains 0.1 wt% [1,4 — [succinic anhydride and 0.3 wt% methylene blue. (From Ref. 

Hydroxamic acids are an important class of compounds targeted as potential therapeutic agents. A-Fmoc-aminooxy-2-chlorotrityl polystyrene resin 61 allowed the synthesis and subsequent cleavage under mild conditions of both peptidyl and small molecule hydroxamic acids (Fig. 14) [70]. An alternative hydroxylamine linkage 62 was prepared from trityl chloride resin and tV-hydroxyphthalimide followed by treatment with hydrazine at room temperature (Scheme 30) [71]. A series of hydroxamic acids were prepared by the addition of substituted succinic anhydrides to the resin followed by coupling with a variety of amines, and cleavage with HCOOH-THF(l 3). 

Block (cap) residual lysine residues with a carboxylic acid by acylation using succinic anhydride prepared in l-methyl-2-pyrrolidinone,... 

Octahydrodibenzothiophene (73) has been prepared by the following sequence. Friedel-Crafts acylation of 4,5,6,7-tetra-hydrobenzo[6]thiophene with succinic anhydride (87%) or with the ester chloride of succinic acid followed by hydrolysis (80%), yields the keto acid (74). Huang-Minlon reduction of 74 followed by cyclization of the derived acid chloride with stannic chloride yields l-keto-1,2,3,4,6,7,-8,9-octahydrodibenzothiophene (53) (Section V,A). Reduction of 53 gives 73 as a solid (overall yield 32%). 

Methyl- 1,3-cyclopentanedione is a key intermediate for the total synthesis of steroids.2 A number of methods have been described for its preparation, among them the condensation of succinic acid with propionyl chloride,3 and that of succinic anhydride with 2-buten-2-ol acetate,4 both in the presence of aluminum chloride. It has also been obtained from 3-methylcyclopentane-1,2,4-trione by catalytic hydrogenation5 and Wolff-Kishner reduction 6 The base-promoted cyclization of 4-oxohexanoic acid ethyl ester and diethyl propionylsuccinate with tertiary alkoxides was first reported by Bucourt.7 The present cyclization process provides an experimentally simple route to 2-methyl-1,3-cyclopentanedione. Using the same procedure, 4-oxoheptanoic acid ethyl ester has been cyclized to give 2-ethyl-l,3-cyclopentanedione in 46% yield... 

A 72 per cent yield of succinic anhydride was obtained by treatment of succinic acid with acetic anhydride according to the method for preparing benzoic anhydride (Org. Syn. 3, 21). 

Succinic anhydride has been obtained by distillation of succinic acid with phosphorus pentachloride, or from benzoyl chloride and sodium succinate.1 It has been prepared from succinic acid and phosphorus oxychloride or phosphorus pentachloride 2 by distillation of succinic acid with phosphorus pent-oxide 3 from acetyl chloride and barium succinate, or from sue-cinyl chloride and sodium acetate 4 from ethyl succinate and benzoyl chloride 5 from succinic acid and acetyl chloride, or from sucdnyl chloride and oxalic acid 6 from succinic acid and suc-cinyl chloride from succinic acid and acetic anhydride 7 from succinic add and acetyl chloride 8 and from sodium succinate and acetic anhydride.9... 

Methyl hydrogen succinate has been prepared by heating succinic acid with methyl succinate,2 by treating ethyl succinate with sodium methoxide,3 and by heating succinic anhydride with methanol.4 5 ... 

The preparation of maleic anhydride (U.S.P., 1,515,299) by the oxidation of benzene by oxygen in presence of V205 constitutes an important industrial development, the anhydride being converted into succinic acid by reduction with hydrogen and nickel (U.S.P., 1,491,465), and into malic acid by hydration. 

Diphenylocta-1,3,5,7-tetraene can be prepared (Expt 6.140) by condensing two mols of cinnamaldehyde with succinic acid in the presence of acetic anhydride and lead oxide, in a reaction which bears similarities with those of the Perkin type discussed above. 

The hydrogen succinates are prepared by procedures closely similar to those followed for the phthalates, except that succinic anhydride is used.10 The crude ester is best taken up at once in ether or benzene, and the solution is washed with water to remove succinic acid. The hydrogen succinates are more soluble in the usual solvents than the corresponding phthalates and often do not crystallize readily. Their alkaloid salts also... 

Process chemists studied an approach to 8 using the readily available indan-1-one-3-carboxylic acid 20 prepared from phenyl succinic anhydride via Friedel-Crafts closure (Scheme 6). After esterification (yielding 21), homologation of the carbonyl via aminomethylation proceeded in high efficiency to give 25. In the presence of... 

A very convenient method of preparation is that of ANSCHUTZ, Ann. 226, 8 (1884). In a i-l. round-bottomed flask fitted with a reflux condenser and a gas trap (Org. Syn. 14, 2) are placed 118 g. (1 mole) of succinic acid and 215 cc. (235 g., 3 moles) of acetyl chloride, and the mixture is gently refluxed on the steam bath until the solid is all dissolved (1.5-2 hours). The solution is allowed to cool undisturbed and finally cooled in an ice bath. The anhydride, which separates in beautiful crystals, is collected on a Buchner funnel, washed with two 75-cc. portions of ether, and dried in a vacuum desiccator. The yield of material melting at 118-1190 is 93-95 g. (93-95 per cent of the theoretical amount). 

Diorgano tellurium dicarboxylates were prepared from dialkyl and diaryl tellurium derivatives. Aliphatic carboxylic acids, aromatic carboxylic acids, their sodium or silver salts, and carboxylic acid anhydrides were used as reagents. Dicarboxylic acids such as succinic acid and phthalic acid were reported to give monomeric carboxylates when... 

Swelling data for macronet crosslinked polyesters were reported by Takahashi [144], His polymers were prepared by causing a mixture of propylene glycol and an equivalent amount of diacid (maleic anhydride plus succinic acid) to undergo... 

Sodium amalgam serves to reduce selectively the double bond in an olefinic acid containing the thiophene or furan ring. " This reagent is also employed to prepare olefinic acids by partial reduction of certain polyenoic acids, e.g., 3-pentenoic acid (60%) from vinylacrylic acid. Among the dibasic acids prepared by this method are succinic acid from maleic acid (98%) by catalytic hydrogenation over Raney nickel catalyst and alkylsuccinic acids from alkenylsuccinic acids made by the Diels-Alder reaction of simple olefins and maleic anhydride. ... 

Starches have been chemically modified to improve their solution and gelling characteristics for food applications. Common modifications involve the cross linking of the starch chains, formation of esters and ethers, and partial depolymerization. Chemical modifications that have been approved in the United States for food use, involve esterification with acetic anhydride, succinic anhydride, mixed acid anhydrides of acetic and adipic acids, and 1-octenylsuccinic anhydride to give low degrees of substitution (d.s.), such as 0.09 [31]. Phosphate starch esters have been prepared by reaction with phosphorus oxychloride, sodium trimetaphosphate, and sodium tripolyphosphate the maximum phosphate d.s. permitted in the US is 0.002. Starch ethers, approved for food use, have been prepared by reaction with propylene oxide to give hydroxypropyl derivatives [31]. 

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