Succinic acid: anhydride from

A mixture consisting of 8 grams of estriol, 20 grams of succinic acid anhydride and 60 ml of pyridine is heated at 90 C for 4 hours, after which the reaction mixture is poured into water. The aqueous solution is extracted with ether, the ether layer is separated, washed with diluted sulfuric acid and after that with water until neutral, then evaporated to dryness to obtain 14 grams of an amorphous substance. Melting point 82° to 86°C. This drying residue proves to consist of a mixture of estriol disuccinate and estriol monosuccinate, which are separated by repeated crystallization from a mixture of methanol and water. 

Succinic Acid-Mono [3-Nitryloxy-2,2-Bis-Nitryloxymethyl-Propylester] (or 0-[-3- Car-boxy-propionyl]-0, 0 ,0w-trinitro-pentaerythritol). C9H, 3N30 3 mw 371.25 N 11.32% OB to C02 —49,65% cryst (from ethanol) mp 92— 92.5°. Prepn is by warming succinic acid anhydride with 0,0 0f,-Pentaerythritol Trinitrate (see in Vol 8, P84-R to 86-L) in acet. Its expl... 

The relationship between Tg and (q(E.) has been calculated from Eq. (9) for

cured resins with different e are shown in Fig. 4. The curing agents used are DETA 25), EDA 26), and DDM 8) as a diamine, succinic acid anhydride (Sue A)21) as an acid anhydride and 2-ethy 1-4-methyl imidazole (Im) 21) as a catalytic curing agent. 

In addition, there are reports of the following syntheses 4,5-dimethoxycanthin-6-one (8) from I-methoxy methyl-)8-carboline and succinic acid anhydride (96), 1 using 4-oxo-1,4,6,7,12,12b-hexahydroindo... 

Besides the more often-used acyl donors mentioned above, others which would also ensure an irreversible type of reaction have been investigated [170]. Bearing in mind that most of the problems of irreversible enzymatic acyl transfer arise from the formation of unavoidable byproducts, emphasis has been put on finding acyl donors that possess cyclic structures, which would not liberate any byproducts at all. However, with candidates such as lactones, lactams, cyclic anhydrides (e.g., succinic acid anhydride [171]), enol lactones (e.g., diketene [172, 173]), and oxazolin-5-one derivatives [174], the drawbacks often outweighed their merits. 

Alkyd resins completely based on renewable resources have been the subject of a few studies. EP 0741 175 A2 to Hoechst describes waterborne alkyd emulsions based on renewable resources. The patent describes the use of sorbitol (easily derived from starch) as the polyhydric alcohol part and succinic acid anhydride as the polycarboxylic acid part. Hajek described the use of sorbitol and xylitol in alkyd resin synthesis, whereas Bagchi et al. described the partial replacement of conventional polyols, i.e., glycerol and pentaerythritol, by sorbitol. 

To distinguish these anhydrides from the corresponding acids, note that succinic anhydride (m.p. 120°) is almost insoluble in cold water, whereas succinic acid (m.p. 185 ) is readily soluble. Phthalic anhydride has m.p. 132° and phthalic acid has m.p. 196-199° with decomposition. Each of these anhydrides when heated with water hydrolyses to the corresponding acids. 

Method B. In a 500 ml. round-bottomed flask, provided with a reflux condenser protected by a cotton wool (or calcium chloride) drying tube, place 59 g. of succinic acid and 102 g. (94-5 ml.) of redistilled acetic anhydride. Reflux the mixture gently on a water bath with occasional shaking until a clear solution is obtamed ca. 1 hour), and then for a further hour to ensure the completeness of the reaction. Remove the complete assembly from the water bath, allow it to cool (observe the formation of crystals), and finally cool in ice. Collect the succinic anhydride as in Method A. The yield is 45 g., m.p. 119-120°. 

Cydopentane reagents used in synthesis are usually derived from cyclopentanone (R.A. Ellison, 1973). Classically they are made by base-catalyzed intramolecular aldol or ester condensations (see also p. 55). An important example is 2-methylcydopentane-l,3-dione. It is synthesized by intramolecular acylation of diethyl propionylsucdnate dianion followed by saponification and decarboxylation. This cyclization only worked with potassium t-butoxide in boiling xylene (R. Bucourt, 1965). Faster routes to this diketone start with succinic acid or its anhydride. A Friedel-Crafts acylation with 2-acetoxy-2-butene in nitrobenzene or with pro-pionyl chloride in nitromethane leads to acylated adducts, which are deacylated in aqueous acids (V.J. Grenda, 1967 L.E. Schick, 1969). A new promising route to substituted cyclopent-2-enones makes use of intermediate 5-nitro-l,3-diones (D. Seebach, 1977). 

From the chemical point of view, succinic acid and its anhydride are characterized by the reactivity of the two carboxyUc functions and of the two methylene groups. Uses range from pharmaceuticals to food, detergents, cosmetics, plastics and resins, plant growth regulators, textiles, photography, and gas and water treatment. 

Succinic acid is absorbed from aqueous solutions by anion-exchange resins or active carbon (9—11). Succinic anhydride forms rhombic pyramidal or bipyramidal crystals. It is relatively insoluble in ether, but soluble in boiling chloroform and ethyl acetate. Succinic anhydride reacts with water and alcohols, giving the acid and monoesters, respectively. 

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). 

Succinyl chloride [543-20-4] is obtained from phosphorous pentachloride and succinic acid, from thionyl chloride and succinic acid or anhydride (91,92), or from phosgene and succinic anhydride (93). 

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). 

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). 

Succinic acid and succinic anhydride are sold in 25-kg net polyethylene (PE) bags having cardboard box protection for the anhydride, in 70-liter (50-kg net) fiber dmms, and in 55-gaHon (275-lb 125-kg net) dmms. The two products must be stored in a fresh, dry, ventilated area. Succinic anhydride must be carefully protected from moisture during transportation and storage to avoid hydrolysis to succinic acid. 

Various methods can be used to analy2e succinic acid and succinic anhydride, depending on the characteristics of the material. Methods generally used to control specifications of pure products include acidimetric titration for total acidity or purity comparison with Pt—Co standard calibrated solutions for color oxidation with potassium permanganate for unsaturated compounds subtracting from the total acidity the anhydride content measured by titration with morpholine for content of free acid in the anhydride atomic absorption or plasma spectroscopy for metals titration with AgNO or BaCl2 for chlorides and sulfates, respectively and comparison of the color of the sulfide solution of the metals with that of a solution with a known Pb content for heavy metals. 

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 symmetrical dialkyl succinic acids exist in tw o forms, each yielding a separate anhydride. From their similaritv to... 

The author is aware that there is a difficulty here, for he states that this result from (102) may be due to some accidental arrangement of atoms however, it is not possible with any arrangement of atoms in his unit to explain the observed reflection. The analogy suggested to (100) of succinic acid and (010) of succinic anhydride [Yardley, Proc. Roy. Soc., 105A, 451 (1924)] is not pertinent, for in these cases dajod- is twice d/ 0b -> not one-half of it. 

Convincing evidence for a surface erosion process is shown in Fig. 8, which shows the concomitant release of the incorporated marker, methylene blue, release of the anhydride excipient hydrolysis product, succinic acid, and total weight loss of the device. According to these data, the release of an incorporated drug from an anhydride-catalyzed erosion of poly (ortho esters) can be unambiguously described by a polymer surface erosion mechanism. 

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. 

The principles set forth above account reasonably well for the course of bifunctional condensations under ordinary conditions and for the relative difficulty of ring formation with units of less than five or more than seven members. They do not explain the formation of cyclic monomers from five-atom units to the total exclusion of linear polymers. Thus 7-hydroxy acids condense exclusively to lactones such as I, 7-amino acids give the lactams II, succinic acid yields the cyclic anhydride III, and ethylene carbonate and ethylene formal occur only in the cyclic forms IV and V. 

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