Succinic acid esters

Following the synthesis of the sodium, potassium, and succinic acid esters of CA-4, which were not soluble in water [35], CA-4P (9), the disodium phosphate pro-drug was developed and is currently in phase II of clinical trials [36]. CA-4P is a promising candidate for combination anti-cancer therapy because it is inactive as a phosphate but is rapidly hydrolyzed in vivo to the active CA-4, 7 compound [31,37]. 

The DuPont company used the succinic acid ester process, in which diethyl succinate is first cyclised to diethyl succinylsuccinate (2.39) in a sodium/alcohol mixture. One mole of the product is next condensed with two moles of aniline under oxidising conditions, forming diethyl 2,5-dianilino-3,6-dihydroterephthalate (2.40). Ring closure at 250 °C gives dihydroquinacridone, from which quinacridone is obtained by oxidising away the two extra hydrogen atoms. 

The fourth synthesis, developed by the Swiss Lonza company and known as the diketene process, resembles the succinic acid ester process of DuPont in that the central ring of the... 

According to Thurston (702), the lower dibasic esters yield pure carbox5unonoguanamines so readily that this reaction is an excellent synthetic route, when confined to the lower esters. It has been apphed to 1-aryl- and alkyl-biguanides as usual, and to the alkali metal salts of half esters. The reaction involving diethyl malonate is represented below succinic acid esters (292, 699) react similarly. 

CH2,CH2,C02Et. From the latter the three-carbon unit of diethyl succinate may be recognised, and the Stobbe condensation is a suitable illustration of this process. Thus the reaction of aldehydes or ketones with succinic esters in the presence of potassium t-butoxide (or with sodium hydride) gives alkylidene-succinic acid esters (25). The reaction is somewhat slower in the case of the less basic sodium ethoxide. 

Succinylated Monoglycerides occur as waxy solids having an off white color. They are a mixture of succinic acid esters of mono- and diglycerides produced by the succinylation of a product obtained by the glycerolysis of edible fats and oils, or by the direct esterification of glycerol with edible fatforming fatty acids. They melt at about 60°. They are soluble in warm methanol, in ethanol, and in n-propanol. 

Knorr, L. Synthesis of furan derivatives from succinic acid esters. Ber. 1884, 17, 2863-2870. 

Not unexpectedly, marine crankcase oils are sometimes contaminated with water, which is normally removed by the lubricating oil centrifuge. To assist further in protecting against rusting, inhibitors such as alkyl sulphonates, phosphonates, amines and alkyl succinic acids/esters can be added. They work by forming a hydrophobic film on the metal surface but must be selected with due regard to the other additives present. 

Alkylation of succinic acid esters 4-Iiydroxy-2-naphthoic acids s. 1, 645... 

Piperidazine derivative (491) treated with substituted succinic acid ester chloride (490) provides (492). The intermediate after deprotection with hydrogen bromide in acetic acid is cyclized into (493) by a sequential treatment with phosphorus pentachloride and pyridine (Scheme 104) <84JCS(Pl)l55>. 

A rhodium complex with chiral phosphane ligand was also intercalated into sodium hectorite by cation exchange (Sento et al. ). The intercalated compound was characterized by FTIR, XRD, and TEM and the basal spacing of the compound was estimated to be 2.29 nm. This novel het-erogenized eatalyst exhibited a characteristic chiral as well as size recognition of the substrate molecule (like the "Tailor-made compounds" method used earlier by Balandin in the hydrogenation of tripticene derivatives over Ni) and was used in enantioselective hydrogenation of the itaconates (methylene-succinic acid esters). 

Miglyol 829 Tricaprylic acid, capric acid, and succinic acid esters of glycerol — Tween 80 PEG-20 sorbitan monooleate 15... 

Definition Propylammonium dimethicone amine salt of the succinic acid ester of a polyoxypropylene, polyoxyethylene ether of glycerin... 

Definition Mixt. of semi- and neutral succinic acid esters of mono- and diglycerides produced from edible fats and oils or edible fatty acids Properties M.p. 50-60 C HLB 5-7 acid no. 70-120 HLB 5.0-7.0... 

Moreover, succinic acid is also a platform chemical used as a precursor of many commodity or specialty chemicals, including adipic acid, 1,4-butanediol, tetrahydro-furan, N-methyl pyrroUdinone, 2-pyrrohdinone, succinic acid esters, succinate salts, and y-butyrolactone (Fig. 1) The derivatives of succinic acid are estimated have a maiket potential of 270,000 tons per year (Zeikus et al. 1999 Willke and Vorlop 2004). 

Cyclohexa-l,4-diene-l,4-diols from 2 succinic acid ester molecules... 

When Bruni shows that dimethyl succinate crystallizes with dimethyl fumarate, it means that the succinic acid ester has a structure resembling the trans-form, i.e. must have a zig-zag form—at least, as long as it is incorporated in the fumarate crystal. 

Succinic acid esters of monoglycerides (SMG) are anionic active emulsifiers made by reacting saturated Cie/Cis fatty acid monoglycerides (preferably distilled) with pure succinic anhydride at a ratio of approximately 4 1 by weight for about 1 h at 120 °C. The resulting succinic acid half ester of monoglycerides has a free carboxyl group which may be partially neutralized with alkali. 

Sodium bis(trimethylsilyl) amide Succinic acid esters from 3-acyl-2-oxazolidones via asym. a-carbalkoxymethylation... 

The author was responsible for the investigation of the reactions of halo-dicarboxylic acid esters, such as halo-succinic acid esters and halo-methylsuccinic acid esters [5]. 

Organotin, organolead, and organogermanium complexes have been prepared from phthalate or succinate acid esters derived from sucrose. ... 

Succinic acid esters (s. a. Acyl-succnic acid esters. Diethyl succinate)... 

DicarboxyNc Acid dl- kar- bak- si-lik n Any of a large family of organic acids containing two carboxylic (-COOH) groups. Those of greatest importance in the plastics industry are the adipic, azelaic, glutaric, pimelic, sebacic, and succinic acids, esters of which are widely used as plasticizers that impart low-temperature flexibility. They are also used in the production of alkyd and polyester resins, polyurethanes, and nylons. 

---