Alkyl lactate esters

Among other surface active esters, polyglycol esters of fatty acids, alkanoyl glycerol acetates and lactates, alkyl lactates, esters of fatty acids and pentaerythritol, glucose, methylglucose, mannose, sucrose, and, especially, sorbitol are often exploited. The latter, sorbitan acylates, are particularly known as Spans , Arlacels , and Arlamol ISML - all of ICI production. These mild and low-toxic emulsifiers are widely applied in food, pharmaceutical, personal care and other consumer and industrial products. 

Within this group of surfactants we can mention the fatty acid esters of lactic acid, lactylates (esters of the fatty acid with the hydroxyl group of lactic acid and lactylates) and the alkyl lactates (esters of the lactic acid with a fatty alcohol) (Figure 5.6), all of them commercially available as safe products for food and personal care formulations. Some examples of manufacturers are Eurolabs Limited, Stepan Co., Cognis GmbH and Spectrum Chemical Mfg Corp. 

Reaction of a metal lactate (such as silver lactate) with an alkyl haUde is a classic method of preparation of the ester, but it is too expensive to be of commercial relevance. Lactamide [2043-43-8] is another high yielding condensation product from lactic acid. It can be produced by aminolysis of dilactide or lactate ester such as methyl or ethyl lactate. 

Rehberg, C. E. and M. B. Dixon, Mixed Esters of Lactic and Carbonic Acids n-Alkyl Carbonates of Methyl and Butyl Lactates, and Butyl Carbonates of n-Alkyl Lactates. J. Org. Chem., 1950 15, 565-571. 

Similar straight-line correlations between aqueous solubility and Nc or M have been found for certain homologous series of mono- and multifunctional compounds such as 1-alkanols, 2-alkanols [6], 2-alkanones [9], n-alkyl acetates [10], n-alkyl /3-ethoxypropionates [11], n-alkyl a-acetoxypropionates, and n-alkyl lactates [12]. In contrast, Sobotka and Kahn [13] have found significant deviations from simple linear correlations with Nc for the series of ethyl esters of monocarbonic acids. They report a zig zag curve caused by the relatively higher solubility of the members with odd values for Nq- The odd-even effect is discussed in detail by Burrows [14], with further examples provided. 

Alkylene bromide, 20, 24 Alkylene thioureas, 26, 35 Alkylidenecyanoacetic esters, 25, 48 Alkyl lactate, 26, 6 Alkyl phenyl selenides, 24, 91 S-Alkylthiuronium halides, 22, 60 d/-ALLOTHREONINE, 20, 104 Alloxan, 23, 3... 

Neutral Wilkinson type catalysts with chiral ligands are quite effective for the hydrogenation of C=0 bonds in prochiral 2-oxocarbo Q lic acids or their esters and are applied to the as5mimetric S5mthesis of 2-hydroxyesters with rather high ee s of up to 80-95%. The reduction of alpha- iQ o esters, such as alkyl-pymvates into alkyl-lactates (Scheme 7.18.) on chiral complexes is one of the most important methods of the synthesis of chiral synthones for practical use. 

See Cl 2-13 alkyl lactate 2-Hydroxypropanoic acid, dodecyl ester. See Lauryl lactate... 

Propanoic acid, 2-hydroxy-, C12-13 alkyl ester. See C12-13 alkyl lactate... 

Propanoic acid, 2-hydroxy-, C12-15 alkyl esters. See C12-15 alkyl lactate Propanoic acid, 2-hydroxy-, compd. with N-[3-(dimethylamino) propyl] docosanamide (1 1). See Behenamidopropyl dimethylamine lactate Propanoic acid, 2-hydroxy-, compd. with [R-(Z)]-N-[3-(dimethylamino) propyl]-12-hydroxy-9-octadecenamide (1 1). See Ricinoleamidopropyl dimethylamine lactate Propanoic acid, 2-hydroxy-, compd. with N-[3-(dimethylamino) propyl]-16-methylheptadecanamide (1 1). See Isostearamidopropyl dimethylamine lactate Propanoic acid, 2-hydroxy-, compd. with N-[3-(dimethylamino) propyl] octadecanamide. See Stearamidopropyl dimethylamine lactate Propanoic acid, 2-hydroxy-, compd. with N-[3-(dimethylamino) propyl]-9-octadecenamide (1 1). See Oleamidopropyl dimethylamine lactate... 

Owing to their importance on the commercial scale, the production of lactic acid and PLA will increase (Wee et al., 2006). Because of its reactive structure, the role of lactic acid as a platform chemical is very attractive (Fan et al., 2009). Corma et al. (2007) described many chemical and biotechnological routes that can help transform lactic acid into valuable chemicals. Its potential application is well reviewed by Varadarajan and Miller (1999), Corma et al. (2007), and Fan et al. (2009). Lactic acid has been used for the production of linear esters (alkyl lactates), which possess unique solvation properties. 

Methylsuccinic acid has been prepared by the pyrolysis of tartaric acid from 1,2-dibromopropane or allyl halides by the action of potassium cyanide followed by hydrolysis by reduction of itaconic, citraconic, and mesaconic acids by hydrolysis of ketovalerolactonecarboxylic acid by decarboxylation of 1,1,2-propane tricarboxylic acid by oxidation of /3-methylcyclo-hexanone by fusion of gamboge with alkali by hydrog. nation and condensation of sodium lactate over nickel oxide from acetoacetic ester by successive alkylation with a methyl halide and a monohaloacetic ester by hydrolysis of oi-methyl-o -oxalosuccinic ester or a-methyl-a -acetosuccinic ester by action of hot, concentrated potassium hydroxide upon methyl-succinaldehyde dioxime from the ammonium salt of a-methyl-butyric acid by oxidation with. hydrogen peroxide from /9-methyllevulinic acid by oxidation with dilute nitric acid or hypobromite from /J-methyladipic acid and from the decomposition products of glyceric acid and pyruvic acid. The method described above is a modification of that of Higginbotham and Lapworth. ... 

Preliminary investigations into the generality of this synthesis of lactate-derived ketones using other alkyl lithium reagents including butyllithium and phenyllithium have not been as successful. Product mixtures were typically contaminated with significant amounts of both the tertiary alcohol and the starting ester. 

Ethylbenzene under Benzene and Monosubstituted Benzene Hydrocarbons Ethyl Chloride Chloroethane under Saturated Alkyl Halides Ethyl Lactate Hydroxypropanoic Acid, Ethyl Ester under Esters Ethylene under Alkenes, Cyclic Alkenes, and Dienes... 

Asymmetric reduction of a-keto esters. / lkyl pyruvates are rapidly reduced by this borane to alkyl (S)-lactates (equation I). The jxtent of asymmetric induction depends to some extent on the temperature and the size if the ester group. Quantitative optical... 

---