Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1998-12-08
2000-12-26
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554 63, 554109, 554110, 159 49, 203 34, C07F 902
Patent
active
061662321
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The invention relates to a process for producing ester quats by direct esterification of quaternary ammonium salts with fatty acids.
Ester quats are quaternary ammonium compounds that are present as salts and, in addition to the quaternary ammonium function, exhibit an ester function.
Quaternary ammonium salts react readily under transfer of alkyl groups or under Hofmann elimination. Frequently, both reactions are observed in parallel. For Hofmann elimination, a base is required, and for dealkylation a nucleophile. Suitable as the base or nucleophile are the hydroxide ion and halogenide ions, among others. In the conversion of quaternary ammonium compounds with carboxylates as well, an O alkylation of the carboxylate is accompanied by the corresponding dealkylation of the ammonium component. Depending on the reaction partner, either the dealkylation or the elimination dominates (Hanhart and Ingold, J. Chem. Soc., 1927, 997, V. Meyer, M. Lecco, Liebigs Ann. 180, 184 (1876). W. Lossen, Liebigs Ann. 181, 377 (1876). J. A. Zoltewicz, L. W. Deady, Adv. Heterocycl. Chem. 22, 71 (1978). Lawson, Collie, J. Chem. Soc., 53, 624 (1888)).
For the same reason, quaternary ammonium salts are stable as phase transfer catalysts only up to temperatures of 100-150.degree. C. (D. Landini, A. Maia, A. Rampoldi, J. Org. Chem. 1986, 51, 3187-3191).
Choline chloride also exhibits these properties typical of quaternary ammonium compounds. When heated, it breaks down into (dimethylamino)ethanol and methyl chloride (Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., 1986, Vol. A7, 39) and, via Hofmann elimination, releases ethene (B. A. Kurchii, Fiziol. Biokhim. Kul't. Rast. 1991, 23(1), 17-23, from: Chemical Abstracts 1991; Vol. 114, 223451w).
The Russian Journal of Applied Chemistry, Vol. 67, No. 5, Part 2, 1994, 734-736, describes the Hofmann elimination of choline ester quats.
Consequently, in the direct esterification of choline chloride with fatty acids, both the Hofmann elimination to trimethylamine and ethene and further to the vinyl ester of the corresponding fatty acid, as well as a dealkylation to (dimethylamino)ethanol and further to the (dimethylamino)ethyl ester of the corresponding fatty acid and to methyl chloride and fatty-acid methyl ester can be expected. Moreover, the quaternary ammonium group exercises a -I effect on the hydroxyl function so that the latter is inactivated for esterification (Methoden der organischen Chemie (Houben-Weyl) 1958, Stickstoff-Verbindungen II und III, 631).
For these reasons, industrial synthesis of a choline ester is not performed via direct esterification of choline chloride with the corresponding carboxylic acid. Rather, in a two-stage synthesis, (dimethylamino)ethanol is first converted with the corresponding acid, and the ester is then quaternized with methyl chloride or dimethyl sulfate (Huadong Huagong Xueyuan Xuebao (1993), 19(5), 594-9). These quaternization reagents are highly toxic and also lead to methylation of the solvent.
A single-stage synthesis is described in Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol. (1971), 14(9), 1369-73, whereby choline chloride is converted with fatty-acid chlorides. Acid chlorides, however, must have previously been produced from the free acids, so that the raw-material price is significantly higher. Moreover, they are corrosive, sensitive to moisture, and difficult to handle due to their high reactivity, so that they can be used industrially only at considerable expense. As a result, such choline ester quat synthesis is not economical.
Likewise uneconomical is the transformation of fatty-acid(2-chloroethyl) ester with trimethylamine, since the ester must be produced prior to quaternization (Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. (1977), 20(8), 1243-5).
Compounds of this type are also described, for example, in WO 91/01295. According to the process described therein, an esterification of a fatty acid with an alkanolamine is first conducted, and the ester obtained is quaternized with substances such as dimethyl s
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Methoden der organischen Chemie (Houben-Weyl) 1958, Stickstoff-Verbindungen II und III, p. 631.
Suo, Fuxi et al., "Synthesis and antistatic effect of quaternary ammonium salts of fatty ester," Huadong Huagong Xueyuan Xuebao, 1993, 19(5), pp. 594-599.(Abstract only).
Komkov, I.P. et al., "Surface-active quaternary ammonium salts of 0-acylcholines," Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol., 1971, 14(9), pp. 1369-1373. (Abstract only).
Vorona, N. I. et al., "Synthesis of surface-active acylcholine chlorides," Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol., 1977, 20(8), pp. 1243-1245.(Abstract only).
Ahrens Hartmut
Bergfeld Manfred
Carstens Axel
Akzo Nobel nv
Killos Paul J.
Oh Taylor
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