Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1996-04-16
1999-02-16
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
584134, 584135, 584138, 584141, C07C 5116
Patent
active
058722670
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/01865 filed Jun. 8, 1994.
The present invention relates to a process for producing an omega-functionalized aliphatic carboxylic acid that has over 7 carbon atoms and to the intermediate products of this process.
More particularly, the present invention relates to the production of aliphatic carboxylic acids that have more than 7 carbon atoms and can be used in the production of polyamides with a large number of carbon atoms, even more particularly polyamides with 9 carbon atoms (nylon 9 and nylon 6,9). These polyamides are particularly appreciated due to their mechanical and elastic characteristics. Despite this, current worldwide industrial production of polyamide 9 is practically nonexistent due to lack of an industrially feasible process for producing 9 amino nonanoic acid with the required degree of purity.
The present invention furthermore relates particularly to the production of 1,9-nonandioic acid (azelaic acid), which is used in the field of lubricants, polyester and alkyd resins, as plasticizer and as a drug for dermatological use, and in the production of polyamide 6,9.
A process for oxidizing ketones, including cyclic ketones, by using permonosulfuric acid as an oxidizing agent has been known since the last century as the Baeyer-Villiger reaction (A. Von Baeyer and V. Villiger, Ber. 1899, 32, 3265; 1400, 33, 858). Other oxidizing agents have been used for this reaction, such as for example: peracetic acid, described by R. Criegel (Liebig Annalen, 1948, 560, 127) and in UK patent No. 1,203,752, peracid salts such as magnesium permonophthalate described in Syntesis 1015-1017, 1987, or persalts such as sodium perborate, described in U.S. Pat. No. 4,988,825, whereas the agent used most is m-chloroperbenzoic acid. More recently, methods have been described for synthesizing lactones from ketones, using molecular oxygen in the presence of catalysts, Tetrahedron Lett. 33,75557-60, 1992. In general, the synthesis of lactones starting from cyclic ketones has unpredictable regioselectivity and chemoselectivity.
Processes for producing polyamides 9 are known and are described by K. A. Pollart and R. E. Miller, (J. Am. Chem. Soc., 27, 2392, 1962), by William R. Miller et al. (Ind. Eng. Chem. Prod. Res. Develop., Vol 10, No. 4, 1971) and by R. B. Perkins, Jr. et al. (Journal of the American Oil Chemists' Society, Vol 52, November 1975); processes for producing azelaic acid are also known and described in Ullmann's Encyclopedia of Industrial Chemistry, fifth edition, volume A 8, pages 523-539, and in the Kirk-Othmer Enc., Vol. 7, page 623. These known processes are all based on a complex process for the ozonolysis of fatty acids of natural origin such as oleic acid or soya oil. The ozonolysis step is delicate and intrinsically dangerous and produces, at the end of the process, a mixture of unsaturated products that are very difficult to purify and for which purification is in any case industrially possible only up to 80-90%. Furthermore, the availability and characteristics of the initial starting products fluctuate. Finally, it is unavoidable to also obtain additional co-products. For example, starting from oleic acid one obtains azelaic acid but also, unavoidably, pelargonic acid, with severe limitations to the free use of the individual products.
A process for synthesizing 9 amino nonanoic acid, starting from sabacic acid by means of a monoesterification, ammonolysis and Hofmann degradation has been described (W. Baoren et al, Polymer Communications, (1), 27-32, 1984. However this process has a very low selectivity and after 10 years no industrial application is known.
U.S. Pat. No. 4,322,547 describes a process which is based on the catalytic iron-copper system to obtain 9 amino nonanoic acid and azelaic acid starting from cyclohexanone and acrylonitrile. This process entails the use of amounts of catalyst, by weight, that are extremely high and indeed comparable with the weight of the product obtained. Furthermore, the copper must be introduced in the process before
REFERENCES:
patent: 4322547 (1982-03-01), Minisci et al.
Burns, et al., Highly Reactive Magnesium and its Application to Organic Synthesis, J. of Organic Chemistry, 52(16):3674, 1987.
Zakharkin, et al., Abstract No. 21911 g: 2E-Dodecendioic) Acid from Dodecandioic Acid, Chemical Abstracts, 99(3):569, 1983.
Cotarca Livius
Maggioni Paolo
Nardelli Alfonso
Carr Deborah D.
Coleman Henry D.
Industrie Chimiche Caffaro, S.p.A.
Killos Paul J.
Sudol R. Neil
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