DOI: 10.1007/bf02541095. Polyhydroxy fatty acids and their derivatives from plant oils

Polyhydroxy fatty acids and their derivatives from plant oils

10.1007/bf02541095

Crossref journal-article

Wiley

Journal of the American Oil Chemists' Society (311)

Abstract

AbstractA novel process for the industrial production of hydroxylated fatty acids involves epoxidation of plant oils and their derivatives, followed by catalytic epoxy ring opening in the presence of water or other hydrogen donors, such as alcohols, diols, and amines. Depending on the starting material, epoxidation followed by opening of the oxirane ring leads to fatty acids that contain vicinal diol groups or to other substituted hydroxylated fatty acid derivatives. As an example for the preparation of a substituted hydroxylated fatty acid derivative, the reaction of epoxidized rapeseed oil with monobutylamine as hydrogen donor is described. Apart from the intended formation of hydroxyl groups with vicinal aminoalkyl groups, partial aminolysis of the ester compound was also observed. Another example describes the reaction of epoxidized rapeseed oil with different molar proportions of 1,4‐butanediol as hydrogen donor. Depending on the molar proportion of the hydrogen donor, interesterification, or intermolecular ether formation were observed as side reactions. The properties of various technical hydroxylated fatty acids and their derivatives, prepared according to this novel process, are given, and potential applications of these products are suggested.

Bibliography

Dahlke, B., Hellbardt, S., Paetow, M., & Zech, W. H. (1995). Polyhydroxy fatty acids and their derivatives from plant oils. Journal of the American Oil Chemistsâ Society, 72(3), 349â353. Portico.

Authors 4

B. Dahlke (first)
S. Hellbardt (additional)
M. Paetow (additional)
W. H. Zech (additional)

References 34 Referenced 60

{'key': 'e_1_2_1_2_1', 'first-page': '692', 'volume': '2', 'author': 'Vignolo R.', 'year': '1991', 'journal-title': 'INFORM'} / INFORM by Vignolo R. (1991)
10.1021/ja01377a012
{'key': 'e_1_2_1_4_1', 'first-page': '316', 'volume': '44', 'author': 'Luong T.M.', 'year': '1967', 'journal-title': 'Ibid.'} / Ibid. by Luong T.M. (1967)
{'key': 'e_1_2_1_5_1', 'first-page': '147', 'volume': '89', 'author': 'Gruber B.', 'year': '1987', 'journal-title': 'Fat Sci. Technol.'} / Fat Sci. Technol. by Gruber B. (1987)
Swern D. andJ.T.Scanlan U.S. Patent 2 443 280 (1948). (10.1136/bmj.2.4573.443-c)
Morrisroe J.J. andT.Banigan U.S. Patent 4 101 589 (1978).
Käbisch G. European Patent EP 002594031 (1980).
10.1039/tf9484400905
Jpn. Kokai Tokkyo Koho JP 63–13993.
10.1021/i300009a027
Hellbardt S. K.SchlandtandW.H.Zech German Patent DE 4125031 (1993).
Hellbardt S. K.SchlandtandW.H.Zech German Patent DE 4203077 A1 (1993).
Hellbardt S. K.SchlandtandW.H.Zech European Patent Application EP 92250277.8 (1993).
Hellbardt S. K.SchlandtandW.H.Zech German Patent Application P 4332292.1 (1993).
Frische R. K.Wollmann J.Volkheimer H.Schomann J.Schneider R.Groß‐Lannet A.AchandB.Best German Patent DE 4019087 A1 (1991).
Frische R. andJ.Volkheimer German Patent DE 4024364 A1 (1991).
Frische R. andJ.Volkheimer German Patent DE 4024365 A1 (1991).
Burg D. R.KleimanandS.Erhan PCT/US92/01263 (1992).
Klauck W. andP.Daute PCT/EP92/01308 (1992).
Lincoln R.M. andJ.A.Meyers U.S. Patent 3 607 778 (1971). (10.1677/joe.0.0500607)
Meffert A. German Patent DE 3318596 A1 (1984).
Anzinger H. K.WorschechandB.Wegemund German Patent DE 3442176 A1 (1986).
Anzinger H. H.Fischer H.H.Friese A.MeffertandH.Schulz German Patent DE 3507505 A1 (1986).
Rutzen H. andG.Stoll German Patent DE 3719790 A1 (1987).
Klauck W. andP.Daute German Patent DE 4120432 A1 (1991).
Borggrefe G. German Patent DE 3203491 C2 (1990).
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{'key': 'e_1_2_1_29_1', 'volume-title': 'DIN Deutsches Institut für Normung e.V.', 'year': '1985'} / DIN Deutsches Institut für Normung e.V. (1985)
{'key': 'e_1_2_1_30_1', 'volume-title': 'German Standard Methods for the Analysis of Fats and Other Lipids', 'author': 'German Society for Fat Science (DGF)', 'year': '1994'} / German Standard Methods for the Analysis of Fats and Other Lipids by German Society for Fat Science (DGF) (1994)
10.1016/S0003-2670(00)88781-4
{'key': 'e_1_2_1_32_1', 'volume-title': 'DIN Deutsches Institut für Normung e.V.', 'year': '1985'} / DIN Deutsches Institut für Normung e.V. (1985)
{'key': 'e_1_2_1_33_1', 'volume-title': 'Structure and Mechanism in Organic Chemistry', 'author': 'Ingold C.K.', 'year': '1953'} / Structure and Mechanism in Organic Chemistry by Ingold C.K. (1953)
10.1007/BF02541097
{'key': 'e_1_2_1_35_1', 'first-page': '355', 'volume': '72', 'author': 'Fehling E.', 'year': '1995', 'journal-title': 'Ibid.'} / Ibid. by Fehling E. (1995)

Dates

Type	When
Created	18 years, 7 months ago (Jan. 5, 2007, 1:59 a.m.)
Deposited	1 year, 11 months ago (Sept. 27, 2023, 11:58 a.m.)
Indexed	1 year, 4 months ago (April 16, 2024, 9:29 p.m.)
Issued	30 years, 5 months ago (March 1, 1995)
Published	30 years, 5 months ago (March 1, 1995)
Published Online	30 years, 5 months ago (March 1, 1995)
Published Print	30 years, 5 months ago (March 1, 1995)

Funders 0

None

BibTeX

@article{Dahlke_1995, title={Polyhydroxy fatty acids and their derivatives from plant oils}, volume={72}, ISSN={1558-9331}, url={http://dx.doi.org/10.1007/bf02541095}, DOI={10.1007/bf02541095}, number={3}, journal={Journal of the American Oil Chemists’ Society}, publisher={Wiley}, author={Dahlke, B. and Hellbardt, S. and Paetow, M. and Zech, W. H.}, year={1995}, month=mar, pages={349–353} }

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