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Fatty Amines, Amidoamines, and Their Derivatives From

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Fatty Amines, Amidoamines, and Their Derivatives From (19) TZZ ¥ Z_T (11) EP 2 632 890 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 69/533 (2006.01) C07C 69/593 (2006.01) 11.01.2017 Bulletin 2017/02 C11D 1/28 (2006.01) C11D 1/74 (2006.01) B01F 17/00 (2006.01) (21) Application number: 11838500.4 (86) International application number: (22) Date of filing: 25.10.2011 PCT/US2011/057602 (87) International publication number: WO 2012/061095 (10.05.2012 Gazette 2012/19) (54) FATTY AMINES, AMIDOAMINES, AND THEIR DERIVATIVES FROM NATURAL OIL METATHESIS FETTAMINE, AMIDOAMINE UND DERIVATE DAVON AUS EINER ERDÖLMETATHESE AMINES GRASSES, AMIDOAMINES GRASSES ET LEURS DÉRIVÉS PROVENANT DE LA MÉTATHÈSE D’HUILES NATURELLES (84) Designated Contracting States: • LUEBKE, Gary AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Chicago GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO IL 60660 (US) PL PT RO RS SE SI SK SM TR • LUKA, Renee Park Ridge (30) Priority: 25.10.2010 US 406570 P IL 60068 (US) 25.10.2010 US 406556 P • MALEC, Andrew, D. 25.10.2010 US 406547 P Chicago IL 60657 (US) (43) Date of publication of application: • MASTERS, Ronald, A. 04.09.2013 Bulletin 2013/36 Glenview IL 60025 (US) (73) Proprietor: Stepan Company • MUNIE, Lawrence, A. Northfield, Illinois 60093 (US) Grayslake IL 60030 (US) (72) Inventors: • MURPHY, Dennis, S. • ALLEN, Dave, R. Libertville Chicago IL 60048 (US) IL 60610 (US) • SHAPIRO, Irene •ALONSO,Marcos Buffalo Grove Chicago IL 60089 (US) IL 60660 (US) •SKELTON,Patti • BERNHARDT, Randal, J. Winter Antioch GA 30680 (US) IL 60002 (US) • SOOK, Brian • BROWN, Aaron Lawrenceville Chicago GA 30045 (US) IL 60645 (US) • TERRY, Michael, R. • BUCHEK, Kelly Gurnee Hoffman Estates IL 60031 (US) IL 60169 (US) • WHITLOCK, Laura, Lee Highland Park IL 60035 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 632 890 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 632 890 B1 • WIESTER, Michael • BESSON L ET AL: "Synthesis of Allylic Amines Chicago Through the Palladium-Catalyzed IL 60625 (US) Hydroamination of Allenes", TETRAHEDRON • WOLFE, Patrick, Shane LETTERS, PERGAMON, vol. 36, no. 22, 29 May Palatine 1995 (1995-05-29), pages 3857-3860, IL 60074 (US) XP004028002, ISSN: 0040-4039, DOI: 10.1016/0040-4039(95)00656-W (74) Representative: Müller, Christian Stefan Gerd • CHENG ET AL: "Efficient, asymmetric synthesis ZSP Patentanwälte PartG mbB of(-)-isooncinotine", TETRAHEDRON, ELSEVIER Radlkoferstrasse 2 SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 81373 München (DE) 63, no. 14, 9 March 2007 (2007-03-09) , pages 3000-3005, XP005908467, ISSN: 0040-4020, DOI: (56) References cited: 10.1016/J.TET.2007.01.068 WO-A1-2007/074922 DE-A1- 2 551 483 US-A- 5 226 943 US-A- 5 322 630 US-A1- 2005 245 772 US-A1- 2007 093 393 US-A1- 2007 118 916 • SHELLEY BOWER ET AL: "Ein allgemein einsetzbares, mildes Eintopfverfahren zur Umwandlung von Amiden in Aldehyde", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH), vol. 108, no. 13-14, 15 July 1996 (1996-07-15), pages 1662-1664, XP055075084, ISSN: 0044-8249, DOI: 10.1002/ange.19961081338 2 EP 2 632 890 B1 Description FIELD OF THE INVENTION 5 [0001] The inventionrelates to fatty amines, amidoamines, and derivativesthereof that originate fromnatural resources, particularly natural oils, and their uses. BACKGROUND OF THE INVENTION 10 [0002] "Fatty amines" generally have a nonpolar chain of six or more carbons, typically 6-30 carbons, and at least one polar end group comprising or derived from an amine, for example, a tertiary amine. Fatty amines have value in and of themselves, or they can be modified to provide different utility. For instance, oxidation of a tertiary amine group provides an amine oxide with properties unlike the free amine. A variety of quaternization methods further expand the utility of fatty tertiary amines as intermediate targets. 15 [0003] Fatty amines and/or their derivatives have been used in a wide range of end-use applications, including fabric softening or other antistatic uses (see U.S. Pat. Nos. 3,468,869; 3,943,234; and 6,110,886), shampoos and hair condi- tioning (U.S. Pat. Nos. 4,714,610 and 5,167,864), cleaners and detergents including hard surface cleaners (U.S. Pat. No. 5,858,955 and U.S. Pat. Appl. Publ. Nos. 2010/0184855 and 2009/0305938), corrosion inhibitors (U.S. Pat. No. 5,322,630), and agricultural surfactants (U.S. Pat. Nos. 5,226,943 and 5,668,085). 20 [0004] Fatty tertiary amines can be made by converting fatty esters or acids with a secondary amine to the amide derivative, followed by reduction of the carbonyl to give a terminal tertiary amine. In a preferred approach, the reduction step is avoided by reacting a fatty ester with an aminoalkyl-substituted tertiary amine. For instance, N,N-dimethyl-1,3- propanediamine (DMAPA) reacts with a fatty methyl ester, triglyceride or fatty acid to give a fatty amidoamine. The amidoamine has a terminal tertiary amine group that is well suited to further functionalization by oxidation or quaterni- 25 zation. [0005] Fatty amines can also be made by direct amination of fatty alcohols, usually with a copper and/or nickel-based catalyst (see, e.g., U.S. Pat. Nos. 3,497,555; 4,594,455; and 4,994,622), or in multiple steps from the fatty alcohol by first converting the alcohol to a halide, sulfonate ester, or the like, and then reacting with ammonia or a primary or secondary amine. 30 [0006] The fatty acids or esters used to make fatty amines and their derivatives are usually made by hydrolysis or transesterification of triglycerides, which are typically animal or vegetable fats. Consequently, the fatty portion of the acid or ester will typically have 6-22 carbons with a mixture of saturated and internally unsaturated chains. Depending on source, the fatty acid or ester often has a preponderance of C16 to C22 component. For instance, methanolysis of soybean oil provides the saturated methyl esters of palmitic (C16) and stearic (C18) acids and the unsaturated methyl 35 esters of oleic (C18 mono-unsaturated), linoleic (C18 di-unsaturated), and α-linolenic (C18 tri-unsaturated) acids. The unsaturation in these acids has either exclusively or predominantly cis- configuration. [0007] Recent improvements in metathesis catalysts (see J.C. Mol, Green Chem. 4 (2002) 5) provide an opportunity to generate reduced chain length, monounsaturated feedstocks, which are valuable for making detergents and sur- factants, from C 16 to C 22-rich natural oils such as soybean oil or palm oil. Soybean oil and palm oil can be more economical 40 than, for example, coconut oil, which is a traditional starting material for making detergents. As Professor Mol explains, metathesis relies on conversion of olefins into new products by rupture and reformation of carbon-carbon double bonds mediated by transition metal carbene complexes. Self-metathesis of an unsaturated fatty ester can provide an equilibrium mixture of starting material, an internally unsaturated hydrocarbon, and an unsaturated diester. For instance, methyl oleate (methyl cis-9-octadecenoate) is partially converted to 9-octadecene and dimethyl 9-octadecene-1,18-dioate, with 45 both products consisting predominantly of the trans isomer. Metathesis effectively isomerizes the cis double bond of methyl oleate to give an equilibrium mixture of cis and trans isomers in both the "unconverted" starting material and the metathesis products, with the trans isomers predominating. [0008] Cross-metathesis of unsaturated fatty esters with olefins generates new olefins and new unsaturated esters that can have reduced chain length and that may be difficult to make otherwise. For instance, cross-metathesis of methyl 50 oleate and 3-hexene provides 3-dodecene and methyl 9-dodecenoate (see also U.S. Pat. No. 4,545,941). Terminal olefins are particularly desirable synthetic targets, and Elevance Renewable Sciences, Inc. recently described an im- proved way to prepare them by cross-metathesis of an internal olefin and anα -olefin in the presence of a ruthenium alkylidene catalyst (see U.S. Pat. Appl. Publ. No. 2010/0145086). A variety of cross-metathesis reactions involving an α-olefin and an unsaturated fatty ester (as the internal olefin source) are described. Thus, for example, reaction of 55 soybean oil with propylene followed by hydrolysis gives, among other things, 1-decene, 2-undecenes, 9-decenoic acid, and 9-undecenoic acid. Despite the availability (from cross-metathesis of natural oils and olefins) of unsaturated fatty esters having reduced chain length and/or predominantly trans configuration of the unsaturation, fatty amines and their derivatives made from these feedstocks appear to be unknown. Moreover, fatty amines and their derivatives have not 3 EP 2 632 890 B1 been made from the C18 unsaturated diesters that can be made readily by self-metathesis of a natural oil. [0009] In sum, traditional sources of fatty acids and esters used for making fatty amines and their derivatives generally have predominantly (or exclusively) cis isomers and lack relatively short-chain (e.g., C 10 or C 12) unsaturated fatty portions. Metathesis chemistry provides an opportunity to generate precursors having shorter chains and mostly trans isomers, 5 which could impart improved performance when the precursors are converted to downstream compositions (e.g., in surfactants).
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