GB2396611A - Preparation of wax esters by transesterifying esters with alcohols below atmospheric pressure - Google Patents
Preparation of wax esters by transesterifying esters with alcohols below atmospheric pressure Download PDFInfo
- Publication number
- GB2396611A GB2396611A GB0329456A GB0329456A GB2396611A GB 2396611 A GB2396611 A GB 2396611A GB 0329456 A GB0329456 A GB 0329456A GB 0329456 A GB0329456 A GB 0329456A GB 2396611 A GB2396611 A GB 2396611A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- process according
- mixtures
- acid
- application
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000004164 Wax ester Substances 0.000 title claims abstract description 43
- 235000019386 wax ester Nutrition 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000002148 esters Chemical class 0.000 title description 11
- 150000001298 alcohols Chemical class 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 65
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 17
- 150000002194 fatty esters Chemical class 0.000 claims abstract description 13
- 239000002537 cosmetic Substances 0.000 claims abstract description 6
- 239000004744 fabric Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 26
- -1 cyclic fatty alcohols Chemical class 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 239000006227 byproduct Substances 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 6
- 235000009508 confectionery Nutrition 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 14
- 239000002253 acid Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 4
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 3
- 229940093471 ethyl oleate Drugs 0.000 description 3
- JELGPLUONQGOHF-KTKRTIGZSA-N ethyl palmitoleate Chemical compound CCCCCC\C=C/CCCCCCCC(=O)OCC JELGPLUONQGOHF-KTKRTIGZSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 3
- 229940089456 isopropyl stearate Drugs 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 description 3
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229940087291 tridecyl alcohol Drugs 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- FDVCQFAKOKLXGE-UHFFFAOYSA-N 216978-79-9 Chemical compound C1CC(C)(C)C2=CC(C=O)=CC3=C2N1CCC3(C)C FDVCQFAKOKLXGE-UHFFFAOYSA-N 0.000 description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 229960000735 docosanol Drugs 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
- 229940067592 ethyl palmitate Drugs 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- AANLSOCSNMYRRR-UHFFFAOYSA-N heptane;octane Chemical compound CCCCCCC.CCCCCCCC AANLSOCSNMYRRR-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 229910001867 inorganic solvent Inorganic materials 0.000 description 2
- 239000003049 inorganic solvent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 229940073769 methyl oleate Drugs 0.000 description 2
- IZFGRAGOVZCUFB-HJWRWDBZSA-N methyl palmitoleate Chemical compound CCCCCC\C=C/CCCCCCCC(=O)OC IZFGRAGOVZCUFB-HJWRWDBZSA-N 0.000 description 2
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N methyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BEKZXQKGTDVSKX-UHFFFAOYSA-N propyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCC BEKZXQKGTDVSKX-UHFFFAOYSA-N 0.000 description 2
- BTAXGNQLYFDKEF-UHFFFAOYSA-N propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCC BTAXGNQLYFDKEF-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- URAXDCBRCGSGAT-UHFFFAOYSA-N cyclooctanecarboxylic acid Chemical compound OC(=O)C1CCCCCCC1 URAXDCBRCGSGAT-UHFFFAOYSA-N 0.000 description 1
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- SVEDZEIUAKXCCX-FPLPWBNLSA-N ethyl 9Z-tetradecenoate Chemical compound CCCC\C=C/CCCCCCCC(=O)OCC SVEDZEIUAKXCCX-FPLPWBNLSA-N 0.000 description 1
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
- 229940031016 ethyl linoleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 1
- AJAMRCUNWLZBDF-UHFFFAOYSA-N linoleic acid propyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCCC AJAMRCUNWLZBDF-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RWIPSJUSVXDVPB-SREVYHEPSA-N methyl myristoleate Chemical compound CCCC\C=C/CCCCCCCC(=O)OC RWIPSJUSVXDVPB-SREVYHEPSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XEIOPEQGDSYOIH-MURFETPASA-N propan-2-yl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(C)C XEIOPEQGDSYOIH-MURFETPASA-N 0.000 description 1
- HBDHXDBPCVDGQN-FPLPWBNLSA-N propan-2-yl (z)-tetradec-9-enoate Chemical compound CCCC\C=C/CCCCCCCC(=O)OC(C)C HBDHXDBPCVDGQN-FPLPWBNLSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FDUURQHLBXRCMJ-FPLPWBNLSA-N propyl (z)-tetradec-9-enoate Chemical compound CCCC\C=C/CCCCCCCC(=O)OCCC FDUURQHLBXRCMJ-FPLPWBNLSA-N 0.000 description 1
- AJAMRCUNWLZBDF-MURFETPASA-N propyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCC AJAMRCUNWLZBDF-MURFETPASA-N 0.000 description 1
- DPBVJRXPSXTHOL-UHFFFAOYSA-N propyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCC DPBVJRXPSXTHOL-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the preparation of wax esters by transesterifying a C2-60 fatty ester with a C1-30 fatty alcohol at a pressure below atmospheric pressure. Wax esters in improved chemical yield or with improved purity, reduced colour or reduced odour may be obtained. The process may be performed in the presence of a catalyst, preferably a non-recyclable basic catalyst such as sodium methylate. The process is preferably performed at a pressure below 0.1 atm and at a temperature between 60 and 100 {C. The wax esters may be useful in home care, fabric care, cosmetics, personal care, pharmaceutical or confectionary applications.
Description
1 2396611
Improved Process for the Preparation of Wax Esters Field of the Invention
This invention relates to lower pressure processes for the preparation of esters, more specifically of wax esters.
5 In particular, this invention relates to the preparation of wax esters with improved chemical yield, with improved purity, with reduced color, with reduced odor or any combination thereof.
Background to the Invention
10 Wax esters are widely used materials, e.g., in the candle making industries, in the cosmetic industries, in the pharmaceutical industries, in the confectionery industries, in the car polish industries and in the shoe polish industries to name a few. The growing demand of wax 15 esters, also known as fatty esters, has generated interest in investigating novel and improved processes of preparing such compounds.
U.S. Patent No. 4,112,235 (issued September 5, 1978; UOP Inc.) describes a transesterification process wherein 20 a specific C2-C8 fatty ester is reacted with a C:-C20 carboxylic acid in the presence of a tin halide catalyst to obtain the corresponding ester of the carboxylic acid. The reaction is performed in an autoclave at a pressure between 1 atm to 100 atm and at temperatures from 0 C to 150 C.
25 The document cited is, in relevant part, incorporated herein by reference; the citation of this document is not to be construed as an admission that it is prior art with
respect to the present invention.
The process mentioned above has at least the following 30 disadvantages: (a) the process is performed at high reaction pressures and therefore requires the use of a relatively complicated reaction vessel; and (b) the process requires an expensive catalyst (which generally must be separated and/or re-cycled from the reaction liquor and/or 35 from the reaction product in an expensive and/or time consuming manner).
Therefore, a need exists for an improved process for the preparation of wax esters to deliver desired wax esters without the common disadvantages known in the art.
As described above, the prior art teaches to perform
5 trans-esterification reactions at atmospheric pressure. The same document teaches to perform trans-esterification reactions at even higher pressures than atmospheric pressure, e.g. up to 150 atmospheres. It is evident from the cited art document that problems occur when using such 10 high pressures. Indeed, it is noted from the example section of U.S. Patent No. 4,112,235 that mixtures of products are obtained by high pressure processes. The prior art does not teach to lower the pressure to perform trans-
esterification processes. We have now surprisingly found 15 that wax esters are obtainable in an improved process under reduced pressure. By utilizing such a process with suitable starting materials, wax esters are obtainable with improved chemical yield, with improved purity, with reduced color, with reduced odor or any combination thereof.
20 Summary of the Invention
The present invention relates to processes for the preparation of wax esters comprising the following reaction step performed under reduced pressure: trans-esterification of C7-C60 fatty esters with C-C30 fatty alcohols.
25 As used herein, "reduced pressure" refers to a pressure below atmospheric pressure. Preferably, the processes of the present invention are performed at a pressure below 0.5 atm, more preferably at a pressure below 0.2 atm, and most preferably at a pressure below 0.1 atm.
30 The processes of the present invention are preferably performed at relatively mild reaction temperatures, or in the presence of a catalyst, or in the presence of an inert solvent, or even at any combination of these conditions. As used herein, "relatively mild reaction temperatures" refers 35 to temperatures below 105 C. Preferably, the reaction temperature is below 100 C, and more preferably the reaction temperature is between 60 C and 100 C.
To prepare the final wax ester by the process of the present invention, one or more additional processing steps may be necessary, e.g., steps in which the intermediate products or final products or raw products are washed, 5 neutralized, separated and/or purified from impurities and/or side products and/or starting materials or any combination thereof.
The present invention also relates to a method of using the wax esters obtained by the processes of the 10 present invention in applications known for utilizing wax esters, including but not limiting to any home care application, fabric care application, cosmetics application, personal care application, pharmaceutical application, confectionery application and any combination 15 thereof. The present invention further relates to the use of the wax esters obtained by the processes of the present invention in any home care application, fabric care application, cosmetics application, personal care application, pharmaceutical application, confectionery 20 application and any combination thereof.
Detailed Description of the Invention
The processes of the present invention provide a way to prepare the desired wax esters with improved chemical yield, with improved purity, with reduced color, with 25 reduced odor or any combination thereof.
The following reaction has been found to be suitable to deliver the desired wax esters under reduced pressure: The reaction of C2-C60 fatty esters with C1-C30 fatty alcohols (trans-esterification).
30It has been found that this reaction performed at reduced pressure for the preparation of such esters provides improvements as mentioned above.
In the chemical reactions of the present invention, the group Ri is selected from the group consisting of 35 hydrogen and C1 to C29 saturated or unsaturated, linear, branched, cyclic, substituted or unsubstituted hydrocarbons, preferably from Cg to Cal saturated or
unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and more preferably from Cal to Ci7 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and mixtures 5 thereof. The group Red is selected from the group consisting of C1 to C30 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons, preferably from ClO to C22 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted 10 hydrocarbons and more preferably from C:2 to Cue saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and mixtures thereof. The group R3 is selected from the group consisting of Cat to C30 saturated or unsaturated, linear, branched or cyclic, 15 substituted or unsubstituted hydrocarbons, preferably from Cl to C6 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and more preferably from Cat to C3 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted 20 hydrocarbons and mixtures thereof.
When using the term substituted, it is meant that the respective hydrocarbon chain may comprise any heteroatom in addition to already containing carbon and hydrogen. Non-
limiting examples of heteroatoms useful herein include 25 silicone, nitrogen, phosphorous, arsenic, oxygen, sulfur, fluorine, chlorine, bromine, iodine, and mixtures thereof.
These heteroatoms may be part of the main carbon chain or of a functional group attached to the main carbon chain of the hydrocarbon. When using the term unsubstituted, it is 30 meant that the respective hydrocarbon chain only contains carbon and hydrogen and none of the above-mentioned heteroatoms. Non-limiting examples of suitable esters to be used in the processes of the present invention include any C2 to C60 35 esters derivable from formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, 2-ethyl hexanoic acid, oenanthylic acid, caprylic acid, pelargonic
acid, capric acid, undecylic acid, lauric acid, tridecoic acid, myristic acid, pentadecanonic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, cyclopentanecarboxylic acid, cyclohexanecarboxylic acid, 5 cycloheptanecarboxylic acid, cyclooctanecarboxylic acid, benzoic acid, phentylacetic acid, phenylpropionic acid, phenylbutyric acid, o-toluic acid, m-toliuc acid, ptoluic acid, naphthalenecarboxylic acid, acryclic acid, crotonic acid, isocrotonic acid, tiglic acid, angelic acid, 10 senecioic acid, myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eleosteraic acid, eicosenic acid, erucic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, sebacic acid, brassic acid, amleic acid, boxylic acid and mixtures thereof.
15 Preferably, suitable esters to be used in the processes of the present invention include methyl laureate, ethyl laureate, propyl laureate, isopropyl laureate, methyl myristate, ethyl myristate, propyl myristate, isopropyl myristate, methyl palmitate, ethyl palmitate, propyl 20 palmitate, isopropyl palmitate, methyl stearate, ethyl stearate, propyl stearate, isopropyl stearate, methyl myristoleate, ethyl myristoleate, propyl myristoleate, isopropyl myristoleate, methyl palmitoleate, ethyl palmitoleate, propyl palmitoleate, isopropyl palmitoleate, 25 methyl oleate, ethyl oleate, propyl oleate, isopropyl oleate, methyl linoleate, ethyl linoleate, propyl linoleate, isopropyl linoleate, and mixtures thereof. More preferably, suitable esters to be used in the processes of the present invention include methyl palmitate, ethyl 30 palmitate, propyl palmitate, isopropyl palmitate, methyl stearate, ethyl stearate, propyl stearate, isopropyl stearate, methyl palmitoleate, ethyl palmitoleate, propyl palmitoleate, isopropyl palmitoleate, methyl oleate, ethyl oleate, propyl oleate, isopropyl oleate, and mixtures 35 thereof. Most preferably, suitable esters to be used in the processes of the present invention include ethyl palmitate, isopropyl palmitate, ethyl stearate, isopropyl stearate,
ethyl palmitoleate, isopropyl palmitoleate, ethyl oleate, isopropyl oleate, and mixtures thereof.
Non-limiting examples of suitable alcohols to be used in the processes of the present invention include methanol, 5 ethanol, propanol, butanol, pentanol, hexanol, 2-ethyl hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, lauryl alcohol, tridecyl alcohol, myristiryl alcohol, pentadecyl alcohol, palmyl alcohol, margaryl alcohol, stearyl alcohol, arachyl alcohol, behenyl alcohol, 10 cyclopentanol, cyclohexanol, cycloheptanol, cyclooctanol, phenol, and mixtures thereof. Preferably, suitable alcohols to be used in the processes of the present invention include decanol, undecanol, dodecanol, lauryl alcohol, tridecyl alcohol, myristiryl alcohol, pentadecyl alcohol, 15 palmyl alcohol, margaryl alcohol, stearyl alcohol, arachyl alcohol, behenyl alcohol, and mixtures thereof. More preferably, suitable alcohols to be used in the processes of the present invention include dodecanol, lauryl alcohol, tridecyl alcohol, myristiryl alcohol, pentadecyl alcohol, 20 palmyl alcohol, margaryl alcohol, stearyl alcohol, and mixtures thereof.
The esters and alcohols suitable for use in the present invention can be of natural or synthetic origin.
The ratio of the fatty esters to the fatty alcohols in 25 the processes of the present invention ranges from about 10:1 to about 1:10, preferably from about 5:1 to about 1:5, more preferably from about 2:1 to about 1:2, even more preferably from about 1.2:1 to about 1:1.2 and most preferably from about 1.05:1 to about 1:1.05.
30 In the processes of the present invention, it is required that side products formed during the reaction are withdrawn at least in part from the reaction mixture.
Preferably, the side products are continuously withdrawn at least in part from the reaction mixture. For a trans 35 esterification reaction, the side product is typically an alcohol. In order to withdraw the side products, the pressure inside the reaction vessel is set below
atmospheric pressure, preferably at a pressure below 0.5 atm, more preferably at a pressure below 0.2 atm, and most preferably at a pressure below 0.1 atm. Without being bound by theory, it is believed that the improved chemical yield 5 of wax ester products obtained from the processes of the present invention results from driving the reaction until its completion by the continuous removal of side products.
It is further believed that the improved purity, the reduced color, the reduced odor or any combination thereof 10 also result from reducing the pressure in the reaction vessel. Furthermore, the withdraw of side products may be assisted by an inert gas flow, e.g. nitrogen, and/or argon, passing through the reaction mixture to further 15 the stripping effect of the reduced pressure.
Alternatively or in addition to using an inert gas, the withdraw of side products may be assisted by applying heat to the reaction vessel. However, it is preferred that the temperature is maintained below 105 C at any 20 time during the process.
In order to substantially remove the side products from the reaction mixtures, it is preferred to have a combination of reducing the pressure inside the reaction vessel and applying heat.
25 In a preferred embodiment of the present invention, the processes of the present invention are performed under relatively mild conditions. This means that in a preferred embodiment, the reaction temperature inside the reaction vessel is below 105 C, preferably the reaction temperature 30 is below 100 C, and more preferably the reaction temperature is between 60 C and 100 C.
Without being bound by theory, it is believed that the improved purity is also effected by these relatively mild reaction conditions. It is believed that these relatively 35 mild reaction conditions reduce the possibility of unwanted side reactions, thereby increasing the chemical yield of desired wax esters.
Unwanted side products often cause an undesired darkening and/or off odor formation, e.g., a brownish color and/or a burnt odor of the wax esters. By preventing the formation of side products, the desired wax esters in 5 themselves can be obtained in reduced color and/or in reduced odor, which is specifically true for the wax esters obtained by the processes of the present invention.
In another preferred embodiment of the present invention, the processes are performed in the presence of 10 a catalyst, more preferably in the presence of a non-
recyclable catalyst. Even more preferably, the trans-
esterification is performed in the presence of a basic catalyst. Suitable basic catalysts include inorganic and organic bases, selected from NaOH, KOH, NaOCH3, and 15 mixtures thereof. More preferably, the catalyst is NaOCH3.
The catalyst may be used in an inert solvent such as an inorganic solvent, organic solvent or combination thereof.
Non-limiting examples of suitable solvents to be used in the processes of the present invention include substituted 20 and unsubstituted hydrocarbons, such as C-C1s hydrocarbons.
Preferably, the solvent is selected from hexane; heptane; octane; toluene; halocarbons, such as CBr4, CCl4, CHCl3, CH2Cl2; and mixtures thereof.
Typically, the catalyst is present in a catalytic 25 amount, that is, less than stochiometric quantity based on the fatty ester. By being able to utilize only catalytic amounts of catalyst, it is possible to prepare the desired wax esters at a relatively low costs and thus render the process more attractive from an economic point of view.
30 Preferably, the volume inside the reaction vessel is flooded with an inert gas, e.g. nitrogen and/or argon prior to letting in any starting materials of any of the claimed processes. The processes of the present invention may optionally 35 be performed in the presence of an inert solvent. Suitable solvents to be used in the processes of the present invention include any organic solvent or inorganic solvent
or mixtures thereof, which do not react with any of the reactants, namely with the fatty ester or with the fatty alcohol or with the wax esters or with the catalyst, if present. Non-limiting examples of suitable solvents to be 5 used in the processes of the present invention include substituted and unsubstituted hydrocarbons, such as C1-C5 hydrocarbons. Preferably, the solvent is selected from hexane; heptane; octane; toluene; halocarbons, such as CBr4, CCl4, CHCl3, CH2Cl2; and mixtures thereof.
10 In a preferred embodiment of the present invention, the reaction is performed at a pressure below about 0.1 atm, the ratio of the fatty esters to the fatty alcohols ranges from about 1.05:1 to about 1:1.05, the reaction is performed at a temperature below about 105 C, the reaction 15 is performed in the presence of a catalyst, the reaction is performed in the presence of an inert solvent or any combination thereof.
The process of the present invention may be effected in any suitable manner and may comprise either a batch or 20 continuous type operation. For example, when a batch type operation is used, a quantity of the reactants, namely the fatty ester and the fatty alcohol set forth hereinbefore in greater detail, are placed in an appropriate reaction vessel which may comprise a flask. In a preferred 25 embodiment of the present invention, the catalyst and/or any other additional component is added. Optionally, alternatively or in addition, the catalyst may be admixed with one or both of the reactants and the resulting mixture charged thereto into the reaction vessel. The pressure is 30 then adjusted by activating the vacuum pump and by adjusting the desired pressure controlled by any suitable pressure controlling device. The temperature at which the reaction is effected may be controlled by external means, that is either cooling means or conversely heating means.
35 The reaction is allowed to proceed for a predetermined period of time which may range from about 0.5 hours to about 24 hours or more in duration. This residence time
being dependent upon the various parameters of the reaction including pressure, temperature and type of reactants employed. Upon completion of the desired residence time, heating or cooling is discontinued and the apparatus and 5 contents thereof are allowed to return to room temperature.
The reaction mixture is then recovered and subjected to conventional means of separation as described below in more greater detail.
It is also contemplated within the scope of the 10 present invention that the process in which a fatty ester is treated with a fatty alcohol may be effected in a continuous manner of operation. When such a type of operation is employed, the starting materials comprising the fatty ester and the fatty alcohol are continuously 15 charged to a reaction zone which is maintained at the proper operation condition of pressure and optionally of temperature. In addition, the catalyst may be also charged to the reactor through a separate line, or if so desired, may be admixed with one or both of the reactants and the 20 resulting mixture charged thereto in a single stream.
Alternatively, the catalyst may be added to one of the reactants and the mixture charged through one line, the other reactant being charged through another line. Upon completion of the desired reaction time, the reactor 25 effluent is continuously withdrawn and subjected to conventional means of separation whereby the desired product is separated and recovered as described in greater detail below.
Additional Processing steps 30 Depending on the desired purity level of the wax esters products from the reaction of the present invention, further processing steps may be desired. The additional processing steps useful herein include one or more steps in which the intermediate or final or raw products are washed, 35 neutralized, separated and/or purified from impurities and/or side products and/or starting materials or any combination thereof.
Preferably, the catalysts are neutralized before refurbishing the reaction liquor and before isolating the desired wax ester. The basic catalyst is preferably neutralized with an acidic (pH of from about 6.5 to about 5 1) medium, preferably strongly acidic (pH of from about 3.0 to about 1) medium, in order to completely neutralize a strong basic catalyst. Preferably, an aqueous solution of the acidic, preferably strongly acidic medium is applied to the reaction mixture. Examples include H2SO4, HNO3, and HC1.
10 The washing step may be performed by adding either pure water or an aqueous solution of an inorganic salt, e.g. an about 10% wt. solution of sodium chloride, calcium chloride, and/or magnesium sulfate to the reaction mixture.
Often due to the hydrophobic nature of the wax esters 15 products of the present invention, a two phase solution will result after the washing step. These two phases should be separated from each other, wherein the desired wax ester is usually dissolved in the organic phase, and wherein the aqueous phase can usually be discarded. The solvent, if 20 present, is removed from the retained organic phase by any method applicable, e.g., vacuum distillation, and/or evaporation under reduced pressure with or without added heat. Finally, the desired wax esters product will be obtained as raw product. If desirable, the raw product can 25 be further purified by vacuum distillation, and/or re-
crystallization or any other method as known in the art.
Furthermore, if a colorless product is desired the resulting wax ester may be either bleached with active carbon and/or reacted with bleaching earths or any other 30 method known in the art.
Examples
The following non-limiting examples are illustrative of the present invention. Percentages are by weight unless otherwise specified.
For the purpose of the present invention, the reaction vessel can be any suitable one as known by the person skilled in the art. This includes reaction vessels made from glass ware as well as stainless steel reactors. The 5 reduced pressure inside the reaction vessel is constituted by any conventional means as known by the skilled person.
Non-limiting examples include mechanical vacuum pumps such as rotary vane pumps from Edwards, UK, e.g. Edwards RV12, and membrane pumps from IMLVAC, Germany, e.g. IMLVAC MPC 10 052Z. The reduced pressure inside the reaction vessel is measured by any conventional means as known by the skilled person. Non-limiting examples include a field mounted
pressure indicating controller with a stainless steel Bourbon tube. Furthermore, a Jordan Valve Mark 65 Vacuum 15 Regulator has been used for pressure control. The pressure indicating controller and the vacuum regulator are located in a position between the reactor and the vacuum pump. The pressure controller indicates the pressure for the entire process above the liquid phase in the reactor, including 20 the reactor headspace, the condenser and the receiver.
Example I
A reactor, which is a 12 liter flask equipped with thermometer, stirrer, heating mantle, overhead condenser, and receiver with dry ice trap is connected to a vacuum 25 pump. The stirrer is turned on and the flask is charged with 4114 grams (11.75 gram moles) of C22 methyl ester, 3147 grams (11.6 gram moles) of Cue fatty alcohol, and 29.05 grams (0.54 gram moles) of sodium methylate. The latter ingredient is added as a 25 solution in methanol for ease 30 of handling. The reactor is heated to a temperature of 100 C and the pressure is slowly reduced to 5 mm Hg over a period of four hours. The methanol is constantly removed from the reaction mixture to drive the reaction to completion while the reaction product remains in the 35 reactor.
After ventilating to atmospheric pressure, the reaction mixture is neutralized with 23.3 grams (0.20 gram
moles) of 85% phosphoric acid. 1800 grams of deionized water with 18 grams of sodium chloride present are then added to the reactor and are mixed for five minutes at a temperature of 85 C. Then the stirrer is turned off and the 5 water phase is settled and decanted. A total of 1866 grams of water is collected with a pH of 8.0. The wax ester left in the reactor is dried at a temperature of 75 C and a pressure of 5 mm Hg for a period of 30 minutes. 6583 grams of product is collected with a purity of 91% wax ester and 10 a moisture content of less than 0.1%.
Example II
A C24 wax ester is prepared using a procedure similar to that in Example 1. The product purity is 86% wax ester.
In order to reduce odor originating from residual levels of 15 C12 methyl ester and Cry fatty alcohol, the product is processed in a 2" short path continuous evaporator with internal condenser (Pope Scientific). The evaporator conditions are a pressure of 3 mm Hg and a jacket temperature of 180 C. The internal condenser uses 20 C 20 cooling water. Using a dropping funnel, 200 grams of material is processed in the evaporator over a period of two hours. The final residue out of the evaporator has a purity of 98% wax ester and a much reduced odor impression.
The distillate from the evaporator is a blend of C24 25 wax ester, C12 methyl ester, and C12 fatty alcohol and has a very sharp odor.
Claims (13)
1. A process for the preparation of wax esters comprising the reaction step of: 5 trans-esterifying C2-C60 fatty esters with C-C30 fatty alcohols wherein the reaction step is performed at a pressure below atmospheric pressure.
2. A process according to Claim 1, wherein the reaction 10 step is performed at a pressure below 0.5 atm, more preferably at a pressure below 0.2 atm, and most preferably at a pressure below 0.1 atm.
3. A process according to any of the preceding claims, wherein the reaction step is performed in the presence 15 of a catalyst, preferably in the presence of a non recyclable catalyst and even more preferably in the presence of a basic catalyst.
4. A process according to any of the preceding claims, wherein the reaction step is performed in the presence 20 of an inert solvent.
5. A process according any of the preceding claims, wherein the reaction step is performed at a temperature below 105 C, preferably at a temperature below 100 C, and more preferably at a temperature 25 between 60 C and 100 C.
6. A process according any of the preceding claims, wherein the ratio of the fatty esters to the fatty alcohols ranges from 10:1 to 1:10, preferably from 5:1 to 1:5, more preferably from 2:1 to 1:2, even more 30 preferably from 1.2:1 to 1:1.2, and most preferably from 1.05:1 to 1:1. 05.
7. A process according any of the preceding claims, wherein the fatty alcohols are selected from the group consisting of Car to C30 saturated or unsaturated, 35 linear, branched or cyclic fatty alcohols of natural or synthetic origin, and mixtures thereof; preferably from CIO to C22 saturated or unsaturated, linear,
branched or cyclic, substituted or unsubstituted fatty alcohols of natural or synthetic origin, and mixtures thereof; and most preferably from C2 to Cl8 saturated or unsaturated, linear, branched or cyclic, 5 substituted or unsubstituted fatty alcohols of natural or synthetic origin, and mixtures thereof.
8. A process according any of the preceding claims, wherein the fatty esters are selected from the group consisting of C2 to C60 saturated or unsaturated, 10 linear, branched or cyclic fatty esters of natural or synthetic origin, and mixtures thereof; preferably from the group consisting of CIO to C22 saturated or unsaturated, linear, branched or cyclic fatty esters of natural or synthetic origin; and mixtures thereof; 15 and more preferably from the group consisting of C:2 to C:8 saturated or unsaturated, linear, branched or cyclic fatty esters of natural or synthetic origin; and mixtures thereof.
9. A process according any of the preceding claims, 20 wherein the process to obtain the final wax esters comprises one or more additional processing steps selected from the group consisting of: steps in which the intermediate product or final product or raw product are washed, neutralized, separated and/or 25 purified from impurities and/or side products and/or starting materials or any combination thereof.
10. A process according any of the preceding claims, wherein the reaction step is performed at a pressure below 0.1 atm, wherein the ratio of the fatty esters 30 to the fatty alcohols ranges from 1.05:1 to 1:1.05, and wherein the reaction step is performed at a temperature below 105 C.
11. A process for the preparation of wax esters substantially as described herein with reference to 35 examples I and II.
12. A method of using the wax esters obtained by the process according to any of the preceding claims in
any home care application and/or fabric care application and/or cosmetics application and/or personal care application and/or pharmaceutical application and/or confectionery application.
5
13. The use of the wax esters obtained by the process according to any of the preceding claims in any home care application and/or fabric care application and/or cosmetics application and/or personal care application and/or pharmaceutical application and/or confectionery 10 application.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US43506802P | 2002-12-19 | 2002-12-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
GB0329456D0 GB0329456D0 (en) | 2004-01-28 |
GB2396611A true GB2396611A (en) | 2004-06-30 |
Family
ID=31188750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB0329456A Withdrawn GB2396611A (en) | 2002-12-19 | 2003-12-19 | Preparation of wax esters by transesterifying esters with alcohols below atmospheric pressure |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB2396611A (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4002667A (en) * | 1974-03-26 | 1977-01-11 | Imperial Chemical Industries Limited | Bis-(2-hydroxyethyl)-terephthalate |
JPS57185235A (en) * | 1981-05-07 | 1982-11-15 | Mitsui Toatsu Chem Inc | Preparation of neopentyl polyol ester from fatty acid |
JPS62185051A (en) * | 1986-02-10 | 1987-08-13 | Mitsui Toatsu Chem Inc | Method for producing cyclohexyl ester of acrylic acid or methacrylic acid |
JPH0648988A (en) * | 1992-07-29 | 1994-02-22 | Dainippon Ink & Chem Inc | Process for producing tetrakis [3- (3,5-dialkyl-4-hydroxyphenyl) propionyloxyalkyl] methane |
WO1999057092A1 (en) * | 1998-05-02 | 1999-11-11 | Cognis Deutschland Gmbh | Method for producing polyolesters |
JP2001271090A (en) * | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | Method for producing fatty acid ester and fuel containing fatty acid ester |
-
2003
- 2003-12-19 GB GB0329456A patent/GB2396611A/en not_active Withdrawn
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4002667A (en) * | 1974-03-26 | 1977-01-11 | Imperial Chemical Industries Limited | Bis-(2-hydroxyethyl)-terephthalate |
JPS57185235A (en) * | 1981-05-07 | 1982-11-15 | Mitsui Toatsu Chem Inc | Preparation of neopentyl polyol ester from fatty acid |
JPS62185051A (en) * | 1986-02-10 | 1987-08-13 | Mitsui Toatsu Chem Inc | Method for producing cyclohexyl ester of acrylic acid or methacrylic acid |
JPH0648988A (en) * | 1992-07-29 | 1994-02-22 | Dainippon Ink & Chem Inc | Process for producing tetrakis [3- (3,5-dialkyl-4-hydroxyphenyl) propionyloxyalkyl] methane |
WO1999057092A1 (en) * | 1998-05-02 | 1999-11-11 | Cognis Deutschland Gmbh | Method for producing polyolesters |
JP2001271090A (en) * | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | Method for producing fatty acid ester and fuel containing fatty acid ester |
Also Published As
Publication number | Publication date |
---|---|
GB0329456D0 (en) | 2004-01-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5175323A (en) | Preparation of esterified propoxylated glycerin by transesterification | |
US4983329A (en) | Preparation of esterified propoxylated glycerin from free fatty acids | |
CN110312700B (en) | Method for purifying natural vanillin | |
US5455370A (en) | Process for the production of fatty acid lower alkyl esters | |
EP0759422B1 (en) | Direct esterification of propoxylated glycerin | |
CA2156155A1 (en) | A process for the production of light-colored polyol esters | |
KR20160055808A (en) | Method for post-treating polyol esters | |
JP3365422B2 (en) | Method for producing high-purity polyglycerin fatty acid ester | |
US4377686A (en) | Method of purifying fatty acid ester products | |
GB2396611A (en) | Preparation of wax esters by transesterifying esters with alcohols below atmospheric pressure | |
FR2584711A1 (en) | PROCESS FOR THE PREPARATION OF METHACRYL ESTERS BY TRANSESTERIFICATION | |
US5773636A (en) | Process for the production of fatty acid lower alkyl esters | |
GB2396612A (en) | Preparation of wax esters by esterifying acids with alcohols below atmospheric pressure | |
EP1770082A1 (en) | Process for producing sorbitan fatty acid ester | |
US5908922A (en) | Method for producing a sucrose fatty acid ester | |
US5641816A (en) | Process for the production of polyol compounds | |
JPH07145104A (en) | Method for producing polyglycerin fatty acid ester | |
KR100441030B1 (en) | Preparation method of high purity diglyceride | |
JP3168695B2 (en) | Method for lowering substitution degree of sucrose fatty acid ester | |
GB2256869A (en) | Process for preparing sucrose fatty acid esters | |
JPS60105690A (en) | Method for purifying sucrose fatty acid ester | |
JPH0381252A (en) | Production of highly purified polyglycerin fatty ester | |
CA1093049A (en) | Residue treatment process | |
JP3546462B2 (en) | Method for separating polyglycerin fatty acid ester | |
EP2861704B1 (en) | Process for the production of fatty acid esters |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |