KR0167750B1 - 알코올의 제조방법 - Google Patents
알코올의 제조방법 Download PDFInfo
- Publication number
- KR0167750B1 KR0167750B1 KR1019900702047A KR900702047A KR0167750B1 KR 0167750 B1 KR0167750 B1 KR 0167750B1 KR 1019900702047 A KR1019900702047 A KR 1019900702047A KR 900702047 A KR900702047 A KR 900702047A KR 0167750 B1 KR0167750 B1 KR 0167750B1
- Authority
- KR
- South Korea
- Prior art keywords
- esters
- alcohols
- transesterification
- fatty
- mixture
- 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.)
- Expired - Lifetime
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 28
- 238000004519 manufacturing process Methods 0.000 title description 9
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 103
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 96
- 239000003054 catalyst Substances 0.000 claims abstract description 80
- 150000002148 esters Chemical class 0.000 claims abstract description 71
- -1 fatty acid esters Chemical class 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 239000000194 fatty acid Substances 0.000 claims abstract description 60
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 59
- 229930195729 fatty acid Natural products 0.000 claims abstract description 59
- 150000001298 alcohols Chemical class 0.000 claims abstract description 53
- 239000004164 Wax ester Substances 0.000 claims abstract description 45
- 235000019386 wax ester Nutrition 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 32
- 238000004821 distillation Methods 0.000 claims abstract description 29
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 55
- 238000005984 hydrogenation reaction Methods 0.000 claims description 44
- 150000004665 fatty acids Chemical class 0.000 claims description 22
- 150000004702 methyl esters Chemical class 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 16
- 238000001704 evaporation Methods 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 239000013067 intermediate product Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 6
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims 2
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 239000002253 acid Substances 0.000 description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- 239000006227 byproduct Substances 0.000 description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- GFCDJPPBUCXJSC-UHFFFAOYSA-N [O-2].[Zn+2].[Cu]=O Chemical compound [O-2].[Zn+2].[Cu]=O GFCDJPPBUCXJSC-UHFFFAOYSA-N 0.000 description 4
- 239000003240 coconut oil Substances 0.000 description 4
- 235000019864 coconut oil Nutrition 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229940013317 fish oils Drugs 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241001465754 Metazoa Species 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
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HABLENUWIZGESP-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O HABLENUWIZGESP-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- AGDANEVFLMAYGL-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCCCCCC(O)=O AGDANEVFLMAYGL-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- GAFMQXDECDEWTD-UHFFFAOYSA-N heptadecanoic acid;hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCC(O)=O GAFMQXDECDEWTD-UHFFFAOYSA-N 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- JEGNXMUWVCVSSQ-UHFFFAOYSA-N octadec-1-en-1-ol Chemical compound CCCCCCCCCCCCCCCCC=CO JEGNXMUWVCVSSQ-UHFFFAOYSA-N 0.000 description 1
- RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 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
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001868 water Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898900993A GB8900993D0 (en) | 1989-01-17 | 1989-01-17 | Process |
| GB8900993.0 | 1989-01-17 | ||
| PCT/GB1990/000065 WO1990008123A1 (en) | 1989-01-17 | 1990-01-16 | Process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910700221A KR910700221A (ko) | 1991-03-14 |
| KR0167750B1 true KR0167750B1 (ko) | 1999-03-20 |
Family
ID=10650169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900702047A Expired - Lifetime KR0167750B1 (ko) | 1989-01-17 | 1990-01-16 | 알코올의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5138106A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0454720B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2781274B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR0167750B1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE116633T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU637998B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR9007039A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2045547A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69015806T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2069731T3 (cg-RX-API-DMAC7.html) |
| GB (1) | GB8900993D0 (cg-RX-API-DMAC7.html) |
| IN (1) | IN175663B (cg-RX-API-DMAC7.html) |
| MY (1) | MY106264A (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ232138A (cg-RX-API-DMAC7.html) |
| OA (1) | OA09381A (cg-RX-API-DMAC7.html) |
| PH (1) | PH27251A (cg-RX-API-DMAC7.html) |
| WO (1) | WO1990008123A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA90331B (cg-RX-API-DMAC7.html) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1006287A3 (fr) * | 1992-04-30 | 1994-07-12 | Gheorghiu Mihail | Procede de fabrication d'esters methyliques d'acides gras a partir d'une huile ou graisse naturelle, esters methyliques tels qu'ainsi obtenus et leur utilisation. |
| ZA938109B (en) * | 1992-10-29 | 1994-06-06 | Davy Mckee London | Process for the production of fatty alcohols |
| DE4335781C2 (de) * | 1993-10-20 | 1998-02-19 | Henkel Kgaa | Fettalkohole auf pflanzlicher Basis und Verfahren zu Ihrer Herstellung |
| EP0654528A1 (fr) * | 1993-11-22 | 1995-05-24 | Mihail Gheorghiu | Procédé de fabrication d'esters méthyliques d'acides gras à partir d'une huile ou graisse naturelle, esters méthyliques tels qu'ainsi obtenus et leur utilisation |
| US5532392A (en) * | 1994-01-13 | 1996-07-02 | Gheorghiu; Mihail | Process for the preparation of methyl fatty acid esters starting from natural oil or fat, methyl esters obtained in this way and use thereof |
| US5536889A (en) * | 1995-09-29 | 1996-07-16 | Shell Oil Company | Process for the two-stage hydrogenation of methyl esters |
| DE19939566C1 (de) * | 1999-08-20 | 2001-04-05 | Cognis Deutschland Gmbh | Verzweigte, weitgehend ungesättigte Esteröle, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von kosmetischen und/oder pharmazeutischen Zubereitungen |
| US20040047830A1 (en) * | 2002-09-05 | 2004-03-11 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Shaving composition |
| JP4034289B2 (ja) * | 2004-04-02 | 2008-01-16 | 花王株式会社 | 脂肪アルコールの製造方法 |
| DE102007033636A1 (de) | 2007-07-19 | 2009-01-22 | Cognis Ip Management Gmbh | Reinigung von Fettalkoholen |
| US20090119979A1 (en) * | 2007-11-08 | 2009-05-14 | Imperial Petroleum, Inc. | Catalysts for production of biodiesel fuel and glycerol |
| WO2010063780A1 (en) * | 2008-12-04 | 2010-06-10 | Shell Internationale Research Maatschappij B.V. | Process for preparing alkanediol and dialkyl carbonate |
| WO2010103549A2 (en) * | 2009-03-12 | 2010-09-16 | Godavari Biorefineries Ltd | A method of obtaining policosanols from natural material |
| EP2522650B1 (en) * | 2011-05-13 | 2016-03-09 | Cognis IP Management GmbH | Process for purifying crude fatty alcohols |
| US9045715B2 (en) * | 2011-05-13 | 2015-06-02 | Cognis Ip Management Gmbh | Process for purifying crude fatty alcohols |
| GB201119871D0 (en) * | 2011-11-17 | 2011-12-28 | Davy Process Techn Ltd | Process |
| DE112013004222T5 (de) * | 2012-08-31 | 2015-06-03 | Dow Global Technologies Llc | Verfahren zum Herstellen von Alkoholen aus organischen Säuren |
| GB201218078D0 (en) | 2012-10-09 | 2012-11-21 | Davy Process Techn Ltd | Process |
| GB201219983D0 (en) | 2012-11-06 | 2012-12-19 | Davy Process Techn Ltd | Apparatus and process |
| DE102013106382A1 (de) | 2013-06-19 | 2014-12-24 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Verfahren zum Herstellen von Fettalkoholen aus Fettsäuremethylester |
| EP3294453A4 (en) | 2015-03-26 | 2018-10-24 | BASF Corporation | Hydrogenolysis catalysts with high acid tolerance |
| CN108516924A (zh) * | 2018-03-30 | 2018-09-11 | 江苏丰益化工科技有限公司 | 一种用于高纯度脂肪醇的生产系统 |
| CN110860284B (zh) * | 2019-11-28 | 2021-04-02 | 浙江大学 | 一种负载型催化剂及其制备方法和应用 |
| US20240025826A1 (en) * | 2020-08-12 | 2024-01-25 | Conopco, Inc., D/B/A Unilever | Oleyl alcohol and process of production |
| WO2024062008A1 (en) * | 2022-09-23 | 2024-03-28 | Firmenich Sa | Transesterification process |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3173959A (en) * | 1965-03-16 | Process for the production of saturated fatty alcohols | ||
| US1491076A (en) * | 1921-04-05 | 1924-04-22 | Us Ind Alcohol Co | Process of alcoholysis |
| GB795573A (en) * | 1955-05-10 | 1958-05-28 | Belge Produits Chimiques Sa | An improved process for the preparation of higher aliphatic alcohols |
| FR1154907A (fr) * | 1955-07-05 | 1958-04-18 | California Research Corp | Alcools gras supérieurs |
| FR1402133A (fr) * | 1964-04-30 | 1965-06-11 | Sinnova Ou Sadic | Procédé de préparation d'alcools gras supérieurs à partir d'huiles ou graisses acides d'origine végétale ou animale |
| US3949007A (en) * | 1969-08-01 | 1976-04-06 | Bayer Aktiengesellschaft | Process for the production of primary alkenols |
| GB1290094A (cg-RX-API-DMAC7.html) * | 1970-03-13 | 1972-09-20 | ||
| SU734182A1 (ru) * | 1977-07-07 | 1980-05-15 | Ярославский политехнический институт | Способ получени вторичного бутилового спирта |
| JPS60188334A (ja) * | 1984-03-08 | 1985-09-25 | Nisshin Oil Mills Ltd:The | 高級アルコ−ルの製造法 |
| ES2064715T3 (es) * | 1989-01-17 | 1995-02-01 | Davy Mckee London | Procedimiento para la obtencion de alcoholes grasos. |
-
1989
- 1989-01-17 GB GB898900993A patent/GB8900993D0/en active Pending
-
1990
- 1990-01-16 PH PH39894A patent/PH27251A/en unknown
- 1990-01-16 ES ES90901859T patent/ES2069731T3/es not_active Expired - Lifetime
- 1990-01-16 AU AU49466/90A patent/AU637998B2/en not_active Ceased
- 1990-01-16 DE DE69015806T patent/DE69015806T2/de not_active Expired - Fee Related
- 1990-01-16 AT AT90901859T patent/ATE116633T1/de not_active IP Right Cessation
- 1990-01-16 BR BR909007039A patent/BR9007039A/pt not_active Application Discontinuation
- 1990-01-16 KR KR1019900702047A patent/KR0167750B1/ko not_active Expired - Lifetime
- 1990-01-16 WO PCT/GB1990/000065 patent/WO1990008123A1/en not_active Ceased
- 1990-01-16 CA CA002045547A patent/CA2045547A1/en not_active Abandoned
- 1990-01-16 US US07/721,437 patent/US5138106A/en not_active Expired - Lifetime
- 1990-01-16 EP EP90901859A patent/EP0454720B1/en not_active Expired - Lifetime
- 1990-01-16 JP JP2502361A patent/JP2781274B2/ja not_active Expired - Lifetime
- 1990-01-17 NZ NZ232138A patent/NZ232138A/en unknown
- 1990-01-17 MY MYPI90000087A patent/MY106264A/en unknown
- 1990-01-17 ZA ZA90331A patent/ZA90331B/xx unknown
- 1990-01-17 IN IN49MA1990 patent/IN175663B/en unknown
-
1991
- 1991-07-15 OA OA60040A patent/OA09381A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2069731T3 (es) | 1995-05-16 |
| AU4946690A (en) | 1990-08-13 |
| GB8900993D0 (en) | 1989-03-08 |
| AU637998B2 (en) | 1993-06-17 |
| JPH04504411A (ja) | 1992-08-06 |
| EP0454720A1 (en) | 1991-11-06 |
| DE69015806D1 (de) | 1995-02-16 |
| OA09381A (en) | 1992-09-15 |
| KR910700221A (ko) | 1991-03-14 |
| PH27251A (en) | 1993-05-04 |
| ATE116633T1 (de) | 1995-01-15 |
| US5138106A (en) | 1992-08-11 |
| NZ232138A (en) | 1992-06-25 |
| CA2045547A1 (en) | 1990-07-18 |
| IN175663B (cg-RX-API-DMAC7.html) | 1995-08-05 |
| WO1990008123A1 (en) | 1990-07-26 |
| EP0454720B1 (en) | 1995-01-04 |
| MY106264A (en) | 1995-04-29 |
| ZA90331B (en) | 1991-01-30 |
| JP2781274B2 (ja) | 1998-07-30 |
| DE69015806T2 (de) | 1995-05-18 |
| BR9007039A (pt) | 1991-11-12 |
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| Date | Code | Title | Description |
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| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19900915 |
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| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19950116 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19900915 Comment text: Patent Application |
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Comment text: Notification of reason for refusal Patent event date: 19980227 Patent event code: PE09021S01D |
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