DE19950593A1 - Verfahren zur Gewinnung einfacher Fettsäure-Ester aus Fett und/oder Öl biologischen Ursprungs - Google Patents
Verfahren zur Gewinnung einfacher Fettsäure-Ester aus Fett und/oder Öl biologischen UrsprungsInfo
- Publication number
- DE19950593A1 DE19950593A1 DE19950593A DE19950593A DE19950593A1 DE 19950593 A1 DE19950593 A1 DE 19950593A1 DE 19950593 A DE19950593 A DE 19950593A DE 19950593 A DE19950593 A DE 19950593A DE 19950593 A1 DE19950593 A1 DE 19950593A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- salt
- oil
- fat
- amino
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims abstract description 48
- 230000008569 process Effects 0.000 title claims description 13
- -1 fatty acid esters Chemical class 0.000 title claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 8
- 229930195729 fatty acid Natural products 0.000 title claims description 8
- 239000000194 fatty acid Substances 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 150000001413 amino acids Chemical class 0.000 claims abstract 7
- 235000021588 free fatty acids Nutrition 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000011541 reaction mixture Substances 0.000 claims description 17
- ODKSFYDXXFIFQN-UHFFFAOYSA-N Arginine Chemical compound OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 16
- 238000005809 transesterification reaction Methods 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 229910052746 lanthanum Inorganic materials 0.000 claims description 7
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 7
- 150000003751 zinc Chemical class 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 3
- 150000002910 rare earth metals Chemical class 0.000 claims description 3
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229940024606 amino acid Drugs 0.000 claims 6
- 235000001014 amino acid Nutrition 0.000 claims 6
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims 5
- 150000002815 nickel Chemical class 0.000 claims 5
- 150000001868 cobalt Chemical class 0.000 claims 3
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims 2
- 229960005261 aspartic acid Drugs 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- 150000002603 lanthanum Chemical class 0.000 claims 1
- 150000002696 manganese Chemical class 0.000 claims 1
- 229910052712 strontium Inorganic materials 0.000 claims 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 1
- 150000003862 amino acid derivatives Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 50
- 150000004702 methyl esters Chemical class 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000003921 oil Substances 0.000 description 32
- 235000019198 oils Nutrition 0.000 description 32
- 229960005150 glycerol Drugs 0.000 description 23
- 235000011187 glycerol Nutrition 0.000 description 23
- RLSBGGURBSZJLQ-SCGRZTRASA-N (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid zinc Chemical compound [Zn].N[C@@H](CCCN=C(N)N)C(O)=O.N[C@@H](CCCN=C(N)N)C(O)=O RLSBGGURBSZJLQ-SCGRZTRASA-N 0.000 description 21
- 235000019482 Palm oil Nutrition 0.000 description 21
- 239000003925 fat Substances 0.000 description 21
- 235000019197 fats Nutrition 0.000 description 21
- 239000002540 palm oil Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 239000012071 phase Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 150000003626 triacylglycerols Chemical class 0.000 description 9
- 235000019486 Sunflower oil Nutrition 0.000 description 8
- 239000002600 sunflower oil Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 150000002357 guanidines Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000007210 heterogeneous catalysis Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229940071566 zinc glycinate Drugs 0.000 description 4
- UOXSXMSTSYWNMH-UHFFFAOYSA-L zinc;2-aminoacetate Chemical compound [Zn+2].NCC([O-])=O.NCC([O-])=O UOXSXMSTSYWNMH-UHFFFAOYSA-L 0.000 description 4
- 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 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000006140 methanolysis reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VSCBATMPTLKTOV-UHFFFAOYSA-N 2-tert-butylimino-n,n-diethyl-1,3-dimethyl-1,3,2$l^{5}-diazaphosphinan-2-amine Chemical compound CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1C VSCBATMPTLKTOV-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-M creatinate Chemical compound NC(=N)N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-M 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000010932 ethanolysis reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229960004198 guanidine Drugs 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003112 potassium compounds Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- FUPAJKKAHDLPAZ-UHFFFAOYSA-N 1,2,3-triphenylguanidine Chemical compound C=1C=CC=CC=1NC(=NC=1C=CC=CC=1)NC1=CC=CC=C1 FUPAJKKAHDLPAZ-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical class OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-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
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical class NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 1
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 1
- KNJKCQQJXJVQGA-UHFFFAOYSA-N 5-(diaminomethylideneamino)-2-methylpentanoic acid Chemical compound OC(=O)C(C)CCCN=C(N)N KNJKCQQJXJVQGA-UHFFFAOYSA-N 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
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- 241000220317 Rosa Species 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 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
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- 150000003868 ammonium compounds Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000001483 arginine derivatives Chemical class 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
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- 229940009098 aspartate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001582 butter acid Substances 0.000 description 1
- YCGZGGJSAXLJFQ-UHFFFAOYSA-L calcium 2-amino-5-(diaminomethylideneamino)pentanoate Chemical compound [Ca+2].[O-]C(=O)C(N)CCCN=C(N)N.[O-]C(=O)C(N)CCCN=C(N)N YCGZGGJSAXLJFQ-UHFFFAOYSA-L 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
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- 239000010962 carbon steel Substances 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 235000005473 carotenes Nutrition 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
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- JCICJTXQTSTBTE-UHFFFAOYSA-N ctk0h9578 Chemical class NP(N)(N)=N JCICJTXQTSTBTE-UHFFFAOYSA-N 0.000 description 1
- GICLSALZHXCILJ-UHFFFAOYSA-N ctk5a5089 Chemical compound NCC(O)=O.NCC(O)=O GICLSALZHXCILJ-UHFFFAOYSA-N 0.000 description 1
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- RWXOJQGSZWUIEJ-UHFFFAOYSA-K lanthanum(3+);octadecanoate Chemical compound [La+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RWXOJQGSZWUIEJ-UHFFFAOYSA-K 0.000 description 1
- 238000002386 leaching Methods 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
- 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
- 239000007788 liquid Substances 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XIYLJKDSPVXWSV-UHFFFAOYSA-N n-[bis(dimethylamino)-methylimino-$l^{5}-phosphanyl]-n-methylmethanamine Chemical compound CN=P(N(C)C)(N(C)C)N(C)C XIYLJKDSPVXWSV-UHFFFAOYSA-N 0.000 description 1
- 229910001453 nickel ion Inorganic materials 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical class OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19950593A DE19950593A1 (de) | 1999-10-20 | 1999-10-20 | Verfahren zur Gewinnung einfacher Fettsäure-Ester aus Fett und/oder Öl biologischen Ursprungs |
| CNB008023026A CN1228303C (zh) | 1999-10-20 | 2000-10-19 | 用醇解方法使生物来源的脂肪和/或油进行酯交换的工艺 |
| JP2001531947A JP2003512507A (ja) | 1999-10-20 | 2000-10-19 | 加アルコール分解による生物由来の脂肪および／又は油のエステル交換方法 |
| AT00981204T ATE267862T1 (de) | 1999-10-20 | 2000-10-19 | Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse |
| EP00981204A EP1141183B1 (de) | 1999-10-20 | 2000-10-19 | Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse |
| UA2001075130A UA66904C2 (en) | 1999-10-20 | 2000-10-19 | A method for the reesterification of fat and/or oil of biological origin by means of alcoholysis and fatty acids monosters |
| PL00348256A PL348256A1 (en) | 1999-10-20 | 2000-10-19 | Method for the reesterification of fat and/or oil of biological origin by means of alcoholysis |
| TR2001/01774T TR200101774T1 (tr) | 1999-10-20 | 2000-10-19 | Alkooliz vasìtasìyla yaĞ ve/veya biyolojik orijinli yaĞìn transesterifikasyonu iin proses. |
| DK00981204T DK1141183T3 (da) | 1999-10-20 | 2000-10-19 | Fremgangsmåde til omesterificering af fedt og/eller olie af biologisk oprindelse ved hjælp af alkoholyse |
| DE50006589T DE50006589D1 (de) | 1999-10-20 | 2000-10-19 | Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse |
| RU2001119276/04A RU2263660C2 (ru) | 1999-10-20 | 2000-10-19 | Способ переэтерификации жира и/или масла биологического происхождения путем алкоголиза |
| AU18536/01A AU778807B2 (en) | 1999-10-20 | 2000-10-19 | Method for the reesterification of fat and/or oil of biological origin by means of alcoholysis |
| ES00981204T ES2219420T3 (es) | 1999-10-20 | 2000-10-19 | Procedimiento para la transesterificacion de grasa y/o aceite de origen biologico por medio de alcoholisis. |
| PCT/EP2000/010314 WO2001029160A1 (de) | 1999-10-20 | 2000-10-19 | Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse |
| KR1020017007538A KR20010080766A (ko) | 1999-10-20 | 2000-10-19 | 알코올 분해에 의한 생물학적 기원의 지방 및/또는 오일의에스테르교환 방법 |
| IDW00200101309A ID29472A (id) | 1999-10-20 | 2000-10-19 | Proses untuk transesterifikasi lemak dan/atau minyak asal biologi dengan menggunakan alkoholisis |
| CA002352352A CA2352352A1 (en) | 1999-10-20 | 2000-10-19 | Method for the reesterification of fat and/or oil of biological origin by means of alcoholysis |
| IL14360500A IL143605A (en) | 1999-10-20 | 2000-10-19 | Process for transesterification of fat and / or oil from a biological source through decomposition by alcohol |
| BR0007224-9A BR0007224A (pt) | 1999-10-20 | 2000-10-19 | Processo para a transesterificação de gorduras e/ou óleo de origem biológica por meio de alcoólise |
| NZ512283A NZ512283A (en) | 1999-10-20 | 2000-10-19 | Method for the reesterification of fat and/or oil of biological origin consisting of glycerides by means of alcoholysis |
| ARP000105540A AR026196A1 (es) | 1999-10-20 | 2000-10-20 | Procedimiento para transesterificar grasas y/o aceites de origen biologico por medio de la alcoholisis, y los monoesteres de acido graso obtenidos condicho procedimiento |
| US09/884,328 US6359157B2 (en) | 1999-10-20 | 2001-06-19 | Process for the transesterification of fat and/or oil of biological origin by means of alcoholysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19950593A DE19950593A1 (de) | 1999-10-20 | 1999-10-20 | Verfahren zur Gewinnung einfacher Fettsäure-Ester aus Fett und/oder Öl biologischen Ursprungs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19950593A1 true DE19950593A1 (de) | 2001-05-17 |
Family
ID=7926318
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19950593A Withdrawn DE19950593A1 (de) | 1999-10-20 | 1999-10-20 | Verfahren zur Gewinnung einfacher Fettsäure-Ester aus Fett und/oder Öl biologischen Ursprungs |
| DE50006589T Expired - Fee Related DE50006589D1 (de) | 1999-10-20 | 2000-10-19 | Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50006589T Expired - Fee Related DE50006589D1 (de) | 1999-10-20 | 2000-10-19 | Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6359157B2 (enExample) |
| EP (1) | EP1141183B1 (enExample) |
| JP (1) | JP2003512507A (enExample) |
| KR (1) | KR20010080766A (enExample) |
| CN (1) | CN1228303C (enExample) |
| AR (1) | AR026196A1 (enExample) |
| AT (1) | ATE267862T1 (enExample) |
| AU (1) | AU778807B2 (enExample) |
| BR (1) | BR0007224A (enExample) |
| CA (1) | CA2352352A1 (enExample) |
| DE (2) | DE19950593A1 (enExample) |
| DK (1) | DK1141183T3 (enExample) |
| ES (1) | ES2219420T3 (enExample) |
| ID (1) | ID29472A (enExample) |
| IL (1) | IL143605A (enExample) |
| NZ (1) | NZ512283A (enExample) |
| PL (1) | PL348256A1 (enExample) |
| RU (1) | RU2263660C2 (enExample) |
| TR (1) | TR200101774T1 (enExample) |
| UA (1) | UA66904C2 (enExample) |
| WO (1) | WO2001029160A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004031119A1 (de) * | 2002-10-01 | 2004-04-15 | Siegfried Peter | Verfahren zur herstellung von fettsäureestern einwertiger alkohole mittels alkoholyse unter verwendung spezieller basischer katalysatoren |
| EP1660619A4 (en) * | 2003-08-29 | 2009-08-05 | Nippon Catalytic Chem Ind | METHOD FOR PRODUCING FATTY ACID ESTERS AND / OR GLYCERINE AND FATTY ACID ELECTRIC COMPOSITION |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10155241C1 (de) | 2001-11-09 | 2003-07-03 | Gmk Ges Fuer Motoren Und Kraft | Verfahren zur Herstellung von Kraftstoffen aus sauren Fetten und Anlage zu dessen Durchführung |
| US20060013892A1 (en) * | 2001-11-28 | 2006-01-19 | Albion International Inc. | Administration of amino acid chelates for reduction in alcohol dependency |
| US7910137B2 (en) * | 2001-11-28 | 2011-03-22 | Albion International, Inc. | Metal carnitine chelates |
| US20030158171A1 (en) * | 2001-11-28 | 2003-08-21 | Albion International, Inc. | Chelates and complexes for reduction in alcohol dependency |
| DE10200528A1 (de) * | 2002-01-09 | 2003-07-10 | Siegfried Peter | Verfahren zur Emesterung von Fett und/oder Öl durch heterogene Katalyse |
| DE102004044660A1 (de) * | 2004-09-15 | 2006-03-30 | Siegfried Prof. Dr. Peter | Verfahren zur Umesterung von Fetten und Ölen biologischen Ursprungs mittels Alkoholyse unter Verwendung spezieller Kohlensäuresalze |
| US7473539B2 (en) * | 2004-09-20 | 2009-01-06 | Sunho Biodiesel Corporation | Methods for producing alkyl esters |
| CN1301322C (zh) * | 2005-01-12 | 2007-02-21 | 李搏 | 快速制备生物柴油的方法 |
| CN100439474C (zh) * | 2005-09-30 | 2008-12-03 | 中国科学院山西煤炭化学研究所 | 高酸值油脂同时酯化酯交换制备生物柴油的方法 |
| US7828978B2 (en) * | 2006-01-11 | 2010-11-09 | Doug Geier | Simultaneous synthesis and purification of a fatty acid monoester biodiesel fuel |
| ITRM20060377A1 (it) * | 2006-07-19 | 2008-01-20 | Angelis Nazzareno De | Procedimento integrato per la produzione di biocombustibili e biocarburanti da diverse tipologie di materie prime e relativi prodotti |
| BRPI0716831A2 (pt) * | 2006-09-14 | 2013-10-29 | Biofuelbox Corp | Método de conversão consistente e eficiente de lipídeos celulares em biocombustíveis |
| WO2008055131A2 (en) * | 2006-10-30 | 2008-05-08 | Greenline Industries, Llc | Optimized biodiesel reaction kinetics system |
| CN101200674B (zh) * | 2006-12-13 | 2010-05-19 | 中国石油化工股份有限公司 | 一种降低油脂酸值的方法 |
| WO2009002880A1 (en) * | 2007-06-22 | 2008-12-31 | Biofuelbox Corporation | Vessels and methods for synthesis of biofuel |
| WO2009002878A1 (en) * | 2007-06-22 | 2008-12-31 | Biofuelbox Corporation | System for production and purification of biofuel |
| FR2919303B1 (fr) * | 2007-07-24 | 2012-11-30 | Jean Pierre Esterez | Procede de preparation d'esters d'acides gras a partir de flocon de graines oleagineuses. |
| US8070836B2 (en) * | 2007-10-16 | 2011-12-06 | Wayne State University | Combined homogeneous and heterogeneous catalytic transesterification process for biodiesel production |
| US20090119979A1 (en) * | 2007-11-08 | 2009-05-14 | Imperial Petroleum, Inc. | Catalysts for production of biodiesel fuel and glycerol |
| RU2365625C1 (ru) * | 2007-12-07 | 2009-08-27 | Государственное образовательное учреждение высшего профессионального образования Российский государственный университет нефти и газа им.И.М.Губкина | Способ обработки растительного масла |
| US7851645B2 (en) * | 2008-02-11 | 2010-12-14 | Catalytic Distillation Technologies | Process for continuous production of organic carbonates or organic carbamates and solid catalysts therefore |
| CA2650365C (en) * | 2008-02-28 | 2011-09-13 | Rohm And Haas Company | Guanidine-substituted resin for transesterification |
| CN101544928B (zh) * | 2008-03-27 | 2012-12-12 | 中国石油化工股份有限公司 | 一种降低生物油料酸值的方法 |
| RU2366503C1 (ru) * | 2008-04-14 | 2009-09-10 | Институт Катализа Им. Г.К. Борескова Сибирского Отделения Российской Академии Наук | Катализатор, способ его приготовления (варианты) и способ получения биотоплива |
| BRPI0913099A2 (pt) * | 2008-05-19 | 2019-09-24 | Univ Wayne State | métodos e catalizadores para preparar biodiesel a partir da transesterificação de óleo não refinados |
| US8895764B2 (en) * | 2008-05-19 | 2014-11-25 | Wayne State University | ZnO nanoparticle catalysts for use in biodiesel production and method of making |
| US8975426B2 (en) | 2008-05-19 | 2015-03-10 | Wayne State University | ZnO nanoparticle catalysts for use in transesterification and esterification reactions and method of making |
| DE102009006777A1 (de) | 2009-01-30 | 2010-08-05 | Wolfgang F. Prof. Dr. Hölderich | Verfahren zur Herstellung von Fettsäureestern und Glycerin durch Umesterung von pflanzlichen und tierischen Fetten und Ölen |
| RU2405627C1 (ru) * | 2009-07-07 | 2010-12-10 | Федеральное государственное унитарное предприятие "Государственный научно-исследовательский институт органической химии и технологии" (ФГУП "ГосНИИОХТ") | Катализатор для производства метиловых эфиров жирных кислот (биодизеля) |
| GB201119871D0 (en) | 2011-11-17 | 2011-12-28 | Davy Process Techn Ltd | Process |
| GB201218078D0 (en) | 2012-10-09 | 2012-11-21 | Davy Process Techn Ltd | Process |
| CN102965202B (zh) * | 2012-10-31 | 2014-02-19 | 潍坊金信达生物化工有限公司 | 一种用非均相催化剂制备生物柴油的方法 |
| US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
| EP3342930B1 (en) * | 2016-12-28 | 2020-04-29 | Advanced Polymer Technology Corp. | Floor pavement structure with gel layer |
| CN109678703B (zh) * | 2019-01-29 | 2021-07-13 | 河南工业大学 | 一种单甘脂的合成方法 |
| CN115385812A (zh) * | 2022-07-29 | 2022-11-25 | 宁夏太康药业有限公司 | 一种肌氨酸锌螯合物的制备方法 |
| CN118995282B (zh) * | 2024-10-25 | 2025-02-07 | 洛阳恒玖生物能源有限公司 | 一种生物油脂制备高质燃油的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB979523A (en) * | 1961-03-30 | 1965-01-06 | Boake Roberts & Co Ltd | Improvements in or relating to the production of terpene esters and alcohols |
| IE34977B1 (en) * | 1970-03-06 | 1975-10-15 | Unilever Ltd | Process for preparing diglycerides |
| GB8418274D0 (en) * | 1984-07-18 | 1984-08-22 | Inst Penyelidikan Minyak Kelap | Carboxylic acid esterification |
| RU2050347C1 (ru) * | 1992-09-16 | 1995-12-20 | Центральный научно-исследовательский и проектный институт лесохимической промышленности | Способ получения эфиров дистиллированного таллового масла |
| FR2752242B1 (fr) * | 1996-08-08 | 1998-10-16 | Inst Francais Du Petrole | Procede de fabrication d'esters a partir d'huiles vegetales ou animales et d'alcools |
| JP3837950B2 (ja) * | 1998-09-09 | 2006-10-25 | 住友化学株式会社 | 脂肪酸エステルの製造方法および脂肪酸エステルを含む燃料 |
-
1999
- 1999-10-20 DE DE19950593A patent/DE19950593A1/de not_active Withdrawn
-
2000
- 2000-10-19 AU AU18536/01A patent/AU778807B2/en not_active Ceased
- 2000-10-19 ID IDW00200101309A patent/ID29472A/id unknown
- 2000-10-19 AT AT00981204T patent/ATE267862T1/de not_active IP Right Cessation
- 2000-10-19 IL IL14360500A patent/IL143605A/en not_active IP Right Cessation
- 2000-10-19 DK DK00981204T patent/DK1141183T3/da active
- 2000-10-19 TR TR2001/01774T patent/TR200101774T1/xx unknown
- 2000-10-19 JP JP2001531947A patent/JP2003512507A/ja active Pending
- 2000-10-19 NZ NZ512283A patent/NZ512283A/xx unknown
- 2000-10-19 EP EP00981204A patent/EP1141183B1/de not_active Expired - Lifetime
- 2000-10-19 CN CNB008023026A patent/CN1228303C/zh not_active Expired - Fee Related
- 2000-10-19 CA CA002352352A patent/CA2352352A1/en not_active Abandoned
- 2000-10-19 WO PCT/EP2000/010314 patent/WO2001029160A1/de not_active Ceased
- 2000-10-19 DE DE50006589T patent/DE50006589D1/de not_active Expired - Fee Related
- 2000-10-19 KR KR1020017007538A patent/KR20010080766A/ko not_active Ceased
- 2000-10-19 BR BR0007224-9A patent/BR0007224A/pt not_active IP Right Cessation
- 2000-10-19 ES ES00981204T patent/ES2219420T3/es not_active Expired - Lifetime
- 2000-10-19 PL PL00348256A patent/PL348256A1/xx unknown
- 2000-10-19 UA UA2001075130A patent/UA66904C2/xx unknown
- 2000-10-19 RU RU2001119276/04A patent/RU2263660C2/ru not_active IP Right Cessation
- 2000-10-20 AR ARP000105540A patent/AR026196A1/es unknown
-
2001
- 2001-06-19 US US09/884,328 patent/US6359157B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004031119A1 (de) * | 2002-10-01 | 2004-04-15 | Siegfried Peter | Verfahren zur herstellung von fettsäureestern einwertiger alkohole mittels alkoholyse unter verwendung spezieller basischer katalysatoren |
| EP1660619A4 (en) * | 2003-08-29 | 2009-08-05 | Nippon Catalytic Chem Ind | METHOD FOR PRODUCING FATTY ACID ESTERS AND / OR GLYCERINE AND FATTY ACID ELECTRIC COMPOSITION |
| US7605281B2 (en) | 2003-08-29 | 2009-10-20 | Nippon Shokubai Co., Ltd. | Method of production of fatty acid alkyl esters and/or glycerine and fatty acid alkyl ester-containing composition |
Also Published As
| Publication number | Publication date |
|---|---|
| UA66904C2 (en) | 2004-06-15 |
| NZ512283A (en) | 2002-10-25 |
| ID29472A (id) | 2001-08-30 |
| RU2263660C2 (ru) | 2005-11-10 |
| US20010053860A1 (en) | 2001-12-20 |
| ATE267862T1 (de) | 2004-06-15 |
| PL348256A1 (en) | 2002-05-20 |
| AU1853601A (en) | 2001-04-30 |
| BR0007224A (pt) | 2001-09-25 |
| EP1141183B1 (de) | 2004-05-26 |
| WO2001029160A1 (de) | 2001-04-26 |
| CN1327472A (zh) | 2001-12-19 |
| EP1141183A1 (de) | 2001-10-10 |
| ES2219420T3 (es) | 2004-12-01 |
| DK1141183T3 (da) | 2004-09-27 |
| DE50006589D1 (de) | 2004-07-01 |
| TR200101774T1 (tr) | 2002-03-21 |
| IL143605A (en) | 2004-09-27 |
| AR026196A1 (es) | 2003-01-29 |
| CA2352352A1 (en) | 2001-04-26 |
| CN1228303C (zh) | 2005-11-23 |
| IL143605A0 (en) | 2002-04-21 |
| AU778807B2 (en) | 2004-12-23 |
| KR20010080766A (ko) | 2001-08-22 |
| US6359157B2 (en) | 2002-03-19 |
| JP2003512507A (ja) | 2003-04-02 |
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