CA2352352A1 - Method for the reesterification of fat and/or oil of biological origin by means of alcoholysis - Google Patents
Method for the reesterification of fat and/or oil of biological origin by means of alcoholysis Download PDFInfo
- Publication number
- CA2352352A1 CA2352352A1 CA002352352A CA2352352A CA2352352A1 CA 2352352 A1 CA2352352 A1 CA 2352352A1 CA 002352352 A CA002352352 A CA 002352352A CA 2352352 A CA2352352 A CA 2352352A CA 2352352 A1 CA2352352 A1 CA 2352352A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- oil
- catalyst
- fat
- fatty acids
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 53
- 238000006136 alcoholysis reaction Methods 0.000 title claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000001413 amino acids Chemical class 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 150000003862 amino acid derivatives Chemical class 0.000 claims abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 63
- 235000021588 free fatty acids Nutrition 0.000 claims description 34
- 235000011187 glycerol Nutrition 0.000 claims description 31
- 238000005809 transesterification reaction Methods 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 22
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 239000011701 zinc Substances 0.000 claims description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000005456 glyceride group Chemical group 0.000 claims description 12
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 12
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 10
- 150000003751 zinc Chemical class 0.000 claims description 10
- -1 fatty-acid esters Chemical class 0.000 claims description 8
- 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
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 6
- 239000004475 Arginine Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 229960004203 carnitine Drugs 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 229910001385 heavy metal Inorganic materials 0.000 claims description 6
- 229960003080 taurine Drugs 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 5
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 150000001661 cadmium Chemical class 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 108700003601 dimethylglycine Proteins 0.000 claims description 2
- 150000002603 lanthanum Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 229960003624 creatine Drugs 0.000 claims 1
- 239000006046 creatine Substances 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 229940078490 n,n-dimethylglycine Drugs 0.000 claims 1
- 229910052761 rare earth metal Inorganic materials 0.000 claims 1
- 150000002910 rare earth metals Chemical class 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- 238000006243 chemical reaction Methods 0.000 description 37
- 150000004702 methyl esters Chemical class 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 32
- 235000019198 oils Nutrition 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- 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 27
- 235000019482 Palm oil Nutrition 0.000 description 27
- 239000002540 palm oil Substances 0.000 description 27
- 239000003925 fat Substances 0.000 description 21
- 235000019197 fats Nutrition 0.000 description 21
- 239000012071 phase Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 238000012856 packing Methods 0.000 description 10
- 239000000344 soap Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000002357 guanidines Chemical class 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 150000003626 triacylglycerols Chemical class 0.000 description 8
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical class C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 235000019486 Sunflower oil Nutrition 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000002600 sunflower oil Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 229960002449 glycine Drugs 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000007210 heterogeneous catalysis Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 229960003237 betaine Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052793 cadmium Inorganic materials 0.000 description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
- 230000003292 diminished effect Effects 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- 229940071566 zinc glycinate Drugs 0.000 description 3
- UOXSXMSTSYWNMH-UHFFFAOYSA-L zinc;2-aminoacetate Chemical compound [Zn+2].NCC([O-])=O.NCC([O-])=O UOXSXMSTSYWNMH-UHFFFAOYSA-L 0.000 description 3
- 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
- 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
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
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- 238000010924 continuous production 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
- 230000007423 decrease Effects 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010932 ethanolysis reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 238000006140 methanolysis reaction Methods 0.000 description 2
- 230000007935 neutral effect Effects 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
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- 150000003388 sodium compounds Chemical class 0.000 description 2
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-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
- 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
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 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
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 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
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229930003802 tocotrienol Natural products 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- 229940068778 tocotrienols Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 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)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19950593.4 | 1999-10-20 | ||
| DE19950593A DE19950593A1 (de) | 1999-10-20 | 1999-10-20 | Verfahren zur Gewinnung einfacher Fettsäure-Ester aus Fett und/oder Öl biologischen Ursprungs |
| PCT/EP2000/010314 WO2001029160A1 (de) | 1999-10-20 | 2000-10-19 | Verfahren zur umesterung von fett und/oder öl biologischen ursprungs mittels alkoholyse |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2352352A1 true CA2352352A1 (en) | 2001-04-26 |
Family
ID=7926318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002352352A Abandoned CA2352352A1 (en) | 1999-10-20 | 2000-10-19 | Method for the reesterification of fat and/or oil of biological origin by means of alcoholysis |
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) |
Families Citing this family (39)
| 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 |
| US20030158171A1 (en) * | 2001-11-28 | 2003-08-21 | Albion International, Inc. | Chelates and complexes for reduction in alcohol dependency |
| 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 |
| DE10200528A1 (de) * | 2002-01-09 | 2003-07-10 | Siegfried Peter | Verfahren zur Emesterung von Fett und/oder Öl durch heterogene Katalyse |
| DE10245806A1 (de) * | 2002-10-01 | 2004-04-15 | Siegfried Prof. Dr. Peter | Verfahren zur Herstellung von Fettsäureestern einwertiger Alkohole mittels Alkoholyse unter Verwendung spezieller basischer Katalysatoren |
| AU2004269265B2 (en) * | 2003-08-29 | 2009-11-26 | Nippon Shokubai Co., Ltd. | Method of production of fatty acid alkyl esters and/or glycerine and fatty acid alkyl ester-containing composition |
| 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 |
| US20080188676A1 (en) * | 2006-09-14 | 2008-08-07 | Anderson Gregory A | Methods of robust and efficient conversion of cellular lipids to biofuels |
| 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 |
| US20090005582A1 (en) * | 2007-06-22 | 2009-01-01 | Greg Anderson | Vessels and methods for synthesis of biofuel |
| US20080318763A1 (en) * | 2007-06-22 | 2008-12-25 | Greg Anderson | 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 |
| US8895764B2 (en) * | 2008-05-19 | 2014-11-25 | Wayne State University | ZnO nanoparticle catalysts for use in biodiesel production and method of making |
| EP2313479B1 (en) * | 2008-05-19 | 2018-05-16 | Wayne State University | Methods and catalysts for making biodiesel from the transesterification and esterification of unrefined oils |
| 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 CN CNB008023026A patent/CN1228303C/zh not_active Expired - Fee Related
- 2000-10-19 ID IDW00200101309A patent/ID29472A/id unknown
- 2000-10-19 DK DK00981204T patent/DK1141183T3/da active
- 2000-10-19 JP JP2001531947A patent/JP2003512507A/ja active Pending
- 2000-10-19 BR BR0007224-9A patent/BR0007224A/pt not_active IP Right Cessation
- 2000-10-19 TR TR2001/01774T patent/TR200101774T1/xx unknown
- 2000-10-19 KR KR1020017007538A patent/KR20010080766A/ko not_active Ceased
- 2000-10-19 RU RU2001119276/04A patent/RU2263660C2/ru not_active IP Right Cessation
- 2000-10-19 PL PL00348256A patent/PL348256A1/xx unknown
- 2000-10-19 DE DE50006589T patent/DE50006589D1/de not_active Expired - Fee Related
- 2000-10-19 UA UA2001075130A patent/UA66904C2/xx unknown
- 2000-10-19 EP EP00981204A patent/EP1141183B1/de not_active Expired - Lifetime
- 2000-10-19 NZ NZ512283A patent/NZ512283A/xx unknown
- 2000-10-19 IL IL14360500A patent/IL143605A/en not_active IP Right Cessation
- 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 AU AU18536/01A patent/AU778807B2/en not_active Ceased
- 2000-10-19 AT AT00981204T patent/ATE267862T1/de not_active IP Right Cessation
- 2000-10-19 ES ES00981204T patent/ES2219420T3/es not_active Expired - Lifetime
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| IL143605A (en) | 2004-09-27 |
| US6359157B2 (en) | 2002-03-19 |
| DE50006589D1 (de) | 2004-07-01 |
| UA66904C2 (en) | 2004-06-15 |
| EP1141183A1 (de) | 2001-10-10 |
| DK1141183T3 (da) | 2004-09-27 |
| AU778807B2 (en) | 2004-12-23 |
| TR200101774T1 (tr) | 2002-03-21 |
| BR0007224A (pt) | 2001-09-25 |
| ID29472A (id) | 2001-08-30 |
| ES2219420T3 (es) | 2004-12-01 |
| CN1327472A (zh) | 2001-12-19 |
| WO2001029160A1 (de) | 2001-04-26 |
| PL348256A1 (en) | 2002-05-20 |
| CN1228303C (zh) | 2005-11-23 |
| IL143605A0 (en) | 2002-04-21 |
| AU1853601A (en) | 2001-04-30 |
| KR20010080766A (ko) | 2001-08-22 |
| JP2003512507A (ja) | 2003-04-02 |
| US20010053860A1 (en) | 2001-12-20 |
| DE19950593A1 (de) | 2001-05-17 |
| EP1141183B1 (de) | 2004-05-26 |
| RU2263660C2 (ru) | 2005-11-10 |
| AR026196A1 (es) | 2003-01-29 |
| ATE267862T1 (de) | 2004-06-15 |
| NZ512283A (en) | 2002-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |