ZA200201238B - Single-phase process for production of fatty acid methyl esters from mixtures of triglycerides and fatty acids. - Google Patents
Single-phase process for production of fatty acid methyl esters from mixtures of triglycerides and fatty acids. Download PDFInfo
- Publication number
- ZA200201238B ZA200201238B ZA200201238A ZA200201238A ZA200201238B ZA 200201238 B ZA200201238 B ZA 200201238B ZA 200201238 A ZA200201238 A ZA 200201238A ZA 200201238 A ZA200201238 A ZA 200201238A ZA 200201238 B ZA200201238 B ZA 200201238B
- Authority
- ZA
- South Africa
- Prior art keywords
- oil
- alcohol
- triglycerides
- fatty acids
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 73
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 60
- 239000000194 fatty acid Substances 0.000 title claims abstract description 60
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 60
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 56
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 150000003626 triacylglycerols Chemical class 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title description 12
- 235000019387 fatty acid methyl ester Nutrition 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000006184 cosolvent Substances 0.000 claims abstract description 36
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 150000002148 esters Chemical class 0.000 claims abstract description 20
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 19
- 239000003377 acid catalyst Substances 0.000 claims abstract description 11
- 238000005886 esterification reaction Methods 0.000 claims abstract description 10
- 230000032050 esterification Effects 0.000 claims abstract description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 56
- 239000003921 oil Substances 0.000 claims description 48
- 235000019198 oils Nutrition 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
- 239000003549 soybean oil Substances 0.000 claims description 25
- 235000012424 soybean oil Nutrition 0.000 claims description 23
- 239000002585 base Substances 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 13
- -1 lard Substances 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 239000001117 sulphuric acid Substances 0.000 claims description 8
- 235000011149 sulphuric acid Nutrition 0.000 claims description 8
- 239000002551 biofuel Substances 0.000 claims description 7
- 238000010924 continuous production Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 241000273930 Brevoortia tyrannus Species 0.000 claims description 3
- 241000219992 Cuphea Species 0.000 claims description 3
- 241001048891 Jatropha curcas Species 0.000 claims description 3
- 235000019482 Palm oil Nutrition 0.000 claims description 3
- 235000019483 Peanut oil Nutrition 0.000 claims description 3
- 235000004347 Perilla Nutrition 0.000 claims description 3
- 244000124853 Perilla frutescens Species 0.000 claims description 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 3
- 244000057114 Sapium sebiferum Species 0.000 claims description 3
- 235000005128 Sapium sebiferum Nutrition 0.000 claims description 3
- 239000010480 babassu oil Substances 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 235000015278 beef Nutrition 0.000 claims description 3
- 239000000828 canola oil Substances 0.000 claims description 3
- 235000019519 canola oil Nutrition 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- 235000012343 cottonseed oil Nutrition 0.000 claims description 3
- 150000004292 cyclic ethers Chemical group 0.000 claims description 3
- 229940013317 fish oils Drugs 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 3
- 235000021388 linseed oil Nutrition 0.000 claims description 3
- 239000000944 linseed oil Substances 0.000 claims description 3
- 235000019488 nut oil Nutrition 0.000 claims description 3
- 239000010466 nut oil Substances 0.000 claims description 3
- 239000004006 olive oil Substances 0.000 claims description 3
- 235000008390 olive oil Nutrition 0.000 claims description 3
- 239000002540 palm oil Substances 0.000 claims description 3
- 239000000312 peanut oil Substances 0.000 claims description 3
- 235000011803 sesame oil Nutrition 0.000 claims description 3
- 239000008159 sesame oil Substances 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000003346 palm kernel oil Substances 0.000 claims description 2
- 235000019865 palm kernel oil Nutrition 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 239000002383 tung oil Substances 0.000 claims description 2
- 150000001339 alkali metal compounds Chemical class 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 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 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 50
- 235000019441 ethanol Nutrition 0.000 description 33
- 150000004702 methyl esters Chemical class 0.000 description 25
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 239000010410 layer Substances 0.000 description 18
- 239000003925 fat Substances 0.000 description 13
- 235000019197 fats Nutrition 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000004817 gas chromatography Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 235000021314 Palmitic acid Nutrition 0.000 description 10
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 238000001212 derivatisation Methods 0.000 description 7
- 239000008158 vegetable oil Substances 0.000 description 7
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
- 238000006140 methanolysis reaction Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 5
- 239000003225 biodiesel Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- RZYHXKLKJRGJGP-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C(F)(F)F RZYHXKLKJRGJGP-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 235000021588 free fatty acids Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 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
- 239000002028 Biomass Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 239000005639 Lauric acid Substances 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
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 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
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010932 ethanolysis reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
- 235000019421 lipase Nutrition 0.000 description 1
- 150000004668 long chain fatty acids Chemical group 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004704 methoxides Chemical class 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003541 multi-stage reaction Methods 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
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
- C10G2300/1014—Biomass of vegetal origin
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
- C10G2300/1018—Biomass of animal origin
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4025—Yield
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/44—Solvents
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2280289 | 1999-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201238B true ZA200201238B (en) | 2002-11-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201238A ZA200201238B (en) | 1999-08-18 | 2002-02-13 | Single-phase process for production of fatty acid methyl esters from mixtures of triglycerides and fatty acids. |
Country Status (16)
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| EP (1) | EP1206437B9 (es) |
| JP (2) | JP4990455B2 (es) |
| CN (1) | CN1177794C (es) |
| AT (1) | ATE308505T1 (es) |
| AU (1) | AU771781C (es) |
| BR (1) | BR0013396B1 (es) |
| CA (2) | CA2381394C (es) |
| CY (1) | CY1107516T1 (es) |
| DE (1) | DE60023710T2 (es) |
| DK (1) | DK1206437T3 (es) |
| ES (1) | ES2252040T3 (es) |
| HK (1) | HK1046129B (es) |
| MX (1) | MXPA02001636A (es) |
| NZ (1) | NZ517447A (es) |
| WO (1) | WO2001012581A1 (es) |
| ZA (1) | ZA200201238B (es) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60023710T2 (de) * | 1999-08-18 | 2006-07-20 | Biox Corp., Oakville | Einphaseverfahren zur herstellung von fettsäuremethylestern aus gemischen von triglyceriden und fettsäuren |
| FI114280B (fi) | 2001-01-11 | 2004-09-30 | Eriksson Capital Ab | Polyamidiin ja polyamidilohkoja ja polyeetterilohkoja sisältäviin polymeereihin perustuva makkarankuori, joka on savustettavissa |
| DE10132842C1 (de) * | 2001-07-06 | 2002-11-28 | Siegfried Peter | Verfahren zur Umesterung von Fett und/oder Öl mittels Alkoholyse |
| HU0104786D0 (en) | 2001-11-08 | 2002-01-28 | Kovacs Andras Dr | Method for producing of vegetable oil-methyl-esther |
| 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 |
| ES2201894B2 (es) * | 2002-01-18 | 2005-03-01 | Industrial Management, S.A | Procedimiento para producir combustibles biodiesel con propiedades mejoradas a baja temperatura. |
| US7279018B2 (en) | 2002-09-06 | 2007-10-09 | Fortum Oyj | Fuel composition for a diesel engine |
| CN1181161C (zh) * | 2003-03-13 | 2004-12-22 | 清华大学 | 一种制备生物柴油的方法 |
| ATE468318T1 (de) | 2003-04-25 | 2010-06-15 | Dow Global Technologies Inc | Von samenölen abgeleitete aldehyd- und alkoholzusammensetzungen |
| JP4122433B2 (ja) * | 2003-08-18 | 2008-07-23 | 独立行政法人農業・食品産業技術総合研究機構 | 副産物を生成しないバイオディーゼル燃料の無触媒製造法 |
| 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 |
| FR2884819B1 (fr) * | 2005-04-22 | 2011-08-12 | Air Liquide | Procede de purification par lavage a l'eau des phases liquides issues d'une reaction de transesterification |
| WO2006133437A1 (en) * | 2005-06-09 | 2006-12-14 | Biosphere Environmental Energy Llc | Systems and methods for esterification and transesterification of fats and oils |
| WO2007000913A1 (ja) * | 2005-06-27 | 2007-01-04 | Tokyo Institute Of Technology | 高級脂肪酸エステルの製造方法 |
| US8022258B2 (en) | 2005-07-05 | 2011-09-20 | Neste Oil Oyj | Process for the manufacture of diesel range hydrocarbons |
| ES2245270B1 (es) * | 2005-07-22 | 2006-09-16 | Fundacion Cidaut | Procedimiento para la obtencion de comustible para motores de ciclo diesel a partir de aceites vegetales usados. |
| US20070031354A1 (en) * | 2005-08-03 | 2007-02-08 | Brown James H | Cosmetic and topical compositions comprising cuphea oil and derivatives thereof |
| FI120684B (fi) * | 2005-10-21 | 2010-01-29 | Valtion Teknillinen | Menetelmä oligo-/polyestereiden valmistamiseksi suberiinin ja/tai kutiinin karboksyylihapposeoksesta |
| JP2007153943A (ja) * | 2005-12-01 | 2007-06-21 | Japan Energy Corp | エステル交換反応によるエステルの製造方法 |
| ITMI20060082A1 (it) * | 2006-01-19 | 2007-07-20 | Maurizio Germani | Processo per la preparazione di biodiesel |
| BRPI0710853A2 (pt) | 2006-05-15 | 2011-05-17 | Dow Global Technologies Inc | processo de hidroformilação não aquoso |
| MX2009004868A (es) * | 2006-11-07 | 2009-12-14 | Sued Chemie Ag | Metodo para la purificacion de biodiesel. |
| EP1920829A1 (en) | 2006-11-07 | 2008-05-14 | Süd-Chemie Ag | Amorphous adsorbent, method of obtaining the same and its use in the bleaching of fats and/or oils |
| CZ17221U1 (cs) * | 2006-11-23 | 2007-02-05 | Stv Group A. S. | Trhavina |
| GB2445355A (en) * | 2007-01-05 | 2008-07-09 | Biofuel Systems Group Ltd | Fuel and method of production thereof |
| BRPI0807093A2 (pt) | 2007-02-06 | 2014-04-22 | Janos Thesz | Uso de combustíveis ou aditivos de combustíveis à base de triglicerídeos de estrutura modificada e processo para sua preparação |
| JP2008260819A (ja) * | 2007-04-11 | 2008-10-30 | National Institute Of Advanced Industrial & Technology | バイオディーゼル燃料の製造方法 |
| CN101311247B (zh) * | 2007-05-23 | 2012-11-21 | 中国科学院过程工程研究所 | 一种溶剂强化快速制备生物柴油的方法 |
| WO2008143593A2 (en) * | 2007-05-24 | 2008-11-27 | Sie Hendery Hendery | Bbn 100 to substitute diesel fuel |
| JP5334462B2 (ja) * | 2007-06-11 | 2013-11-06 | 花王株式会社 | 脂肪酸エステルの製造法 |
| CN101802046B (zh) | 2007-07-12 | 2014-06-18 | 陶氏环球技术有限责任公司 | 室温可固化聚合物及其前体 |
| AU2007357902B2 (en) * | 2007-08-17 | 2013-03-14 | Energy & Environmental Research Center Foundation | Energy efficient process to produce biologically based fuels |
| 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 |
| DE102008052795B4 (de) | 2008-10-22 | 2012-01-26 | Balchem Corp. | Verfahren zur Herstellung von Fettsäureestern ein- oder mehrwertiger Alkohole unter Verwendung spezieller hydroxyfunktioneller quartärer Ammoniumverbindungen als Katalysatoren |
| US8192696B2 (en) | 2008-11-18 | 2012-06-05 | Stephanie Marie Gurski | System and process of biodiesel production |
| JP5167110B2 (ja) | 2008-12-26 | 2013-03-21 | 独立行政法人日本原子力研究開発機構 | バイオディーゼル製造用触媒とその製造方法並びにバイオディーゼルの製造方法 |
| EP2585507A1 (en) | 2010-06-22 | 2013-05-01 | Dow Global Technologies LLC | Curable silyl polymers |
| WO2012003187A1 (en) | 2010-06-30 | 2012-01-05 | Dow Global Technologies Llc | Silyl-terminated polymers |
| US8563482B2 (en) | 2010-09-22 | 2013-10-22 | Saudi Arabian Oil Company | Environment friendly base fluid to replace the toxic mineral oil-based base fluids |
| WO2013083692A1 (de) * | 2011-12-06 | 2013-06-13 | Sika Technology Ag | Stabilisierung von rohpolyolen aus biomasse |
| RU2553988C1 (ru) | 2014-03-21 | 2015-06-20 | Евгений Валентинович Пантелеев | Биотопливная композиция |
| WO2015155858A1 (ja) * | 2014-04-09 | 2015-10-15 | 信和化工株式会社 | 脂肪酸アルキルエステルを調製する方法及びキット |
| US9834718B2 (en) | 2014-05-06 | 2017-12-05 | Saudi Arabian Oil Company | Ecofriendly lubricating additives for water-based wellbore drilling fluids |
| CA2998289A1 (en) * | 2015-09-11 | 2017-03-16 | Resiway - Solucoes Sustentaveis, Lda. | Glycerol ester production from wastes containing organic oils and/or fats |
| ES2585706B1 (es) * | 2016-04-21 | 2017-08-14 | Soluciones Industriales Extremeñas Sll | Procedimiento mejorado para el refino y esterificación continua de cualquier material graso de origen vegetal o animal, especialmente diseñado para subproductos animales de categoría 1 y 2 |
| GB202005461D0 (en) * | 2020-04-15 | 2020-05-27 | Trio Plus Bio Energy Ag | Additive |
| US11352545B2 (en) | 2020-08-12 | 2022-06-07 | Saudi Arabian Oil Company | Lost circulation material for reservoir section |
| CN114717056B (zh) * | 2022-04-25 | 2023-07-18 | 广东省农业科学院农业质量标准与监测技术研究所 | 一种酸催化油脂甲酯化的方法 |
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| JPS6025478B2 (ja) * | 1977-03-17 | 1985-06-18 | 花王株式会社 | 脂肪酸低級アルコ−ルエステルの製造法 |
| FR2577569B1 (fr) * | 1985-02-15 | 1987-03-20 | Inst Francais Du Petrole | Procede de fabrication d'une composition d'esters d'acide gras utilisables comme carburant de substitution du gazole avec de l'alcool ethylique hydrate et composition d'esters ainsi formes |
| CA2131654A1 (en) * | 1994-09-08 | 1996-03-09 | David G. B. Boocock | Process for producing lower alkyl fatty acid esters |
| DE60023710T2 (de) * | 1999-08-18 | 2006-07-20 | Biox Corp., Oakville | Einphaseverfahren zur herstellung von fettsäuremethylestern aus gemischen von triglyceriden und fettsäuren |
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- 2000-08-15 DE DE60023710T patent/DE60023710T2/de not_active Expired - Lifetime
- 2000-08-15 CA CA2381394A patent/CA2381394C/en not_active Expired - Lifetime
- 2000-08-15 NZ NZ517447A patent/NZ517447A/xx not_active IP Right Cessation
- 2000-08-15 JP JP2001516882A patent/JP4990455B2/ja not_active Expired - Fee Related
- 2000-08-15 WO PCT/CA2000/000930 patent/WO2001012581A1/en active IP Right Grant
- 2000-08-15 MX MXPA02001636A patent/MXPA02001636A/es active IP Right Grant
- 2000-08-15 ES ES00952823T patent/ES2252040T3/es not_active Expired - Lifetime
- 2000-08-15 AU AU65519/00A patent/AU771781C/en not_active Ceased
- 2000-08-15 DK DK00952823T patent/DK1206437T3/da active
- 2000-08-15 BR BRPI0013396-5B1A patent/BR0013396B1/pt not_active IP Right Cessation
- 2000-08-15 CA CA002316141A patent/CA2316141C/en not_active Expired - Lifetime
- 2000-08-15 AT AT00952823T patent/ATE308505T1/de active
- 2000-08-15 EP EP00952823A patent/EP1206437B9/en not_active Expired - Lifetime
- 2000-08-15 CN CNB008117497A patent/CN1177794C/zh not_active Expired - Fee Related
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2002
- 2002-02-13 ZA ZA200201238A patent/ZA200201238B/en unknown
- 2002-10-17 HK HK02107530.0A patent/HK1046129B/zh not_active IP Right Cessation
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2006
- 2006-01-31 CY CY20061100123T patent/CY1107516T1/el unknown
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2009
- 2009-09-18 JP JP2009217549A patent/JP2010018810A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU771781B2 (en) | 2004-04-01 |
| EP1206437B9 (en) | 2006-06-28 |
| HK1046129A1 (en) | 2002-12-27 |
| HK1046129B (zh) | 2006-01-20 |
| EP1206437A1 (en) | 2002-05-22 |
| DE60023710D1 (de) | 2005-12-08 |
| CA2381394C (en) | 2010-04-27 |
| CN1177794C (zh) | 2004-12-01 |
| AU771781C (en) | 2005-04-21 |
| BR0013396B1 (pt) | 2015-03-10 |
| JP2003507495A (ja) | 2003-02-25 |
| ATE308505T1 (de) | 2005-11-15 |
| MXPA02001636A (es) | 2003-07-14 |
| BR0013396A (pt) | 2002-04-30 |
| JP2010018810A (ja) | 2010-01-28 |
| CA2316141A1 (en) | 2001-02-18 |
| CA2381394A1 (en) | 2001-02-22 |
| WO2001012581A1 (en) | 2001-02-22 |
| EP1206437B1 (en) | 2005-11-02 |
| NZ517447A (en) | 2003-03-28 |
| AU6551900A (en) | 2001-03-13 |
| CN1370140A (zh) | 2002-09-18 |
| DE60023710T2 (de) | 2006-07-20 |
| ES2252040T3 (es) | 2006-05-16 |
| CY1107516T1 (el) | 2013-03-13 |
| CA2316141C (en) | 2009-10-20 |
| DK1206437T3 (da) | 2006-03-20 |
| JP4990455B2 (ja) | 2012-08-01 |
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