JP4944125B2 - 炭化水素の製造方法 - Google Patents
炭化水素の製造方法 Download PDFInfo
- Publication number
- JP4944125B2 JP4944125B2 JP2008545029A JP2008545029A JP4944125B2 JP 4944125 B2 JP4944125 B2 JP 4944125B2 JP 2008545029 A JP2008545029 A JP 2008545029A JP 2008545029 A JP2008545029 A JP 2008545029A JP 4944125 B2 JP4944125 B2 JP 4944125B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- catalyst
- decarbonylation
- decarboxylation
- product
- 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.)
- Active
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims description 24
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 93
- 239000000194 fatty acid Substances 0.000 claims description 93
- 229930195729 fatty acid Natural products 0.000 claims description 93
- 150000004665 fatty acids Chemical class 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 50
- 239000002994 raw material Substances 0.000 claims description 32
- -1 fatty acid esters Chemical class 0.000 claims description 31
- 238000006317 isomerization reaction Methods 0.000 claims description 29
- 238000006114 decarboxylation reaction Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 25
- 238000006606 decarbonylation reaction Methods 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 238000006392 deoxygenation reaction Methods 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 19
- 230000006324 decarbonylation Effects 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 13
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910003294 NiMo Inorganic materials 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000010457 zeolite Substances 0.000 claims description 7
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 6
- 229910021536 Zeolite Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000006213 oxygenation reaction Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 241000269350 Anura Species 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 150000002194 fatty esters Chemical class 0.000 claims 1
- 230000008929 regeneration Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 52
- 239000002283 diesel fuel Substances 0.000 description 28
- 239000003225 biodiesel Substances 0.000 description 21
- 239000000446 fuel Substances 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 235000015112 vegetable and seed oil Nutrition 0.000 description 12
- 239000008158 vegetable oil Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000003784 tall oil Substances 0.000 description 9
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 150000003626 triacylglycerols Chemical class 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000012620 biological material Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 229910052680 mordenite Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-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
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-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
- 239000013618 particulate matter Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- VCLJODPNBNEBKW-UHFFFAOYSA-N 2,2,4,4,6,8,8-heptamethylnonane Chemical compound CC(C)(C)CC(C)CC(C)(C)CC(C)(C)C VCLJODPNBNEBKW-UHFFFAOYSA-N 0.000 description 1
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 1
- 235000019737 Animal fat Nutrition 0.000 description 1
- 208000023514 Barrett esophagus Diseases 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 238000006576 Kolbe electrolysis reaction Methods 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000004177 carbon cycle Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007233 catalytic pyrolysis Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical group [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
-
- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/45—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
- C10G3/46—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof in combination with chromium, molybdenum, tungsten metals or compounds thereof
-
- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/47—Catalytic treatment characterised by the catalyst used containing platinum group metals or compounds thereof
-
- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
- C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
-
- 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
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/50—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids in the presence of hydrogen, hydrogen donors or hydrogen generating 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
- C10L1/32—Liquid carbonaceous fuels consisting of coal-oil suspensions or aqueous emulsions or oil emulsions
-
- 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
- C10G2300/44—Solvents
-
- 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/04—Diesel oil
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
骨格異性化とは、化合物の炭素数が変わることなしに、炭素主鎖に分岐が形成されることを意味すると解される。
本発明は、草木、植物、動物ならびに魚類の脂肪および油ならびに脂肪酸といった再生可能資源から、ディーゼル燃料プールとして適切な、分岐の飽和炭化水素の製造のための触媒方法に関する。本発明は、脂肪酸または低級アルコールとの脂肪酸エステルを含む原料を、酸性触媒を用いて分岐の脂肪酸または脂肪酸エステルに変換すること、それに続いて、得られた分岐の脂肪酸または脂肪酸エステルを、脱炭酸化/脱カルボニル化不均一系触媒または水素化脱酸素化触媒のどちらかと接触させることによって、分岐の炭化水素に変換することに関する。
原料は脂肪酸またはC1〜C5、好ましくはC1〜C3アルコールとの脂肪酸エステル、またはそれらの混合物を含む。原料は好ましくは草木、植物、動物ならびに魚の油および脂肪といった生物由来原料に由来する。生物由来原料は、加水分解などの、脂肪酸または脂肪酸エステルを原料として有用なものとして得るために、先行技術である、いかなる前処理または精製法を用いて処理されてもよい。原料は少なくとも20重量%、好ましくは少なくとも50重量%、そして特に好ましくは80重量%の不飽和の脂肪酸または脂肪酸エステルを含む。原料は、脂肪酸および脂肪酸エステルの混合物を含むが、脂肪酸または脂肪酸エステルのどちらかを使用することが好ましい。
本発明による方法の第一の段階では、分岐鎖を有する脂肪酸または脂肪酸のアルキルエステルが製造される。上記に記載した原料が骨格異性化段階に付される。骨格異性化は150〜400℃の温度で、0〜5MPaの圧力下、好ましくは200〜350℃および0.1〜5MPaそして特に好ましくは220〜300℃および0.1〜2MPaで、酸性触媒を使用して行われた。適切な酸性触媒はシリコアルミノリン酸塩およびゼオライト、好ましくはフォージャサイト、オファールタイト、モンモリロナイトおよびモルデナイトである。特に好ましくは、触媒はモルデナイトである。
骨格異性化段階から得られた分岐の生成物はその後、脱炭酸化/脱カルボニル化または水素化脱酸素化によって行われる脱酸素化に付される。
本発明による方法は、ディーゼル燃料プールに適切な分岐のパラフィン系炭化水素生成物を生じる。生成物は、一般的にはいくつかの短い炭素−炭素側鎖の分岐を含み、その結果、公知の方法によって得られた生成物に比べて、群を抜いた低い曇点および低温でのフィルター目詰まり点(cold filter plugging point)を有するにも関わらず、良好なセタン価をもつ。表2に示されるように、本発明による方法を用いて製造された生成物の特性(1)が公知の技術に基づく方法によって得られた生成物(2〜6)と比較された。全ての生成物は100%(B100)ディーゼル構成成分である。
(1)は本発明による方法によって、脂肪酸の骨格異性化および脱酸素化によって製造される。
(2)はトリグリセリドの水素化脱酸素化および水素化異性化によって製造される。
(3)は菜種油のエステル交換反応によって製造される脂肪酸メチルエステルである。
(4)は気体の液化および水素化異性化方法によって製造される天然ガス由来のディーゼル燃料である。
(5)および(6)は極寒の条件で使用される異なる規格をもつ鉱物油由来のディーゼル燃料である。
トール油脂肪酸の骨格異性化および脱酸素化
低温でのトール油脂肪酸の骨格異性化および脱酸素化
水無添加でのトール油脂肪酸の骨格異性化、低温での脱酸素化および最終生成物の冷却下でのろ過
水無添加でのトール油脂肪酸の骨格異性化、および脱炭酸化/脱カルボニル化による脱酸素化
Claims (17)
- 分岐の飽和炭化水素の製造方法であって、生物由来原料の前処理または精製によって得られる不飽和の脂肪酸もしくはC1〜C5アルコールとの脂肪酸エステル、またはそれらの混合物を含む原料を骨格異性化段階およびその後の脱酸素化段階に付すことを特徴とする方法。
- 原料が、少なくとも20重量%の不飽和の脂肪酸またはC1〜C5アルコールとの脂肪酸エステルを含むことを特徴とする請求項1記載の方法。
- 不飽和の脂肪酸またはC1〜C5アルコールとの脂肪酸エステルの全炭素数が、8〜26であることを特徴とする請求項1または2記載の方法。
- 骨格異性化段階が、150〜400℃の温度で、0〜5MPaの圧力下で行われることを特徴とする請求項1〜3のいずれかに記載の方法。
- 骨格異性化段階が、シリコアルミノリン酸塩およびゼオライトより選択される酸性触媒の存在下で行われることを特徴とする請求項1〜4のいずれかに記載の方法。
- 全反応混合物を基準にして、0〜8重量%の水またはC1〜C5アルコールが原料に添加されることを特徴とする請求項1〜5のいずれかに記載の方法。
- 原料が脂肪酸を含む場合には水が添加され、そして原料が脂肪酸エステルを含む場合にはアルコールが添加されることを特徴とする請求項6記載の方法。
- 骨格異性化段階の後に、前水素化段階が行われることを特徴とする請求項1〜7のいずれかに記載の方法。
- 前水素化段階が、1または複数の第VIII族および/または第VIA族の金属を含む水素化触媒の存在下、50〜400℃の温度で0.1〜20MPaの水素圧の下で行われることを特徴とする請求項8記載の方法。
- 原料が脂肪酸エステルを含む場合に、前水素化段階が、金属触媒の存在下、25〜30MPaの水素圧、および200〜230℃の温度で行われることを特徴とする請求項8記載の方法。
- 骨格異性化および任意の前水素化段階から得られる生成物を、脱炭酸化/脱カルボニル化または水素化脱酸素化によって行われる脱酸素化段階に付すことを特徴とする請求項1〜10のいずれかに記載の方法。
- 脱炭酸化および/または脱カルボニル化において、生成物および任意には溶媒または溶媒の混合物を、1または複数の周期系の第VIII族および/または第VIA族の金属を含む担持触媒より選択される、脱炭酸化/脱カルボニル化不均一系触媒と、100〜400℃の温度で、大気圧から、不活性気体/水素混合物の20MPaまでの圧力下で接触させることを特徴とする請求項11記載の方法。
- 脱炭酸化および/または脱カルボニル化不均一系触媒が、炭素担持Pdまたはアルミナ担持硫化NiMoであることを特徴とする請求項12記載の方法。
- 水素化脱酸素化において、生成物および任意には溶媒または溶媒の混合物を、周期系の第VIII族および/または第VIA族の金属を含む水素化触媒と、1〜20MPaの間の圧力下、200〜500℃の間の温度で接触させることを特徴とする請求項13記載の方法。
- 水素化脱酸素化触媒が、担持されたPd、Pt、Ni、NiMoまたはCoMo触媒であって、かつ担持体が、アルミナおよび/またはシリカであることを特徴とする請求項14記載の方法。
- 脱炭酸化/脱カルボニル化および/または水素化脱酸素化段階において、溶媒が炭化水素、炭化水素を含む再生処理蒸気およびそれらの混合物からなる群より選択されることを特徴とする請求項11〜15のいずれかに記載の方法。
- 炭化水素が、150〜350℃の沸点範囲を有するパラフィン、イソパラフィン、ナフテンおよび芳香族炭化水素であることを特徴とする請求項16記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05028780.4 | 2005-12-12 | ||
EP05028780.4A EP1795576B1 (en) | 2005-12-12 | 2005-12-12 | Process for the manufacture of hydrocarbons |
US74958105P | 2005-12-13 | 2005-12-13 | |
US60/749,581 | 2005-12-13 | ||
PCT/FI2006/050551 WO2007068798A2 (en) | 2005-12-12 | 2006-12-12 | Process for the manufacture of hydrocarbons |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009518533A JP2009518533A (ja) | 2009-05-07 |
JP2009518533A5 JP2009518533A5 (ja) | 2012-03-15 |
JP4944125B2 true JP4944125B2 (ja) | 2012-05-30 |
Family
ID=36000954
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008545029A Active JP4944125B2 (ja) | 2005-12-12 | 2006-12-12 | 炭化水素の製造方法 |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1795576B1 (ja) |
JP (1) | JP4944125B2 (ja) |
KR (1) | KR101016643B1 (ja) |
CN (1) | CN101331210B (ja) |
BR (1) | BRPI0619737B1 (ja) |
CA (1) | CA2631879C (ja) |
DK (1) | DK1795576T3 (ja) |
ES (1) | ES2491871T3 (ja) |
HK (1) | HK1128038A1 (ja) |
MY (1) | MY141968A (ja) |
PL (1) | PL1795576T3 (ja) |
RU (1) | RU2394872C2 (ja) |
WO (1) | WO2007068798A2 (ja) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007141293A1 (en) * | 2006-06-09 | 2007-12-13 | Albemarle Netherlands B.V. | Catalytic hydrodeoxygenation of an oxygenate feedstock |
US8067653B2 (en) | 2006-07-14 | 2011-11-29 | The Governors Of The University Of Alberta | Methods for producing fuels and solvents |
CA2663592C (en) | 2006-09-19 | 2011-08-09 | Applied Research Associates, Inc. | Method of converting triglycerides to biofuels |
EP2351845A1 (en) | 2007-06-01 | 2011-08-03 | Solazyme, Inc. | Renewable chemicals and fuels from oleaginous yeast |
FR2917423B1 (fr) * | 2007-06-12 | 2012-11-30 | Inst Francais Du Petrole | Hydrotraitement en deux etapes d'une charge issue d'une source renouvelable mettant en oeuvre un premier catalyseur metallique et un deuxieme catalyseur sulfure |
US8119847B2 (en) * | 2007-06-15 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Catalytic process for converting renewable resources into paraffins for use as diesel blending stocks |
US7955401B2 (en) * | 2007-07-16 | 2011-06-07 | Conocophillips Company | Hydrotreating and catalytic dewaxing process for making diesel from oils and/or fats |
WO2009011639A2 (en) * | 2007-07-19 | 2009-01-22 | Sunpine Ab | Diesel range fuels from carboxylic acids with plant origin |
US8523959B2 (en) | 2007-07-26 | 2013-09-03 | Chevron U.S.A. Inc. | Paraffinic biologically-derived distillate fuels with bio-oxygenates for improved lubricity and methods of making same |
US7999143B2 (en) * | 2007-09-20 | 2011-08-16 | Uop Llc | Production of diesel fuel from renewable feedstocks with reduced hydrogen consumption |
US8766025B2 (en) | 2008-06-24 | 2014-07-01 | Uop Llc | Production of paraffinic fuel from renewable feedstocks |
US8304592B2 (en) | 2008-06-24 | 2012-11-06 | Uop Llc | Production of paraffinic fuel from renewable feedstocks |
ES2742527T3 (es) | 2008-11-28 | 2020-02-14 | Corbion Biotech Inc | Fabricación de aceites personalizados en microorganismos heterotróficos recombinantes |
FR2940314B1 (fr) * | 2008-12-23 | 2011-11-18 | Total Raffinage Marketing | Carburant de type gazole pour moteur diesel a fortes teneurs en carbone d'origine renouvelable et en oxygene |
WO2010096812A2 (en) * | 2009-02-23 | 2010-08-26 | Maria Flytzani-Stephanopoulos | Converting biomass to gaseous fuel hydrocarbons |
FR2943071B1 (fr) * | 2009-03-10 | 2011-05-13 | Inst Francais Du Petrole | Procede d'hydrodesoxygenation de charges issues de sources renouvelables avec conversion limitee en decarboxylation mettant en oeuvre un catalyseur a base de nickel et de molybdene |
JP5273724B2 (ja) * | 2009-03-13 | 2013-08-28 | 独立行政法人産業技術総合研究所 | トリグリセリドの水素化分解用触媒 |
EP2275514A1 (en) | 2009-07-17 | 2011-01-19 | Neste Oil Oyj | Process for the preparation of light fuels |
JP2013503947A (ja) * | 2009-09-04 | 2013-02-04 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | 植物油のエステル交換アルコキシル化からの安定なアルコキシル化脂肪酸アルキルエステル |
US8471081B2 (en) * | 2009-12-28 | 2013-06-25 | Uop Llc | Production of diesel fuel from crude tall oil |
US20110203253A1 (en) * | 2010-02-23 | 2011-08-25 | General Electric Company | Advanced fuel compositions from renewable sources, and related methods for making and using the fuel |
WO2011104626A2 (en) | 2010-02-24 | 2011-09-01 | The Governors Of The University Of Alberta | Methods for producing fuels and solvents substantially free of fatty acids |
FI126337B (fi) * | 2010-03-26 | 2016-10-14 | Forchem Oy | Menetelmä mäntyöljypien hyödyntämiseksi |
CA2801057C (en) | 2010-05-28 | 2019-06-18 | Solazyme, Inc. | Tailored oils produced from recombinant heterotrophic microorganisms |
US8366907B2 (en) | 2010-08-02 | 2013-02-05 | Battelle Memorial Institute | Deoxygenation of fatty acids for preparation of hydrocarbons |
MY162451A (en) * | 2010-11-04 | 2017-06-15 | Albemarle Europe Sprl | Hydrodeoxygenation of pyrolysis oil in presence of admixed alcohol |
CN110066836A (zh) | 2011-02-02 | 2019-07-30 | 柯碧恩生物技术公司 | 产自重组产油微生物的定制油 |
JP2015110523A (ja) * | 2012-03-29 | 2015-06-18 | 日清オイリオグループ株式会社 | ペースト状組成物及びその製造方法 |
JP2015110524A (ja) * | 2012-03-29 | 2015-06-18 | 日清オイリオグループ株式会社 | ワックス状組成物及びその製造方法 |
FI125507B2 (en) * | 2012-04-13 | 2021-12-15 | Stora Enso Oyj | Methods for deoxygenating tall oil and producing polymerizable monomers therefrom |
CN110358686A (zh) | 2012-04-18 | 2019-10-22 | 柯碧恩生物技术公司 | 定制油 |
US20140081065A1 (en) * | 2012-09-20 | 2014-03-20 | Ei Du Pont De Nemours And Company | Process for making linear long chain alkanes using renewable feedstocks |
TWI481584B (zh) * | 2012-11-22 | 2015-04-21 | Ind Tech Res Inst | 酯類脫氧的方法 |
US9816079B2 (en) | 2013-01-29 | 2017-11-14 | Terravia Holdings, Inc. | Variant thioesterases and methods of use |
US9567615B2 (en) | 2013-01-29 | 2017-02-14 | Terravia Holdings, Inc. | Variant thioesterases and methods of use |
US20140275670A1 (en) * | 2013-03-14 | 2014-09-18 | Ted R. Aulich | Process for low-hydrogen-consumption conversion of renewable feedstocks to alkanes |
US9783836B2 (en) | 2013-03-15 | 2017-10-10 | Terravia Holdings, Inc. | Thioesterases and cells for production of tailored oils |
KR102273722B1 (ko) * | 2013-03-15 | 2021-07-15 | 포지 하이드로카본스 코포레이션 | 알켄의 존재 하에서의 열분해 반응들 |
US9290749B2 (en) | 2013-03-15 | 2016-03-22 | Solazyme, Inc. | Thioesterases and cells for production of tailored oils |
FI126330B (en) * | 2013-04-02 | 2016-10-14 | Upm Kymmene Corp | Renewable hydrocarbon composition |
WO2014176515A2 (en) | 2013-04-26 | 2014-10-30 | Solazyme, Inc. | Low polyunsaturated fatty acid oils and uses thereof |
ES2526617B1 (es) | 2013-06-10 | 2015-09-09 | Neol Biosolutions, S.A. | Producción de aceites microbianos |
WO2015001141A1 (es) | 2013-07-02 | 2015-01-08 | Repsol, S.A. | Composiciones y métodos para la producción de biocombustibles utilizando pseudomonas brassicacearum |
US20150057477A1 (en) * | 2013-08-23 | 2015-02-26 | Uop Llc | Systems and methods for producing fuel from a renewable feedstock |
CN103614155B (zh) * | 2013-09-11 | 2016-08-10 | 浙江工业大学 | 一种藻油生产烃类燃料的制备方法 |
EP3052636A2 (en) | 2013-10-04 | 2016-08-10 | Solazyme, Inc. | Tailored oils |
US9469583B2 (en) * | 2014-01-03 | 2016-10-18 | Neste Oyj | Composition comprising paraffin fractions obtained from biological raw materials and method of producing same |
CA2884216A1 (en) * | 2014-03-14 | 2015-09-14 | Energy & Environmental Research Center Foundation | Process for low-hydrogen-consumption conversion of renewable feedstocks to alkanes |
TW201602336A (zh) | 2014-06-09 | 2016-01-16 | W R 康格雷氏公司 | 天然油及脂之催化脫氧方法 |
BR112017001404A2 (pt) | 2014-07-24 | 2017-11-21 | Terravia Holdings Inc | tioesterases variantes e métodos de utilização |
US10125382B2 (en) | 2014-09-18 | 2018-11-13 | Corbion Biotech, Inc. | Acyl-ACP thioesterases and mutants thereof |
US20160348119A1 (en) | 2015-04-06 | 2016-12-01 | Terravia Holdings, Inc. | Oleaginous Microalgae Having an LPAAT Ablation |
CN106608804B (zh) * | 2015-10-22 | 2019-06-28 | 中国石油化工股份有限公司 | 一种脱除含氧轻烃中氧气的方法 |
EP3487959A4 (en) | 2016-07-25 | 2020-02-19 | The Governors of the University of Alberta | METHOD FOR PRODUCING HYDROCARBON COMPOSITIONS WITH A REDUCED NUMBER OF ACID AND FOR INSULATING SHORT-CHAIN FATTY ACIDS |
BR112020005798A2 (pt) * | 2017-09-26 | 2020-09-24 | Valero Services, Inc. | produção de combustíveis e intermediários renováveis |
CN108940341B (zh) * | 2018-07-17 | 2020-08-28 | 中国石油大学(北京) | 一种催化加氢制备烷烃的催化剂及其制备方法 |
WO2020074870A1 (en) * | 2018-10-11 | 2020-04-16 | Scg Chemicals Co., Ltd. | Catalytic process |
FI130601B (en) * | 2018-12-14 | 2023-12-07 | Neste Oyj | Diesel fuel composition |
BR112023001291A2 (pt) * | 2020-07-24 | 2023-04-04 | Reg Synthetic Fuels Llc | Processo de codimerização descarboxilativa e combustíveis sintéticos produzidos a partir do mesmo |
CN112973697A (zh) * | 2021-03-01 | 2021-06-18 | 广东工业大学 | 一种加氢反应用催化剂及其催化脂肪酸甲酯的合成方法 |
WO2023126588A1 (en) * | 2021-12-30 | 2023-07-06 | Neste Oyj | Producing hydrocarbons from organic material of biological origin |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59108088A (ja) * | 1982-11-10 | 1984-06-22 | Honda Motor Co Ltd | パラフイン系炭化水素の製造法 |
ATE187954T1 (de) * | 1995-11-16 | 2000-01-15 | Unichema Chemie Bv | Isomerisierung der fettsäure |
JP2003171670A (ja) * | 2001-12-07 | 2003-06-20 | Kawaken Fine Chem Co Ltd | 炭化水素類の製造方法および炭化水素類製造用触媒 |
EP1398364A1 (en) * | 2002-09-06 | 2004-03-17 | Fortum OYJ | Fuel composition for a diesel engine |
EP1396531B2 (en) * | 2002-09-06 | 2016-11-30 | Neste Oil Oyj | Process for producing a hydrocarbon component of biological origin |
US7279018B2 (en) * | 2002-09-06 | 2007-10-09 | Fortum Oyj | Fuel composition for a diesel engine |
US7232935B2 (en) * | 2002-09-06 | 2007-06-19 | Fortum Oyj | Process for producing a hydrocarbon component of biological origin |
-
2005
- 2005-12-12 DK DK05028780.4T patent/DK1795576T3/da active
- 2005-12-12 ES ES05028780.4T patent/ES2491871T3/es active Active
- 2005-12-12 PL PL05028780T patent/PL1795576T3/pl unknown
- 2005-12-12 EP EP05028780.4A patent/EP1795576B1/en active Active
-
2006
- 2006-12-12 JP JP2008545029A patent/JP4944125B2/ja active Active
- 2006-12-12 WO PCT/FI2006/050551 patent/WO2007068798A2/en active Application Filing
- 2006-12-12 MY MYPI20064660A patent/MY141968A/en unknown
- 2006-12-12 CN CN2006800467883A patent/CN101331210B/zh not_active Expired - Fee Related
- 2006-12-12 RU RU2008128480/04A patent/RU2394872C2/ru active
- 2006-12-12 BR BRPI0619737A patent/BRPI0619737B1/pt active IP Right Grant
- 2006-12-12 KR KR1020087016895A patent/KR101016643B1/ko active IP Right Grant
- 2006-12-12 CA CA2631879A patent/CA2631879C/en active Active
-
2009
- 2009-06-19 HK HK09105525.4A patent/HK1128038A1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
KR101016643B1 (ko) | 2011-02-25 |
CN101331210A (zh) | 2008-12-24 |
MY141968A (en) | 2010-08-16 |
EP1795576A1 (en) | 2007-06-13 |
RU2008128480A (ru) | 2010-01-20 |
HK1128038A1 (en) | 2009-10-16 |
KR20080078889A (ko) | 2008-08-28 |
CA2631879C (en) | 2013-07-02 |
RU2394872C2 (ru) | 2010-07-20 |
CN101331210B (zh) | 2012-10-31 |
CA2631879A1 (en) | 2007-06-21 |
BRPI0619737A2 (pt) | 2011-10-11 |
PL1795576T3 (pl) | 2014-10-31 |
ES2491871T3 (es) | 2014-09-08 |
DK1795576T3 (da) | 2014-07-14 |
BRPI0619737B1 (pt) | 2016-06-21 |
JP2009518533A (ja) | 2009-05-07 |
WO2007068798A3 (en) | 2007-08-02 |
WO2007068798A2 (en) | 2007-06-21 |
EP1795576B1 (en) | 2014-05-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4944125B2 (ja) | 炭化水素の製造方法 | |
US7459597B2 (en) | Process for the manufacture of hydrocarbons | |
US10550332B2 (en) | Process for the manufacture of diesel range hydrocarbons | |
De Sousa et al. | Producing hydrocarbons for green diesel and jet fuel formulation from palm kernel fat over Pd/C | |
JP5616784B2 (ja) | 分枝状炭化水素の製造方法 | |
FI100248B (fi) | Keskitisleen valmistus | |
KR101038004B1 (ko) | 디젤 등급 탄화수소류의 제조 공정 | |
JP4741662B2 (ja) | ディーゼルレンジ炭化水素の製造方法 | |
RU2514918C2 (ru) | Конверсия растительных масел в базовые масла и топлива для транспортных средств | |
KR101008266B1 (ko) | 포화 탄화수소 성분의 제조방법 | |
US8841494B2 (en) | Thermal decomposition process of triglyceride containing mixtures, co-processed with low molecular weight olefins to produce a renewable fuel composition | |
RU2495081C2 (ru) | Конверсия растительных масел в базовые масла и топлива для транспортных средств | |
JP2009518533A5 (ja) | ||
KR20200019898A (ko) | 카르복실산 및 에스테르를 기유 탄화수소로 전환하기 위한 방법 | |
US20080066374A1 (en) | Reaction system for production of diesel fuel from vegetable and animals oils | |
JP2005538204A (ja) | 脂肪酸を水素化および分解することによって得られる生物学的原材料にもとづく成分を含むディーゼル燃料組成物 | |
BRPI0619628B1 (pt) | processo para a produção de um componente de hidrocarboneto saturado | |
RU2429909C1 (ru) | Катализатор, способ его приготовления и способ получения дизельного топлива из сырья природного происхождения | |
RU2376062C1 (ru) | Способ приготовления катализатора и способ получения дизельного топлива с использованием этого катализатора | |
RU2558948C2 (ru) | Способ получения дизельного топлива из возобновляемого сырья растительного происхождения (варианты) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20100616 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110916 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110927 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20111222 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120105 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20120126 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120221 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120301 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4944125 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150309 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |