JP2008545034A - ディーゼルレンジ炭化水素の製造方法 - Google Patents
ディーゼルレンジ炭化水素の製造方法 Download PDFInfo
- Publication number
- JP2008545034A JP2008545034A JP2008518886A JP2008518886A JP2008545034A JP 2008545034 A JP2008545034 A JP 2008545034A JP 2008518886 A JP2008518886 A JP 2008518886A JP 2008518886 A JP2008518886 A JP 2008518886A JP 2008545034 A JP2008545034 A JP 2008545034A
- Authority
- JP
- Japan
- Prior art keywords
- feedstock
- oil
- catalyst
- fatty acids
- unused
- 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.)
- Granted
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 35
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title abstract description 15
- 239000000194 fatty acid Substances 0.000 claims abstract description 74
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 73
- 229930195729 fatty acid Natural products 0.000 claims abstract description 73
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 58
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 38
- 230000008569 process Effects 0.000 claims abstract description 38
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 37
- 239000011593 sulfur 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 19
- -1 C 16 fatty acid ester Chemical class 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims description 84
- 239000003925 fat Substances 0.000 claims description 51
- 235000019197 fats Nutrition 0.000 claims description 46
- 239000003921 oil Substances 0.000 claims description 34
- 235000019198 oils Nutrition 0.000 claims description 33
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 21
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 19
- 239000008158 vegetable oil Substances 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 16
- 235000021588 free fatty acids Nutrition 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 11
- 239000003240 coconut oil Substances 0.000 claims description 11
- 235000019864 coconut oil Nutrition 0.000 claims description 11
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 150000003464 sulfur compounds Chemical group 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 229910003294 NiMo Inorganic materials 0.000 claims description 7
- 235000019871 vegetable fat Nutrition 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 6
- 150000002898 organic sulfur compounds Chemical group 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 241000251468 Actinopterygii Species 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 240000002791 Brassica napus Species 0.000 claims description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000828 canola oil Substances 0.000 claims description 2
- 235000019519 canola oil Nutrition 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 229910001657 ferrierite group Inorganic materials 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 238000010353 genetic engineering Methods 0.000 claims description 2
- 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 2
- 239000010460 hemp oil Substances 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 239000008267 milk Substances 0.000 claims description 2
- 210000004080 milk Anatomy 0.000 claims description 2
- 239000008164 mustard oil Substances 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 239000003784 tall oil Substances 0.000 claims description 2
- 239000003760 tallow Substances 0.000 claims description 2
- 239000010698 whale oil Substances 0.000 claims description 2
- 229910021472 group 8 element Inorganic materials 0.000 claims 1
- 150000002484 inorganic compounds Chemical group 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 49
- 239000001257 hydrogen Substances 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000000047 product Substances 0.000 description 41
- 238000006114 decarboxylation reaction Methods 0.000 description 19
- 150000003626 triacylglycerols Chemical class 0.000 description 16
- 238000005262 decarbonization Methods 0.000 description 15
- 238000006392 deoxygenation reaction Methods 0.000 description 15
- 239000007789 gas Substances 0.000 description 12
- 238000007086 side reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 10
- 239000012188 paraffin wax Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 238000006606 decarbonylation reaction Methods 0.000 description 9
- 239000002283 diesel fuel Substances 0.000 description 9
- 235000019737 Animal fat Nutrition 0.000 description 8
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 8
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000006324 decarbonylation Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000012263 liquid product Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000003904 phospholipids Chemical class 0.000 description 6
- 239000010775 animal oil Substances 0.000 description 5
- 239000012075 bio-oil Substances 0.000 description 5
- 238000004061 bleaching Methods 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 235000019482 Palm oil Nutrition 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 238000004517 catalytic hydrocracking Methods 0.000 description 4
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 4
- 239000002540 palm oil Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical compound [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000005899 aromatization reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000021466 carotenoid Nutrition 0.000 description 2
- 150000001747 carotenoids Chemical class 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940013317 fish oils Drugs 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003060 catalysis inhibitor Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000006280 diesel fuel additive Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000004508 fractional distillation Methods 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
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004831 organic oxygen compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Images
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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
- C10G45/06—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof
- C10G45/08—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof in combination with chromium, molybdenum, or 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
-
- 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
- C10G3/50—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
- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
-
- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
- C10G45/10—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
-
- 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
- C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
- C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
- C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps
- C10G65/043—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps at least one step being a change in the structural skeleton
-
- 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
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
-
- 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
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/205—Metal content
-
- 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
- C10G2300/80—Additives
- C10G2300/802—Diluents
-
- 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
- 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
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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
脱カルボニル: C17H35COOH+H2 → C17H36+CO+H2O (B1)
C17H35COOH → C17H34+CO+H2O (B2)
水素化: C17H35COOH+3H2 → C18H38+2H2O (C)
メタン化: CO+3H2 → CH4+H2O (D)
水性ガスシフト:CO+H2O → H2+CO2 (E)
本発明の目的は、水素消費量が低減された、バイオ油脂からのディーゼルレンジ炭化水素の製造のための改善された方法である。
本明細書において、水素化加工処理とは、分子状水素のあらゆる手段による有機材料の触媒的処理と理解される。
本発明は、水素化処理工程および異性化工程を含み、再生可能な供給源、たとえば、植物油/脂肪および動物油/脂肪および魚の油/脂肪などのバイオ油脂など、特に、C12〜C16脂肪酸および/またはその誘導体から、ディーゼルレンジ炭化水素を、イオウの存在下で製造するための改善された方法に関する。本発明は、水素化処理中の水素消費量を低減させて、イオウの存在下、トリグリセリド、脂肪酸および脂肪酸の誘導体、特にC12〜C16脂肪酸および/またはその誘導体またはそれらの組合せを含む供給原料をn−パラフィンに水素化処理した後、異性化により高ディーゼル収率でn−パラフィンをディーゼルレンジ分枝アルカンに変換することに関する。この方法によって生成する炭化水素油生成物は、高品質のディーゼル成分である。水素化処理工程では、イオウの存在下で、供給原料を硫化水素化処理触媒と接触させた後、異性化触媒を用いた異性化工程を行なう。
本発明の方法において未使用供給原料として使用されるバイオ油および/または脂肪は、再生可能な供給源由来のもの、たとえば、植物および/または動物および/または魚由来の油脂ならびにこれらから誘導される化合物などである。原料油として有用である代表的な植物または植物性または動物油/脂肪の基本構造単位はトリグリセリドであり、これは、グリセロールと3つの脂肪酸分子とのトリエステルであり、下記式Iで表される構造を有する。
水素化処理ユニットへ向けられる供給原料は、未使用供給原料および任意で少なくとも1種類の希釈剤を含む。希釈剤は、生物学的起源および/または非生物学的起源の炭化水素でよい。供給原料がさらに少なくとも1種類の希釈剤を含む場合、供給原料は、20重量%未満の未使用供給原料を含有することが好ましい。
生成物の低温特性を改善するためには、n−パラフィンの異性化が必要である。異性化の際、分枝イソパラフィンが生成する。イソパラフィンは、通常は、モノ−、ジ−、トリ−またはテトラメチル分枝を有する。
本発明による方法は、脂肪酸およびその誘導体を含有することのある未使用供給原料の水素化処理の際に、高分子量化合物の生成を低減する方法を提供する。本発明による方法は、ディーゼル収率が高く、重大な副反応のない、バイオ油脂からのディーゼルレンジ炭化水素の選択的な製造を提供する。分枝炭化水素は、植物油脂や植物性油脂ならびに動物および魚の油脂から、水素化脱酸素中の脱炭素反応の促進性補助を用いて製造することができ、従って、水素消費量は20〜60%、一般的には20〜40%低減される。
0.3面積%の遊離脂肪酸を含有するヤシ油を未使用供給原料として、水素の存在下、再利用生成物とともに5:1で使用した。未使用供給原料中のトリグリセリドC12〜C16脂肪酸の含有量は58.3重量%であった。全供給原料は、アルカリ金属およびアルカリ土類金属(アルカリ金属およびアルカリ土類金属元素として換算)を10w−ppm未満の量で含んでいた。供給原料中の他の金属の量(金属元素として換算)は10w−ppm未満であった。リンの量(リン元素として換算)は30w−ppmm未満であった。
44.8重量%のトリグリセリドC12〜C16脂肪酸を含有するヤシ油を未使用供給原料において使用した。ジメチルジスルフィドをヤシ油に添加し、供給原料中でのイオウ含量(イオウ元素として換算)を約600w−ppmとした。供給原料の純度は実施例1と同じであったが、遊離脂肪酸量は0.2面積%であった。希釈剤は使用しなかった。供給原料は、水素存在下、305℃で水素化処理し、未使用供給原料に対して、反応器圧力を5MPa、空間速度を2g/gとした。生成物は、主にn−パラフィンを含んでいた。n−パラフィン供給原料は317℃、4MPaで異性化し、WHSVは、水素の存在下、3l/hとした。触媒(A)は、Pt、SAPO−11およびアルミナ担持体を含むものであった。生成物中、>C10の炭化水素の量は97重量%であった。該液状生成物の曇り点は−22℃であった。生成物の分析の結果を表4に示す。
実施例2で得られた水素化処理ヤシ油を312℃、4MPaで異性化し、WHSVは、水素の存在下、触媒Aで31/hとした。これにより、−14℃の曇り点を有する液状生成物が得られた。生成物中、>C10の炭化水素の量は、今度は、98重量%であった。表4からわかるように、生成物の引火点および蒸留曲線から、少量の軽質炭化水素が推測され得る。表4は、菜種油およびヤシ油の水素化処理および異性化した生成物の分析結果を示し、HRO=水素化処理菜種油、HPO=水素化処理ヤシ油である。
30重量%のトリグリセリドC12〜C16脂肪酸を含有する動物脂肪を、未使用供給原料として使用した。供給原料は、アルカリ金属およびアルカリ土類金属(アルカリ金属およびアルカリ土類金属元素として換算)を10w−ppm未満の量で含んでいた。供給原料中の他の金属の量(金属元素として換算)は10w−ppm未満であった。リンの量(リン元素として換算)は30w−ppm未満であった。ジメチルジスルフィドを動物脂肪に添加し、供給原料中でのイオウ含量を約100w−ppmとした。未使用供給原料は遊離脂肪酸を0.6面積%含んでいた。供給原料を、水素の存在下、300℃で水素化処理し、未使用供給原料に対して、反応器圧力を5MPa、空間速度を2g/gとし、希釈剤は伴わなかった。生成物は、主にn−パラフィンを含んでいた。n−パラフィン供給原料を316℃、4MPaで異性化し、WHSVは、水素の存在下、1.51/hとした。触媒(B)は、Pt、SAPO−11およびアルミナ担持体を含むものであった。生成物中、>C10の炭化水素の量は95重量%であった。該液状生成物の曇り点は−20℃であった。
実施例4で得られた水素化処理動物脂肪を、312℃、4MPaで異性化し、WHSVは、水素の存在下、触媒Bで1.51/hとした。これにより、−13℃の曇り点を有する液状生成物が得られた。>C10の炭化水素の量は、今度は、98重量%であった。
Claims (20)
- 供給原料が、少なくとも20重量%のトリグリセリドC12〜C16脂肪酸もしくはC12〜C16脂肪酸エステルもしくはC12〜C16脂肪酸またはその組合せを含有する未使用供給原料を含み、全供給原料が、50〜20000w−ppmのイオウ(イオウ元素として換算)を含有することを特徴とし、供給原料が水素化処理工程において水素化処理され、異性化工程において異性化される、ディーゼルレンジ炭化水素の製造方法。
- 未使用供給原料が、少なくとも30重量%、好ましくは少なくとも40重量%のトリグリセリドC12〜C16脂肪酸もしくは他の脂肪酸エステルまたはその組合せを含有することを特徴とする請求項1記載の方法。
- 未使用供給原料が5重量%より多くの遊離脂肪酸を含有することを特徴とする請求項1または2記載の方法。
- 供給原料が、10w−ppm未満のアルカリ金属およびアルカリ土類金属(アルカリ金属およびアルカリ土類金属の元素として換算)、10w−ppm未満の他の金属(金属元素として換算)、および30w−ppm未満のリン(リン元素として換算)を含有することを特徴とする請求項1〜3のいずれか1項に記載の方法。
- 供給原料が、20重量%未満の未使用供給原料およびさらに少なくとも1種類の希釈剤を含むことを特徴とする請求項1〜4のいずれか1項に記載の方法。
- 希釈剤が、炭化水素および前記方法の再利用生成物またはその混合物から選択される希釈剤であり、希釈剤/未使用供給原料比が5〜30:1、好ましくは10〜30:1、最も好ましくは12〜25:1であることを特徴とする請求項5記載の方法。
- 供給原料が、1000〜8000w−ppm、好ましくは2000〜5000w−ppmのイオウ(イオウ元素として換算)を含有することを特徴とする請求項1〜6のいずれか1項に記載の方法。
- 少なくとも1種類の無機または有機イオウ化合物またはイオウ化合物を含有する精油所ガスおよび/または液体流が供給原料に添加されることを特徴とする請求項1〜7のいずれか1項に記載の方法。
- 未使用供給原料が、植物油/脂肪、動物脂肪/油、魚の脂肪/油、遺伝子操作によって栽培された植物中に含有される脂肪、食品業界の再利用脂肪およびその混合物から選択される生物学的起源のものであることを特徴とする請求項1〜8のいずれか1項に記載の方法。
- 未使用供給原料が、菜種油、コルザ油(colza oil)、キャノーラ油、トール油、ヒマワリ油、大豆油、麻実油、オリーブ油、アマニ油、カラシ油、ヤシ油、ピーナッツ油、ヒマシ油、ココナッツ油、ラード、獣脂、鯨油もしくは乳汁中に含有される脂肪またはその混合物から選択されることを特徴とする請求項1〜9のいずれか1項に記載の方法。
- 未使用供給原料が、生物学的起源の供給原料および1種類/複数の炭化水素である供給原料を含むことを特徴とする請求項1〜10のいずれか1項に記載の方法。
- 水素化処理工程において、1種類以上の触媒床を含む触媒床系が使用されることを特徴とする請求項1〜11のいずれか1項に記載の方法。
- 水素化処理工程において、圧力が2〜15MPaの範囲、好ましくは3〜10MPaの範囲で変動し、温度が200〜400℃、好ましくは250〜350℃、最も好ましくは280〜345℃のあいだで変動することを特徴とする請求項1〜12のいずれか1項に記載の方法。
- 異性化工程において、圧力が2〜15MPaの範囲、好ましくは3〜10MPaの範囲で変動し、温度が200〜500℃、好ましくは280〜400℃で変動することを特徴とする請求項1〜13のいずれか1項に記載の方法。
- 水素化処理が水素化触媒の存在下で行なわれ、前記水素化触媒が周期律表の第VIIIおよび/またはVIB族の金属を含有することを特徴とする請求項1〜14のいずれか1項に記載の方法。
- 水素化処理触媒が、担持されたPd、Pt、Ni、NiMoまたはCoMo触媒であり、該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15記載の方法。
- 分子篩を含む異性化触媒が異性化工程において使用されることを特徴とする請求項1〜16のいずれか1項に記載の方法。
- 異性化触媒が第VIII族元素の金属を含有することを特徴とする請求項17記載の方法。
- 異性化触媒がAl2O3またはSiO2を含有することを特徴とする請求項17または18記載の方法。
- 異性化触媒が、SAPO−11またはSAPO−41またはZSM−22またはZSM−23またはフェリエライトおよびPtまたはPdまたはNiおよびAl2O3またはSiO2を含有することを特徴とする請求項17〜19のいずれか1項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05014426.0A EP1741767B2 (en) | 2005-07-04 | 2005-07-04 | Process for the manufacture of diesel range hydrocarbons |
EP05014426.0 | 2005-07-04 | ||
US69585205P | 2005-07-05 | 2005-07-05 | |
US60/695,852 | 2005-07-05 | ||
PCT/FI2006/050300 WO2007003708A1 (en) | 2005-07-04 | 2006-06-29 | Process for the manufacture of diesel range hydrocarbons |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008545034A true JP2008545034A (ja) | 2008-12-11 |
JP4741661B2 JP4741661B2 (ja) | 2011-08-03 |
Family
ID=36440865
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008518886A Active JP4741661B2 (ja) | 2005-07-04 | 2006-06-29 | ディーゼルレンジ炭化水素の製造方法 |
Country Status (15)
Country | Link |
---|---|
EP (2) | EP1741767B2 (ja) |
JP (1) | JP4741661B2 (ja) |
CN (1) | CN101233212B (ja) |
AP (1) | AP2645A (ja) |
BR (1) | BRPI0614043B1 (ja) |
DK (1) | DK1741767T3 (ja) |
ES (1) | ES2550244T5 (ja) |
FI (1) | FI1741767T4 (ja) |
HU (1) | HUE025943T2 (ja) |
NZ (1) | NZ565051A (ja) |
PL (1) | PL1741767T3 (ja) |
PT (1) | PT1741767E (ja) |
SI (1) | SI1741767T1 (ja) |
UA (1) | UA90906C2 (ja) |
ZA (1) | ZA200800056B (ja) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007153927A (ja) * | 2005-11-30 | 2007-06-21 | Nippon Oil Corp | 水素化精製方法及び水素化精製油 |
JP2010511750A (ja) * | 2006-12-01 | 2010-04-15 | ノース・キャロライナ・ステイト・ユニヴァーシティ | バイオマスの燃料への変換のためのプロセス |
JP2010529992A (ja) * | 2007-06-15 | 2010-09-02 | ユーオーピー エルエルシー | 熱分解油からの化学物質の製造 |
JP2010540700A (ja) * | 2007-09-20 | 2010-12-24 | ユーオーピー エルエルシー | 減少した水素消費量での再生可能な供給材料からのディーゼル燃料の製造 |
JP2012514073A (ja) * | 2008-12-24 | 2012-06-21 | 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 | ディーゼルバイオ原料と灯油範囲炭化水素の同時処理 |
JP2012519744A (ja) * | 2009-03-04 | 2012-08-30 | イエフペ エネルジ ヌヴェル | トリグリセリドを含有する原材料の連続的水素化方法 |
JP5110607B2 (ja) * | 2007-02-28 | 2012-12-26 | 独立行政法人産業技術総合研究所 | バイオディーゼル燃料の製造方法及びバイオディーゼル燃料組成物 |
JP2013503246A (ja) * | 2009-08-28 | 2013-01-31 | 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 | バイオ成分供給材料の水素処理における水素消費量の低減方法 |
JP2013100501A (ja) * | 2011-11-08 | 2013-05-23 | IFP Energies Nouvelles | 水素下での前処理工程を含む連続的水素化処理による、再生可能材料を用いるパラフィン燃料の製造 |
JP2013100500A (ja) * | 2011-11-08 | 2013-05-23 | IFP Energies Nouvelles | 前処理工程を含む連続的水素化処理による、再生可能な材料を用いるパラフィン燃料の製造 |
JP2013522396A (ja) * | 2010-03-09 | 2013-06-13 | 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 | ディーゼル範囲バイオ分子の水素処理 |
JP2013522395A (ja) * | 2010-03-09 | 2013-06-13 | 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 | 再生可能ディーゼル燃料の脱ロウ処理 |
JP2015504937A (ja) * | 2011-12-14 | 2015-02-16 | ユーオーピー エルエルシー | バイオマス由来熱分解油を脱酸素化するための方法 |
JP2019518823A (ja) * | 2016-05-11 | 2019-07-04 | アールイージー シンセティック フューエルス リミテッド ライアビリティ カンパニー | バイオ再生可能ケロシン、ジェット燃料、ジェット燃料ブレンドストック、および製造方法 |
JP2020524199A (ja) * | 2017-06-19 | 2020-08-13 | ネステ オサケ ユキチュア ユルキネン | RBOを製造するためのケトン化反応におけるTiO2触媒 |
JP2021518859A (ja) * | 2018-04-30 | 2021-08-05 | グリーン テクノロジー リサーチ シーオー.,エルティーディーGreen Technology Research Co.,Ltd | バイオベース素材の処理方法及びそれを処理するための装置 |
Families Citing this family (93)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200801175A (en) * | 2006-02-28 | 2008-01-01 | Grace Gmbh & Amp Co Kg | Physical refining process using adsorbent particles for the production of biodiesel fuel |
FR2910483B1 (fr) * | 2006-12-21 | 2010-07-30 | Inst Francais Du Petrole | Procede de conversion de charges issues de sources renouvelables en bases carburants gazoles de bonne qualite. |
DE102006061604A1 (de) * | 2006-12-27 | 2008-07-03 | Alois Dotzer | Verfahren zur Herstellung eines Kraftstoffs aus Pflanzenöl |
GB2447684B (en) * | 2007-03-21 | 2011-11-23 | Statoil Asa | Biogasoline |
US8802422B2 (en) | 2007-06-01 | 2014-08-12 | Solazyme, Inc. | Renewable diesel and jet fuel from microbial sources |
US20080312480A1 (en) | 2007-06-15 | 2008-12-18 | E. I. Du Pont De Nemours And Company | Catalytic process for converting renewable resources into paraffins for use as diesel blending stocks |
FR2919299B1 (fr) | 2007-07-25 | 2009-10-09 | Inst Francais Du Petrole | Procede d'hydroconversion en lit bouillonnant de charges d'origine bio-renouvelable pour la production de bases carburants. |
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 |
US7982076B2 (en) * | 2007-09-20 | 2011-07-19 | Uop Llc | Production of diesel fuel from biorenewable feedstocks |
US7982075B2 (en) * | 2007-09-20 | 2011-07-19 | Uop Llc | Production of diesel fuel from biorenewable feedstocks with lower hydrogen consumption |
US7999142B2 (en) * | 2007-09-20 | 2011-08-16 | Uop Llc | Production of diesel fuel from biorenewable feedstocks |
US7744742B2 (en) | 2007-11-28 | 2010-06-29 | Chevron U.S.A. Inc. | Integration of molecular redistribution and hydroisomerization processes for the production of paraffinic base oil |
US8551327B2 (en) | 2007-12-27 | 2013-10-08 | Exxonmobil Research And Engineering Company | Staged co-processing of biofeeds for manufacture of diesel range hydrocarbons |
AU2009234176B2 (en) | 2008-04-09 | 2014-08-07 | Corbion Biotech, Inc. | Direct chemical modification of microbial biomass and microbial oils |
GB2462054A (en) * | 2008-04-29 | 2010-01-27 | Statoilhydro Asa | Biodiesel |
US7960597B2 (en) * | 2008-07-24 | 2011-06-14 | Chevron U.S.A. Inc. | Conversion of vegetable oils to base oils and transportation fuels |
US7960596B2 (en) * | 2008-07-24 | 2011-06-14 | Chevron U.S.A. Inc. | Conversion of vegetable oils to base oils and transportation fuels |
US8772555B2 (en) * | 2008-07-24 | 2014-07-08 | Chevron U.S.A. Inc. | Conversion of vegetable oils to base oils and transportation fuels |
ES2433220T5 (es) * | 2008-09-10 | 2024-02-12 | Haldor Topsoe As | Proceso y catalizador de hidroconversión |
AU2008363825B2 (en) | 2008-11-06 | 2016-03-03 | Exxonmobil Research And Engineering Company | Hydroprocessing of biodiesel fuels and blends |
JP5859311B2 (ja) | 2008-11-28 | 2016-02-10 | ソラザイム, インコーポレイテッドSolazyme Inc | 組み換え従属栄養微生物における、用途に応じた油の生産 |
CN102439118B (zh) * | 2008-12-12 | 2015-04-01 | 纳幕尔杜邦公司 | 从可再生资源制备直链二元羧酸的方法 |
US8632675B2 (en) | 2008-12-24 | 2014-01-21 | Exxonmobil Research And Engineering Company | Co-processing of diesel biofeed and heavy oil |
FI122957B (fi) | 2009-06-24 | 2012-09-14 | Neste Oil Oyj | Menetelmä rasvan tuottamiseksi |
JP2012533655A (ja) | 2009-07-17 | 2012-12-27 | 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 | Fccオフガスによるバイオ成分原材料の水素処理 |
EP4371970A2 (en) | 2009-07-17 | 2024-05-22 | Neste Oyj | Process for the preparation of light fuels |
EP2290045A1 (en) * | 2009-07-27 | 2011-03-02 | Total Petrochemicals Research Feluy | A process for the production of bio-naphtha from complex mixtures of natural occurring fats and oils |
EP2290035A1 (en) * | 2009-07-27 | 2011-03-02 | Total Petrochemicals Research Feluy | A process for the production of bio-naptha from complex mixtures of natural occurring fats and oils |
FR2950895B1 (fr) * | 2009-10-06 | 2012-02-17 | Inst Francais Du Petrole | Procede d'hydrotraitement et d'hydroisomerisation de charges issues de source renouvelable mettant en oeuvre un catalyseur a base de carbure de silicium |
FR2953854B1 (fr) * | 2009-12-16 | 2012-12-28 | Inst Francais Du Petrole | Procede de conversion de charges issues de sources renouvelables avec pretraitement des charges par dephosphatation a chaud |
US8853474B2 (en) | 2009-12-29 | 2014-10-07 | Exxonmobil Research And Engineering Company | Hydroprocessing of biocomponent feedstocks with low purity hydrogen-containing streams |
EP2390341B1 (en) | 2010-05-25 | 2018-06-27 | Neste Oyj | Process and microorganisms for production of lipids |
FI125632B (fi) | 2010-05-25 | 2015-12-31 | Upm Kymmene Corp | Menetelmä ja laite hiilivetyjen tuottamiseksi |
CA3039432A1 (en) | 2010-05-28 | 2011-12-01 | Corbion Biotech, Inc. | Tailored oils produced from recombinant heterotrophic microorganisms |
US20120016167A1 (en) | 2010-07-15 | 2012-01-19 | Exxonmobil Research And Engineering Company | Hydroprocessing of biocomponent feeds with low pressure hydrogen-containing streams |
US8366907B2 (en) | 2010-08-02 | 2013-02-05 | Battelle Memorial Institute | Deoxygenation of fatty acids for preparation of hydrocarbons |
CA3024641A1 (en) | 2010-11-03 | 2012-05-10 | Corbion Biotech, Inc. | Microbial oils with lowered pour points, dielectric fluids produced therefrom, and related methods |
DK2465868T3 (en) | 2010-12-17 | 2016-05-17 | Neste Oyj | Enhancement of lipid production |
PL2468875T3 (pl) | 2010-12-22 | 2022-11-07 | Neste Oyj | Zintegrowany sposób wytwarzania biopaliw |
ES2748848T3 (es) | 2010-12-22 | 2020-03-18 | Neste Oyj | Proceso para la producción de enzimas |
PT2468857E (pt) | 2010-12-22 | 2014-12-22 | Neste Oil Oyj | Um sistema de processo integrado para produção de lípidos e polpação |
FR2969642B1 (fr) * | 2010-12-22 | 2012-12-28 | IFP Energies Nouvelles | Production de carburants paraffiniques a partir de matieres renouvelables par un procede d'hydrotraitement en continu |
ES2626658T5 (es) | 2011-01-18 | 2021-01-26 | Neste Oyj | Método y disposición para alimentar materiales sensibles al calor a reactores de lecho fijo |
CA2825691C (en) | 2011-02-02 | 2020-08-25 | Solazyme, Inc. | Tailored oils produced from recombinant oleaginous microorganisms |
DK2489276T3 (da) | 2011-02-17 | 2014-01-20 | Neste Oil Oyj | Fremgangsmåde til udvinding af olie |
WO2012154626A1 (en) | 2011-05-06 | 2012-11-15 | Solazyme, Inc. | Genetically engineered microorganisms that metabolize xylose |
EP2546352A1 (en) | 2011-07-15 | 2013-01-16 | Neste Oil Oyj | Process for producing lipids from palm oil production residues |
CN103059902B (zh) * | 2011-10-24 | 2015-05-20 | 中国石油化工股份有限公司 | 一种以动植物油为原料制备喷气燃料调合组分的方法 |
CN103059901B (zh) * | 2011-10-24 | 2015-11-25 | 中国石油化工股份有限公司 | 一种动植物油脂制备柴油组分或喷气燃料组分的方法 |
FR2981942B1 (fr) * | 2011-10-27 | 2013-11-15 | IFP Energies Nouvelles | Procede d'hydrotraitement et d'hydroisomerisation de charges issues de la biomasse dans lequel l'effluent a hydrosiomeriser et le flux d'hydrogene contiennent une teneur limitee en oxygene |
CN103102919B (zh) * | 2011-11-10 | 2015-04-15 | 中国石油化工股份有限公司 | 一种生产优质溶剂油的两段法加氢方法 |
ES2744868T3 (es) | 2012-04-18 | 2020-02-26 | Corbion Biotech Inc | Aceites hechos a medida |
CN103773459B (zh) * | 2012-10-24 | 2015-11-18 | 中国石油化工股份有限公司 | 一种动植物油与催化柴油联合加氢工艺 |
CN103773457B (zh) * | 2012-10-24 | 2016-04-27 | 中国石油化工股份有限公司 | 一种动植物油与柴油联合加氢方法 |
CN103773455B (zh) * | 2012-10-24 | 2016-05-18 | 中国石油化工股份有限公司 | 一种动植物油、催化柴油联合加氢工艺方法 |
EP2735610A1 (en) | 2012-11-26 | 2014-05-28 | Neste Oil Oyj | Oleaginous bacterial cells and methods for producing lipids |
EP2938707B1 (en) * | 2012-12-31 | 2019-11-13 | Shell International Research Maatschappij B.V. | A process for converting one or more c3-c12 oxygenates |
US20150353864A1 (en) * | 2013-01-21 | 2015-12-10 | Total Research & Technology Feluy | Process for the Production of Bio-Naphtha from Complex Mixtures of Natural Occurring Fats & Oils |
US10098371B2 (en) | 2013-01-28 | 2018-10-16 | Solazyme Roquette Nutritionals, LLC | Microalgal flour |
US9567615B2 (en) | 2013-01-29 | 2017-02-14 | Terravia Holdings, Inc. | Variant thioesterases and methods of use |
US9816079B2 (en) | 2013-01-29 | 2017-11-14 | Terravia Holdings, Inc. | Variant thioesterases and methods of use |
US9290749B2 (en) | 2013-03-15 | 2016-03-22 | Solazyme, Inc. | Thioesterases and cells for production of tailored oils |
US9783836B2 (en) | 2013-03-15 | 2017-10-10 | Terravia Holdings, Inc. | Thioesterases and cells for production of tailored oils |
WO2014176515A2 (en) | 2013-04-26 | 2014-10-30 | Solazyme, Inc. | Low polyunsaturated fatty acid oils and uses thereof |
FR3009619B1 (fr) | 2013-08-07 | 2017-12-29 | Roquette Freres | Compositions de biomasse de microalgues riches en proteines de qualite sensorielle optimisee |
EP3052636A2 (en) | 2013-10-04 | 2016-08-10 | Solazyme, Inc. | Tailored oils |
WO2015086783A1 (en) | 2013-12-11 | 2015-06-18 | Neste Oil Oyj | Method of processing lignocellulosic material using a cationic compound |
UA121025C2 (uk) | 2013-12-11 | 2020-03-25 | Несте Оій | Спосіб виробництва одноклітинної олії з лігноцелюлозних матеріалів |
EP3080287A1 (en) | 2013-12-11 | 2016-10-19 | Neste Oyj | Method of processing lignocellulosic material using an alkaline delignification agent |
CN103756720A (zh) * | 2014-01-26 | 2014-04-30 | 陈恒顺 | 一种提高蒽油加氢柴油十六烷值的生产方法 |
CN103756723A (zh) * | 2014-01-26 | 2014-04-30 | 陈恒顺 | 一种生物柴油和煤焦油加氢生产高十六烷值柴油的方法 |
WO2015149026A1 (en) | 2014-03-28 | 2015-10-01 | Solazyme, Inc. | Lauric ester compositions |
WO2016007862A2 (en) | 2014-07-10 | 2016-01-14 | Solazyme, Inc. | Novel ketoacyl acp synthase genes and uses thereof |
BR112017001404A2 (pt) | 2014-07-24 | 2017-11-21 | Terravia Holdings Inc | tioesterases variantes e métodos de utilização |
BR112017005370A2 (pt) | 2014-09-18 | 2017-12-12 | Terravia Holdings Inc | acil-acp tioesterases e mutantes das mesmas |
CN105733646B (zh) * | 2014-12-08 | 2017-11-03 | 中国石油化工股份有限公司 | 一种高级脂肪酸酯加氢制烃的方法 |
WO2016142806A1 (en) * | 2015-03-10 | 2016-09-15 | Sabic Global Technologies, B.V. | Process for hydrocracking of hydrocarbon streams and pyrolysis oils |
WO2016142807A1 (en) * | 2015-03-10 | 2016-09-15 | Sabic Global Technologies, B.V. | Process for preparation of hydrocracking catalyst for use in hydrocracking of hydrocarbon streams |
WO2016164495A1 (en) | 2015-04-06 | 2016-10-13 | Solazyme, Inc. | Oleaginous microalgae having an lpaat ablation |
CN106190277B (zh) * | 2016-08-18 | 2017-12-15 | 深圳市中创新能源科技有限公司 | 一种催化裂化制备生物质燃料的方法 |
CN107974266B (zh) * | 2016-10-25 | 2020-06-12 | 中国石油化工股份有限公司 | 一种由废弃油脂生产航空燃料组分的方法及系统 |
CN107974265B (zh) * | 2016-10-25 | 2020-08-18 | 中国石油化工股份有限公司 | 一种由废弃油脂生产航空燃料组分的方法 |
CN106833716A (zh) * | 2017-03-27 | 2017-06-13 | 天津南开大学蓖麻工程科技有限公司 | 以蓖麻油为原料催化加氢脱氧及异构化生产生物航煤方法 |
FI129178B (en) * | 2017-12-29 | 2021-08-31 | Neste Oyj | Purification of biomass-based lipid material |
FI20176201A1 (en) | 2017-12-29 | 2019-06-30 | Neste Oyj | A method for determining the amount of renewable fuel in a fuel mixture. |
AU2019262044B2 (en) * | 2018-05-03 | 2024-05-30 | Renewable Energy Group, Inc. | Methods and devices for producing biodiesel, diesel-range hydrocarbons, and products obtained therefrom |
FI130601B (en) | 2018-12-14 | 2023-12-07 | Neste Oyj | Diesel fuel composition |
FI20195647A1 (en) | 2019-07-22 | 2021-01-23 | Neste Oyj | Paraffin products, method of production of paraffin products and use of paraffin products |
IT201900014778A1 (it) * | 2019-08-14 | 2021-02-14 | Nextchem S P A | Processo per il pretrattamento di alimentazioni destinate alla produzione di bio-carburanti, mediante idrolisi di grassi ad alta temperatura e pressione |
US20220243132A1 (en) * | 2019-08-29 | 2022-08-04 | Haldor Topsøe A/S | A process for monitoring the operation of hydrodeoxygenation of a feedstock |
CN112592730A (zh) * | 2020-10-10 | 2021-04-02 | 中国科学院青岛生物能源与过程研究所 | 一种生产生物柴油的加氢工艺 |
CN116648493A (zh) * | 2020-12-11 | 2023-08-25 | 耐思特公司 | 具有良好十六烷值和良好冷特性的可再生烃组合物 |
FI20216353A1 (en) | 2021-12-27 | 2023-06-28 | Neste Oyj | RENEWABLE STABILIZED NAFTA AREA HYDROCARBON FEED, THERMAL CRACKING METHOD AND ITS PRODUCTS |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP1396531A2 (en) * | 2002-09-06 | 2004-03-10 | Fortum OYJ | Process for producing a hydrocarbon component of biological origin |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2551056B1 (fr) | 1983-08-25 | 1985-11-29 | Inst Francais Du Petrole | Nouveau procede de fabrication d'olefine lineaire a partir d'acide gras ou d'ester d'acide gras sature |
FR2607803A1 (fr) | 1986-12-08 | 1988-06-10 | Univ Paris Curie | Procede d'hydrocraquage sous pression des huiles vegetales ou des acides gras derives desdites huiles |
US4992605A (en) | 1988-02-16 | 1991-02-12 | Craig Wayne K | Production of hydrocarbons with a relatively high cetane rating |
CA2149685C (en) † | 1994-06-30 | 1999-09-14 | Jacques Monnier | Conversion of depitched tall oil to diesel fuel additive |
US5612273A (en) | 1994-12-30 | 1997-03-18 | Intevep, S.A. | Catalyst for the hydroisomerization of contaminated hydrocarbon feedstock |
CZ283575B6 (cs) | 1996-01-17 | 1998-05-13 | Chemopetrol, A. S. | Způsob výroby automobilového benzínu |
FI100248B (fi) | 1996-02-05 | 1997-10-31 | Fortum Oil Oy | Keskitisleen valmistus |
FI102767B (fi) | 1997-05-29 | 1999-02-15 | Fortum Oil Oy | Menetelmä korkealuokkaisen dieselpolttoaineen valmistamiseksi |
EP1000132A1 (fr) | 1997-07-09 | 2000-05-17 | Crystallisation and Degumming Sprl | Procede d'elimination des metaux des corps gras et des gommes associes a ces metaux |
CN100347278C (zh) | 2002-05-30 | 2007-11-07 | 科学与工业研究委员会 | 物理精炼植物油的预处理方法 |
US7232935B2 (en) * | 2002-09-06 | 2007-06-19 | Fortum Oyj | Process for producing a hydrocarbon component of biological origin |
DE10327059B4 (de) * | 2003-06-16 | 2005-12-22 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zum Konvertieren von fett- oder ölhaltigen Roh- und Abfallstoffen in Gemische mit hohem Kohlenwasserstoffanteil, mit diesem Verfahren hergestellte Produkte und deren Verwendung |
-
2005
- 2005-07-04 PT PT50144260T patent/PT1741767E/pt unknown
- 2005-07-04 SI SI200532017T patent/SI1741767T1/sl unknown
- 2005-07-04 EP EP05014426.0A patent/EP1741767B2/en active Active
- 2005-07-04 ES ES05014426T patent/ES2550244T5/es active Active
- 2005-07-04 HU HUE05014426A patent/HUE025943T2/en unknown
- 2005-07-04 DK DK05014426.0T patent/DK1741767T3/en active
- 2005-07-04 FI FIEP05014426.0T patent/FI1741767T4/fi active
- 2005-07-04 PL PL05014426T patent/PL1741767T3/pl unknown
- 2005-07-04 EP EP15174588.2A patent/EP2990462A1/en active Pending
-
2006
- 2006-06-29 BR BRPI0614043A patent/BRPI0614043B1/pt active IP Right Grant
- 2006-06-29 CN CN2006800274255A patent/CN101233212B/zh active Active
- 2006-06-29 UA UAA200801408A patent/UA90906C2/ru unknown
- 2006-06-29 AP AP2008004335A patent/AP2645A/xx active
- 2006-06-29 JP JP2008518886A patent/JP4741661B2/ja active Active
- 2006-06-29 NZ NZ565051A patent/NZ565051A/en unknown
-
2008
- 2008-01-02 ZA ZA200800056A patent/ZA200800056B/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP1396531A2 (en) * | 2002-09-06 | 2004-03-10 | Fortum OYJ | Process for producing a hydrocarbon component of biological origin |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007153927A (ja) * | 2005-11-30 | 2007-06-21 | Nippon Oil Corp | 水素化精製方法及び水素化精製油 |
JP2010511750A (ja) * | 2006-12-01 | 2010-04-15 | ノース・キャロライナ・ステイト・ユニヴァーシティ | バイオマスの燃料への変換のためのプロセス |
JP5110607B2 (ja) * | 2007-02-28 | 2012-12-26 | 独立行政法人産業技術総合研究所 | バイオディーゼル燃料の製造方法及びバイオディーゼル燃料組成物 |
JP2010529992A (ja) * | 2007-06-15 | 2010-09-02 | ユーオーピー エルエルシー | 熱分解油からの化学物質の製造 |
JP2010540700A (ja) * | 2007-09-20 | 2010-12-24 | ユーオーピー エルエルシー | 減少した水素消費量での再生可能な供給材料からのディーゼル燃料の製造 |
JP2012514073A (ja) * | 2008-12-24 | 2012-06-21 | 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 | ディーゼルバイオ原料と灯油範囲炭化水素の同時処理 |
JP2012519744A (ja) * | 2009-03-04 | 2012-08-30 | イエフペ エネルジ ヌヴェル | トリグリセリドを含有する原材料の連続的水素化方法 |
JP2015007238A (ja) * | 2009-03-04 | 2015-01-15 | イエフペ エネルジ ヌヴェルIfp Energies Nouvelles | トリグリセリドを含有する原材料の連続的水素化方法 |
JP2013503246A (ja) * | 2009-08-28 | 2013-01-31 | 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 | バイオ成分供給材料の水素処理における水素消費量の低減方法 |
JP2013522396A (ja) * | 2010-03-09 | 2013-06-13 | 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 | ディーゼル範囲バイオ分子の水素処理 |
JP2013522395A (ja) * | 2010-03-09 | 2013-06-13 | 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 | 再生可能ディーゼル燃料の脱ロウ処理 |
JP2013100500A (ja) * | 2011-11-08 | 2013-05-23 | IFP Energies Nouvelles | 前処理工程を含む連続的水素化処理による、再生可能な材料を用いるパラフィン燃料の製造 |
JP2013100501A (ja) * | 2011-11-08 | 2013-05-23 | IFP Energies Nouvelles | 水素下での前処理工程を含む連続的水素化処理による、再生可能材料を用いるパラフィン燃料の製造 |
JP2015504937A (ja) * | 2011-12-14 | 2015-02-16 | ユーオーピー エルエルシー | バイオマス由来熱分解油を脱酸素化するための方法 |
JP2019518823A (ja) * | 2016-05-11 | 2019-07-04 | アールイージー シンセティック フューエルス リミテッド ライアビリティ カンパニー | バイオ再生可能ケロシン、ジェット燃料、ジェット燃料ブレンドストック、および製造方法 |
JP2020524199A (ja) * | 2017-06-19 | 2020-08-13 | ネステ オサケ ユキチュア ユルキネン | RBOを製造するためのケトン化反応におけるTiO2触媒 |
JP2020524197A (ja) * | 2017-06-19 | 2020-08-13 | ネステ オサケ ユキチュア ユルキネン | 再生可能なベースオイル、ディーゼルおよびナフサを製造するための方法 |
JP7229180B2 (ja) | 2017-06-19 | 2023-02-27 | ネステ オサケ ユキチュア ユルキネン | RBOを製造するためのケトン化反応におけるTiO2触媒 |
JP7266539B2 (ja) | 2017-06-19 | 2023-04-28 | ネステ オサケ ユキチュア ユルキネン | 再生可能なベースオイル、ディーゼルおよびナフサを製造するための方法 |
JP2021518859A (ja) * | 2018-04-30 | 2021-08-05 | グリーン テクノロジー リサーチ シーオー.,エルティーディーGreen Technology Research Co.,Ltd | バイオベース素材の処理方法及びそれを処理するための装置 |
JP7490851B2 (ja) | 2018-04-30 | 2024-05-27 | グリーン テクノロジー リサーチ シーオー.,エルティーディー | バイオベース素材の処理方法及びそれを処理するための装置 |
Also Published As
Publication number | Publication date |
---|---|
EP1741767A1 (en) | 2007-01-10 |
JP4741661B2 (ja) | 2011-08-03 |
PL1741767T3 (pl) | 2015-12-31 |
UA90906C2 (ru) | 2010-06-10 |
CN101233212A (zh) | 2008-07-30 |
BRPI0614043B1 (pt) | 2016-04-19 |
AP2645A (en) | 2013-04-17 |
CN101233212B (zh) | 2012-10-03 |
DK1741767T3 (en) | 2015-10-26 |
PT1741767E (pt) | 2015-11-03 |
ZA200800056B (en) | 2008-12-31 |
ES2550244T5 (es) | 2023-06-08 |
BRPI0614043A2 (pt) | 2011-03-09 |
EP1741767B1 (en) | 2015-07-22 |
EP2990462A1 (en) | 2016-03-02 |
NZ565051A (en) | 2011-04-29 |
HUE025943T2 (en) | 2016-05-30 |
ES2550244T3 (es) | 2015-11-05 |
SI1741767T1 (sl) | 2016-02-29 |
FI1741767T4 (fi) | 2023-04-25 |
EP1741767B2 (en) | 2023-04-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4741661B2 (ja) | ディーゼルレンジ炭化水素の製造方法 | |
US11473018B2 (en) | Process for the manufacture of diesel range hydrocarbons | |
JP4741662B2 (ja) | ディーゼルレンジ炭化水素の製造方法 | |
KR101037583B1 (ko) | 디젤 등급 탄화수소류의 제조 공정 | |
US8278492B2 (en) | Process for the manufacture of diesel range hydrocarbons | |
CA2614020C (en) | Process for the manufacture of diesel range hydrocarbons | |
US20230014266A1 (en) | Process for the manufacture of diesel range hydrocarbons |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20100616 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20101221 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110322 |
|
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: 20110412 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110506 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 4741661 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: 20140513 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 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |