CN109836329A - The method for preparing hydrocarbon hydrocarbon from scenedesmus - Google Patents
The method for preparing hydrocarbon hydrocarbon from scenedesmus Download PDFInfo
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- CN109836329A CN109836329A CN201910195707.5A CN201910195707A CN109836329A CN 109836329 A CN109836329 A CN 109836329A CN 201910195707 A CN201910195707 A CN 201910195707A CN 109836329 A CN109836329 A CN 109836329A
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- CN
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- Prior art keywords
- scenedesmus
- alcohol
- hydrocarbon
- renewable oils
- renewable oil
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- 238000000034 method Methods 0.000 title claims abstract description 32
- 241000195663 Scenedesmus Species 0.000 title claims abstract description 30
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 28
- -1 hydrocarbon hydrocarbon Chemical class 0.000 title claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 title abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 43
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 6
- 239000000543 intermediate Substances 0.000 claims description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 241000195493 Cryptophyta Species 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011973 solid acid Substances 0.000 claims description 3
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 2
- 239000010457 zeolite Substances 0.000 claims 2
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- 229910017116 Fe—Mo Inorganic materials 0.000 claims 1
- 229910003296 Ni-Mo Inorganic materials 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000007669 thermal treatment Methods 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 48
- 239000003225 biodiesel Substances 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 3
- 235000019441 ethanol Nutrition 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000003610 charcoal Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 4
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 4
- 239000003863 metallic catalyst Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 229910003178 Mo2C Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RZJRJXONCZWCBN-UHFFFAOYSA-N alpha-octadecene Natural products CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- QIJNJJZPYXGIQM-UHFFFAOYSA-N 1lambda4,2lambda4-dimolybdacyclopropa-1,2,3-triene Chemical compound [Mo]=C=[Mo] QIJNJJZPYXGIQM-UHFFFAOYSA-N 0.000 description 2
- 229910039444 MoC Inorganic materials 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910003076 TiO2-Al2O3 Inorganic materials 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 229940067592 ethyl palmitate Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- KWUUWVQMAVOYKS-UHFFFAOYSA-N iron molybdenum Chemical compound [Fe].[Fe][Mo][Mo] KWUUWVQMAVOYKS-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229940038384 octadecane Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- YBADLXQNJCMBKR-UHFFFAOYSA-M (4-nitrophenyl)acetate Chemical compound [O-]C(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-M 0.000 description 1
- 229910019626 (NH4)6Mo7O24 Inorganic materials 0.000 description 1
- 229910003208 (NH4)6Mo7O24·4H2O Inorganic materials 0.000 description 1
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- BGHNPAUUBTXCBM-UHFFFAOYSA-N CC(CCCCCCCCCCCCP)C Chemical compound CC(CCCCCCCCCCCCP)C BGHNPAUUBTXCBM-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropyl alcohol Natural products CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012378 ammonium molybdate tetrahydrate Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- FIXLYHHVMHXSCP-UHFFFAOYSA-H azane;dihydroxy(dioxo)molybdenum;trioxomolybdenum;tetrahydrate Chemical compound N.N.N.N.N.N.O.O.O.O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O FIXLYHHVMHXSCP-UHFFFAOYSA-H 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- HRSXWUSONDBHSP-UHFFFAOYSA-N benzyl hexanoate Chemical compound CCCCCC(=O)OCC1=CC=CC=C1 HRSXWUSONDBHSP-UHFFFAOYSA-N 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000005255 carburizing Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 235000020057 cognac Nutrition 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NXDICBYIUGMBNM-UHFFFAOYSA-N ethyl hexadeca-9,12-dienoate Chemical compound CCCC=CCC=CCCCCCCCC(=O)OCC NXDICBYIUGMBNM-UHFFFAOYSA-N 0.000 description 1
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
- 229940031016 ethyl linoleate Drugs 0.000 description 1
- JELGPLUONQGOHF-KTKRTIGZSA-N ethyl palmitoleate Chemical compound CCCCCC\C=C/CCCCCCCC(=O)OCC JELGPLUONQGOHF-KTKRTIGZSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- IIYJCOKOQWJTHO-UHFFFAOYSA-N hexadec-5-ene Chemical compound CCCCCCCCCCC=CCCCC IIYJCOKOQWJTHO-UHFFFAOYSA-N 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 1
- 238000002803 maceration Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 235000016768 molybdenum Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000005067 remediation Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 239000002002 slurry Substances 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
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The present invention describes a kind of method for preparing hydrocarbon by scenedesmus, and method includes by mixing wet scenedesmus in proportion with alcohol, and thermally treated mixture is to generate renewable oils intermediate, by adding catalyst hydrogenation to handle renewable oils intermediate to generate hydrocarbon.The invention further relates to the techniques from renewable oils intermediate preparation biodiesel and ammonia.
Description
Technical field
Production technology the present invention relates to hydrocarbon compound be by adjust the concentration of alcohol, heat treatment, recycling alcohol, to heat at
Hydrocarbon caused by the carry out hydrotreating and separation of product liquid after reason.Present invention further relates to be formed after hydrotreating
Biodiesel and separation of ammonia.
Background technique
It is considered as promising biology combustion due to the superior growth rate of microalgae, high oil content and the property of environmental protection
Expect raw material.Algae passes through photosynthesis effectively from many source absorbing carbon dioxides, and can be processed to a variety of productions
Product, for example, ethyl alcohol, biodiesel, green diesel, methane, soil remediation and animal feed.The scenedesmus that the present invention uses, scenedesmus
Resourceful is planktonic algae common in fresh water, and many types have stronger patience to organic pollutant, in water body
There is certain effect in self-cleaning and sewage purification, is the dominant species in organic sewage oxidation pond biofacies.Scenedesmus breeding is fast, cell
Interior protein rich in and vitamin, can be used as the material of artificial mass propgation.Part scenedesmus can accumulate greatly into the cell
Fatty acid is measured, biodiesel can be converted into.
Mainly there are 3 classes by the method that microalgae prepares bio-fuel at present.The first kind is conventional method, using micro- after drying
Algae is extracted by organic solvent (such as hexane), directly obtains microalgae oil, then carry out esterification to microalgae oil and prepare biological bavin
Oil.Carbohydrate fermentation in microalgae is ethyl alcohol using zymotechnique by the 2nd kind of method, and algae oil is then extracted from residue using hexane.
3rd kind of method is using hydrothermal liquefaction in 300-374 DEG C of temperature range in continuous plug flow reactor or batch reactor
It is heated 5-90 minutes with 4-22MPa pressure limit, microalgae slurries are converted to water-insoluble bio-crude oil.Bio-crude oil carries out again
Refining production fuels and chemicals.
Above method is all respectively defective.Conventional method requires high energy consumption to cross range drying microalgae, while requiring containing for microalgae
Oil mass has to be higher than 25% dry weight, but the oil content of most of microalgae is all in 20% dry weight hereinafter, be not achieved economical production
It is required that.2nd class fermentation process then requires the sugar content of microalgae to want high, and otherwise increased zymotechnique can not play a role.3rd class
Hydro-thermal process method needs to complete under high temperature and pressure.
Higher about 56% dry weight of scenedesmus protein content, and oil content is generally 20% dry weight or so, sugared content is then relatively low
It is 10% or so.In view of the foregoing, the present invention is according to the specific components of scenedesmus, using wet scenedesmus as raw material, it is expected that finding from grid
The alternative of algae production multi-products.
Summary of the invention
Therefore, the present invention provides the new methods from scenedesmus production hydrocarbon.It the use of wet scenedesmus is raw material, with renewable chemicals
Agent is write supplemented by alcohol, and wet scenedesmus handle under medium temperature (200-290 DEG C), is obtained in the relatively stable renewable oils of high yield
Mesosome.It carries out adding the process such as hydrogen for oily intermediate again, it is orientable to prepare hydrocarbon hydrocarbon, fatty acid methyl ester, fatty-acid ethyl ester
And ammonia.Alcohol used herein refers to or mixtures thereof ethyl alcohol, methanol.Renewable oils intermediate is formed after heat treatment, organizes subpackage
Include the chemical substances such as hydrocarbon, aliphatic ester, fatty acid, ethyl alcohol, methanol.Renewable oils intermediate can be distilled first to separate second
Alcohol, first alcohol and water are to form second level renewable oils intermediate.Second level renewable oils intermediate can be processed on metallic catalyst
Or hydrotreating is to generate hydrocarbon, biodiesel and ammonia.It is described in more detail below about some other implementations of these and other
The additional detail of scheme.
The above-mentioned general introduction of some embodiments, which is not intended to, describes each disclosed embodiment or each patent currently invented.
These embodiments are more particularly exemplified in following attached drawing, detailed description and embodiment.
Detailed description of the invention
In view of the detailed description below in conjunction with attached drawing to various embodiments of the present invention, this hair can be more fully understood
It is bright, in which: Fig. 1 is process flow diagram flow chart
Specific embodiment
It should be described below with reference to attached drawing reading, wherein identical appended drawing reference indicates identical member in entire several views
Part.The detailed description and the accompanying drawings show the example embodiment of claimed invention.Therefore, in embodiments, the present invention mentions
Supply a kind of new method that hydrocarbon is formed from scenedesmus, comprising:
A) alcohol is added into wet scenedesmus
B) it is heat-treated scenedesmus at a certain temperature to form renewable oils intermediate；
C) from renewable oils intermediate separation alcohol to form second level renewable oils intermediate；
D) alcohol is recycled；
E) product liquid obtained by metallic catalyst hydrotreating is to form hydrocarbon.
In order to efficiently use all the components in scenedesmus, a kind of new technique by scenedesmus production hydrocarbon is developed.Fig. 1 is aobvious
Show procedure chart.The wet scenedesmus range of solid content of raw material used is 2-20%, the preferably solid content of 10-15%.By the alcohol of addition with
Wet scenedesmus mixing.The volume of alcohol is 1-7 times of wet scenedesmus volume, preferably 3-5 times.Catalyst, catalyst can also be added simultaneously
It can be but not limited to sulfonation solid, sulfuric acid, solid base, potassium hydroxide or sodium hydroxide.The mixture is heated to 190-300
DEG C, preferable temperature is 240-290 DEG C.Heating time depends on the size of reactor and the power of heater.When reactor reaches
When required temperature, heat treatment reaction is carried out 10-120 minutes, preferably 15-30 minutes.It, will when reaction is completed at desired temperatures
Reactor is cooled to room temperature.Heat treatment reaction generates a kind of renewable oils intermediate.This renewable oils intermediate may include
But it is not limited to hydrocarbon, alcohol, aliphatic ester, water, acid, ketone, aldehyde and nitrogenous chemicals.By renewable oils intermediate distillation to separate and recover
Unreacted alcohol, volatile compound (such as acetic acid) and water, and form secondary renewable oils intermediate.In secondary renewable oils
Mesosome with metallic catalyst by mixing, and at 300-400 DEG C under high pressure hydrogen, hydrotreating is carried out at preferably 320-350 DEG C
Form hydrocarbon.The metal of catalyst can be selected from the VIth race's metal (such as Mo and W), and by selected from group VIII metal (such as Fe, Co
And Ni) second of metal promoted.The carrier of catalyst can be selected from but not limited to carbon material, aluminium oxide, silica, boiling
Stone, molecular sieve or combinations thereof.
In one embodiment, the present invention provides a kind of new methods for being used to form biodiesel.Biodiesel is
The diesel fuel being made of chain alkyl (methyl, ethyl or propyl) ester.Aliphatic ester can from secondary by extraction process
The separation of reclaimed oil intermediate direct purification.The process may further include: in methyl alcohol in hydrotreating secondary renewable oils
Mesosome primarily forms fatty acid methyl ester.
In another embodiment, the nitrogenous chemicals in secondary renewable oils intermediate is broken to form ammonia.Ammonia quilt
It is recycled with water, is then used as fertilizer.
On the basis of not departing from essence of the invention, the present invention can be implemented in other specific forms.The present invention includes
All combinations of the aspect and embodiment of invention as described herein.It should be appreciated that any and all embodiments of the invention can
Additional embodiment is described to combine any other embodiments or embodiment (or example).It is also understood that each of embodiment
Individual component is intended to be separately considered to be its independent embodiment.In addition, any element of embodiment is provided to and comes from appoint
Any and all other elements of what embodiment are combined to describe additional embodiment.
Example
The present invention can be further appreciated that by reference to following embodiment, these embodiments are some preferred for illustrating
Embodiment, rather than limit the invention in any way.
The heat treatment of 1 scenedesmus of example
The solid content of wet scenedesmus is 15%.Multiple experiments are carried out by following design: scenedesmus being mixed with additional ethyl alcohol, body
Product ratio is adjusted to 9:1,1:1,1:9.Gained mixture is heat-treated at a temperature of 210,240,290 DEG C three kinds.Reaction time is
0.5,1,2 hour.Experiment the results are shown in Table 1.After the reaction was completed, solid residue is filtered from the liquid of renewable oils intermediate
It separates, dry weighing.The yield of renewable oils intermediate product is the 60-84% of raw material.Gas yield between 1-10%,
Wherein carbon dioxide accounts for 70-90%, remaining group is divided into hydrogen, methane, carbon monoxide and ethane.In higher treatment temperature (example
Such as 240 DEG C and 290 DEG C) typically result in higher gas yield.According to Gc-mss, renewable oils intermediate includes fat
Acid esters, fatty acid, hydrocarbon (such as benzene, toluene and dimethylbenzene), (such as pyridine, pyrazine, pyrroles, indoles and its spread out nitrogenous compound
Biology) and oxygenatedchemicals (such as ketone, furfural, aldehyde and phenol).
Table 1 is heat-treated products obtained therefrom yield (no catalyst) using the scenedesmus of the auxiliary work of ethyl alcohol
Example 2 is heat-treated scenedesmus using ethanol solution under the auxiliary work of catalyst
In another embodiment, by SO4 2-/TiO2-Al2O3Solid acid be added together with ethyl alcohol in wet microalgae.It is real
Design is tested with example 1.It the results are shown in Table 2.The yield of renewable oils intermediate product is the 72-94% of raw material.With no catalysts conditions
Example 1 compares, and renewable oils intermediate product yield significantly improves, and solid residue amount and gas products are all reduced.
Table 2 uses SO4 2-/TiO2-Al2O3Solid acid and the auxiliary work of ethyl alcohol scenedesmus be heat-treated products obtained therefrom yield
Being directly separated and analyzing for 3 fatty-acid ethyl ester of example steams the renewable oils intermediate of embodiment 1 in distilling apparatus
It evaporates with ethanol evaporation and volatile matter.Hexane is added in remaining product liquid, 5mins is then centrifuged with 3200rpm.Extraction contains
The top organic layer of non-polar lipid, and pass through silica column, fractionation of fatty acetoacetic ester (FAEE).FAEE and fatty acid methyl ester
(FAME) it is commonly known as biodiesel.For quantitative analysis, is prepared by gas chromatography and analyze C4-C24The one of compound
Series fatty acid ethyl ester standard quantitatively calculates the content of fatty-acid ethyl ester.
The Gc-mss of fatty-acid ethyl ester in the renewable oils intermediate of 3. embodiment 1 of table
| Fatty-acid ethyl ester title | Content % in the product |
| Cognac oil | 0.085 |
| 4- methylvaleric acid ethyl valerate | 0.330 |
| 4- ketovaleric acid ethyl ester | 0.074 |
| 2- monoxone 1- cyclopentyl ethyl | 0.022 |
| Succinic acid, cis- -6-3- alkenyl stearyl | 0.019 |
| Diethyl succinate | 0.165 |
| Ethyl caprilate | 0.249 |
| Hydroxy functional urethane | 0.088 |
| Ethyl phenylacetate | 0.217 |
| Benzyl hexanoate | 0.094 |
| Ethyl caprate | 0.097 |
| 4- nitrophenyl acetate | 0.122 |
| Phenylpropyl alcohol acetoacetic ester | 0.684 |
| Ethyl caprate | 0.423 |
| Ethyl laurate | 2.052 |
| 9,12- hexadecadienoic acid ethyl ester | 2.116 |
| Palmitoleic acid ethyl ester | 17.564 |
| 13- methyltetradecylphosphine acetoacetic ester | 6.915 |
| Ethyl palmitate | 42.201 |
| 11- hexadecene acetoacetic ester | 4.594 |
| 15- methyihexadecanoic acid methyl esters | 2.541 |
| Ethyl linoleate | 13.995 |
| 9,12,15- octadecane triolefin acetoacetic ester | 5.347 |
The preparation of 4 charcoal base hydrogenation catalyst of example
Charcoal is to be generated using sawdust as raw material by catalysis fast pyrolysis.The drying charcoal of collection is screened to first
The particle size range of 0.18-0.25mm, then in nitric acid solution (HNO3) in further pre-process.Usually by 10g charcoal and
The 0.1M HNO of 250mL3Solution flows back 12 hours at 100 DEG C.Pretreated purpose is to remove biology remaining on charcoal
Oil and ash content, also increase metal deposit of the quantity of its surface oxygen functional group advantageous as catalyst load when and divide
It dissipates.Charcoal after pickling is washed by filtering, and with hot deionized water until pH ≈ 7 is to remove excessive acid, finally by place
The charcoal managed is dried overnight at 105 DEG C.Early-stage study the result shows that, pretreatment make charcoal surface area from 612 promoted
To 780m2g-1, Kong Rongcong 0.4 be promoted to 0.5cm3g-1, the carbon content in charcoal is about 86wt%.
The hydrogenation catalyst preparation of charcoal load uses equi-volume impregnating.With single-metal reforming catalyst Mo2C/
For Biochar, by ammonium molybdate tetrahydrate (NH4)6Mo7O24·4H2The aqueous solution of O is immersed on dry charcoal, Mo's
Load capacity can reach 30% (weight).Material is dried at room temperature for 6 hours after mixing, is then dried overnight at 105 DEG C.It is dry
Catalyst precursor afterwards carries out carburization reaction in tube furnace, 100mL/min argon Ar purging protection under, with 5 DEG C/
The heating rate of min is warming up to 800 DEG C, and constant temperature is kept for 2 hours at 800 DEG C.Catalyst is cooling in argon gas, is used for further table
Sign.The molybdenum carbide of charcoal load is expressed as Mo2C/Biochar。
One kind of bimetallic catalyst Fe, Co or Ni are prepared with Mo presoma using co-impregnation.By a certain amount of (NH4)6Mo7O24·4H2O solution and a certain amount of Fe, the mixing of Co or Ni salting liquid, are configured to nickel molybdenum, iron molybdenum or cobalt molybdenum maceration extract.So
Mixed impregnant liquor is loaded on charcoal afterwards.All samples are dried at room temperature for 6 hours after dipping, are then done at 105 DEG C
It is dry overnight.According to different nickel molybdenums/iron molybdenum/cobalt molybdenum atom molar ratio, obtaining the Mo load capacity on material is 0-15% (weight
Amount), Fe, Co or Ni load capacity is 0-15% (weight).The temperature programming carbonisation of catalyst is as follows: weighing a certain amount of
Catalyst precursor is placed in tube furnace, is 20%CH in volume fraction4- 80%H2Mixed gas in the liter of 10 DEG C/min
Warm rate rises to 300 DEG C from room temperature, rises to carburizing temperature 800 after temperature reaches 300 DEG C, then with the heating rate of 1 DEG C/min
DEG C, it in 800 DEG C of constant temperature 2h, is finally cooled to room temperature under the atmosphere of inert gas Ar, obtains bimetallic catalyst X-Mo2C/
Bichar (X=Fe, Co or Ni).
Example 5 improves biodiesel production rate
By the renewable oils intermediate distillation evaporating volatile substances formed in embodiment 1 and formed among secondary renewable oils
Body.Secondary renewable oils intermediate is diluted in methyl alcohol and is mixed with the molybdenum carbide of charcoal load.In secondary renewable oils
The hydrotreating of mesosome carries out under the initial hydrogen pressure of 3.44MPa at 300 DEG C and 340 DEG C.Table 3 shows hydrotreating
The composition analysis of product.The lipid chemical concentration that can be used as biodiesel has been increased to 82-88% by 42.1%.Gas chromatography mass spectrometry
Analysis shows main component is fatty acid methyl ester.
Component analysis after 3 grade renewable oils intermediates of table dilute in methyl alcohol at obstructed temperature plus before and after hydrogen
6 hydrotreating renewable oils intermediate of example is to form hydrocarbon
By the renewable oils intermediate distillation evaporating volatile substances formed in embodiment 1 and formed among the second renewable oils
Body.The metallic catalyst X-Mo that secondary renewable oils intermediate is diluted in hexane and loaded with biological carbon2C/Bichar(X
=Fe, Co or Ni) mixing.At 340 DEG C, initial hydrogen pressure is to carry out under 3.44MPa for the hydrotreating of secondary renewable oils intermediate.
Table 3 shows the composition analysis of hydrotreatment products.Total hydrocarbon increases to 67.9%.The kind of oxidation and nitridation chemicals
Class at least reduces half.Most of pre-existing fatty-acid ethyl esters are converted to hydrocarbon.For example, the conversion ratio of ethyl palmitate is
95%.Gained hydro carbons mainly within the scope of diesel oil one's share of expenses for a joint undertaking, usually contains 12-20 carbon atom.Hydrocarbon samples include hexadecane, and 17
Alkane, octadecane, tetradecene, the ring tetradecane and eicosylene.
4 grade renewable oils intermediates of table dilute the component analysis before and after back end hydrogenation in hexane
The production of 7 ammonia of example
Method described in embodiment 5 and 6 can produce ammonia flow.Nitrogenous chemicals in secondary renewable oils intermediate turns
Turn to hydro carbons.Nitrogen-atoms in these chemical substances is removed in the form of ammonia.Ammonia can be recycled with water, be then used as fertilizer.
Claims (10)
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