JP7372815B2 - C5+化合物の製造方法及びこれに用いられる触媒 - Google Patents
C5+化合物の製造方法及びこれに用いられる触媒 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims description 58
- 239000003054 catalyst Substances 0.000 title claims description 57
- 238000004519 manufacturing process Methods 0.000 title claims description 22
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 35
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000005846 sugar alcohols Chemical class 0.000 claims description 17
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 13
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
- 238000000508 aqueous-phase reforming Methods 0.000 claims description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 10
- 238000006555 catalytic reaction Methods 0.000 claims description 9
- 239000002028 Biomass Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000600 sorbitol Substances 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 15
- 238000012360 testing method Methods 0.000 description 13
- 229910004298 SiO 2 Inorganic materials 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 238000010304 firing Methods 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 6
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 5
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 5
- 239000000811 xylitol Substances 0.000 description 5
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 5
- 229960002675 xylitol Drugs 0.000 description 5
- 235000010447 xylitol Nutrition 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- -1 diol compound Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000002029 lignocellulosic biomass Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
収率(%)=(着目する生成物の総炭素モル数)/(ソルビトールの総炭素モル数)×100
例えば、「着目する生成物の総炭素モル数」は、ガスクロマトグラフ及び高速液体クロマトグラフによって分析された着目する生成物のモル数に、その生成物の炭素数をかけて算出できる。また、「ソルビトールの総炭素モル数」も同様に、加熱容器に仕込んだソルビトールのモル数に、炭素数をかけて算出できる。
転化率(%)=100-(反応後のソルビトール量)/(反応前のソルビトール量)×100
Claims (6)
- 植物由来バイオマスから触媒反応により炭素数5又は6のモノアルコール及びアルカンからなるC5+化合物を製造する方法であって、
炭素数5及び6の少なくとも何れかの糖アルコールの水素化分解を行う水素化分解工程を含み、
前記水素化分解工程において、ルチル型TiO2にIr-ReOxを担持させた触媒を用いることを特徴とするC5+化合物の製造方法。 - C5及びC6のアルカン並びにC5及びC6のモノアルコールの合計の収率を30%以上とするように、前記触媒の担体比表面積を100m2/g以下で調整したことを特徴とする請求項1記載のC5+化合物の製造方法。
- 前記Ir-ReOxにおいて、ReのIrに対するモル比を0.5以上としたことを特徴とする請求項1又は2に記載のC5+化合物の製造方法。
- 前記水素化分解工程では、前記糖アルコールを水相改質させることにより生成した水素及び外部から供給される水素の少なくとも何れかを用いて前記水素化分解を行うことを特徴とする請求項1乃至3のうちの1つに記載のC5+化合物の製造方法。
- 前記C5+化合物は、主としてペンタノール及びヘキサノールの少なくとも何れかであることを特徴とする請求項1乃至4のうちの1つに記載のC5+化合物の製造方法。
- 植物由来バイオマスから炭素数5及び6の少なくとも何れかの糖アルコールの水素化分解を行う工程を経て触媒反応により炭素数5又は6のモノアルコール及びアルカンからなるC5+化合物を製造する方法に用いられる触媒であって、
ルチル型TiO2にIr-ReOxを担持させたものである、ことを特徴とする触媒。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008505103A (ja) | 2004-07-01 | 2008-02-21 | イネオス ユーエスエイ エルエルシー | マレイン酸の1,4−ブタンジオールへの水素化用触媒 |
JP2009521387A (ja) | 2005-12-21 | 2009-06-04 | ヴァイレント エナジー システムズ インク. | 触媒、および含酸素化合物の製造方法 |
US20140051872A1 (en) | 2012-08-15 | 2014-02-20 | Virent, Inc. | Catalysts for hydrodeoxygenation of oxygenated hydrocarbons |
JP2016033129A (ja) | 2014-07-30 | 2016-03-10 | 昭和シェル石油株式会社 | ヘキサノール/ペンタノールの製造方法 |
JP2018080122A (ja) | 2016-11-14 | 2018-05-24 | 昭和シェル石油株式会社 | C5+モノアルコールの製造方法 |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2008505103A (ja) | 2004-07-01 | 2008-02-21 | イネオス ユーエスエイ エルエルシー | マレイン酸の1,4−ブタンジオールへの水素化用触媒 |
JP2009521387A (ja) | 2005-12-21 | 2009-06-04 | ヴァイレント エナジー システムズ インク. | 触媒、および含酸素化合物の製造方法 |
US20140051872A1 (en) | 2012-08-15 | 2014-02-20 | Virent, Inc. | Catalysts for hydrodeoxygenation of oxygenated hydrocarbons |
JP2016033129A (ja) | 2014-07-30 | 2016-03-10 | 昭和シェル石油株式会社 | ヘキサノール/ペンタノールの製造方法 |
JP2018080122A (ja) | 2016-11-14 | 2018-05-24 | 昭和シェル石油株式会社 | C5+モノアルコールの製造方法 |
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