JP5605797B2 - リグニンの可溶化方法 - Google Patents
リグニンの可溶化方法 Download PDFInfo
- Publication number
- JP5605797B2 JP5605797B2 JP2010254271A JP2010254271A JP5605797B2 JP 5605797 B2 JP5605797 B2 JP 5605797B2 JP 2010254271 A JP2010254271 A JP 2010254271A JP 2010254271 A JP2010254271 A JP 2010254271A JP 5605797 B2 JP5605797 B2 JP 5605797B2
- Authority
- JP
- Japan
- Prior art keywords
- lignin
- water
- reaction
- alcohol
- butanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229920005610 lignin Polymers 0.000 title claims description 69
- 238000000034 method Methods 0.000 title claims description 39
- 230000003381 solubilizing effect Effects 0.000 title claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 24
- 239000002028 Biomass Substances 0.000 claims description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000011973 solid acid Substances 0.000 claims description 12
- 238000000354 decomposition reaction Methods 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000005063 solubilization Methods 0.000 description 20
- 230000007928 solubilization Effects 0.000 description 20
- 229920002678 cellulose Polymers 0.000 description 13
- 235000010980 cellulose Nutrition 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000001913 cellulose Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 cyclic ester Chemical class 0.000 description 9
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
- 235000005822 corn Nutrition 0.000 description 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 229920002488 Hemicellulose Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000010902 straw Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 229920000704 biodegradable plastic Polymers 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 239000012978 lignocellulosic material Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 241001133760 Acoelorraphe Species 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000221089 Jatropha Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000010905 bagasse Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002029 lignocellulosic biomass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000004537 pulping Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010907 stover Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002154 agricultural waste Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000006731 degradation 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
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001575 sodium mineral Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000007968 uric acids Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010254271A JP5605797B2 (ja) | 2010-11-12 | 2010-11-12 | リグニンの可溶化方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010254271A JP5605797B2 (ja) | 2010-11-12 | 2010-11-12 | リグニンの可溶化方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012102297A JP2012102297A (ja) | 2012-05-31 |
| JP2012102297A5 JP2012102297A5 (hu) | 2014-01-23 |
| JP5605797B2 true JP5605797B2 (ja) | 2014-10-15 |
Family
ID=46393056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010254271A Active JP5605797B2 (ja) | 2010-11-12 | 2010-11-12 | リグニンの可溶化方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5605797B2 (hu) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6274478B2 (ja) * | 2012-07-11 | 2018-02-07 | 出光興産株式会社 | リグニン分解物の製造方法 |
| JP6090897B2 (ja) * | 2012-08-10 | 2017-03-08 | 出光興産株式会社 | フェノール類の製造方法 |
| JP5817794B2 (ja) | 2012-11-30 | 2015-11-18 | トヨタ自動車株式会社 | メトキシ基を有する芳香族化合物の脱メチル化又は脱メトキシ化方法 |
| JP6344724B2 (ja) * | 2013-03-15 | 2018-06-20 | 出光興産株式会社 | リグニン分解物の製造方法 |
| ES2517990B1 (es) * | 2013-04-30 | 2015-07-23 | Council Of Scientific & Industrial Research | Despolimerización lignina usando catalizadores ácidos sólidos |
| JP2015003955A (ja) * | 2013-06-19 | 2015-01-08 | 独立行政法人産業技術総合研究所 | リグニンの分解方法 |
| US20150034109A1 (en) * | 2013-08-02 | 2015-02-05 | R.J. Reynolds Tobacco Company | Process for Producing Lignin from Tobacco |
| JP6369168B2 (ja) * | 2014-07-01 | 2018-08-08 | 富士電機株式会社 | 電子写真用感光体及びそれを搭載する画像形成装置 |
| JP6402051B2 (ja) * | 2014-08-29 | 2018-10-10 | 日本化薬株式会社 | 低分子リグニンの製造方法 |
| JP2016060813A (ja) * | 2014-09-17 | 2016-04-25 | 出光興産株式会社 | 熱硬化性樹脂組成物 |
| JP2017000093A (ja) * | 2015-06-11 | 2017-01-05 | 出光興産株式会社 | セルロース含有固形物の製造方法及びグルコースの製造方法 |
| CN110914341B (zh) | 2017-08-10 | 2023-02-21 | 出光兴产株式会社 | 改质木质素的制造方法和改质木质素、以及含改质木质素的树脂组成材料 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1131415A (en) * | 1978-11-27 | 1982-09-14 | Bau- Und Forschungsgesellschaft Thermoform A.G. | Pulping of lignocellulose with aqueous methanol/ catalyst mixture |
| JPS59146594A (ja) * | 1983-02-10 | 1984-08-22 | Sanyo Kokusaku Pulp Co Ltd | 加水分解方法 |
| JP3155603B2 (ja) * | 1992-03-17 | 2001-04-16 | 信夫 白石 | リグノセルロース物質の液化溶液の製造法 |
| JP2001170601A (ja) * | 1999-12-17 | 2001-06-26 | Noritsu Koki Co Ltd | バイオマス系廃棄物処理方法 |
| JP4982036B2 (ja) * | 2004-04-16 | 2012-07-25 | 志朗 坂 | バイオマスの分解・液化方法 |
| JP4604194B2 (ja) * | 2004-11-02 | 2010-12-22 | 国立大学法人広島大学 | 触媒を用いたセルロースの加水分解方法および触媒を用いたグルコースの生産方法 |
| JP2008248202A (ja) * | 2007-03-30 | 2008-10-16 | Toyota Motor Corp | セルロース精製方法及びセルロース精製装置 |
| JP4957661B2 (ja) * | 2007-07-25 | 2012-06-20 | トヨタ自動車株式会社 | バイオマスを原料とする液化燃料油の製造方法 |
| JP5549067B2 (ja) * | 2008-10-22 | 2014-07-16 | 株式会社豊田中央研究所 | 糖又はその誘導体の製造方法 |
| JP2011224499A (ja) * | 2010-04-21 | 2011-11-10 | Toyota Central R&D Labs Inc | 糖又はその誘導体の製造方法 |
| JP5522683B2 (ja) * | 2010-07-07 | 2014-06-18 | 独立行政法人産業技術総合研究所 | 炭化水素の製造方法 |
-
2010
- 2010-11-12 JP JP2010254271A patent/JP5605797B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012102297A (ja) | 2012-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5605797B2 (ja) | リグニンの可溶化方法 | |
| Li et al. | Recent advances in biomass pretreatment using biphasic solvent systems | |
| Yu et al. | Tailored one-pot lignocellulose fractionation to maximize biorefinery toward versatile xylochemicals and nanomaterials | |
| US10155853B2 (en) | Method for manufacturing lignin degradation product | |
| Sannigrahi et al. | Fundamentals of biomass pretreatment by fractionation | |
| Madadi et al. | One-step lignocellulose fractionation using acid/pentanol pretreatment for enhanced fermentable sugar and reactive lignin production with efficient pentanol retrievability | |
| Zhao et al. | Organosolv pretreatment of lignocellulosic biomass for enzymatic hydrolysis | |
| Zhang | Catalytic transformation of carbohydrates and lignin in ionic liquids | |
| CN110734582B (zh) | 用于生产纳米纤维素、以及由其产生的组合物和产品的方法和装置 | |
| Zhang et al. | Pretreatment of sugarcane bagasse by acid-catalysed process in aqueous ionic liquid solutions | |
| Brosse et al. | Organosolv processes | |
| Feng et al. | Acidolysis mechanism of lignin from bagasse during p-toluenesulfonic acid treatment | |
| Mazar et al. | Integrated multiproduct biorefinery for furfural production with acetic acid and lignin recovery: design, scale-up evaluation, and technoeconomic analysis | |
| Peleteiro et al. | Furfural production in biphasic media using an acidic ionic liquid as a catalyst | |
| WO2014092873A1 (en) | Processes and apparatus for lignin separation in biorefineries | |
| Yu et al. | Fractionation of corn stover for efficient enzymatic hydrolysis and producing platform chemical using p-toluenesulfonic acid/water pretreatment | |
| WO2014106221A1 (en) | Processes and apparatus for producing fermentable sugars, cellulose solids, and lignin from lignocellulosic biomass | |
| Semerci et al. | Hornbeam pretreatment with protic ionic liquids: Cation, particle size, biomass loading and recycling effects | |
| Kim et al. | Challenges and perspective of recent biomass pretreatment solvents | |
| Dutta et al. | Ionic liquid pretreatment of lignocellulosic biomass for biofuels and chemicals | |
| Dutta et al. | Catalytic valorisation of various paper wastes into levulinic acid, hydroxymethylfurfural, and furfural: Influence of feedstock properties and ferric chloride | |
| Wang et al. | Rapid and mild fractionation of hemicellulose through recyclable mandelic acid pretreatment | |
| Yang et al. | Integrated forest biorefinery: value-added utilization of dissolved organics in the prehydrolysis liquor of prehydrolysis kraft (PHK) dissolving pulp production process | |
| Kammoun et al. | The key role of pretreatment for the one-step and multi-step conversions of European lignocellulosic materials into furan compounds | |
| Bao et al. | Deep eutectic solvents for fractionation and valorization of lignocellulose |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101216 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20101216 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20131108 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131108 Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20131108 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140218 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140318 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140519 |
|
| 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: 20140729 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140819 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5605797 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| 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 |