DE102015006926A1 - Neuartiges durch RIBIL' s katalysiertes Verfahren zur Fraktionierung von Lignocellulose-haltiger Biomasse - Google Patents
Neuartiges durch RIBIL' s katalysiertes Verfahren zur Fraktionierung von Lignocellulose-haltiger Biomasse Download PDFInfo
- Publication number
- DE102015006926A1 DE102015006926A1 DE102015006926.8A DE102015006926A DE102015006926A1 DE 102015006926 A1 DE102015006926 A1 DE 102015006926A1 DE 102015006926 A DE102015006926 A DE 102015006926A DE 102015006926 A1 DE102015006926 A1 DE 102015006926A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butoxy
- lignin
- propane
- hydroxymethyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 58
- 239000002029 lignocellulosic biomass Substances 0.000 title 1
- 229920005610 lignin Polymers 0.000 claims abstract description 61
- 230000029087 digestion Effects 0.000 claims abstract description 53
- 239000001913 cellulose Substances 0.000 claims abstract description 25
- 229920002678 cellulose Polymers 0.000 claims abstract description 25
- 229920002488 Hemicellulose Polymers 0.000 claims abstract description 21
- 229920005989 resin Polymers 0.000 claims abstract description 18
- 239000011347 resin Substances 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 12
- 150000007975 iminium salts Chemical class 0.000 claims abstract description 10
- 238000001704 evaporation Methods 0.000 claims abstract description 9
- 230000008020 evaporation Effects 0.000 claims abstract description 8
- 229920001864 tannin Polymers 0.000 claims abstract description 7
- 235000018553 tannin Nutrition 0.000 claims abstract description 7
- 239000001648 tannin Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims abstract description 5
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 2
- 239000002608 ionic liquid Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000000605 extraction Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000006184 cosolvent Substances 0.000 claims description 12
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- -1 heterocyclic radical Chemical class 0.000 claims description 11
- 238000004537 pulping Methods 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002028 Biomass Substances 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 8
- 235000013312 flour Nutrition 0.000 claims description 8
- 241000196324 Embryophyta Species 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000011121 hardwood Substances 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
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- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- 240000000111 Saccharum officinarum Species 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 238000000855 fermentation Methods 0.000 claims description 3
- 230000004151 fermentation Effects 0.000 claims description 3
- 235000013772 propylene glycol Nutrition 0.000 claims description 3
- 239000010902 straw Substances 0.000 claims description 3
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- HRBWXJNAGJSBIF-UHFFFAOYSA-N 2-methyl-2-[3-[(2-methylpropan-2-yl)oxy]propoxy]propane Chemical compound CC(C)(C)OCCCOC(C)(C)C HRBWXJNAGJSBIF-UHFFFAOYSA-N 0.000 claims description 2
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims description 2
- 235000017491 Bambusa tulda Nutrition 0.000 claims description 2
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 239000011425 bamboo Substances 0.000 claims description 2
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 235000005822 corn Nutrition 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 4
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 229960004592 isopropanol Drugs 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- YAXKTBLXMTYWDQ-UHFFFAOYSA-N 1,2,3-butanetriol Chemical compound CC(O)C(O)CO YAXKTBLXMTYWDQ-UHFFFAOYSA-N 0.000 claims 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims 2
- BOHGAOWOIJMTPZ-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethanol Chemical compound OCC1COCO1 BOHGAOWOIJMTPZ-UHFFFAOYSA-N 0.000 claims 2
- VCGPODFDWMEQGI-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-2-propan-2-yloxybutane Chemical compound C(C)(C)(C)OCC(CC)OC(C)C VCGPODFDWMEQGI-UHFFFAOYSA-N 0.000 claims 2
- CXZURZLAFDWWFD-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-2-propoxybutane Chemical compound C(C)(C)(C)OCC(CC)OCCC CXZURZLAFDWWFD-UHFFFAOYSA-N 0.000 claims 2
- JQPQGHSESNJJBC-UHFFFAOYSA-N 1-ethoxybutan-2-ol Chemical compound CCOCC(O)CC JQPQGHSESNJJBC-UHFFFAOYSA-N 0.000 claims 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims 2
- CSZZMFWKAQEMPB-UHFFFAOYSA-N 1-methoxybutan-2-ol Chemical compound CCC(O)COC CSZZMFWKAQEMPB-UHFFFAOYSA-N 0.000 claims 2
- LHVVHKMPOOYTEZ-UHFFFAOYSA-N 1-propan-2-yloxybutan-2-ol Chemical compound CCC(O)COC(C)C LHVVHKMPOOYTEZ-UHFFFAOYSA-N 0.000 claims 2
- AFHJYKBGDDJSRR-UHFFFAOYSA-N 1-propan-2-yloxypropan-2-ol Chemical compound CC(C)OCC(C)O AFHJYKBGDDJSRR-UHFFFAOYSA-N 0.000 claims 2
- NVHNPNNZMBSXIF-UHFFFAOYSA-N 1-propoxybutan-2-ol Chemical compound CCCOCC(O)CC NVHNPNNZMBSXIF-UHFFFAOYSA-N 0.000 claims 2
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 claims 2
- XACLNMMXAHCFGN-UHFFFAOYSA-N 2-(2-ethoxypropoxy)-2-methylpropane Chemical compound C(C)OC(COC(C)(C)C)C XACLNMMXAHCFGN-UHFFFAOYSA-N 0.000 claims 2
- HSEBJONSSRBHCL-UHFFFAOYSA-N 2-(2-methoxypropoxy)-2-methylpropane Chemical compound COC(C)COC(C)(C)C HSEBJONSSRBHCL-UHFFFAOYSA-N 0.000 claims 2
- HMKJIROAFZEFGU-UHFFFAOYSA-N 2-ethoxy-1-[(2-methylpropan-2-yl)oxy]butane Chemical compound C(C)(C)(C)OCC(CC)OCC HMKJIROAFZEFGU-UHFFFAOYSA-N 0.000 claims 2
- YHTBJYLPKQOJAY-UHFFFAOYSA-N 2-ethoxybutan-1-ol Chemical compound CCOC(CC)CO YHTBJYLPKQOJAY-UHFFFAOYSA-N 0.000 claims 2
- DEDUBNVYPMOFDR-UHFFFAOYSA-N 2-ethoxypropan-1-ol Chemical compound CCOC(C)CO DEDUBNVYPMOFDR-UHFFFAOYSA-N 0.000 claims 2
- KUSJUCTZLKQSLT-UHFFFAOYSA-N 2-methoxy-1-[(2-methylpropan-2-yl)oxy]butane Chemical compound C(C)(C)(C)OCC(CC)OC KUSJUCTZLKQSLT-UHFFFAOYSA-N 0.000 claims 2
- IPUDBCXGMBSQGH-UHFFFAOYSA-N 2-methoxybutan-1-ol Chemical compound CCC(CO)OC IPUDBCXGMBSQGH-UHFFFAOYSA-N 0.000 claims 2
- UOYHLYHKFSXAEY-UHFFFAOYSA-N 2-methyl-2-(2-propan-2-yloxypropoxy)propane Chemical compound CC(C)OC(C)COC(C)(C)C UOYHLYHKFSXAEY-UHFFFAOYSA-N 0.000 claims 2
- QCVGDPQTUAKOHM-UHFFFAOYSA-N 2-methyl-2-(2-propoxypropoxy)propane Chemical compound CCCOC(C)COC(C)(C)C QCVGDPQTUAKOHM-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C3/00—Pulping cellulose-containing materials
- D21C3/20—Pulping cellulose-containing materials with organic solvents or in solvent environment
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C11/00—Regeneration of pulp liquors or effluent waste waters
- D21C11/0007—Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C3/00—Pulping cellulose-containing materials
- D21C3/02—Pulping cellulose-containing materials with inorganic bases or alkaline reacting compounds, e.g. sulfate processes
- D21C3/024—Pulping cellulose-containing materials with inorganic bases or alkaline reacting compounds, e.g. sulfate processes with NH3 or H2O
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C5/00—Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| CN109134708A (zh) * | 2018-07-25 | 2019-01-04 | 中国科学院广州能源研究所 | 一种木质纤维素类生物质组分分离的方法 |
| EP3549968A1 (en) | 2018-04-06 | 2019-10-09 | RAMPF Holding GmbH & Co. KG | Lignin-containing polyurethanes |
| CN115703699A (zh) * | 2021-08-06 | 2023-02-17 | 深圳有为技术控股集团有限公司 | 新型叔丁醚取代多元醇及其丙烯酸酯型化合物 |
| WO2024064164A1 (en) * | 2022-09-21 | 2024-03-28 | The Regents Of The University Of California | Methods and compositions useful for fractionating biomass using a schiff-base ionic liquid |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3549968A1 (en) | 2018-04-06 | 2019-10-09 | RAMPF Holding GmbH & Co. KG | Lignin-containing polyurethanes |
| WO2019193142A1 (en) | 2018-04-06 | 2019-10-10 | Rampf Holding Gmbh & Co. Kg | Lignin-containing polyurethanes |
| CN109134708A (zh) * | 2018-07-25 | 2019-01-04 | 中国科学院广州能源研究所 | 一种木质纤维素类生物质组分分离的方法 |
| CN109134708B (zh) * | 2018-07-25 | 2021-02-09 | 中国科学院广州能源研究所 | 一种木质纤维素类生物质组分分离的方法 |
| CN115703699A (zh) * | 2021-08-06 | 2023-02-17 | 深圳有为技术控股集团有限公司 | 新型叔丁醚取代多元醇及其丙烯酸酯型化合物 |
| WO2024064164A1 (en) * | 2022-09-21 | 2024-03-28 | The Regents Of The University Of California | Methods and compositions useful for fractionating biomass using a schiff-base ionic liquid |
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| DE102015006926B4 (de) | 2022-09-22 |
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