JP5933578B2 - セルロースを酸触媒解重合する方法 - Google Patents
セルロースを酸触媒解重合する方法 Download PDFInfo
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- JP5933578B2 JP5933578B2 JP2013540239A JP2013540239A JP5933578B2 JP 5933578 B2 JP5933578 B2 JP 5933578B2 JP 2013540239 A JP2013540239 A JP 2013540239A JP 2013540239 A JP2013540239 A JP 2013540239A JP 5933578 B2 JP5933578 B2 JP 5933578B2
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- 239000001913 cellulose Substances 0.000 title claims description 58
- 229920002678 cellulose Polymers 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 22
- 239000000047 product Substances 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- 150000007522 mineralic acids Chemical class 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 14
- 150000007524 organic acids Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 4
- 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 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims 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 claims 2
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 claims 1
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 238000003801 milling Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 229910000831 Steel Inorganic materials 0.000 description 25
- 239000010959 steel Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000227 grinding Methods 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000002023 wood Substances 0.000 description 5
- 241000609240 Ambelania acida Species 0.000 description 4
- 241001070947 Fagus Species 0.000 description 4
- 235000010099 Fagus sylvatica Nutrition 0.000 description 4
- 240000000111 Saccharum officinarum Species 0.000 description 4
- 235000007201 Saccharum officinarum Nutrition 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000010905 bagasse Substances 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
- 235000011613 Pinus brutia Nutrition 0.000 description 3
- 241000018646 Pinus brutia Species 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- -1 halogen alkane carboxylic acids Chemical class 0.000 description 2
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 2
- 239000002029 lignocellulosic biomass Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H8/00—Macromolecular compounds derived from lignocellulosic materials
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
- C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/007—Separation of sugars provided for in subclass C13K
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
例1
硫酸(95〜97%、J. T. Baker社、USAの市販品)0.52mLを、ジエチルエーテル150mL中に溶解させた。α−セルロース10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカー中で粉砕した。該メインディスクの回転時間は800rpmであった。得られた固体の試料を、フェニルイソシアナートでGPC分析のために誘導体化した。別の試料を水中に溶解させ、HPLC分析を用いて調べた。
硫酸(95〜97%、J. T. Baker社、USAの市販品)0.52mLを、ジエチルエーテル150mL中に溶解させた。α−セルロース10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカー中で粉砕した。該メインディスクの回転時間は800rpmであった。得られた固体の試料を、フェニルイソシアナートでGPC分析のために誘導体化した。別の試料を水中に溶解させ、HPLC分析を用いて調べた。
塩酸(85%、Fluka社、USAの市販品)0.76mLを、ジエチルエーテル150mL中に溶解させた。α−セルロース10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカー中で粉砕した。該メインディスクの回転時間は800rpmであった。試料を水中に溶解させ、HPLC分析を用いて調べた。
オルトリン酸(85%、Fluka社、USAの市販品)0.58mLを、ジエチルエーテル150mL中に溶解させた。α−セルロース10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカー中で粉砕した。該メインディスクの回転時間は800rpmであった。試料を水中に溶解させ、HPLC分析を用いて調べた。
硫酸(95〜97%、J. T. Baker社、USAの市販品)0.52mLを、ジエチルエーテル150mL中に溶解させた。粉砕したサトウキビバガス10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカー中で粉砕した。該メインディスクの回転時間は800rpmであった。該水溶性生成物を、HPLC分析を用いて調べた。
硫酸(95〜97%、J. T. Baker社、USAの市販品)0.52mLを、ジエチルエーテル150mL中に溶解させた。ブナ材おがくず10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカー中で粉砕した。該メインディスクの回転時間は800rpmであった。該水溶性生成物を、HPLC分析を用いて調べた。
硫酸(95〜97%、J. T. Baker社、USAの市販品)0.52mLを、ジエチルエーテル150mL中に溶解させた。マツ材おがくず10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカーで粉砕した。該メインディスクの回転時間は800rpmであった。該水溶性生成物を、HPLC分析を用いて調べた。
硫酸(95〜97%、J. T. Baker社、USAの市販品)0.52mLを、ジエチルエーテル150mL中に溶解させた。干し草10gを引き続き添加し、該懸濁液をシェーカー(IKA、KS 130 control)で1時間、350 1/分の振動数で振盪した。その後、該溶剤を除去した。乾燥混合物1.00gを、Fritsch社のPulverisette P7中で鋼球(5個の鋼球;個々の質量3.95g)を有する鋼製ビーカー中で粉砕した。該メインディスクの回転時間は800rpmであった。該水溶性生成物を、HPLC分析を用いて調べた。
Claims (6)
- セルロース含有材料を、セルロース含有材料1gあたり0.0001〜6.2mmolの量の無機酸及び/又は有機酸の存在下で機械的に処理することによって、セルロースを酸触媒解重合する方法であって、
該セルロースを、該機械的処理前に、溶剤中の該酸の混合物で処理し、該溶剤を機械的処理前に除去し、該機械的処理がミル中での粉砕であり、その際に該粉砕物を粉砕媒体を使用して粉砕する、
セルロースを酸触媒解重合する方法。 - 該酸が−14〜2のpKa値を有する、請求項1記載の方法。
- 該無機酸が、硫酸、塩酸、リン酸、硝酸、タングストリン酸及びそれらの任意の混合物から選択されている、請求項1又は2記載の方法。
- 該有機酸が、ベンゼンスルホン酸、p−トルエンスルホン酸、ニトロベンゼンスルホン酸、2,4,6−トリメチルベンゼンスルホン酸、又は前記の酸の誘導体、メタンスルホン酸、マレイン酸、シュウ酸、ハロゲンアルカンカルボン酸及びそれらの任意の混合物から選択されている、請求項1から3までのいずれか1項記載の方法。
- 該ミルが、振動ミル、撹拌ミル、撹拌ボールミル及びボールミルから選択されている、請求項1から4までのいずれか1項記載の方法。
- 反応生成物として水溶性のセルロースオリゴマー、セロビオース、グルコース及びグリセリンを得る、請求項1から5までのいずれか1項記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102010052602A DE102010052602A1 (de) | 2010-11-25 | 2010-11-25 | Verfahren zur säurekatalysierten Depolymerisation von Cellulose |
DE102010052602.9 | 2010-11-25 | ||
DE201110012102 DE102011012102A1 (de) | 2011-02-23 | 2011-02-23 | Verfahren zur säurekatalysierten Depolymerisation von Cellulose |
DE102011012102.1 | 2011-02-23 | ||
PCT/DE2011/075282 WO2012097781A1 (de) | 2010-11-25 | 2011-11-22 | Verfahren zur säurekatalysierten depolymerisation von cellulose |
Publications (2)
Publication Number | Publication Date |
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JP2013543735A JP2013543735A (ja) | 2013-12-09 |
JP5933578B2 true JP5933578B2 (ja) | 2016-06-15 |
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JP2013540239A Expired - Fee Related JP5933578B2 (ja) | 2010-11-25 | 2011-11-22 | セルロースを酸触媒解重合する方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US20130239955A1 (ja) |
EP (1) | EP2643485B1 (ja) |
JP (1) | JP5933578B2 (ja) |
BR (1) | BR112013012614A2 (ja) |
CA (1) | CA2818041C (ja) |
EA (1) | EA023989B1 (ja) |
ES (1) | ES2519618T3 (ja) |
MX (1) | MX342572B (ja) |
PL (1) | PL2643485T3 (ja) |
PT (1) | PT2643485E (ja) |
WO (1) | WO2012097781A1 (ja) |
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DE102012109595A1 (de) * | 2012-10-09 | 2014-04-24 | Studiengesellschaft Kohle Mbh | Verfahren zur Gewinnung von Zuckeralkoholen mit fünf bis sechs Kohlenstoffatomen |
CA2904425A1 (en) * | 2013-03-12 | 2014-09-18 | Studiengesellschaft Kohle Mbh | Method for breaking down lignocellulosic biomass |
WO2014176531A2 (en) * | 2013-04-27 | 2014-10-30 | The Regents Of The University Of California | Co-solvent to produce reactive intermediates from biomass |
JP6692024B2 (ja) * | 2014-07-30 | 2020-05-13 | 出光興産株式会社 | ペンタノールの製造方法 |
JP7414686B2 (ja) * | 2020-10-22 | 2024-01-16 | 信越化学工業株式会社 | 解重合されたセルロースエーテルの製造方法 |
DE102022125975A1 (de) | 2022-10-07 | 2024-04-18 | Holy Technologies Gmbh | Faserverstärktes und recycelbares Strukturbauteil sowie Verfahren zu dessen Bereitstellung |
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---|---|---|---|---|
GB376323A (en) * | 1931-03-07 | 1932-07-07 | Henry Dreyfus | Improvements in or relating to the manufacture of dextrins, sugars and other products from cellulosic materials |
CH625251A5 (ja) * | 1978-10-04 | 1981-09-15 | Battelle Memorial Institute | |
CA1190923A (en) * | 1980-03-18 | 1985-07-23 | Barry Rugg | Process and apparatus for chemical conversion of materials and particularly the conversion of cellulose waste to glucose |
DE3040850C2 (de) * | 1980-10-30 | 1982-11-18 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Gewinnung wasserlöslicher Saccharide aus cellulosehaltigem Material |
AR227462A1 (es) * | 1981-03-26 | 1982-10-29 | Thermoform Bau Forschung | Procedimiento mejorado para la produccion de hidrolizados de carbohidratos a partir de material celulosico triturado |
BR8102802A (pt) * | 1981-04-30 | 1982-12-14 | Villares Ind | Processo e instalacao para obtencao de etanol por hidrolise acida continua de materiais celulosicos |
DE3149587A1 (de) * | 1981-12-15 | 1983-06-23 | Werner & Pfleiderer, 7000 Stuttgart | Verfahren und vorrichtung zur hydrolytischen spaltung von cellulose |
FR2525236A1 (fr) * | 1982-04-15 | 1983-10-21 | Creusot Loire | Procede et dispositif d'hydrolyse d'une matiere cellulosique |
DE3312450C2 (de) * | 1983-04-07 | 1985-02-07 | Knauth, Hans, Dipl.-Ing., 7758 Meersburg | Zweistufiges Verfahren zur Herstellung von Furfurol und Glucose aus cellulosehaltigen Stoffen durch saure Hydrolyse |
US5972118A (en) * | 1995-10-27 | 1999-10-26 | Tennessee Valley Authority | Concentrated sulfuric acid hydrolysis of lignocellulosics |
US6423145B1 (en) * | 2000-08-09 | 2002-07-23 | Midwest Research Institute | Dilute acid/metal salt hydrolysis of lignocellulosics |
DE10158120A1 (de) * | 2001-11-27 | 2003-06-18 | Ties Karstens | Verfahren zum Abtrennen von Xylose aus xylanreichen Lignocellulosen, insbesondere Holz |
JP4619917B2 (ja) * | 2005-10-14 | 2011-01-26 | 月島機械株式会社 | リグノセルロースの前処理方法 |
JP4877045B2 (ja) * | 2007-04-25 | 2012-02-15 | トヨタ自動車株式会社 | 植物系繊維材料の分解方法 |
US8062428B2 (en) * | 2007-11-06 | 2011-11-22 | University Of Central Florida Research Foundation, Inc. | Solid acid catalyzed hydrolysis of cellulosic materials |
DE102008030892A1 (de) * | 2008-06-30 | 2009-12-31 | Süd-Chemie AG | Abbau von kohlehydrathaltigen Materialien mit anorganischen Katalysatoren |
WO2010035832A1 (ja) * | 2008-09-29 | 2010-04-01 | 株式会社日本触媒 | 単糖類の製造方法 |
CN102325893A (zh) * | 2008-12-19 | 2012-01-18 | 诺维信股份有限公司 | 在过氧化物酶存在下增加纤维素材料酶法水解的方法 |
WO2010094240A1 (en) * | 2009-02-18 | 2010-08-26 | Rongxiu Li | Process for biomass conversion |
CN105200095A (zh) * | 2009-06-30 | 2015-12-30 | 诺维信公司 | 生物质水解方法 |
WO2011103180A2 (en) * | 2010-02-16 | 2011-08-25 | Grain Processing Corporation | Process for hydrolysis of wet fiber and method for producing fermentation products from wet fiber |
-
2011
- 2011-11-22 BR BR112013012614A patent/BR112013012614A2/pt not_active Application Discontinuation
- 2011-11-22 CA CA2818041A patent/CA2818041C/en not_active Expired - Fee Related
- 2011-11-22 MX MX2013005790A patent/MX342572B/es active IP Right Grant
- 2011-11-22 EA EA201300605A patent/EA023989B1/ru not_active IP Right Cessation
- 2011-11-22 PL PL11818994T patent/PL2643485T3/pl unknown
- 2011-11-22 PT PT118189943T patent/PT2643485E/pt unknown
- 2011-11-22 ES ES11818994.3T patent/ES2519618T3/es active Active
- 2011-11-22 JP JP2013540239A patent/JP5933578B2/ja not_active Expired - Fee Related
- 2011-11-22 US US13/989,439 patent/US20130239955A1/en not_active Abandoned
- 2011-11-22 EP EP11818994.3A patent/EP2643485B1/de not_active Not-in-force
- 2011-11-22 WO PCT/DE2011/075282 patent/WO2012097781A1/de active Application Filing
Also Published As
Publication number | Publication date |
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MX2013005790A (es) | 2013-06-18 |
BR112013012614A2 (pt) | 2016-09-20 |
WO2012097781A1 (de) | 2012-07-26 |
EA023989B1 (ru) | 2016-08-31 |
PT2643485E (pt) | 2014-11-13 |
ES2519618T3 (es) | 2014-11-07 |
CA2818041A1 (en) | 2012-07-26 |
EP2643485B1 (de) | 2014-08-13 |
CA2818041C (en) | 2015-10-13 |
US20130239955A1 (en) | 2013-09-19 |
MX342572B (es) | 2016-10-05 |
JP2013543735A (ja) | 2013-12-09 |
EA201300605A1 (ru) | 2013-12-30 |
EP2643485A1 (de) | 2013-10-02 |
PL2643485T3 (pl) | 2015-02-27 |
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