JP2007514047A - リグノセルロース材料の液状化方法 - Google Patents
リグノセルロース材料の液状化方法 Download PDFInfo
- Publication number
- JP2007514047A JP2007514047A JP2006544430A JP2006544430A JP2007514047A JP 2007514047 A JP2007514047 A JP 2007514047A JP 2006544430 A JP2006544430 A JP 2006544430A JP 2006544430 A JP2006544430 A JP 2006544430A JP 2007514047 A JP2007514047 A JP 2007514047A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- solvent
- compound
- levulinic
- levulinic acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 57
- 239000000463 material Substances 0.000 title claims abstract description 44
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims abstract description 112
- 239000002904 solvent Substances 0.000 claims abstract description 62
- 229940040102 levulinic acid Drugs 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical group O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000002253 acid Substances 0.000 claims abstract description 37
- 239000001913 cellulose Substances 0.000 claims abstract description 28
- 229920002678 cellulose Polymers 0.000 claims abstract description 28
- 230000018044 dehydration Effects 0.000 claims abstract description 13
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 13
- 239000003377 acid catalyst Substances 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 12
- 239000011343 solid material Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 8
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract description 7
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 6
- 230000032050 esterification Effects 0.000 claims abstract description 5
- 238000005886 esterification reaction Methods 0.000 claims abstract description 5
- 125000000962 organic group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000000686 lactone group Chemical group 0.000 claims abstract description 3
- 125000000457 gamma-lactone group Chemical group 0.000 claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 18
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 7
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- QOTQFLOTGBBMEX-UHFFFAOYSA-N alpha-angelica lactone Chemical compound CC1=CCC(=O)O1 QOTQFLOTGBBMEX-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- GVUKXGZRYIFDES-UHFFFAOYSA-N 4-methyl-6-oxononanedioic acid Chemical compound OC(=O)CCC(C)CC(=O)CCC(O)=O GVUKXGZRYIFDES-UHFFFAOYSA-N 0.000 claims description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- WFCVTCIMBXTXFJ-UHFFFAOYSA-N 2-methyl-5-oxooxolane-2-carboxylic acid Chemical compound OC(=O)C1(C)CCC(=O)O1 WFCVTCIMBXTXFJ-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- GTZCVFVGUGFEME-HNQUOIGGSA-N trans-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C/C(O)=O GTZCVFVGUGFEME-HNQUOIGGSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- ISBWNEKJSSLXOD-UHFFFAOYSA-N Butyl levulinate Chemical compound CCCCOC(=O)CCC(C)=O ISBWNEKJSSLXOD-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 229940005460 butyl levulinate Drugs 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 claims description 2
- NLDFWNCRMVSDMC-UHFFFAOYSA-N pentyl 4-oxopentanoate Chemical compound CCCCCOC(=O)CCC(C)=O NLDFWNCRMVSDMC-UHFFFAOYSA-N 0.000 claims description 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005523 4-oxopentanoic acid group Chemical group 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002028 Biomass Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000012978 lignocellulosic material Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 229920002488 Hemicellulose Polymers 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 150000007513 acids Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- GPDXFYPVHRESMA-UHFFFAOYSA-N 2,4,5-trihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=C(O)C=C1O GPDXFYPVHRESMA-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013064 chemical raw material Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- SXFBQAMLJMDXOD-UHFFFAOYSA-N (+)-hydrogentartrate bitartrate salt Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O SXFBQAMLJMDXOD-UHFFFAOYSA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- GIEGKXINITVUOO-UHFFFAOYSA-N 2-methylidenebutanedioic acid Chemical compound OC(=O)CC(=C)C(O)=O.OC(=O)CC(=C)C(O)=O GIEGKXINITVUOO-UHFFFAOYSA-N 0.000 description 1
- HWKRAUXFMLQKLS-UHFFFAOYSA-N 2-oxidanylidenepropanoic acid Chemical compound CC(=O)C(O)=O.CC(=O)C(O)=O HWKRAUXFMLQKLS-UHFFFAOYSA-N 0.000 description 1
- PCSKKIUURRTAEM-UHFFFAOYSA-N 5-hydroxymethyl-2-furoic acid Chemical compound OCC1=CC=C(C(O)=O)O1 PCSKKIUURRTAEM-UHFFFAOYSA-N 0.000 description 1
- 235000003932 Betula Nutrition 0.000 description 1
- 241000219429 Betula Species 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 235000021463 dry cake Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03257858 | 2003-12-15 | ||
| PCT/EP2004/053450 WO2005058856A1 (en) | 2003-12-15 | 2004-12-14 | A process for the liquefaction of lignocellulosic material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007514047A true JP2007514047A (ja) | 2007-05-31 |
| JP2007514047A5 JP2007514047A5 (enExample) | 2008-01-17 |
Family
ID=34684622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006544430A Pending JP2007514047A (ja) | 2003-12-15 | 2004-12-14 | リグノセルロース材料の液状化方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20070100162A1 (enExample) |
| EP (1) | EP1699771A1 (enExample) |
| JP (1) | JP2007514047A (enExample) |
| CN (1) | CN1894230A (enExample) |
| AU (1) | AU2004298440B2 (enExample) |
| BR (1) | BRPI0417599A (enExample) |
| CA (1) | CA2549458A1 (enExample) |
| RU (1) | RU2006125433A (enExample) |
| WO (1) | WO2005058856A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014519476A (ja) * | 2011-03-28 | 2014-08-14 | エージェンシー フォー サイエンス，テクノロジー アンド リサーチ | 二価酸の合成 |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1828095B1 (en) * | 2004-12-23 | 2011-10-05 | Shell Internationale Research Maatschappij B.V. | A process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group |
| US20070034345A1 (en) * | 2005-06-15 | 2007-02-15 | Leonardus Petrus | Process for organosolv pulping and use of a gamma lactone in a solvent for organosolv pulping |
| EP1991518A2 (en) | 2006-01-20 | 2008-11-19 | Archer-Daniels-Midland Company | Levulinic acid ester derivatives as reactive plasticizers and coalescent solvents |
| WO2008122029A1 (en) * | 2007-04-02 | 2008-10-09 | Inventure Chemical, Inc. | Simultaneous esterification and alcohol ysis/hydrolysis of oil-containing materials with cellulosic and peptidic content |
| US7943792B2 (en) * | 2007-04-02 | 2011-05-17 | Inventure Chemical Inc. | Production of biodiesel, cellulosic sugars, and peptides from the simultaneous esterification and alcoholysis/hydrolysis of materials with oil-containing substituents including phospholipids and peptidic content |
| 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 |
| FI121541B (fi) * | 2008-04-21 | 2010-12-31 | Kemira Oyj | Menetelmä muurahaishapon talteenottamiseksi |
| US7777085B2 (en) * | 2008-10-01 | 2010-08-17 | Inventure Chemical, Inc. | Method for conversion of oil-containing algae to 1,3-propanediol |
| US8871989B2 (en) * | 2009-02-27 | 2014-10-28 | Uop Llc | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
| US8138371B2 (en) | 2009-03-11 | 2012-03-20 | Biofine Technologies Llc | Production of formic acid |
| US8653312B2 (en) * | 2009-06-05 | 2014-02-18 | Toyota Jidosha Kabushiki Kaisha | Method for producing water-insoluble liquefied fuel oil from biomass |
| US8580978B2 (en) | 2009-08-07 | 2013-11-12 | Shell Oil Company | Process for preparing a hydroxyacid or hydroxyester |
| US20110112326A1 (en) * | 2009-08-07 | 2011-05-12 | Jean-Paul Lange | Process for hydrogenation |
| US20110173877A1 (en) * | 2009-12-24 | 2011-07-21 | Jeroen Van Buijtenen | Process for preparing a hydrocarbon or mixture of hydrocarbons |
| BR112012028765A2 (pt) * | 2010-05-12 | 2016-07-19 | Shell Int Research | processo para liquefazer um material celulósico |
| BR112012028438A2 (pt) * | 2010-05-12 | 2016-07-19 | Shell Int Research | processos para liquefazer um material celulósico para sintetizar um produto liquefeito, e para produzir um componente biocombustível a partir de um material celulósico, produto, e, biocombustível |
| CA2805881C (en) * | 2010-07-30 | 2019-10-22 | Purdue Research Foundation | Biomass liquefaction processes, and uses of same |
| US20140007492A1 (en) | 2011-11-14 | 2014-01-09 | Shell Oil Company | Process for conversion of a cellulosic material |
| US20140316161A1 (en) | 2011-11-23 | 2014-10-23 | Segetis, Inc. | Process to prepare levulinic acid |
| CN103304821B (zh) * | 2012-03-09 | 2016-01-20 | 东北林业大学 | 一种木质素的精制方法 |
| CN104704083B (zh) | 2012-10-08 | 2016-08-31 | 国际壳牌研究有限公司 | 液化纤维素材料的方法 |
| US9073841B2 (en) | 2012-11-05 | 2015-07-07 | Segetis, Inc. | Process to prepare levulinic acid |
| US9359650B2 (en) * | 2013-12-20 | 2016-06-07 | Wisconsin Alumni Research Foundation | Biomass pre-treatment for co-production of high-concentration C5- and C6-carbohydrates and their derivatives |
| BR112018072577A2 (pt) * | 2016-05-03 | 2019-02-19 | Shell Internationale Research Maatschappij B.V. | solventes à base de lignina e métodos para a preparação dos mesmos |
| WO2019014602A1 (en) | 2017-07-14 | 2019-01-17 | Battelle Memorial Institute | LIGNIN FOR LIQUID FUELS AND POLYOLS USING SOLVENTS DERIVED FROM BIOMASS |
| CN109053906B (zh) * | 2018-09-10 | 2021-02-12 | 北京理工大学 | 一种纳米纤维素纤维干粉的制备方法 |
| CN113293637B (zh) * | 2021-04-30 | 2022-09-20 | 中国林业科学研究院林产化学工业研究所 | 一种木质纤维组分分离的方法 |
| US12479962B2 (en) * | 2021-05-20 | 2025-11-25 | The Board Of Trustees Of Western Michigan University | Fractionation of woody biomass using phenol-4-sulfonic acid (PSA) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04106128A (ja) * | 1990-08-24 | 1992-04-08 | Nobuo Shiraishi | リグノセルロース物質の液化溶液の製造法 |
| JPH08225653A (ja) * | 1992-03-17 | 1996-09-03 | Nobuo Shiraishi | リグノセルロース物質の液化溶液の製造法 |
| JPH11130872A (ja) * | 1997-10-30 | 1999-05-18 | Nobuo Shiraishi | リグノセルロース物質の液化物の製造方法 |
| JP2000273310A (ja) * | 1999-03-29 | 2000-10-03 | Ibaraki Prefecture | 植物系物質からの樹脂原料組成物の製造方法 |
| JP2002037867A (ja) * | 2000-07-21 | 2002-02-06 | Fuji Carbon Kk | バイオマス由来のポリオール及び生分解性ポリウレタン |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594130A (en) * | 1978-11-27 | 1986-06-10 | Chang Pei Ching | Pulping of lignocellulose with aqueous alcohol and alkaline earth metal salt catalyst |
| US4462865A (en) * | 1981-09-30 | 1984-07-31 | The Dow Chemical Company | Delignification of lignocellulosic materials with 2-imidazolidinones and 2-oxazolidinones |
| US4652685A (en) * | 1985-11-15 | 1987-03-24 | General Electric Company | Hydrogenation of lactones to glycols |
| GB8721528D0 (en) * | 1987-09-14 | 1987-10-21 | Shell Int Research | Pulping lignocellulose-containing material |
| CA2048388C (en) * | 1990-08-16 | 1996-12-03 | Yasuo Tamura | Laminated material and process for manufacturing the same |
| US5508435A (en) * | 1992-07-29 | 1996-04-16 | Merck & Co., Inc. | Asymmetric hydrogenation of beta- or gamma-ketoesters and beta- or gamma-ketoamides |
| US5614564A (en) * | 1993-07-28 | 1997-03-25 | Samsung General Chemicals Co., Ltd. | Degradable foam and the method for its production |
| US5608105A (en) * | 1995-06-07 | 1997-03-04 | Biofine Incorporated | Production of levulinic acid from carbohydrate-containing materials |
| US5892107A (en) * | 1996-11-08 | 1999-04-06 | Arkenol, Inc. | Method for the production of levulinic acid |
| US5883266A (en) * | 1998-01-16 | 1999-03-16 | Battelle Memorial Institute | Hydrogenated 5-carbon compound and method of making |
| US20020069987A1 (en) * | 2000-08-08 | 2002-06-13 | Pye Edward Kendall | Integrated processing of biomass and liquid effluents |
| US6767565B2 (en) * | 2001-03-22 | 2004-07-27 | Archer Daniels Midland Company | Process for obtaining lignan |
| US6894199B2 (en) * | 2001-04-27 | 2005-05-17 | Danisco Sweeteners Oy | Process for the production of xylitol |
| FI117632B (fi) * | 2001-07-13 | 2006-12-29 | Chempolis Oy | Menetelmä massan valmistamiseksi |
| US6527914B1 (en) * | 2002-01-30 | 2003-03-04 | Ondeo Nalco Company | Method of enhancing brightness and brightness stability of paper made with mechanical pulp |
| US7439280B2 (en) * | 2004-04-06 | 2008-10-21 | Basf Corporation | Lignocellulosic composite material and method for preparing the same |
| US20060135793A1 (en) * | 2004-11-26 | 2006-06-22 | Blessing Robert W | Process for the dimerisation of levulinic acid, dimers obtainable by such process and esters of such dimers |
| EP1828095B1 (en) * | 2004-12-23 | 2011-10-05 | Shell Internationale Research Maatschappij B.V. | A process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group |
| US20070034345A1 (en) * | 2005-06-15 | 2007-02-15 | Leonardus Petrus | Process for organosolv pulping and use of a gamma lactone in a solvent for organosolv pulping |
-
2004
- 2004-12-14 JP JP2006544430A patent/JP2007514047A/ja active Pending
- 2004-12-14 EP EP04804809A patent/EP1699771A1/en not_active Withdrawn
- 2004-12-14 AU AU2004298440A patent/AU2004298440B2/en not_active Ceased
- 2004-12-14 BR BRPI0417599-9A patent/BRPI0417599A/pt not_active IP Right Cessation
- 2004-12-14 CN CNA200480037424XA patent/CN1894230A/zh active Pending
- 2004-12-14 US US10/582,888 patent/US20070100162A1/en not_active Abandoned
- 2004-12-14 RU RU2006125433/04A patent/RU2006125433A/ru not_active Application Discontinuation
- 2004-12-14 WO PCT/EP2004/053450 patent/WO2005058856A1/en not_active Ceased
- 2004-12-14 CA CA002549458A patent/CA2549458A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04106128A (ja) * | 1990-08-24 | 1992-04-08 | Nobuo Shiraishi | リグノセルロース物質の液化溶液の製造法 |
| JPH08225653A (ja) * | 1992-03-17 | 1996-09-03 | Nobuo Shiraishi | リグノセルロース物質の液化溶液の製造法 |
| JPH11130872A (ja) * | 1997-10-30 | 1999-05-18 | Nobuo Shiraishi | リグノセルロース物質の液化物の製造方法 |
| JP2000273310A (ja) * | 1999-03-29 | 2000-10-03 | Ibaraki Prefecture | 植物系物質からの樹脂原料組成物の製造方法 |
| JP2002037867A (ja) * | 2000-07-21 | 2002-02-06 | Fuji Carbon Kk | バイオマス由来のポリオール及び生分解性ポリウレタン |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014519476A (ja) * | 2011-03-28 | 2014-08-14 | エージェンシー フォー サイエンス，テクノロジー アンド リサーチ | 二価酸の合成 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1699771A1 (en) | 2006-09-13 |
| CA2549458A1 (en) | 2005-06-30 |
| AU2004298440A1 (en) | 2005-06-30 |
| BRPI0417599A (pt) | 2007-03-20 |
| US20070100162A1 (en) | 2007-05-03 |
| CN1894230A (zh) | 2007-01-10 |
| AU2004298440B2 (en) | 2007-10-04 |
| RU2006125433A (ru) | 2008-01-27 |
| WO2005058856A1 (en) | 2005-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007514047A (ja) | リグノセルロース材料の液状化方法 | |
| Li et al. | Recent advances in biomass pretreatment using biphasic solvent systems | |
| Inkrod et al. | Characteristics of lignin extracted from different lignocellulosic materials via organosolv fractionation | |
| US8901325B2 (en) | Method for producing furfural from lignocellulosic biomass material | |
| Cai et al. | THF co-solvent enhances hydrocarbon fuel precursor yields from lignocellulosic biomass | |
| Ramli et al. | Catalytic hydrolysis of cellulose and oil palm biomass in ionic liquid to reducing sugar for levulinic acid production | |
| RU2739567C2 (ru) | Получение мономеров из лигнина в процессе деполимеризации содержащей лигноцеллюлозу композиции | |
| Wang et al. | Rapid and simultaneous production of furfural and cellulose-rich residue from sugarcane bagasse using a pressurized phosphoric acid-acetone-water system | |
| CN102112432A (zh) | 从生物质生产3-乙酰丙酸酯的方法 | |
| CN104292193B (zh) | 一种生物质分级处理后制备糠醛和两步制备乙酰丙酸的方法 | |
| CN103797004B (zh) | 用于制备糠醛的方法 | |
| Liu et al. | Selective conversion of hemicellulose into furfural over low-cost metal salts in a γ-valerolactone/water solution | |
| KR101791852B1 (ko) | 이관능성 하이드록시메틸기를 가지는 퓨란 모노머 및 이의 제조 방법 | |
| WO2012156479A1 (fr) | Procédé de préparation de 5-hydroxyméthylfurfural | |
| CA2611152A1 (en) | A process for organosolv pulping and use of a gamma lactone in a solvent for organosolv pulping | |
| CN102892864B (zh) | 液化纤维素材料的方法 | |
| JP2018536656A (ja) | ５−（ヒドロキシメチル）フルフラール及び特定のｈｍｆエステルを含む混合物を調製する方法 | |
| NL2021194B1 (en) | A comprehensive utilization method for preparing levulinic acid through directional liquefaction of lignocellulosic biomass | |
| CN104292195A (zh) | 一种生物质分级处理后制备糠醛和调变流量制备乙酰丙酸的方法 | |
| Feng et al. | One-step method to produce methyl-D-glucoside from lignocellulosic biomass | |
| CN104292194B (zh) | 一种生物质分级处理后制备糠醛和快速变温法制备乙酰丙酸的方法 | |
| CN108675928B (zh) | 一种糠醛直接制备乙酰丙酸酯的方法 | |
| US10125079B2 (en) | Methods of making levulinic acid and alkyl levulinates from saccharides | |
| Salgado-Ramos et al. | One-pot, microwave (MW)-assisted production of furfural from almond-, oil-, and wine-derived co-products through biorefinery-based approaches | |
| Ganado et al. | Towards the Valorization of Biomass to 5-Hydroxymethylfurfural: A Promising Biochemical and Biofuel Feedstock |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071120 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20071120 |
|
| RD13 | Notification of appointment of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7433 Effective date: 20090608 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090622 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20090713 |
|
| RD14 | Notification of resignation of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7434 Effective date: 20090713 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20100803 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20100825 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20101019 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20101116 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110510 |