CA2968409A1 - Methods for converting cellulose to furanic products - Google Patents
Methods for converting cellulose to furanic products Download PDFInfo
- Publication number
- CA2968409A1 CA2968409A1 CA2968409A CA2968409A CA2968409A1 CA 2968409 A1 CA2968409 A1 CA 2968409A1 CA 2968409 A CA2968409 A CA 2968409A CA 2968409 A CA2968409 A CA 2968409A CA 2968409 A1 CA2968409 A1 CA 2968409A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- stream
- ionic liquid
- glucose
- hydroxymethyl furfural
- 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 193
- 229920002678 cellulose Polymers 0.000 title claims description 173
- 239000001913 cellulose Substances 0.000 title claims description 173
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 152
- 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 abstract description 152
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims abstract description 152
- 239000008103 glucose Substances 0.000 claims abstract description 151
- 230000008569 process Effects 0.000 claims abstract description 151
- 229920005610 lignin Polymers 0.000 claims abstract description 67
- 239000005715 Fructose Substances 0.000 claims abstract description 61
- 229930091371 Fructose Natural products 0.000 claims abstract description 61
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims abstract description 61
- 239000000047 product Substances 0.000 claims abstract description 36
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 28
- 238000000926 separation method Methods 0.000 claims abstract description 26
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 25
- 230000018044 dehydration Effects 0.000 claims abstract description 19
- 239000000413 hydrolysate Substances 0.000 claims abstract description 15
- 239000002608 ionic liquid Substances 0.000 claims description 231
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 133
- 239000000203 mixture Substances 0.000 claims description 131
- 229910001868 water Inorganic materials 0.000 claims description 106
- 239000007787 solid Substances 0.000 claims description 97
- 239000011347 resin Substances 0.000 claims description 87
- 229920005989 resin Polymers 0.000 claims description 87
- 239000002904 solvent Substances 0.000 claims description 77
- 239000002253 acid Substances 0.000 claims description 74
- 239000000243 solution Substances 0.000 claims description 71
- 150000001768 cations Chemical class 0.000 claims description 64
- 235000000346 sugar Nutrition 0.000 claims description 64
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 54
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 54
- 150000008163 sugars Chemical class 0.000 claims description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 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 37
- 238000004587 chromatography analysis Methods 0.000 claims description 31
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 28
- 150000001720 carbohydrates Chemical class 0.000 claims description 28
- 235000019253 formic acid Nutrition 0.000 claims description 28
- 150000007524 organic acids Chemical class 0.000 claims description 28
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 27
- 229940040102 levulinic acid Drugs 0.000 claims description 27
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 26
- 239000003550 marker Substances 0.000 claims description 26
- 238000004064 recycling Methods 0.000 claims description 26
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical group CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 235000014633 carbohydrates Nutrition 0.000 claims description 21
- -1 levulinate anion Chemical class 0.000 claims description 21
- 235000005985 organic acids Nutrition 0.000 claims description 21
- 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 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 238000001704 evaporation Methods 0.000 claims description 14
- 230000008020 evaporation Effects 0.000 claims description 14
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 11
- 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 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000003729 cation exchange resin Substances 0.000 claims description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims description 10
- 150000002772 monosaccharides Chemical class 0.000 claims description 10
- 238000007670 refining Methods 0.000 claims description 10
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 claims description 9
- 230000003750 conditioning effect Effects 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 7
- 229940058352 levulinate Drugs 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 230000001143 conditioned effect Effects 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 claims description 5
- 229910001415 sodium ion Inorganic materials 0.000 claims description 5
- 229920001503 Glucan Polymers 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- 229920001002 functional polymer Polymers 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 239000003957 anion exchange resin Substances 0.000 claims description 2
- 239000011324 bead Substances 0.000 claims description 2
- 238000003795 desorption Methods 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002028 Biomass Substances 0.000 abstract description 20
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000012084 conversion product Substances 0.000 abstract description 5
- 239000012978 lignocellulosic material Substances 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 25
- 238000006460 hydrolysis reaction Methods 0.000 description 23
- 230000007062 hydrolysis Effects 0.000 description 22
- 239000002585 base Substances 0.000 description 17
- 239000003929 acidic solution Substances 0.000 description 16
- 229920002488 Hemicellulose Polymers 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000011084 recovery Methods 0.000 description 11
- 241000609240 Ambelania acida Species 0.000 description 9
- 239000010905 bagasse Substances 0.000 description 9
- 244000004281 Eucalyptus maculata Species 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000010586 diagram Methods 0.000 description 8
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 7
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 7
- 241000219927 Eucalyptus Species 0.000 description 7
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 7
- 241000018646 Pinus brutia Species 0.000 description 7
- 235000011613 Pinus brutia Nutrition 0.000 description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000005496 eutectics Effects 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000013375 chromatographic separation Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000002952 polymeric resin Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229920003002 synthetic resin Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical group CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000002663 humin Substances 0.000 description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 230000003381 solubilizing effect Effects 0.000 description 4
- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
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- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019534 high fructose corn syrup Nutrition 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
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- 229910052700 potassium Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
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- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 2
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- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
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- BXOAIZOIDUQOFA-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;hydroxide Chemical compound [OH-].CCCC[N+]=1C=CN(C)C=1 BXOAIZOIDUQOFA-UHFFFAOYSA-M 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
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- XIYUIMLQTKODPS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1 XIYUIMLQTKODPS-UHFFFAOYSA-M 0.000 description 1
- VRFOKYHDLYBVAL-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCN1C=C[N+](C)=C1 VRFOKYHDLYBVAL-UHFFFAOYSA-M 0.000 description 1
- PTAWFMIDYHSANN-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;hydroxide Chemical compound [OH-].CC[N+]=1C=CN(C)C=1 PTAWFMIDYHSANN-UHFFFAOYSA-M 0.000 description 1
- STCBHSHARMAIOM-UHFFFAOYSA-N 1-methyl-1h-imidazol-1-ium;chloride Chemical compound Cl.CN1C=CN=C1 STCBHSHARMAIOM-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000006538 C11 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
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- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
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- 239000000852 hydrogen donor Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- TVEOIQKGZSIMNG-UHFFFAOYSA-N hydron;1-methyl-1h-imidazol-1-ium;sulfate Chemical compound OS([O-])(=O)=O.C[NH+]1C=CN=C1 TVEOIQKGZSIMNG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 238000004989 laser desorption mass spectroscopy Methods 0.000 description 1
- 150000004722 levulinic acids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CBKJDTFDVVXSJR-UHFFFAOYSA-M methyl sulfate;1,2,4-trimethylpyrazol-2-ium Chemical compound COS([O-])(=O)=O.CC1=CN(C)[N+](C)=C1 CBKJDTFDVVXSJR-UHFFFAOYSA-M 0.000 description 1
- FIMHASWLGDDANN-UHFFFAOYSA-M methyl sulfate;tributyl(methyl)azanium Chemical compound COS([O-])(=O)=O.CCCC[N+](C)(CCCC)CCCC FIMHASWLGDDANN-UHFFFAOYSA-M 0.000 description 1
- WLTHPEHYBIKNHR-UHFFFAOYSA-M methyl sulfate;tris(2-hydroxyethyl)-methylazanium Chemical compound COS([O-])(=O)=O.OCC[N+](C)(CCO)CCO WLTHPEHYBIKNHR-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- 238000004730 pulsed amperometry Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical class C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 239000012266 salt solution Substances 0.000 description 1
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- 239000011973 solid acid Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
- C07D307/50—Preparation from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/06—Ethanol, i.e. non-beverage
- C12P7/08—Ethanol, i.e. non-beverage produced as by-product or from waste or cellulosic material substrate
- C12P7/10—Ethanol, i.e. non-beverage produced as by-product or from waste or cellulosic material substrate substrate containing cellulosic material
-
- 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
- C13K1/04—Purifying
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K11/00—Fructose
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P5/00—Preparation of hydrocarbons or halogenated hydrocarbons
- C12P5/02—Preparation of hydrocarbons or halogenated hydrocarbons acyclic
- C12P5/023—Methane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Furan Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462091319P | 2014-12-12 | 2014-12-12 | |
| US62/091,319 | 2014-12-12 | ||
| US201462095673P | 2014-12-22 | 2014-12-22 | |
| US62/095,673 | 2014-12-22 | ||
| PCT/US2015/065403 WO2016094878A1 (en) | 2014-12-12 | 2015-12-11 | Methods for converting cellulose to furanic products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2968409A1 true CA2968409A1 (en) | 2016-06-16 |
Family
ID=56108296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2968409A Pending CA2968409A1 (en) | 2014-12-12 | 2015-12-11 | Methods for converting cellulose to furanic products |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10532990B2 (enExample) |
| EP (1) | EP3230270A4 (enExample) |
| JP (1) | JP2017537119A (enExample) |
| CN (1) | CN107250123B (enExample) |
| BR (1) | BR112017011978A2 (enExample) |
| CA (1) | CA2968409A1 (enExample) |
| RU (1) | RU2722487C2 (enExample) |
| WO (1) | WO2016094878A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015171368A1 (en) * | 2014-05-06 | 2015-11-12 | Iowa State University Research Foundation, Inc. | Method for the isomerization of glucose to fructose |
| JP2017537119A (ja) | 2014-12-12 | 2017-12-14 | ヴァーディア， インコーポレイテッド | セルロースをフラン生成物に変換するための方法 |
| WO2017032926A2 (en) * | 2015-08-27 | 2017-03-02 | Teknologian Tutkimuskeskus Vtt Oy | Process for converting biomass |
| ES2652362B1 (es) * | 2016-07-01 | 2018-11-13 | Universidade De Santiago De Compostela | Mezclas de sales para disolver celulosa |
| WO2018009502A1 (en) * | 2016-07-06 | 2018-01-11 | Virdia, Inc. | Methods of refining a lignocellulosic hydrolysate |
| CN108408714A (zh) * | 2018-05-09 | 2018-08-17 | 东莞理工学院 | 一种以胡敏素制备层状结构介孔碳材料的方法 |
| FI129866B (fi) * | 2019-05-15 | 2022-10-14 | Lappeenrannan Lahden Teknillinen Yliopisto Lut | Menetelmä lignoselluloosamateriaalin fraktioimiseksi ja mainitulla menetelmällä saadut tuotteet |
| US20230160026A1 (en) * | 2020-04-08 | 2023-05-25 | Jgc Corporation | Method for recovering sugar |
| CN113070103A (zh) * | 2021-04-26 | 2021-07-06 | 上海邢东化工科技有限公司 | 一种弱酸阳离子交换树脂的提纯工艺及提纯设备 |
| JP2025507027A (ja) * | 2022-03-04 | 2025-03-13 | アバンティウム・ナレッジ・センター・ベー・フェー | 塩酸と共に加水分解されたセルロース繊維及び合成の非セルロース繊維から有機溶媒を用いて５－クロロメチルフルフラールを抽出する方法 |
| CN115160267B (zh) * | 2022-08-04 | 2024-01-16 | 安阳工学院 | 一种离子液体型复合介质及采用其制备糠醛类化合物的方法 |
| CN116987051B (zh) * | 2023-08-04 | 2025-08-26 | 安徽理工大学 | 一种水解法制备5-羟甲基糠醛的方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3684574A (en) | 1970-04-20 | 1972-08-15 | Anheuser Busch | Method of producing sweet syrup by resin isomerization of dextrose syrup |
| US4618579A (en) * | 1984-09-28 | 1986-10-21 | Genencor, Inc. | Raw starch saccharification |
| US4764596A (en) * | 1985-11-05 | 1988-08-16 | Repap Technologies Inc. | Recovery of lignin |
| SU1432121A1 (ru) * | 1986-05-26 | 1988-10-23 | Ioffe Iosif | Способ регенерации варочной жидкости |
| JPH07165781A (ja) * | 1993-12-07 | 1995-06-27 | Asai Gerumaniumu Kenkyusho:Kk | グルコースの異性化方法及び異性化或いはその促進剤 |
| JP2996875B2 (ja) * | 1994-07-04 | 2000-01-11 | 新日本製鐵株式会社 | ステーブクーラーの耐火煉瓦鋳ぐるみ方法 |
| US6177575B1 (en) | 1998-06-12 | 2001-01-23 | E. I. Du Pont De Nemours And Company | Process for manufacture of imidazoles |
| RU2165708C2 (ru) * | 1998-07-31 | 2001-04-27 | Валентина Андреевна Васькина | Состав для производства мучного кондитерского изделия |
| US6518440B2 (en) | 2001-03-05 | 2003-02-11 | Gene E. Lightner | Hydroxymethylfurfural derived from cellulose contained in lignocellulose solids |
| US20060081637A1 (en) * | 2004-10-14 | 2006-04-20 | Lundy Michael J | Bucket |
| CA2856978C (en) * | 2006-03-29 | 2017-07-18 | Virginia Tech Intellectual Properties, Inc. | Cellulose-solvent-based lignocellulose fractionation with modest reaction conditions and reagent recycling |
| US8968811B2 (en) * | 2007-01-26 | 2015-03-03 | Probelte Pharma, S.A. | Hydroxytrosol containing extract obtained from olives and solids containing residues of olive oil extraction |
| ES2451011T3 (es) * | 2007-01-26 | 2014-03-26 | Probelte Pharma, S.A. | Procedimiento para la producción de un extracto que contiene hidroxitirosol a partir de aceitunas y sólidos que contienen residuos de la extracción de aceite de oliva |
| US8999067B2 (en) | 2007-02-07 | 2015-04-07 | Queensland University Of Technology | Fractionation of a lignocellulosic material |
| BRPI0813157B1 (pt) * | 2007-06-18 | 2017-12-12 | Archer Daniels-Midland Company | Method of purification of hmf from a mixture containing reagents and products of the synthesis of hmf from fruit |
| CN101354468B (zh) * | 2007-07-23 | 2010-06-23 | 鸿富锦精密工业（深圳）有限公司 | 变焦装置 |
| US8110667B2 (en) | 2008-04-28 | 2012-02-07 | Battelle Memorial Institute | Method for conversion of carbohydrate polymers to value-added chemical products |
| US20090277841A1 (en) * | 2008-05-07 | 2009-11-12 | Johnson Donald A | Method for minimizing corrosion, scale, and water consumption in cooling tower systems |
| WO2009155297A1 (en) | 2008-06-17 | 2009-12-23 | Wisconsin Alumni Research Foundation | Chemical transformation of lignocellulosic biomass into fuels and chemicals |
| CN102498122B (zh) | 2009-07-01 | 2016-08-03 | 威斯康星校友研究基金会 | 生物质水解 |
| WO2011041455A1 (en) | 2009-09-29 | 2011-04-07 | The Regents Of The University Of California | Recovery of sugars from ionic liquid biomass liquor by solvent extraction |
| US8790542B2 (en) | 2009-09-30 | 2014-07-29 | Sandia Corporation | Compositions and methods useful for ionic liquid treatment of biomass |
| CN102249869A (zh) * | 2010-05-18 | 2011-11-23 | 中国科学院兰州化学物理研究所 | 离子液体催化合成聚甲氧基二甲醚的工艺过程 |
| US9174909B2 (en) * | 2012-02-02 | 2015-11-03 | Wisconsin Alumni Research Foundation | Two-stage, acid-catalyzed conversion of carbohydrates into levulinic acid |
| US8563277B1 (en) * | 2012-04-13 | 2013-10-22 | Sweetwater Energy, Inc. | Methods and systems for saccharification of biomass |
| WO2013166237A1 (en) | 2012-05-02 | 2013-11-07 | The Regents Of The University Of California | Sugar extraction and ionic liquid recycling using alkaline solutions |
| EP2847202B1 (en) | 2012-05-03 | 2019-04-17 | Virdia, Inc. | Methods for treating lignocellulosic materials |
| NZ706072A (en) * | 2013-03-08 | 2018-12-21 | Xyleco Inc | Equipment protecting enclosures |
| BR112015027744B1 (pt) | 2013-05-03 | 2022-05-24 | Virdia, Llc | Composição de lignina e produto compreendendo a dita composição |
| EP2813494A1 (de) | 2013-06-12 | 2014-12-17 | Basf Se | Verfahren zur Herstellung von 5-Hydroxymethylfurfural (HMF) |
| JP2017537119A (ja) | 2014-12-12 | 2017-12-14 | ヴァーディア， インコーポレイテッド | セルロースをフラン生成物に変換するための方法 |
-
2015
- 2015-12-11 JP JP2017530586A patent/JP2017537119A/ja active Pending
- 2015-12-11 RU RU2017124242A patent/RU2722487C2/ru active
- 2015-12-11 CN CN201580076596.6A patent/CN107250123B/zh not_active Expired - Fee Related
- 2015-12-11 CA CA2968409A patent/CA2968409A1/en active Pending
- 2015-12-11 US US15/527,597 patent/US10532990B2/en not_active Expired - Fee Related
- 2015-12-11 EP EP15867656.9A patent/EP3230270A4/en not_active Withdrawn
- 2015-12-11 BR BR112017011978A patent/BR112017011978A2/pt not_active Application Discontinuation
- 2015-12-11 WO PCT/US2015/065403 patent/WO2016094878A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP3230270A1 (en) | 2017-10-18 |
| EP3230270A4 (en) | 2018-07-04 |
| CN107250123A (zh) | 2017-10-13 |
| RU2017124242A (ru) | 2019-01-14 |
| JP2017537119A (ja) | 2017-12-14 |
| BR112017011978A2 (pt) | 2017-12-26 |
| US20170362194A1 (en) | 2017-12-21 |
| WO2016094878A1 (en) | 2016-06-16 |
| RU2722487C2 (ru) | 2020-06-01 |
| US10532990B2 (en) | 2020-01-14 |
| WO2016094878A8 (en) | 2016-07-21 |
| CN107250123B (zh) | 2021-06-15 |
| RU2017124242A3 (enExample) | 2019-12-05 |
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