EP2712936A1 - Produits de sucre et son procédé de fabrication - Google Patents
Produits de sucre et son procédé de fabrication Download PDFInfo
- Publication number
- EP2712936A1 EP2712936A1 EP20130186469 EP13186469A EP2712936A1 EP 2712936 A1 EP2712936 A1 EP 2712936A1 EP 20130186469 EP20130186469 EP 20130186469 EP 13186469 A EP13186469 A EP 13186469A EP 2712936 A1 EP2712936 A1 EP 2712936A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- chloride
- mixing solution
- bromide
- sugar product
- fabricating
- 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 55
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002156 mixing Methods 0.000 claims abstract description 191
- 238000004090 dissolution Methods 0.000 claims abstract description 137
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 121
- 238000006243 chemical reaction Methods 0.000 claims abstract description 62
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 61
- 239000011592 zinc chloride Substances 0.000 claims abstract description 59
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 45
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 39
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 34
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims abstract description 31
- 239000001110 calcium chloride Substances 0.000 claims abstract description 27
- 229910001628 calcium chloride Inorganic materials 0.000 claims abstract description 27
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims abstract description 26
- 229910001629 magnesium chloride Inorganic materials 0.000 claims abstract description 25
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 16
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims abstract description 15
- 229910001622 calcium bromide Inorganic materials 0.000 claims abstract description 14
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims abstract description 13
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims abstract description 13
- 229910001623 magnesium bromide Inorganic materials 0.000 claims abstract description 13
- 229940102001 zinc bromide Drugs 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000002028 Biomass Substances 0.000 claims abstract description 11
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 224
- 229920002678 cellulose Polymers 0.000 claims description 160
- 239000001913 cellulose Substances 0.000 claims description 160
- 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 112
- 235000019253 formic acid Nutrition 0.000 claims description 112
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 76
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 56
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 56
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 51
- 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 43
- 239000008103 glucose Substances 0.000 claims description 43
- 241000609240 Ambelania acida Species 0.000 claims description 27
- 239000010905 bagasse Substances 0.000 claims description 27
- 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 23
- 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 18
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 18
- 229920001542 oligosaccharide Polymers 0.000 claims description 18
- 150000002482 oligosaccharides Chemical class 0.000 claims description 18
- 229920002488 Hemicellulose Polymers 0.000 claims description 12
- 229920005610 lignin Polymers 0.000 claims description 12
- -1 salt compound Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 240000008042 Zea mays Species 0.000 claims description 10
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 10
- 235000005822 corn Nutrition 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 6
- 240000007594 Oryza sativa Species 0.000 claims description 4
- 235000007164 Oryza sativa Nutrition 0.000 claims description 4
- 235000009566 rice Nutrition 0.000 claims description 4
- 239000010902 straw Substances 0.000 claims description 4
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims description 2
- 235000017491 Bambusa tulda Nutrition 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 241000195493 Cryptophyta Species 0.000 claims description 2
- 229910020881 PMo12O40 Inorganic materials 0.000 claims description 2
- 244000082204 Phyllostachys viridis Species 0.000 claims description 2
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims description 2
- 229910020628 SiW12O40 Inorganic materials 0.000 claims description 2
- 241000209140 Triticum Species 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 239000011425 bamboo Substances 0.000 claims description 2
- 239000010903 husk Substances 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 239000010893 paper waste Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 174
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 39
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 description 26
- 239000007788 liquid Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 230000007062 hydrolysis Effects 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- 229910000029 sodium carbonate Inorganic materials 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 10
- 239000011667 zinc carbonate Substances 0.000 description 10
- 229910000010 zinc carbonate Inorganic materials 0.000 description 10
- 239000000178 monomer Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000012047 saturated solution Substances 0.000 description 7
- 229910000019 calcium carbonate Inorganic materials 0.000 description 6
- 229920001503 Glucan Polymers 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- 229920001221 xylan Polymers 0.000 description 5
- 150000004823 xylans Chemical class 0.000 description 5
- 235000004416 zinc carbonate Nutrition 0.000 description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 4
- 229910001626 barium chloride Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- NKQIMNKPSDEDMO-UHFFFAOYSA-L barium bromide Chemical compound [Br-].[Br-].[Ba+2] NKQIMNKPSDEDMO-UHFFFAOYSA-L 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 150000004804 polysaccharides Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 229910001620 barium bromide Inorganic materials 0.000 description 2
- 150000003842 bromide salts Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
- HVTQDSGGHBWVTR-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-phenylmethoxypyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound C(C1=CC=CC=C1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CCOCC1 HVTQDSGGHBWVTR-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-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
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000875 Dissolving pulp Polymers 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 229910052925 anhydrite Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
Classifications
-
- 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
Definitions
- the technical field relates to a sugar product and fabricating method thereof.
- the world is facing problems such as the gradual extraction and depletion of petroleum reserves, and changes to the earth's atmosphere due to the greenhouse effect. In order to ensure the sustainability of human life, it has become a world trend to gradually decrease the use of petrochemical energy and petroleum feedstock and to develop new sources of renewable energy and materials.
- Lignocellulose is the main ingredient of biomass, which is the most abundant organic substance in the world. Lignocellulose mainly consists of 38-50% cellulose, 23-32% hemicellulose and 15-25% lignin. Cellulose generates glucose through hydrolysis. However, it is difficult for chemicals to enter the interior of cellulose molecules for depolymerization due to strong intermolecular and intramolecular hydrogen bonding and Van de Waal forces and the complex aggregate structure of cellulose with high-degree crystallinity. The main methods of hydrolyzing cellulose are enzyme hydrolysis and acid hydrolysis. However, there is significant imperfection in these two technologies, therefore, it is difficult to apply widely.
- enzyme hydrolysis can be carried out at room temperature, which is an environmentally friendly method due to the rarity of byproducts, no production of anti-sugar fermentation substances, and integration with the fermentation process.
- a complicated pretreatment process is required, hydrolytic activity is low, the reaction rate is slow, and cellulose hydrolysis enzyme is expensive.
- Dilute acid hydrolysis generally uses comparatively cheap sulfuric acid as a catalyst, but it must operate in a corrosion-resistant pressure vessel at more than 200°C, requiring high-level equipment; simultaneously, the temperature of the dilute acid hydrolysis is high, the byproduct thereof is plentiful, and the sugar yield is low. Concentrated acid hydrolysis can operate at lower temperature and normal pressure. However, there are problems of strong corrosivity of concentrated acid, complications in the post-treatment process of the hydrolyzed solution, large consumption of acid, and difficulties with recycling, among other drawbacks.
- One embodiment of the disclosure provides a sugar product, comprising: a sugar mixture comprising glucose, xylose, mannose, arabinose and oligosaccharides thereof with a weight ratio of 2-15wt%; an acid compound with a weight ratio of 48-97wt%; and a salt compound with a weight ratio of 1-50wt%.
- One embodiment of the disclosure provides a method for fabricating a sugar product, comprising: mixing formic acid or acetic acid and lithium chloride, magnesium chloride, calcium chloride, zinc chloride, iron chloride, lithium bromide, magnesium bromide, calcium bromide, zinc bromide, iron bromide, or heteropoly acid to form a mixing solution; adding a cellulosic biomass to the mixing solution for a dissolution reaction; and adding water to the mixing solution for a hydrolysis reaction to obtain a sugar product.
- a method for fabricating a sugar product comprising the following steps. First, formic acid or acetic acid and lithium chloride, magnesium chloride, calcium chloride, zinc chloride, iron chloride, lithium bromide, magnesium bromide, calcium bromide, zinc bromide, iron bromide, or heteropoly acid are mixed to form a mixing solution. A cellulosic biomass is added to the mixing solution for a dissolution reaction. Water is added to the mixing solution for a hydrolysis reaction to obtain a sugar product.
- the lithium chloride or lithium bromide has a weight ratio of about 5-20wt% or 10-20wt% in the mixing solution.
- the calcium chloride or calcium bromide has a weight ratio of about 12-40wt% or 12-30wt% in the mixing solution.
- the amount of water added is larger than the total molar equivalent of monosaccharides hydrolyzed from the cellulosic biomass.
- the hydrolysis reaction has a reaction temperature of about 50-150°C or 60-105 °C and a reaction time of about 30-180 minutes or 30-120 minutes.
- the sugar product fabricated by the method may comprise a sugar mixture, an acid compound, and a salt compound.
- the sugar mixture may comprise glucose, xylose, mannose, arabinose and oligosaccharides thereof with a weight ratio of about 2-15wt% in the sugar product.
- the acid compound may comprise formic acid or acetic acid with a weight ratio of about 48-97wt% in the sugar product.
- the salt compound may comprise lithium chloride, magnesium chloride, calcium chloride, zinc chloride, iron chloride, lithium bromide, magnesium bromide, calcium bromide, zinc bromide, or iron bromide with a weight ratio of about 1-50wt% in the sugar product.
- the method further comprises adding inorganic acid to the mixing solution before, during or after the dissolution reaction.
- the inorganic acid may comprise sulfuric acid or hydrochloric acid.
- the inorganic acid has a weight ratio of about 1-2wt% in the mixing solution.
- the adding amount of the chloride salt or the bromide salt may be reduced, for example, the weight ratio of the magnesium chloride, the magnesium bromide, the calcium chloride or the calcium bromide in the mixing solution may be reduced to about 1-10wt%, and the weight ratio of the lithium chloride, the lithium bromide, the zinc chloride, the zinc bromide, the iron chloride or the iron bromide in the mixing solution may be reduced to about 1-5wt%.
- Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (75wt% of formic acid, 25wt% of calcium chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (6wt% of Avicel ® cellulose) for a dissolution reaction (65 °C , 90 minutes) to form a yellow, homogeneous, and transparent liquid, as recorded in Table 1.
- Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of magnesium chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65 °C , 120 minutes) to form an amber, homogeneous, and transparent liquid, as recorded in Table 1.
- Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of magnesium chloride).
- ⁇ -cellulose Sigma Corporation, C8002 was added to the mixing solution (5wt% of ⁇ -cellulose) for a dissolution reaction (65°C, 120 minutes) to form an amber, homogeneous, and transparent liquid, as recorded in Table 1.
- Table 1 Examples Salt (wt%) Cellulose (wt%) Dissolution temp.
- Formic acid and lithium chloride (LiCl) were mixed and heated to form a mixing solution (90wt% of formic acid, 10wt% of lithium chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and lithium bromide (LiBr) were mixed and heated to form a mixing solution (90wt% of formic acid, 10wt% of lithium bromide).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 0.5 hour). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and sodium bromide (NaBr) were mixed and heated to form a mixing solution (82wt% of formic acid, 18wt% of sodium bromide).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 9 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and calcium bromide (CaBr 2 ) were mixed and heated to form a mixing solution (88wt% of formic acid, 12wt% of calcium bromide).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and barium bromide (BaBr 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of barium bromide).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of magnesium chloride (saturated solution)).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65 °C , 2 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (90wt% of formic acid, 10wt% of magnesium chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 12 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (75wt% of formic acid, 25wt% of calcium chloride (saturated solution)).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65°C, 1.5 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (82.5wt% of formic acid, 17.5wt% of calcium chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 2 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (88wt% of formic acid, 12wt% of calcium chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (60wt% of formic acid, 40wt% of zinc chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (50°C, 0.25 hour). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of zinc chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65°C, 0.25 hour). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (95wt% of formic acid, 5wt% of zinc chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Formic acid and iron chloride (FeCl 3 ) were mixed and heated to form a mixing solution (98wt% of formic acid, 2wt% of iron chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 3 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
- Magnesium carbonate (MgCO 3 ) precipitate was then removed from the mixing solution.
- the total weight of the reducing sugar was measured using 3,5-dinitro-salicylic acid (DNS) method.
- DNS 3,5-dinitro-salicylic acid
- the yield of the reducing sugar was then calculated.
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 3.
- Formic acid and magnesium chloride (MgCl 2 ) were mixed by stirring and heated to 70°C under 1 atm to form a mixing solution (90wt% of formic acid, 10wt% of magnesium chloride).
- Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours).
- water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (120 minutes).
- saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
- Formic acid and calcium chloride (CaCl 2 ) were mixed by stirring and heated to 50°C under 1 atm to form a mixing solution (85wt% of formic acid, 15wt% of calcium chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (50°C, 4 hours).
- water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (60 minutes).
- saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 4.
- Formic acid and calcium chloride (CaCl 2 ) were mixed by stirring and heated to 70°C under 1 atm to form a mixing solution (88wt% of formic acid, 12wt% of calcium chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 4 hours).
- water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (60 minutes).
- saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 4.
- Formic acid and calcium chloride (CaCl 2 ) were mixed by stirring and heated to 90°C under 1 atm to form a mixing solution (90wt% of formic acid, 10wt% of calcium chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI
- was added to the mixing solution 5wt% of Avicel ® cellulose
- dissolution reaction 90°C, 4 hours.
- water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (60 minutes).
- saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
- Formic acid and zinc chloride (ZnCl 2 ) were mixed by stirring and heated to 50°C under 1 atm to form a mixing solution (60wt% of formic acid, 40wt% of zinc chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (50°C).
- water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (30 minutes).
- saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
- Zinc carbonate (ZnCO 3 ) precipitate was then removed from the mixing solution.
- the total weight of the reducing sugar was measured using 3,5-dinitro-salicylic acid (DNS) method.
- DNS 3,5-dinitro-salicylic acid
- the yield of the reducing sugar was then calculated.
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 5.
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- Formic acid and zinc chloride (ZnCl 2 ) were mixed by stirring and heated to 55 °C under 1 atm to form a mixing solution (60wt% of formic acid, 40wt% of zinc chloride).
- Dried corn stalks (comprising 44.5wt% of glucan, 12.4wt% of xylan, 4.6wt% of acid-soluble lignin, 24.4wt% of acid-insoluble lignin, 2.7wt% of water and 3.8wt% of ash) was added to the mixing solution (5wt% of corn stalks) for a dissolution reaction (55°C).
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- the yield of the glucose is the ratio of the moles of the produced glucose and the moles of the glucose monomers contained in the cellulose in the bagasse.
- the yield of the xylose is the ratio of the moles of the produced xylose and the moles of the xylose monomers contained in the hemicellulose in the bagasse.
- the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the total weight of the cellulose and hemicellulose in the bagasse. The result is shown in Table 9.
- 98wt% of H 2 SO 4 , iron chloride (FeCl 3 ) and formic acid were mixed by stirring and heated to 55°C under 1 atm to form a mixing solution (1wt% of H 2 SO 4 , 2wt% of iron chloride, 97wt% of formic acid).
- Dried bagasse (comprising 40.7wt% of glucan, 20.5wt% of xylan, 2.9wt% of Arab polysaccharides, 27.4wt% of lignin, 3.3wt% of ash and 5.2wt% of other ingredients) was added to the mixing solution (10wt% of bagasse) for a dissolution reaction (65°C).
- the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
- the yield of the glucose is the ratio of the moles of the produced glucose and the moles of the glucose monomers contained in the cellulose in the bagasse.
- the yield of the xylose is the ratio of the moles of the produced xylose and the moles of the xylose monomers contained in the hemicellulose in the bagasse.
- the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the total weight of the cellulose and hemicellulose in the bagasse.
- Formic acid acetic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (54wt% of formic acid, 6wt% of acetic acid and 40wt% of zinc chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (60°C, 60 minutes), forming an amber transparent liquid with an uniform phase. The dissolution of cellulose was observed using a polarizing microscope. The cellulose was completely dissolved.
- Formic acid acetic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (50wt% of formic acid, 10wt% of acetic acid and 40wt% of zinc chloride).
- Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65°C, 60 minutes), forming an amber transparent liquid with an uniform phase. The dissolution of cellulose was observed using a polarizing microscope. The cellulose was completely dissolved.
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US4452640A (en) * | 1982-05-11 | 1984-06-05 | Purdue Research Foundation | Quantitative hydrolysis of cellulose to glucose using zinc chloride |
WO2006007691A1 (fr) * | 2004-07-16 | 2006-01-26 | Iogen Energy Corporation | Procede d'elaboration de flux de produit sucre a partir d'une biomasse cellulosique |
US20080102502A1 (en) * | 2006-10-25 | 2008-05-01 | Brian Foody | Inorganic salt recovery during processing of lignocellulosic feedstocks |
WO2010104371A1 (fr) * | 2009-03-12 | 2010-09-16 | Universiti Malaya | Conversion de matériaux cellulosiques en glucose à utiliser dans la production de bioéthanol |
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US4452640A (en) * | 1982-05-11 | 1984-06-05 | Purdue Research Foundation | Quantitative hydrolysis of cellulose to glucose using zinc chloride |
WO2006007691A1 (fr) * | 2004-07-16 | 2006-01-26 | Iogen Energy Corporation | Procede d'elaboration de flux de produit sucre a partir d'une biomasse cellulosique |
US20080102502A1 (en) * | 2006-10-25 | 2008-05-01 | Brian Foody | Inorganic salt recovery during processing of lignocellulosic feedstocks |
WO2010104371A1 (fr) * | 2009-03-12 | 2010-09-16 | Universiti Malaya | Conversion de matériaux cellulosiques en glucose à utiliser dans la production de bioéthanol |
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