CN118184609A - Method for continuously preparing 5-hydroxymethylfurfural from cellulose by adsorption method - Google Patents
Method for continuously preparing 5-hydroxymethylfurfural from cellulose by adsorption method Download PDFInfo
- Publication number
- CN118184609A CN118184609A CN202211599132.1A CN202211599132A CN118184609A CN 118184609 A CN118184609 A CN 118184609A CN 202211599132 A CN202211599132 A CN 202211599132A CN 118184609 A CN118184609 A CN 118184609A
- Authority
- CN
- China
- Prior art keywords
- cellulose
- hydroxymethylfurfural
- reaction
- adsorbent
- chloride
- 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
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract description 69
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 229920002678 cellulose Polymers 0.000 title claims abstract description 43
- 239000001913 cellulose Substances 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 239000003463 adsorbent Substances 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 23
- 239000003377 acid catalyst Substances 0.000 claims abstract description 15
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 239000000243 solution Substances 0.000 claims description 21
- 239000002808 molecular sieve Substances 0.000 claims description 17
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- -1 magnesium aluminate Chemical class 0.000 claims description 6
- 239000012621 metal-organic framework Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 150000004645 aluminates Chemical class 0.000 claims description 4
- 239000002734 clay mineral Substances 0.000 claims description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 4
- 150000002366 halogen compounds Chemical class 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 3
- 244000060011 Cocos nucifera Species 0.000 claims description 3
- 239000004115 Sodium Silicate Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 235000010981 methylcellulose Nutrition 0.000 claims description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052911 sodium silicate Inorganic materials 0.000 claims description 3
- RFRMMZAKBNXNHE-UHFFFAOYSA-N 6-[4,6-dihydroxy-5-(2-hydroxyethoxy)-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)-5-(2-hydroxypropoxy)oxane-3,4-diol Chemical compound CC(O)COC1C(O)C(O)C(CO)OC1OC1C(O)C(OCCO)C(O)OC1CO RFRMMZAKBNXNHE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000004254 Ammonium phosphate Substances 0.000 claims description 2
- QYEXBYZXHDUPRC-UHFFFAOYSA-N B#[Ti]#B Chemical compound B#[Ti]#B QYEXBYZXHDUPRC-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910021532 Calcite Inorganic materials 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910021555 Chromium Chloride Inorganic materials 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 239000013177 MIL-101 Substances 0.000 claims description 2
- 239000013206 MIL-53 Substances 0.000 claims description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- PZKRHHZKOQZHIO-UHFFFAOYSA-N [B].[B].[Mg] Chemical compound [B].[B].[Mg] PZKRHHZKOQZHIO-UHFFFAOYSA-N 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019289 ammonium phosphates Nutrition 0.000 claims description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 2
- 229910001626 barium chloride Inorganic materials 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910001622 calcium bromide Inorganic materials 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims description 2
- 239000001506 calcium phosphate Substances 0.000 claims description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 2
- 235000011010 calcium phosphates Nutrition 0.000 claims description 2
- 239000000378 calcium silicate Substances 0.000 claims description 2
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 2
- XFWJKVMFIVXPKK-UHFFFAOYSA-N calcium;oxido(oxo)alumane Chemical compound [Ca+2].[O-][Al]=O.[O-][Al]=O XFWJKVMFIVXPKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 229920003086 cellulose ether Polymers 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 2
- 239000003245 coal Substances 0.000 claims description 2
- 229960003280 cupric chloride Drugs 0.000 claims description 2
- 238000003795 desorption Methods 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 claims description 2
- 239000004137 magnesium phosphate Substances 0.000 claims description 2
- 229910000157 magnesium phosphate Inorganic materials 0.000 claims description 2
- 229960002261 magnesium phosphate Drugs 0.000 claims description 2
- 235000010994 magnesium phosphates Nutrition 0.000 claims description 2
- 239000000391 magnesium silicate Substances 0.000 claims description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 2
- 235000019792 magnesium silicate Nutrition 0.000 claims description 2
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 229910001388 sodium aluminate Inorganic materials 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000011775 sodium fluoride Substances 0.000 claims description 2
- 235000013024 sodium fluoride Nutrition 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- 235000011008 sodium phosphates Nutrition 0.000 claims description 2
- 229910052567 struvite Inorganic materials 0.000 claims description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 238000012423 maintenance Methods 0.000 abstract description 8
- 238000007086 side reaction Methods 0.000 abstract description 8
- 239000007864 aqueous solution Substances 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000012071 phase Substances 0.000 abstract description 2
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000005715 Fructose Substances 0.000 description 4
- 229930091371 Fructose Natural products 0.000 description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000011010 flushing procedure Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 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 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 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 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
Landscapes
- Catalysts (AREA)
Abstract
The application discloses a method for continuously preparing 5-hydroxymethylfurfural by cellulose adsorption, which comprises the following steps: the mixed aqueous solution containing cellulose, inorganic salt and acid catalyst flows through a heat exchanger to react under continuous condition, and after the reaction, the aqueous phase passes through an adsorbent to be enriched to obtain 5-hydroxymethylfurfural. The synergistic effect of the specific inorganic salt and the specific acid catalyst added in the method can effectively control the occurrence of side reaction, avoid the occurrence of black rot, improve the selectivity of the reaction and greatly reduce the equipment maintenance and labor cost; the method is a continuous reaction, and has great economic benefit compared with a system for synthesizing 5-hydroxymethylfurfural by using a batch kettle reactor. Meanwhile, the adsorbent is used for adsorbing the 5-hydroxymethylfurfural in the water phase of the reaction liquid, so that side reactions can be effectively inhibited, the reaction selectivity is improved, and the energy consumption in the production process is reduced.
Description
Technical Field
The application relates to a method for continuously preparing 5-hydroxymethylfurfural by cellulose adsorption, belonging to the field of preparation and synthesis of 5-hydroxymethylfurfural.
Background
Typical routes to 5-hydroxymethylfurfural are acid-catalyzed dehydration of carbohydrates such as glucose, fructose, cellulose and sucrose. Various homogeneous or heterogeneous catalysts have been developed, including Lewis and Bronsted acids, which have been found to be effective in the synthesis of 5-hydroxymethylfurfural and which are widely used in processes for the production of 5-hydroxymethylfurfural. However, because the 5-hydroxymethylfurfural generated in the reaction process has higher reactivity, the 5-hydroxymethylfurfural can further react under the catalysis of the catalyst to generate high-molecular black rot through polymerization or generate acetoacetic acid through decomposition. The generation of these byproducts can lead to lower selectivity of the reaction, and can lead to corrosion and blockage of equipment, so that the reaction is difficult to carry out, the maintenance and use cost of the equipment is greatly increased, and the economic benefit is poor. These disadvantages limit their potential industrial application.
Disclosure of Invention
According to one aspect of the application there is provided a process for the preparation of 5-hydroxymethylfurfural which comprises mixing a solution comprising cellulose, an inorganic salt and an acidic catalyst, passing the solution through a heat exchanger, reacting in a continuous manner, passing the reacted solution through a bed of adsorbent, and desorbing to obtain said 5-hydroxymethylfurfural. In the application, the inorganic salt and the specific acid catalyst are added for reaction under the continuous condition, so that the synergistic effect can be achieved, and the production efficiency and the conversion rate of the reaction can be effectively improved compared with the intermittent reaction. Meanwhile, the problems that the yield of the product is reduced and the maintenance cost of equipment is greatly increased due to the fact that the black rot is formed by side reaction of 5-hydroxymethylfurfural are avoided. The system for synthesizing the 5-hydroxymethylfurfural has the advantages of larger economic benefit, lower system cost, less environmental pollution, simple operation, easy repetition, low equipment maintenance cost and high-purity 5-hydroxymethylfurfural production.
A method for continuously preparing 5-hydroxymethylfurfural from cellulose by an adsorption method, which is characterized by comprising the following steps:
Introducing the mixed solution containing cellulose, inorganic salt and acid catalyst into a continuous reactor, reacting at the temperature of 60-180 ℃ and the liquid phase flow rate of 0.1-20L/min, adsorbing the reaction solution by using an adsorbent, and enriching to obtain 5-hydroxymethylfurfural;
the cellulose is at least one selected from cellulose ether, methyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose and carboxymethyl cellulose;
the inorganic salt is at least one selected from halogen compounds, boride, silicate, aluminate, phosphate and borate.
Optionally, the acid catalyst is selected from at least one of acids dissolved in water.
Alternatively, the water-soluble acid is a readily water-soluble acid.
Optionally, the acid catalyst comprises at least one of phosphoric acid, hydrochloric acid, sulfuric acid, boric acid, sulfonic acid, and p-toluenesulfonic acid.
Optionally, the hydrochloric acid is a 35.0 to 40.0wt% hydrochloric acid solution.
Optionally, the sulfuric acid is concentrated sulfuric acid of 95.0 to 99.0 wt%.
Optionally, the halogen compound is selected from at least one of sodium chloride, sodium fluoride, magnesium chloride, calcium chloride, barium chloride, chromium chloride, ferric chloride, cupric chloride, aluminum chloride, sodium bromide, calcium bromide, magnesium bromide;
optionally, the boride is at least one selected from boron fluoride, magnesium boride, titanium boride, chromium boride and calcium boride;
Optionally, the silicate is at least one selected from sodium silicate, calcium silicate, magnesium silicate, ammonium silicate, and the like;
Optionally, the aluminate is at least one selected from sodium aluminate, calcium aluminate, magnesium aluminate, ammonium aluminate and the like;
optionally, the phosphate is at least one selected from sodium phosphate, calcium phosphate, magnesium phosphate, ammonium phosphate, and the like.
Optionally, the mass ratio of the cellulose to the inorganic salt is 0.5-10: 1 to 20.
Optionally, the mass ratio of the cellulose to the inorganic salt is 5-10:5-20.
Optionally, the mass ratio of the cellulose to the inorganic salt is 8-10:6-20.
Optionally, the mass ratio of the cellulose to the inorganic salt is 8-10:15-20.
Optionally, the mass ratio of the cellulose to the acidic catalyst is 0.5-10: 0.01 to 1.
Optionally, the mass ratio of the cellulose to the acid catalyst is 8-10:0.01-1.
Optionally, the mass ratio of the cellulose to the acid catalyst is 10:0.01-1.
Optionally, the solvent of the solution comprises water.
Optionally, the mass ratio of the cellulose to the water is 0.5-10: 1 to 20.
Optionally, the mass ratio of the cellulose to the water is 5-10: 5 to 20.
Optionally, the mass ratio of the cellulose to the water is 8-10: 6-20.
Optionally, the mass ratio of the cellulose to the water is 5-10: 10 to 20.
Optionally, the mass ratio of cellulose to water is 10: 15-20.
Optionally, the mass ratio of cellulose to water satisfies:
Cellulose: water=1:0.8 to 10.
Alternatively, the mass ratio of cellulose to water is independently selected from any value or range of values between any two of 1:0.8, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10.
The mass ratio of the water to the inorganic salt is as follows:
Water: inorganic salt=1:0.05 to 5.
Alternatively, the mass ratio of water to inorganic salt is independently selected from any value or range between any two of 1:0.05, 1:0.10, 1:0.20, 1:0.30, 1:0.40, 1:0.50, 1:0.60, 1:0.70, 1:0.80, 1:0.90, 1:1, 1:2, 1:3, 1:4, 1:5.
The addition amount of the acid catalyst is 0.1-5 wt% of the addition amount of the cellulose.
Alternatively, the ratio of the added amount of the acidic catalyst to the added amount of the cellulose is independently selected from any value or a range between any two of 0.1wt%, 0.2wt%, 0.5wt%, 0.8wt%, 1.0wt%, 1.5wt%, 2.0wt%, 2.5wt%, 3.0wt%, 3.5wt%, 4.0wt%, 4.5wt%, 5.0 wt%.
Optionally, the reaction conditions include: the reaction temperature is 60-180 ℃, and the liquid phase flow rate is 0.1-20L/min.
Alternatively, the temperature of the reaction is independently selected from any value or range of values between any two of 60 ℃, 70 ℃, 90 ℃, 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 150 ℃, 160 ℃, 170 ℃, 175 ℃, 180 ℃.
Alternatively, the reaction time is 2 to 10 hours.
Alternatively, the time of the reaction is independently selected from any value or range of values between any two of 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours.
Alternatively, the pressure of the reaction is not particularly limited, and may be at normal pressure.
Optionally, the reaction conditions include: the flow rate of the reaction is 0.1L/min-20L/min.
Alternatively, the reaction flow rate is independently selected from any value or range of values between any two of 0.1L/min, 0.5L/min, 1L/min, 3L/min, 5L/min, 9L/min, 12L/min, 15L/min, 20L/min.
Optionally, the adsorbent is selected from at least one of activated carbon, molecular sieves, natural clay minerals, amorphous oxides, metal organic framework materials.
Optionally, in the adsorbent, the activated carbon comprises at least one of coal carbon, coconut carbon and wood carbon.
Optionally, in the adsorbent, the molecular sieve is at least one selected from a Y-type molecular sieve, an A-type molecular sieve, a ZSM-5 molecular sieve, a 13X molecular sieve, an MWW molecular sieve and an MOR molecular sieve.
Optionally, in the adsorbent, the natural clay mineral is at least one selected from bentonite, montmorillonite, kaolin and calcite.
Optionally, in the adsorbent, the amorphous oxide is at least one selected from amorphous silica, amorphous alumina, amorphous aluminosilicate.
Optionally, in the adsorbent, the metal-organic framework material is at least one selected from metal-organic framework materials MIL-125, MIL-101, SIFSIX and MIL-53.
Optionally, the mass ratio of the adsorbent to the reaction liquid is 0.5-10: 1 to 50.
Optionally, the mass ratio of the adsorbent to the reaction solution is 5-10: 20 to 50.
Optionally, the mass ratio of the adsorbent to the reaction liquid is 8-10: 35 to 50.
Optionally, the mass ratio of the adsorbent to the reaction solution is 1:1 to 50.
Optionally, the mass ratio of the adsorbent to the reaction liquid is independently selected from any value or range of values between any two of 1:1, 1:5, 1:10, 1:20, 1:30, 1:40, 1:50.
Optionally, after the reaction solution passes through the adsorbent, recycling the reaction solution;
Optionally, after the reaction solution passes through the adsorbent, the adsorbent is rinsed with water for desorption;
optionally, the mass ratio of the water to the adsorbent is 1-10:1.
Optionally, the mass ratio of the water to the adsorbent is 5-10: 1.
Optionally, the mass ratio of the water to the adsorbent is 8-10: 1.
Optionally, the mass ratio of the water to the adsorbent is independently selected from any value or range of values between any two of 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1.
Alternatively, the yield of 5-hydroxymethylfurfural is greater than 80%.
Optionally, the yield of 5-hydroxymethylfurfural is 80% -95%.
The application provides a method for obtaining 5-hydroxymethylfurfural by utilizing inorganic salt, cellulose water solution and acid catalyst to catalyze cellulose to convert into 5-hydroxymethylfurfural under continuous condition, and after reaction, adsorbing and enriching reaction liquid through an adsorbent bed. Compared with the traditional solvent system, the method for synthesizing the 5-HMF by using the cellulose with wide sources and low price as the raw material has the advantages that the inorganic salt added in the reaction process can effectively avoid side reactions of the 5-hydroxymethylfurfural, improves the reaction conversion rate, ensures that the reacted reaction liquid is clear and transparent, has higher conversion rate and selectivity, is environment-friendly, has lower economic cost, is beneficial to industrial production and amplification, has low equipment maintenance cost, and can efficiently produce the high-purity 5-hydroxymethylfurfural. Compared with the traditional method, the preparation method can effectively control the occurrence of side reactions, avoid the occurrence of black rot, improve the selectivity of the reaction and greatly reduce the equipment maintenance and labor cost.
The preparation route of the application is that the raw material of inorganic salt water solution containing cellulose is adopted, and 5-hydroxymethylfurfural is obtained through dehydration reaction under the catalysis of an acid catalyst, which is different from the process of using fructose as the raw material, the fructose has higher water solubility, and the cellulose has poorer water solubility, so that the cellulose can also undergo hydrolysis process in the continuous reaction process, and the cellulose is greatly different from the fructose in the continuous reaction. The added inorganic salt and the continuous reaction different from the intermittent reaction effectively inhibit the further side reaction of the 5-hydroxymethylfurfural, no other impurities or black rot are generated after the reaction, and after the reaction, the reaction liquid is adsorbed and enriched through an adsorbent bed layer to obtain the 5-hydroxymethylfurfural, while the side reaction is difficult to control in the traditional preparation process of the 5-hydroxymethylfurfural, and the generated black rot is extremely easy to cause equipment corrosion and blockage.
As one embodiment, the method comprises:
a) Mixing cellulose, inorganic salt and an acidic catalyst to form an aqueous solution, and allowing the aqueous solution to flow through a heat exchanger for continuous reaction to obtain the 5-hydroxymethylfurfural. The reaction temperature is between 60 and 180 ℃, the reaction time is between 2 and 10 hours, and the flow rate of the reaction is between 0.1 and 20L/min;
b) And c) adsorbing the reaction liquid in the reaction in the step a) through an adsorbent, and flushing and desorbing the 5-hydroxymethylfurfural in the adsorbent by water after the adsorption to obtain an aqueous solution of the product 5-hydroxymethylfurfural.
As a specific embodiment, the method comprises:
1) Uniformly mixing cellulose, inorganic salt aqueous solution and a catalyst, and reacting by a heat exchanger at the reaction temperature of 60-180 ℃ for 2-10 hours at the flow rate of 0.1-20L/min.
2) In the production process, the 5-hydroxymethylfurfural in the reaction liquid is adsorbed and enriched by using an adsorbent, the reaction liquid can be recycled after the 5-hydroxymethylfurfural is adsorbed, the 5-hydroxymethylfurfural is continuously extracted, and the adsorbent is used for desorbing the adsorbed 5-hydroxymethylfurfural by water flushing.
The application has the beneficial effects that:
1) Compared with the traditional method, the preparation method of the 5-hydroxymethylfurfural provided by the application uses cheap and easily available cellulose as a reaction raw material, and the synergistic effect of the added specific inorganic salt and the specific acid catalyst can effectively control the occurrence of side reaction, avoid the generation of black rot, improve the selectivity of the reaction and greatly reduce the equipment maintenance and labor cost.
2) The method is a continuous reaction, is different from a system for synthesizing the 5-hydroxymethylfurfural by an intermittent kettle reactor, has larger economic benefit, lower system cost, less environmental pollution, simple operation, easy repetition, low equipment maintenance cost and can efficiently produce the high-purity 5-hydroxymethylfurfural.
3) The reaction liquid after the reaction is enriched by an adsorption method to obtain the 5-hydroxymethylfurfural, and a traditional distillation step with larger energy consumption is not needed, so that a product with higher purity can be obtained.
Drawings
FIG. 1 is a hydrogen nuclear magnetic resonance spectrum of the product synthesized in example 1 of the present application.
FIG. 2 is a hydrogen nuclear magnetic spectrum of a 5-hydroxymethylfurfural standard.
FIG. 3 is a carbon nuclear magnetic spectrum of the product synthesized in example 1 of the present application.
FIG. 4 is a carbon nuclear magnetic spectrum of a 5-hydroxymethylfurfural standard.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
Unless otherwise indicated, all starting materials in the examples of the present application were purchased commercially.
The analysis method in the embodiment of the application is as follows:
The reaction solution was dissolved in deuteration reagent by using liquid nuclear magnetic resonance spectrometer model AVANCE II 400M manufactured by Bruce company to analyze nuclear magnetic resonance chart of carbon and hydrogen.
High performance liquid chromatography was carried out using water as mobile phase under the conditions of model 7890A from vortical corporation, using uv-vis and differential refraction detector.
In the examples of the present application, the yield and selectivity of 5-hydroxymethylfurfural were calculated by:
Yield of 5-hydroxymethylfurfural = moles of 5-hydroxymethylfurfural produced/moles of reaction substrate added
Selectivity of 5-hydroxymethylfurfural = moles of 5-hydroxymethylfurfural produced/moles of reaction substrate participating in the reaction
Obtaining a liquid chromatography peak area by configuring the content of 5-hydroxymethylfurfural in a standard solution, and obtaining a standard curve by taking the peak area as an abscissa and the concentration of 5-hydroxymethylfurfural as an ordinate; further, the concentration of 5-hydroxymethylfurfural in the reaction liquid after the reaction can be calculated, and the yield of 5-hydroxymethylfurfural is calculated through the concentration.
In the examples of the present application, the concentrations of concentrated sulfuric acid and hydrochloric acid used are described below:
Concentrated sulfuric acid: HSO was 98.0wt%;
Hydrochloric acid: HCl was 37.0wt%.
Example 1
5G of hydroxypropyl methyl cellulose, 6.84g of aluminum chloride and 5g of water are added into a batch kettle type reactor, 0.12g of concentrated sulfuric acid is added dropwise as a catalyst under a stirring state, and after the raw materials are fully dissolved, the raw materials pass through a heat exchanger at a flow rate of 5L/min, are heated to 150 ℃, the continuous reaction time is 6 hours, and the color of a reaction solution is gradually deepened. The reaction solution was passed through 5g of coconut shell activated carbon, followed by washing the adsorbent with 6g of water to obtain an aqueous solution of 5-hydroxymethylfurfural. A small amount of flushing liquid is taken for high performance liquid chromatography analysis, and the result shows that the yield of the 5-hydroxymethylfurfural is 85% and the selectivity is 98%.
Example 2
8G of methyl cellulose, 3g of sodium silicate and 6g of water are added into a batch kettle reactor, 0.1g of phosphoric acid is added into the batch kettle reactor as a catalyst under a stirring state, after the raw materials are fully dissolved, the raw materials pass through a heat exchanger at a flow rate of 5L/min, the temperature is raised to 150 ℃, the continuous reaction time is 5 hours, and the color of a reaction solution is gradually deepened. The reaction solution was passed through 8g of an X-type molecular sieve, followed by washing the adsorbent with 12g of water to obtain an aqueous solution of 5-hydroxymethylfurfural. A small amount of flushing liquid is taken for high performance liquid chromatography analysis, and the result shows that the yield of the 5-hydroxymethylfurfural is 90% and the selectivity is 98%.
Examples 3 to 11
The specific ingredients, materials and reaction conditions are shown in Table 1, and the other operations in the synthesis process are the same as in example 1.
TABLE 1 raw material composition, ratio and adsorption/Desorption conditions for examples 3 to 11
Example 12 liquid Nuclear magnetic resonance analysis
Liquid nuclear magnetic resonance analysis was performed on the 5-hydroxymethylfurfural prepared in examples 1 to 11, and typical examples are shown in fig. 1 and 3, and fig. 2 and 4 are standard spectra of 5-hydroxymethylfurfural. Fig. 1 corresponds to the hydrogen nuclear magnetic resonance spectrum of 5-hydroxymethylfurfural prepared in example 1, and it can be seen from a comparison of fig. 1 and fig. 2 that the 5-hydroxymethylfurfural prepared in example 1 has a typical standard hydrogen nuclear magnetic spectrum of 5-hydroxymethylfurfural.
FIG. 3 corresponds to the carbon nuclear magnetic resonance spectrum of 5-hydroxymethylfurfural prepared in example 1. As can be seen from a comparison of FIGS. 3 and 4, the carbon nuclear magnetic spectrum of 5-hydroxymethylfurfural prepared in example 1 has typical standard 5-hydroxymethylfurfural.
The test results for 5-hydroxymethylfurfural in other examples were similar to those described above, and standard 5-hydroxymethylfurfural was obtained by the present invention.
While the application has been described in terms of preferred embodiments, it will be understood by those skilled in the art that various changes and modifications can be made without departing from the scope of the application, and it is intended that the application is not limited to the specific embodiments disclosed.
Claims (10)
1. A method for continuously preparing 5-hydroxymethylfurfural from cellulose by an adsorption method, which is characterized by comprising the following steps:
Introducing the mixed solution containing cellulose, inorganic salt and acid catalyst into a continuous reactor, reacting at the temperature of 60-180 ℃ and the liquid phase flow rate of 0.1-20L/min, adsorbing the reaction solution by using an adsorbent, and enriching to obtain 5-hydroxymethylfurfural;
the cellulose is at least one selected from cellulose ether, methyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose and carboxymethyl cellulose;
the inorganic salt is at least one selected from halogen compounds, boride, silicate, aluminate, phosphate and borate.
2. The method of claim 1, wherein the acid catalyst comprises at least one of phosphoric acid, hydrochloric acid, sulfuric acid, boric acid, sulfonic acid, and p-toluenesulfonic acid.
3. The method according to claim 1, wherein the halogen compound is at least one selected from the group consisting of sodium chloride, sodium fluoride, magnesium chloride, calcium chloride, barium chloride, chromium chloride, ferric chloride, cupric chloride, aluminum chloride, sodium bromide, calcium bromide, and magnesium bromide;
Preferably, the boride is at least one selected from boron fluoride, magnesium boride, titanium boride, chromium boride and calcium boride;
preferably, the silicate is at least one selected from sodium silicate, calcium silicate, magnesium silicate, ammonium silicate, and the like;
preferably, the aluminate is at least one selected from sodium aluminate, calcium aluminate, magnesium aluminate, ammonium aluminate and the like;
preferably, the phosphate is at least one selected from sodium phosphate, calcium phosphate, magnesium phosphate, ammonium phosphate, and the like.
4. The preparation method according to claim 1, wherein the mass ratio of the cellulose to the inorganic salt is 0.5 to 10:1 to 20.
5. The method according to claim 1, wherein the cellulose and DD220726I
The mass ratio of the acid catalyst is 0.5-10: 0.01 to 1.
6. The preparation method according to claim 1, wherein the mass ratio of the cellulose to the water is 0.5 to 10:1 to 20.
7. The method according to claim 1, wherein the reaction time is 2 to 10 hours.
8. The method according to claim 1, wherein the adsorbent is at least one selected from the group consisting of activated carbon, molecular sieves, natural clay minerals, amorphous oxides, and metal organic framework materials;
Preferably, the activated carbon comprises at least one of coal-based carbon, coconut shell carbon and wood carbon;
Preferably, the molecular sieve is selected from at least one of a Y-type molecular sieve, an A-type molecular sieve, a ZSM-5 molecular sieve, a 13X molecular sieve, an MWW molecular sieve and an MOR molecular sieve;
preferably, the natural clay mineral is at least one selected from bentonite, montmorillonite, kaolin and calcite;
Preferably, the amorphous oxide is at least one selected from amorphous silica, amorphous alumina, amorphous aluminosilicate;
Preferably, the metal organic framework material is selected from at least one of metal organic framework materials MIL-125, MIL-101, SIFSIX and MIL-53.
9. The preparation method according to claim 1, wherein the mass ratio of the adsorbent to the reaction liquid is 0.5 to 10:1 to 50.
10. The method according to claim 1, wherein the reaction solution is recycled after passing through the adsorbent;
Preferably, after the reaction solution passes through the adsorbent, the adsorbent is rinsed with water for desorption.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211599132.1A CN118184609A (en) | 2022-12-12 | 2022-12-12 | Method for continuously preparing 5-hydroxymethylfurfural from cellulose by adsorption method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211599132.1A CN118184609A (en) | 2022-12-12 | 2022-12-12 | Method for continuously preparing 5-hydroxymethylfurfural from cellulose by adsorption method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN118184609A true CN118184609A (en) | 2024-06-14 |
Family
ID=91391747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211599132.1A Pending CN118184609A (en) | 2022-12-12 | 2022-12-12 | Method for continuously preparing 5-hydroxymethylfurfural from cellulose by adsorption method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118184609A (en) |
-
2022
- 2022-12-12 CN CN202211599132.1A patent/CN118184609A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang et al. | Direct conversion of carbohydrates to 5-hydroxymethylfurfural using Sn-Mont catalyst | |
| CN103848730B (en) | Production device system and production process for polymethoxy dimethyl ether (PODE) | |
| CN101475472B (en) | Method for preparing oxalate by coupling reaction of CO in gaseous phase | |
| CN101108843A (en) | Method of synthesizing circularity carbonic acid ester containing water or moisture architecture | |
| CN101347743A (en) | Method for preparing catalyst for producing propylene transformed from methanol with high ratio of propylene/ethylene | |
| CN114805107B (en) | n-alpha arylation method of nitrogen-containing heterocycle realized by photocatalysis | |
| CN113861139A (en) | Method for preparing 5-hydroxymethylfurfural | |
| CN100554231C (en) | The method for preparing butyl glycol ether | |
| CN118184609A (en) | Method for continuously preparing 5-hydroxymethylfurfural from cellulose by adsorption method | |
| CN103435477A (en) | Novel method for synthesizing para-ethoxybenzoic acid | |
| CN102060659A (en) | Method for preparing homoallylic alcohol | |
| CN118126001A (en) | Preparation method of 5-hydroxymethylfurfural | |
| CN118184608A (en) | Method for preparing 5-hydroxymethylfurfural by adsorption method fructose organic-inorganic two-phase continuous process | |
| CN118184607A (en) | Method for preparing 5-hydroxymethylfurfural by adsorption cellulose organic-inorganic two-phase continuous process | |
| CN109438402B (en) | Benzofuranone derivatives and synthesis method thereof | |
| CN115806536A (en) | Method for preparing 5-hydroxymethylfurfural in solvent-free system | |
| KR20110101691A (en) | Improved method for producing catechol and hydroquinone from phenol and hydrogen peroxide | |
| CN103204775B (en) | Oxidation method of acetophenone | |
| CN118125999A (en) | Preparation method of 5-hydroxymethylfurfural | |
| CN118005578A (en) | Preparation method of 5-hydroxymethylfurfural | |
| CN118005583A (en) | Preparation method of 5-hydroxymethylfurfural by using inorganic salt | |
| WO2015095999A1 (en) | Method for preparing polyoxymethylene dimethyl ether carbonyl compound and methyl methoxyacetate | |
| CN118126000A (en) | Preparation method of 5-hydroxymethylfurfural | |
| CN118026971A (en) | Preparation method of 5-hydroxymethylfurfural | |
| CN100469742C (en) | Production of phenyl cyclohexane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination |