CN105753819A - 一种5-羟甲基糠醛纯化的方法 - Google Patents
一种5-羟甲基糠醛纯化的方法 Download PDFInfo
- Publication number
- CN105753819A CN105753819A CN201610260021.6A CN201610260021A CN105753819A CN 105753819 A CN105753819 A CN 105753819A CN 201610260021 A CN201610260021 A CN 201610260021A CN 105753819 A CN105753819 A CN 105753819A
- Authority
- CN
- China
- Prior art keywords
- hydroxymethyl furfural
- adsorbent
- weight
- hydroxymethyl
- furans
- 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
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- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract description 54
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000003463 adsorbent Substances 0.000 claims abstract description 18
- 239000012264 purified product Substances 0.000 claims abstract description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
- 150000002466 imines Chemical class 0.000 claims description 8
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 5
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002460 imidazoles Chemical class 0.000 claims description 5
- 229960004011 methenamine Drugs 0.000 claims description 5
- 229920005990 polystyrene resin Polymers 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 2
- CETXOEGRUBXUAL-UHFFFAOYSA-N 3-(hydroxymethyl)furan-2-carbaldehyde Chemical class OCC=1C=COC=1C=O CETXOEGRUBXUAL-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- 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 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000011964 heteropoly acid Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CMJBUVNYQIMCQH-UHFFFAOYSA-N C(CCCC)OC(=O)C=1OC=CC1C(=O)O Chemical compound C(CCCC)OC(=O)C=1OC=CC1C(=O)O CMJBUVNYQIMCQH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 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 1
- 229920002488 Hemicellulose 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- -1 aldehyde radical Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-Butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Chemical class 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001282 polysaccharide Chemical class 0.000 description 1
- 239000005017 polysaccharide Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
Abstract
Description
编号 | 5-羟甲基糠醛质量百分含量% |
M-1 | 99.6 |
M-2 | 99.2 |
M-3 | 99.9 |
M-4 | 98.2 |
M-5 | 98.4 |
M-6 | 96.9 |
M-7 | 96.4 |
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610260021.6A CN105753819B (zh) | 2016-04-26 | 2016-04-26 | 一种5-羟甲基糠醛纯化的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610260021.6A CN105753819B (zh) | 2016-04-26 | 2016-04-26 | 一种5-羟甲基糠醛纯化的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105753819A true CN105753819A (zh) | 2016-07-13 |
CN105753819B CN105753819B (zh) | 2018-06-08 |
Family
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Family Applications (1)
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CN201610260021.6A Expired - Fee Related CN105753819B (zh) | 2016-04-26 | 2016-04-26 | 一种5-羟甲基糠醛纯化的方法 |
Country Status (1)
Country | Link |
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CN (1) | CN105753819B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107011385A (zh) * | 2016-08-21 | 2017-08-04 | 王琪宇 | 一种六氯环三磷腈提纯助剂的制备方法 |
CN109847715A (zh) * | 2018-12-05 | 2019-06-07 | 广东工业大学 | 一种酰胺基团改性聚苯乙烯系超高交联吸附树脂的制备方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1320483A (zh) * | 2000-04-24 | 2001-11-07 | 邓佑 | 一种离子交换器 |
WO2009076627A2 (en) * | 2007-12-12 | 2009-06-18 | Archer Daniels Midland Co | Conversion of carbohydrates to hydroxy-methylfurfural (hmf) and derivatives |
CN102336856A (zh) * | 2011-07-04 | 2012-02-01 | 常州大学 | 一种特效硼吸附树脂、合成方法及应用 |
CN102459214A (zh) * | 2009-05-14 | 2012-05-16 | 阿彻丹尼尔斯米德兰德公司 | 糠醛化合物的氧化 |
CN104334537A (zh) * | 2012-06-22 | 2015-02-04 | 伊士曼化工公司 | 通过加氢对粗呋喃2,5-二甲酸的纯化 |
WO2015041601A1 (en) * | 2013-09-20 | 2015-03-26 | Agency For Science, Technology And Research | Conversion and purification of biomass |
CN104496946A (zh) * | 2014-11-28 | 2015-04-08 | 林康艺 | 一种从二甲亚砜溶液中提纯2,5-呋喃二甲醛的方法 |
-
2016
- 2016-04-26 CN CN201610260021.6A patent/CN105753819B/zh not_active Expired - Fee Related
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1320483A (zh) * | 2000-04-24 | 2001-11-07 | 邓佑 | 一种离子交换器 |
WO2009076627A2 (en) * | 2007-12-12 | 2009-06-18 | Archer Daniels Midland Co | Conversion of carbohydrates to hydroxy-methylfurfural (hmf) and derivatives |
CN102459214A (zh) * | 2009-05-14 | 2012-05-16 | 阿彻丹尼尔斯米德兰德公司 | 糠醛化合物的氧化 |
CN102336856A (zh) * | 2011-07-04 | 2012-02-01 | 常州大学 | 一种特效硼吸附树脂、合成方法及应用 |
CN104334537A (zh) * | 2012-06-22 | 2015-02-04 | 伊士曼化工公司 | 通过加氢对粗呋喃2,5-二甲酸的纯化 |
WO2015041601A1 (en) * | 2013-09-20 | 2015-03-26 | Agency For Science, Technology And Research | Conversion and purification of biomass |
CN104496946A (zh) * | 2014-11-28 | 2015-04-08 | 林康艺 | 一种从二甲亚砜溶液中提纯2,5-呋喃二甲醛的方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107011385A (zh) * | 2016-08-21 | 2017-08-04 | 王琪宇 | 一种六氯环三磷腈提纯助剂的制备方法 |
CN109847715A (zh) * | 2018-12-05 | 2019-06-07 | 广东工业大学 | 一种酰胺基团改性聚苯乙烯系超高交联吸附树脂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN105753819B (zh) | 2018-06-08 |
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Address after: 432000 Hubei city of Xiaogan province high tech Zone Qun Sheng Cun Nan Qu Bian min Lu 5 floor, room 91 Applicant after: Zhang Ling Address before: 432000 Hubei city of Xiaogan province high tech Zone Danyang District Community Lisi mall two Room 201 Applicant before: Zhang Ling |
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Address after: 432000, 11 business street, Danyang office, hi tech Zone, Hubei, Xiaogan Applicant after: Zhang Ling Address before: 432000 Hubei city of Xiaogan province high tech Zone Qun Sheng Cun Nan Qu Bian min Lu 5 floor, room 91 Applicant before: Zhang Ling |
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Address after: Binwang zipper street 322000 Yiwu city in Zhejiang province Jinhua city 5 District No. 3 room 602 Applicant after: Zhang Ling Address before: 432000, 11 business street, Danyang office, hi tech Zone, Hubei, Xiaogan Applicant before: Zhang Ling |
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TR01 | Transfer of patent right |
Effective date of registration: 20211117 Address after: 157614 Liu Shu Zhen Fu Xing Cun, Linkou County, Mudanjiang City, Heilongjiang Province Patentee after: Linkou Senhao furfural Co.,Ltd. Address before: 322000 Room 602, No. 3, 5 District, Binwang Zipper Street, Yiwu City, Jinhua City, Zhejiang Province Patentee before: Zhang Ling |
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Granted publication date: 20180608 |
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