CN105906587A - Method for purifying 2,5-dihydroxymethylfuran - Google Patents
Method for purifying 2,5-dihydroxymethylfuran Download PDFInfo
- Publication number
- CN105906587A CN105906587A CN201610256466.7A CN201610256466A CN105906587A CN 105906587 A CN105906587 A CN 105906587A CN 201610256466 A CN201610256466 A CN 201610256466A CN 105906587 A CN105906587 A CN 105906587A
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- Prior art keywords
- fdm
- reaction
- adsorbent
- purification
- alcohol
- 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 19
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 title abstract 4
- 239000003463 adsorbent Substances 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000008367 deionised water Substances 0.000 claims abstract description 6
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 6
- 238000001179 sorption measurement Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000000746 purification Methods 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000012264 purified product Substances 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 2
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007278 cyanoethylation reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material 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
- C07D307/42—Singly bound oxygen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
Abstract
The invention provides a method for purifying 2,5-dihydroxymethylfuran. The method comprises the following steps: mixing industrial grade 2,5-dihydroxymethylfuran with deionized water at a suitable temperature, allowing the obtained solution to go through a chromatography column provided with an adsorbent at a suitable temperature and a suitable flow velocity to carry out adsorption, and dehydrating the obtained solution to obtain a purified 2,5-dihydroxymethylfuran product.
Description
Technical field
A kind of method that the present invention relates to purification, a kind of method of 2,5-FDM purification.
Background technology
2,5-FDM outward appearance is white or interior white solid, be dissolved in water, ethanol, acetone, pyridine,
Oxolane, insoluble in ethane, toluene, dichloroethanes.Chemical property: there is the character of dihydroxylic alcohols.Energy
Esterification, alkoxide, glycidyl ether, cyanoethylation, etherificate, urethane, resinification etc..Furfural is
The impurity such as 2,5-FDM prepared by raw material, and product contains the acid of trace, alcohol, need to purify further.
CN101941958A discloses a kind of method preparing 5-HMFA and 2,5-FDM.Should
Method is to be reacted through Connizzaro (Cannizzaro) by 5 hydroxymethyl furfural (5-HMF), can prepare simultaneously
5-HMFA and 2,5-FDM.Method before Xiang Dui, the present invention is not only without extra oxidation
The metallic catalyst of agent, reducing agent and costliness, and it is cheap to produce equipment requirements, production technology safety, simultaneously
This reaction condition is gentle, and reaction efficiency is high, and atom economy obtains two kinds of products simultaneously, meets current Green Chemistry
The requirement that technique and product diversification produce.2,5-FDM method of purification uses the method for distillation to remove
Remove solvent.
CN1546480 discloses the preparation method of a kind of 5-alkyl-2-furfural alcohol.By 2-furancarbinol and gold
Belong to alkyl reagent (RM) react in oxolane, reaction temperature is-30 DEG C～60 DEG C, the response time be 0.5～
5h.Being slowly added into metal halide (M ' X) and halogenated alkane (R ' X) after completion of the reaction, reaction temperature is
-50 DEG C～40 DEG C, the response time is 0.5～6h.Again after acidic hydrolysis, with ether or dichloromethane, benzene,
Toluene equal solvent extracts, and boils off solvent, and product 5-alkyl-2-furfural alcohol shown in title is distilled to obtain in decompression.Whole
Reaction intermediate is not required to separate, purify, and uses " one kettle way " to produce, and easy and simple to handle, the three wastes are few, have substantially
Industrial production prospect.
The method purifying 2,5-FDM reported in document at present, by extraction, distillation etc. purifies
Method, consumes a large amount of organic solvent, needs to be optimized.
Summary of the invention
Present invention aim at solving above-mentioned technical problem present in prior art, it is provided that a kind of 2,5-furan
The method of dimethanol purification.
The method of a kind of 2,5-FDM purification of the present invention, is prepared by following steps:
The preparation of step 1. adsorbent:
Add 100 parts of hydrogen bond type selective adsorption resins, 1-10 part maleics two the most by weight
Diethyl phthalate, 0.1-1 part 2-methyl-4-(2,2,3-trimethyl-3-cyclopentenes-1-base)-2-butylene-1-alcohol,
500-1000 part water, 1-4 part polyvinyl alcohol, 0.5-2 part benzoyl peroxide, heats up after 80 DEG C of reaction 6h
To 85 DEG C of reaction 2h, then it is warming up to 95 DEG C of reaction 6h, filters, after drying, obtain adsorbent；
Step 2. absorption purification 2,5-FDM:
By weight, 100 parts of technical grade 2,5-FDMs, 500-2000 part deionized water 80～
Mix 1-5h under the conditions of 100 DEG C, through adsorbing equipped with in the chromatographic column of adsorbent, temperature 80～
100 DEG C, flow velocity 1-5BV/h, then through dehydration, available 2,5-FDM purified product.
Described hydrogen bond type selective adsorption resin is commercially available prod, such as Tianjin Nankai Hecheng S&T Co., Ltd.
Polar Adsorbent Resin in the ADS-17 produced；2-methyl-4-(2,2,3-trimethyl-3-cyclopentenes-1-base)-2-
Butene-1-ol is commercially available prod, the product produced such as Hubei Ju Sheng Science and Technology Ltd..
Described 2,5-FDM, diethyl maleate, polyvinyl alcohol, benzoyl peroxide is
Commercially available prod.
Compared with prior art, catalyst of the present invention and preparation method thereof, have the advantages that
Nonpolar hydrogen bond type selective adsorption resin can form hydrogen bond with furancarboxylic acid molecule, shows the most affine
Selectivity, introduces the carbonyl of diethyl maleate, 2-methyl-4-(2,2,3-trimethyl-3-on its surface
Cyclopentenes-1-base) hydroxyl functional group of-2-butylene-1-alcohol, improve in technical grade 2,5-FDM
Acids impurity and the absorbability of hydroxyl impurity, the 2 of available weight/mass percentage composition the highest 99.9%, 5-furan
Mutter dimethanol product.
Detailed description of the invention
Following instance only further illustrates the present invention, is not to limit the scope of protection of the invention.
Technical grade 2,5-FDM in embodiment, mass percentage content 95.3%.
Embodiment 1:
The preparation of step 1. adsorbent:
Polar Adsorbent Resin, 5Kg maleic acid diethyl in 100KgADS-17 is added in 2000L reactor
Ester, 0.5Kg2-methyl-4-(2,2,3-trimethyl-3-cyclopentenes-1-base)-2-butylene-1-alcohol, 700Kg water,
2Kg polyvinyl alcohol, 1Kg benzoyl peroxide, after 80 DEG C of reaction 6h, it is warming up to 85 DEG C of reaction 2h, then heats up
To 95 DEG C of reaction 6h, filter, after drying, obtain adsorbent；
Step 2. absorption purification 2,5-FDM:
By 100Kg technical grade 2,5-FDM, 1000Kg deionized water mixes 3h under the conditions of 90 DEG C,
Adsorb in the chromatographic column of dress row adsorbent, temperature 90 DEG C, flow velocity 3BV/h, then through dehydration, can obtain
To 2,5-FDM purified product.In product, 2,5-FDM weight/mass percentage composition is shown in Table 1.
Embodiment 2:
The preparation of step 1. adsorbent:
Polar Adsorbent Resin, 1Kg maleic acid diethyl in 100KgADS-17 is added in 2000L reactor
Ester, 0.1Kg2-methyl-4-(2,2,3-trimethyl-3-cyclopentenes-1-base)-2-butylene-1-alcohol, 500Kg water,
1Kg polyvinyl alcohol, 0.5Kg benzoyl peroxide, after 80 DEG C of reaction 6h, it is warming up to 85 DEG C of reaction 2h, then rises
Temperature, to 95 DEG C of reaction 6h, filters, obtains adsorbent after drying；
Step 2. absorption purification 2,5-FDM:
By 100Kg technical grade 2,5-FDM, 500Kg deionized water mixes 1h under the conditions of 90 DEG C, warp
Cross and adsorb equipped with in the chromatographic column of adsorbent, temperature 80 DEG C, flow velocity 1BV/h, then through dehydration, available
2,5-FDM purified product.In product, 2,5-FDM weight/mass percentage composition is shown in Table 1.
Embodiment 3
The preparation of step 1. adsorbent:
Polar Adsorbent Resin, 10Kg maleic acid diethyl in 100KgADS-17 is added in 2000L reactor
Ester, 1Kg2-methyl-4-(2,2,3-trimethyl-3-cyclopentenes-1-base)-2-butylene-1-alcohol, 1000Kg water,
4Kg polyvinyl alcohol, 2Kg benzoyl peroxide, after 80 DEG C of reaction 6h, it is warming up to 85 DEG C of reaction 2h, then heats up
To 95 DEG C of reaction 6h, filter, after drying, obtain adsorbent；
Step 2. absorption purification 2,5-FDM:
By 100Kg technical grade 2,5-FDM, 2000Kg deionized water mixes 1h under the conditions of 90 DEG C,
Through adsorbing equipped with in the chromatographic column of adsorbent, temperature 100 DEG C, flow velocity 5BV/h, then through dehydration, can obtain
To 2,5-FDM purified product.In product, 2,5-FDM weight/mass percentage composition is shown in Table 1.
Comparative example 1
It is added without diethyl maleate, the other the same as in Example 1.2,5-FDM weight/mass percentage composition
It is shown in Table 1.
Comparative example 2
Being added without 2-methyl-4-(2,2,3-trimethyl-3-cyclopentenes-1-base)-2-butylene-1-alcohol, other is with real
Execute example 1.2,5-FDM weight/mass percentage composition is shown in Table 1.
Comparative example 3
Removing step 1, adsorbent uses activated carbon, the other the same as in Example 1.2,5-FDM quality hundred
Content is divided to be shown in Table 1.
2,5-FDM matter after gas chromatographic detection, embodiment 1-3 and comparative example 1-5 purify
Amount percentage composition be relatively shown in Table 1:
Table 1: the comparison of 2,5-FDM weight/mass percentage composition after the test specimen absorption that different process is made
| Numbering | 2,5-FDM weight/mass percentage composition % |
| Embodiment 1 | 99.6 |
| Embodiment 2 | 99.4 |
| Embodiment 3 | 99.9 |
| Comparative example 1 | 98.5 |
| Comparative example 2 | 98.8 |
| Comparative example 3 | 97.2 |
These are only the specific embodiment of the present invention, but the technical characteristic of the present invention is not limited thereto.Any
Based on the present invention, for solving essentially identical technical problem, it is achieved essentially identical technique effect, institute
Simple change, equivalent or the modifications etc. made, are all covered by among protection scope of the present invention.
Claims (1)
1. the method for a 2,5-FDM purification, it is characterised in that comprise the following steps:
The preparation of step 1. adsorbent:
Add 100 parts of hydrogen bond type selective adsorption resins, 1-10 part maleics two the most by weight
Diethyl phthalate, 0.1-1 part 2-methyl-4-(2,2,3-trimethyl-3-cyclopentenes-1-base)-2-butylene-1-alcohol,
500-1000 part water, 1-4 part polyvinyl alcohol, 0.5-2 part benzoyl peroxide, heats up after 80 DEG C of reaction 6h
To 85 DEG C of reaction 2h, then it is warming up to 95 DEG C of reaction 6h, filters, after drying, obtain adsorbent；
Step 2. absorption purification 2,5-FDM:
By weight, 100 parts of technical grade 2,5-FDMs, 500-2000 part deionized water 80～
Mix 1-5h under the conditions of 100 DEG C, through adsorbing equipped with in the chromatographic column of adsorbent, temperature 80～
100 DEG C, flow velocity 1-5BV/h, then through dehydration, available 2,5-FDM purified product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610256466.7A CN105906587B (en) | 2016-04-25 | 2016-04-25 | A kind of method of 2,5 furyl dimethyl carbinol purifying |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610256466.7A CN105906587B (en) | 2016-04-25 | 2016-04-25 | A kind of method of 2,5 furyl dimethyl carbinol purifying |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105906587A true CN105906587A (en) | 2016-08-31 |
| CN105906587B CN105906587B (en) | 2017-12-26 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101444720A (en) * | 2008-11-28 | 2009-06-03 | 南开大学 | High selective hydrogen bond absorption resin and separation and purification for effective components in folium ginkgo extract |
| WO2009076627A2 (en) * | 2007-12-12 | 2009-06-18 | Archer Daniels Midland Co | Conversion of carbohydrates to hydroxy-methylfurfural (hmf) and derivatives |
| CN102459214A (en) * | 2009-05-14 | 2012-05-16 | 阿彻丹尼尔斯米德兰德公司 | Oxidation of furfural compounds |
| CN104334537A (en) * | 2012-06-22 | 2015-02-04 | 伊士曼化工公司 | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
| WO2015041601A1 (en) * | 2013-09-20 | 2015-03-26 | Agency For Science, Technology And Research | Conversion and purification of biomass |
-
2016
- 2016-04-25 CN CN201610256466.7A patent/CN105906587B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009076627A2 (en) * | 2007-12-12 | 2009-06-18 | Archer Daniels Midland Co | Conversion of carbohydrates to hydroxy-methylfurfural (hmf) and derivatives |
| CN101444720A (en) * | 2008-11-28 | 2009-06-03 | 南开大学 | High selective hydrogen bond absorption resin and separation and purification for effective components in folium ginkgo extract |
| CN102459214A (en) * | 2009-05-14 | 2012-05-16 | 阿彻丹尼尔斯米德兰德公司 | Oxidation of furfural compounds |
| CN104334537A (en) * | 2012-06-22 | 2015-02-04 | 伊士曼化工公司 | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
| WO2015041601A1 (en) * | 2013-09-20 | 2015-03-26 | Agency For Science, Technology And Research | Conversion and purification of biomass |
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| Publication number | Publication date |
|---|---|
| CN105906587B (en) | 2017-12-26 |
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