CN105906587B - A kind of method of 2,5 furyl dimethyl carbinol purifying - Google Patents
A kind of method of 2,5 furyl dimethyl carbinol purifying Download PDFInfo
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- CN105906587B CN105906587B CN201610256466.7A CN201610256466A CN105906587B CN 105906587 B CN105906587 B CN 105906587B CN 201610256466 A CN201610256466 A CN 201610256466A CN 105906587 B CN105906587 B CN 105906587B
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- 238000000034 method Methods 0.000 title claims abstract description 18
- -1 furyl dimethyl carbinol Chemical compound 0.000 title abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title abstract 3
- 239000003463 adsorbent Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012264 purified product Substances 0.000 claims abstract description 4
- 239000008367 deionised water Substances 0.000 claims abstract description 3
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000746 purification Methods 0.000 claims description 10
- 238000010792 warming Methods 0.000 claims description 10
- OHIIGLSGZTXTBM-UHFFFAOYSA-N 1,5,5-trimethylcyclopentene Chemical compound CC1=CCCC1(C)C OHIIGLSGZTXTBM-UHFFFAOYSA-N 0.000 claims description 8
- 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
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical class CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-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
- 238000001035 drying Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 abstract description 5
- 238000006297 dehydration reaction Methods 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000012535 impurity Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 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
- 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
- 239000002184 metal Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 239000004342 Benzoyl peroxide Substances 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
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids 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
- 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
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical class CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 238000007278 cyanoethylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 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
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 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
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a kind of method of 2,5 furyl dimethyl carbinols purifying：After the furyl dimethyl carbinol of technical grade 2,5 and deionized water are mixed under preference temperature, under preference temperature and flow velocity, it is made by being adsorbed in the chromatographic column equipped with adsorbent, then through dehydration, obtain 2,5 furyl dimethyl carbinol purified products.
Description
Technical field
The present invention relates to a kind of method of purification, particularly a kind of method of 2,5-FDM purifying.
Background technology
2,5-FDM outward appearance is white or interior white solid, is dissolved in water, ethanol, acetone, pyridine, tetrahydrofuran,
Insoluble in ethane, toluene, dichloroethanes.Chemical property：Property with dihydric alcohol.Can esterification, alkoxide, glycidol ether
Change, cyanoethylation, etherificate, urethane, resinification etc..Furfural is that raw material prepares 2,5-FDM, and product contains micro
The impurity such as acid, alcohol are, it is necessary to further purify.
CN101941958A discloses a kind of method for preparing 5-HMFA and 2,5-FDM.This method is
By 5 hydroxymethyl furfural (5-HMF) through Connizzaro (Cannizzaro) react, can be prepared simultaneously 5-HMFA and
2,5-FDM.Method before relative, the not only metal without extra oxidant, reducing agent and costliness of the invention
Catalyst, and production equipment requires cheap, production technology safety, while the reaction condition is gentle, reaction efficiency is high, atom warp
Ji, while two kinds of products are obtained, meet the requirement of current green chemistry process and product diversification production.2,5- furans diformazans
Alcohol method of purification removes solvent using the method for distillation.
CN1546480 discloses a kind of preparation method of 5- alkyl-2-furfural alcohols.By 2- furancarbinols and metal alkyl
Reagent (RM) reacts in tetrahydrofuran, and reaction temperature is -30 DEG C~60 DEG C, and the reaction time is 0.5~5h.After completion of the reaction
It is slowly added into metal halide (M ' X) and halogenated alkane (R ' X), reaction temperature is -50 DEG C~40 DEG C, the reaction time is 0.5~
6h.Again after acidic hydrolysis, extracted with ether or dichloromethane, benzene, toluene equal solvent, boil off solvent, be evaporated under reduced pressure to title
Shown product 5- alkyl-2-furfural alcohols.Whole reaction intermediate is not required to separate, purified, and is produced using " one kettle way ", operation letter
Just, the three wastes are few, have obvious industrial production prospect.
The method for the purification 2,5-FDM reported at present in document, by extraction, the method for purification such as distillation, disappear
A large amount of organic solvents are consumed, it is necessary to optimize.
The content of the invention
Present invention aims at solve above-mentioned technical problem present in prior art, there is provided a kind of 2,5-FDM
The method of purifying.
A kind of method of 2,5-FDM purifying 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 parts maleic acid two by weight in a kettle
Ethyl ester, 0.1-1 part 2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -2- butene-1-ols, 500-1000 part water,
1-4 part polyvinyl alcohol, 0.5-2 part benzoyl peroxides, 85 DEG C of reaction 2h are warming up to after reacting 6h at 80 DEG C, then are warming up to 95 DEG C
6h is reacted, filtering, adsorbent is obtained after drying；
Step 2. absorption purification 2,5-FDM：
By weight, 100 parts of technical grade 2,5-FDMs, 500-2000 parts deionized water is in 80~100 DEG C of bars
1-5h is mixed under part, by being adsorbed in the chromatographic column equipped with adsorbent, 80~100 DEG C, flow velocity 1-5BV/h of temperature, then
Through dehydration, 2,5-FDM purified product can obtain.
Described hydrogen bond type selective adsorption resin is commercially available prod, as Tianjin Nankai Hecheng S＆T Co., Ltd. produces
Polar Adsorbent Resin in ADS-17；2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -2- butene-1-ols are commercially available
Product, the product produced such as Hubei Ju Sheng Science and Technology Ltd.s.
Described 2,5-FDM, diethyl maleate, polyvinyl alcohol, benzoyl peroxide are commercially available production
Product.
Compared with prior art, catalyst of the invention and preparation method thereof, has the advantages that：
Nonpolar hydrogen bond type selective adsorption resin can form hydrogen bond with furancarboxylic acid molecule, show significant affine selection
Property, its surface introduce diethyl maleate carbonyl, 2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -
The hydroxyl functional group of 2- butene-1-ols, improve to acids impurity in technical grade 2,5-FDM and hydroxyl impurity
Adsorption capacity, it can obtain the 2,5-FDM product of weight/mass percentage composition highest 99.9%.
Embodiment
Following instance is only to further illustrate the present invention, is not limitation 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 diethyl maleates in 100KgADS-17 are added in 2000L reactors,
0.5Kg2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -2- butene-1-ols, 700Kg water, 2Kg polyvinyl alcohol,
1Kg benzoyl peroxides, 85 DEG C of reaction 2h are warming up to after reacting 6h at 80 DEG C, then are warming up to 95 DEG C of reaction 6h, filtering, after drying
Obtain adsorbent；
Step 2. absorption purification 2,5-FDM：
By 100Kg technical grade 2,5-FDMs, 1000Kg deionized waters mix 3h under the conditions of 90 DEG C, by dress
Adsorbed in the chromatographic column of row adsorbent, 90 DEG C, flow velocity 3BV/h of temperature, then through dehydration, it is pure to can obtain 2,5-FDM
Change product.2,5-FDM weight/mass percentage composition is shown in Table 1 in product.
Embodiment 2：
The preparation of step 1. adsorbent：
Polar Adsorbent Resin, 1Kg diethyl maleates in 100KgADS-17 are added in 2000L reactors,
0.1Kg2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -2- butene-1-ols, 500Kg water, 1Kg polyvinyl alcohol,
0.5Kg benzoyl peroxides, 85 DEG C of reaction 2h are warming up to after reacting 6h at 80 DEG C, then are warming up to 95 DEG C of reaction 6h, filtered, drying
After obtain adsorbent；
Step 2. absorption purification 2,5-FDM：
By 100Kg technical grade 2,5-FDMs, 500Kg deionized waters mix 1h under the conditions of 90 DEG C, by equipped with
Adsorbed in the chromatographic column of adsorbent, 80 DEG C, flow velocity 1BV/h of temperature, then through dehydration, it is pure to can obtain 2,5-FDM
Change product.2,5-FDM weight/mass percentage composition is shown in Table 1 in product.
Embodiment 3
The preparation of step 1. adsorbent：
Polar Adsorbent Resin, 10Kg diethyl maleates in 100KgADS-17 are added in 2000L reactors,
1Kg2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -2- butene-1-ols, 1000Kg water, 4Kg polyvinyl alcohol,
2Kg benzoyl peroxides, 85 DEG C of reaction 2h are warming up to after reacting 6h at 80 DEG C, then are warming up to 95 DEG C of reaction 6h, filtering, after drying
Obtain adsorbent；
Step 2. absorption purification 2,5-FDM：
By 100Kg technical grade 2,5-FDMs, 2000Kg deionized waters mix 1h under the conditions of 90 DEG C, by dress
Have in the chromatographic column of adsorbent and adsorbed, 100 DEG C, flow velocity 5BV/h of temperature, then through dehydration, can obtain 2,5-FDM
Purified product.2,5-FDM weight/mass percentage composition is shown in Table 1 in product.
Comparative example 1
It is added without diethyl maleate, the other the same as in Example 1.2,5-FDM weight/mass percentage composition is shown in Table 1.
Comparative example 2
It is added without 2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -2- butene-1-ols, other same embodiments
1.2,5-FDM weight/mass percentage composition is shown in Table 1.
Comparative example 3
Remove step 1, adsorbent uses activated carbon, the other the same as in Example 1.2,5-FDM weight/mass percentage composition is shown in
Table 1.
By gas chromatographic detection, embodiment 1-3 and comparative example 1-5 purification after 2,5-FDM quality percentage contain
The comparison of amount is 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 |
The specific embodiment of the present invention is these are only, but the technical characteristic of the present invention is not limited thereto.It is any with this hair
Based on bright, to solve essentially identical technical problem, essentially identical technique effect is realized, made simple change, etc.
With replacement or modification etc., all it is covered by among protection scope of the present invention.
Claims (1)
- A kind of 1. method of 2,5-FDM purifying, it is characterised in that comprise the following steps：The preparation of step 1. adsorbent：Add Polar Adsorbent Resin, 1-10 part diethyl maleates in 100 parts of ADS-17 by weight in a kettle, 0.1-1 part 2- methyl -4- (2,2,3- trimethyl -3- cyclopentene -1- bases) -2- butene-1-ols, 500-1000 part water, 1-4 parts Polyvinyl alcohol, 0.5-2 part benzoyl peroxides, 85 DEG C of reaction 2h are warming up to after reacting 6h at 80 DEG C, then are warming up to 95 DEG C of reactions 6h, filtering, adsorbent is obtained after drying；Step 2. absorption purification 2,5-FDM：By weight, 100 parts of technical grade 2,5-FDMs, 500-2000 parts deionized water is under the conditions of 80~100 DEG C 1-5h is mixed, by being adsorbed in the chromatographic column equipped with adsorbent, 80~100 DEG C, flow velocity 1-5BV/h of temperature, then through de- Water, it can obtain 2,5-FDM purified product.
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| CN201610256466.7A CN105906587B (en) | 2016-04-25 | 2016-04-25 | A kind of method of 2,5 furyl dimethyl carbinol purifying |
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| CN201610256466.7A CN105906587B (en) | 2016-04-25 | 2016-04-25 | A kind of method of 2,5 furyl dimethyl carbinol purifying |
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Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2423205B9 (en) * | 2007-12-12 | 2020-03-18 | Archer-Daniels-Midland Company | Conversion of carbohydrates to hydroxymethylfurfural (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 |
| ES2542972T3 (en) * | 2009-05-14 | 2015-08-13 | Archer Daniels Midland Company | Oxidation of furfural compounds |
| US8969404B2 (en) * | 2012-06-22 | 2015-03-03 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
| EP3046913A4 (en) * | 2013-09-20 | 2017-10-25 | Agency For Science, Technology And Research | Conversion and purification of biomass |
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