CN109020931A - A kind of method that SAPO-34 catalysis xylan prepares furfural and solvent recovery - Google Patents
A kind of method that SAPO-34 catalysis xylan prepares furfural and solvent recovery Download PDFInfo
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- CN109020931A CN109020931A CN201810965323.2A CN201810965323A CN109020931A CN 109020931 A CN109020931 A CN 109020931A CN 201810965323 A CN201810965323 A CN 201810965323A CN 109020931 A CN109020931 A CN 109020931A
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- China
- Prior art keywords
- furfural
- sapo
- xylan
- valerolactone
- reaction
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 229920001221 xylan Polymers 0.000 title claims abstract description 20
- 150000004823 xylans Chemical class 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000002904 solvent Substances 0.000 title claims abstract description 11
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 7
- 238000011084 recovery Methods 0.000 title claims abstract description 6
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 238000004064 recycling Methods 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000010926 purge Methods 0.000 claims description 4
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002028 Biomass Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 239000012429 reaction media Substances 0.000 abstract description 2
- 230000004913 activation Effects 0.000 abstract 1
- 238000000895 extractive distillation Methods 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 8
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 229920002488 Hemicellulose Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- CDVZCUKHEYPEQS-FOASUZNUSA-N (2s,3r,4r)-2,3,4,5-tetrahydroxypentanal;(2r,3s,4r)-2,3,4,5-tetrahydroxypentanal Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C=O CDVZCUKHEYPEQS-FOASUZNUSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- -1 hydroxyl furfurol Chemical compound 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000012978 lignocellulosic material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/82—Phosphates
- B01J29/84—Aluminophosphates containing other elements, e.g. metals, boron
- B01J29/85—Silicoaluminophosphates [SAPO compounds]
-
- 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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Furan Compounds (AREA)
Abstract
The invention belongs to biomass chemical field, in particular to a kind of method that SAPO-34 catalysis xylan prepares furfural and solvent recovery.This method mainly comprises the steps that xylan and SAPO-34 are added in reaction kettle by a certain percentage, add gamma-valerolactone/aqueous solution, in 150~230 DEG C of temperature ranges, react 0.5~10h, then mixture after reaction is filtered separation, liquid portion obtains target product furfural by the method for vacuum distillation.MgCl is added2Raffinate part after extractive distillation, recycling design gamma-valerolactone.Use gamma-valerolactone for reaction medium, the activation energy that xylan is converted into during furfurol reaction can be changed, conducive to the generation of furfural, improve furfural yield, this method uses SAPO-34 for catalyst, have the advantages that stable property, catalyzing hydrolysis and dehydration performance are high and reproducible, there is good industrial applications prospect.
Description
Technical field
The invention belongs to biomass chemical field, in particular to a kind of SAPO-34 catalysis xylan prepares furfural and solvent
The method of recycling, this method use SAPO-34 for catalyst, and gamma-valerolactone is reaction dissolvent, under relatively mild reaction condition
Higher furfural yield is obtained, this reaction system has the characteristics that efficient green.
Background technique
Furfural is a kind of platform chemicals by lignocellulose biomass for raw material preparation.The response path of preparation is wood
Hemicellulose component in matter cellulose biomass generates pentose (xylose arabinose) by hydrolysis under the action of catalyst, wood
Isomerization reaction occurs for sugar, and then xylose sloughs trihyarol and generates furfural.
Industrially furfural using very extensive, closed using furfural and furfural derivatives as raw material by furfuryl alcohol condensation reaction
At alkane.Furfural synthesizes furfuryl alcohol by hydrogenation reaction, and furfuryl alcohol can be used as the preparation that solvent can apply to resin again.2- methyl
Tetrahydrofuran is prepared by furfural and hydroxyl furfurol reaction.2- methyltetrahydrofuran energy density is about the two of ethyl alcohol
Times, calorific value is higher than ethyl alcohol.Therefore, 2- methyltetrahydrofuran is a kind of bio-fuel, is the substitute of tetrahydrofuran.
Gamma-valerolactone (GVL) is applied in the reaction process that biomass is converted into platform chemicals, is ideal sustainable
Petroleum derived solvents substitute.GVL has the advantage that and is in a liquid state under (1) GVL room temperature that GVL has lower fusing point,
It is -31 DEG C, it is 96 DEG C that higher boiling point, which is 207 DEG C, and flash-point is higher；(2) there is condition existing for water or oxygen under room temperature
Under, GVL stability with higher.It (3) is reaction medium relative to water, GVL improves the dehydration rate of xylose, reduces
The degradation rate of furfural, GVL make the reaction activity in hemicellulose conversion process change, and promote reaction to being conducive to chaff
The direction of the generation of aldehyde occurs；(4) since the boiling point of GVL is much higher than the boiling point of furfural, rotation can be passed through under high temperature (137 DEG C)
The method separation furfural and GVL for turning evaporation, reduce the loss of furfural.
Domestic furfural production technology is about by the furfural yield of raw material of corncob using " one-step method " at present
45%, every 1 ton of furfural of preparation expends about 20 tons of steam, forms about 24 tons of the high pollution waste water containing a large amount of inorganic acids.In addition,
Cellulose and lignin utilization rate in lignocellulosic material is low, and waste residue produced during the preparation process, waste water, exhaust gas cause sternly
The environmental pollution of weight.Therefore, to solve these problems, need to develop a kind of furfural preparation of green high-efficient.
Summary of the invention
The purpose of the present invention is overcoming the shortcomings of existing furfural production technology, a kind of conversion xylan of green high-efficient is developed
For the reaction system of furfural.
Technical solution of the present invention is summarized as follows:
(1) xylan and SAPO-34 are added in reaction kettle according to mass ratio for 1: 10~10: 1；
(2) 5~100 times of xylan quality of gamma-valerolactone/aqueous solution is added to reaction kettle, is purged with high pure nitrogen anti-
After answering kettle 4~6 times, reacting kettle inner pressure is adjusted to 5~8MPa, at 150~230 DEG C and under stirring, reacts 0.5~10h；
(3) mixture in reaction kettle is cooled to 55~60 DEG C after reaction, is then separated by solid-liquid separation, liquid portion
Divide and be evaporated under reduced pressure within the scope of 95~120 DEG C at 0.1MPa, obtains furfural；
(4) MgCl is added in the raffinate part after distilling2, then ultrasonic vibration 2h is centrifuged under the conditions of 6000rpm
15min arrives recycling design gamma-valerolactone using the water in disposable plastic dropper removal mixed liquor.
Catalyst SAPO-34 used in above-mentioned furfural preparation step is synthesized using hydro-thermal method.
Reaction dissolvent used in above-mentioned furfural preparation step is gamma-valerolactone/aqueous solution, the body of gamma-valerolactone and water
Product is than being 1: 20~20: 1.
Remarkable advantage of the invention is:
Furfural is produced using the method, reaction condition is mild, furfural yield is high.Catalyst SAPO-34 can regenerate and
It is recycled, solvent gamma-valerolactone is a kind of green solvent, and can be recycled, and generation during furfural production is greatly reduced
Waste water, with good application prospect.
Specific embodiment
It will come that the present invention is described in further detail with specific embodiment below, but protection scope of the present invention is not
It is confined to these specific examples.
Embodiment 1:
(1) xylan and SAPO-34 are added in reaction kettle according to mass ratio for 1: 5；
(2) 10 times of xylan quality of gamma-valerolactone/aqueous solution is added to reaction kettle, purges reaction kettle 5 with high pure nitrogen
After secondary, reacting kettle inner pressure is adjusted to 6MPa, at 160 DEG C and under stirring, reacts 1h；
(3) mixture in reaction kettle is cooled to 56 DEG C after reaction, is then separated by solid-liquid separation, liquid portion exists
It is evaporated under reduced pressure under the conditions of 0.1MPa and 100 DEG C, obtains furfural；
(4) MgCl is added in the raffinate part after distilling2, then ultrasonic vibration 2h is centrifuged under the conditions of 6000rpm
15min arrives recycling design gamma-valerolactone using the water in disposable plastic dropper removal mixed liquor.
Embodiment 2:
(1) xylan and SAPO-34 are added in reaction kettle according to mass ratio for 1: 1；
(2) 20 times of xylan quality of gamma-valerolactone/aqueous solution is added to reaction kettle, purges reaction kettle 5 with high pure nitrogen
After secondary, reacting kettle inner pressure is adjusted to 6MPa, at 180 DEG C and under stirring, reacts 2h；
(3) mixture in reaction kettle is cooled to 58 DEG C after reaction, is then separated by solid-liquid separation, liquid portion exists
It is evaporated under reduced pressure under the conditions of 0.1MPa and 115 DEG C, obtains furfural；
(4) MgCl is added in the raffinate part after distilling2, then ultrasonic vibration 2h is centrifuged under the conditions of 6000rpm
15min arrives recycling design gamma-valerolactone using the water in disposable plastic dropper removal mixed liquor.
Embodiment 3:
(1) xylan and SAPO-34 are added in reaction kettles according to mass ratio for 5: 1；
(2) 30 times of xylan quality of gamma-valerolactone/aqueous solution is added to reaction kettle, purges reaction kettle 5 with high pure nitrogen
After secondary, reacting kettle inner pressure is adjusted to 6MPa, at 200 DEG C and under stirring, reacts 5h；
(3) mixture in reaction kettle is cooled to 59 DEG C after reaction, is then separated by solid-liquid separation, liquid portion exists
0.1MPa and 118 DEG C of condition is evaporated under reduced pressure, and furfural is obtained；
(4) MgCl is added in the raffinate part after distilling2, then ultrasonic vibration 2h is centrifuged under the conditions of 6000rpm
15min arrives recycling design gamma-valerolactone using the water in disposable plastic dropper removal mixed liquor.
Claims (3)
1. a kind of method that SAPO-34 catalysis xylan prepares furfural and solvent recovery, it is characterized in that including following characterization step:
(1) xylan and SAPO-34 are added in reaction kettle according to mass ratio for 1: 10~10: 1；
(2) 5~100 times of xylan quality of gamma-valerolactone/aqueous solution is added to reaction kettle, purges reaction kettle 4 with high pure nitrogen
After~6 times, reacting kettle inner pressure is adjusted to 5~8MPa, at 150~230 DEG C and under stirring, reacts 0.5~10h；
(3) mixture in reaction kettle is cooled to 55~60 DEG C after reaction, is then separated by solid-liquid separation, liquid portion exists
It is evaporated under reduced pressure within the scope of 95~120 DEG C under 0.1MPa, obtains furfural；
(4) MgCl is added in the raffinate part after distilling2, then ultrasonic vibration 2h is centrifuged 15min under the conditions of 6000rpm, adopts
The water in mixed liquor is removed with disposable plastic dropper to get recycling design gamma-valerolactone is arrived.
2. the method that SAPO-34 catalysis xylan according to claim 1 prepares furfural and solvent recovery, feature exist
In the SAPO-34 molecular sieve is synthesized using hydro-thermal method.
3. the method that SAPO-34 catalysis xylan according to claim 1 prepares furfural and solvent recovery, feature exist
It is gamma-valerolactone/aqueous solution in, the reaction dissolvent, the volume ratio of gamma-valerolactone and water is 1: 20~20: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810965323.2A CN109020931A (en) | 2018-08-23 | 2018-08-23 | A kind of method that SAPO-34 catalysis xylan prepares furfural and solvent recovery |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810965323.2A CN109020931A (en) | 2018-08-23 | 2018-08-23 | A kind of method that SAPO-34 catalysis xylan prepares furfural and solvent recovery |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109020931A true CN109020931A (en) | 2018-12-18 |
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| CN201810965323.2A Pending CN109020931A (en) | 2018-08-23 | 2018-08-23 | A kind of method that SAPO-34 catalysis xylan prepares furfural and solvent recovery |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483269A (en) * | 2019-09-03 | 2019-11-22 | 天津科技大学 | A kind of method that SAPO-18 catalysis glucan prepares levulic acid |
| CN115819380A (en) * | 2022-11-16 | 2023-03-21 | 安徽金禾化学材料研究所有限公司 | Neutral gas explosion-SO 3 Method for preparing furfural by catalyzing corn cob through ultrasonic coupling pretreatment |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111170A (en) * | 2015-09-14 | 2015-12-02 | 中国科学技术大学 | Preparation method for furan compound |
| CN105601594A (en) * | 2016-01-27 | 2016-05-25 | 浙江大学 | Method for preparing 5-hydroxymethyl furfural through saccharide dehydration catalyzed by metal-organic framework material |
-
2018
- 2018-08-23 CN CN201810965323.2A patent/CN109020931A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111170A (en) * | 2015-09-14 | 2015-12-02 | 中国科学技术大学 | Preparation method for furan compound |
| CN105601594A (en) * | 2016-01-27 | 2016-05-25 | 浙江大学 | Method for preparing 5-hydroxymethyl furfural through saccharide dehydration catalyzed by metal-organic framework material |
Non-Patent Citations (1)
| Title |
|---|
| L. ZHANG ET AL.: "Enhanced formation of 5-HMF from glucose using a highly selective and stable SAPO-34 catalyst", 《CHEMICAL ENGINEERING JOURNAL》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483269A (en) * | 2019-09-03 | 2019-11-22 | 天津科技大学 | A kind of method that SAPO-18 catalysis glucan prepares levulic acid |
| CN115819380A (en) * | 2022-11-16 | 2023-03-21 | 安徽金禾化学材料研究所有限公司 | Neutral gas explosion-SO 3 Method for preparing furfural by catalyzing corn cob through ultrasonic coupling pretreatment |
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Application publication date: 20181218 |