CN1562477A - Catalyzer for preparing furfuryl alcohol through hydrogenation in liquid phase furfural - Google Patents
Catalyzer for preparing furfuryl alcohol through hydrogenation in liquid phase furfural Download PDFInfo
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- CN1562477A CN1562477A CN 200410012190 CN200410012190A CN1562477A CN 1562477 A CN1562477 A CN 1562477A CN 200410012190 CN200410012190 CN 200410012190 CN 200410012190 A CN200410012190 A CN 200410012190A CN 1562477 A CN1562477 A CN 1562477A
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- CN
- China
- Prior art keywords
- furfural
- furfuryl alcohol
- catalyzer
- catalyst
- hydrogenation
- 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.)
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 43
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 9
- 239000007791 liquid phase Substances 0.000 title claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 230000000694 effects Effects 0.000 abstract description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- PMJNEQWWZRSFCE-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-(thiophen-2-ylmethyl)propanoic acid Chemical compound CCOC(=O)C(C(O)=O)CC1=CC=CS1 PMJNEQWWZRSFCE-UHFFFAOYSA-N 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GTUVXOOHBUUGBH-UHFFFAOYSA-N furan;methanol Chemical compound OC.C=1C=COC=1 GTUVXOOHBUUGBH-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- -1 cobalt metals Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
一种液相糠醛加氢制糠醇催化剂各组份重量百分比为CuO 50－53％，Cr2O3 47－50％，Pd 0.08－0.15％。将催化剂和糠醛装在反应釜内，使催化剂的量占糠醛重量的3％，反应条件为温度180－200℃，压力7.5－8.5MPa。本发明的催化剂具有较高的活性，糠醛转化率大于99％，糠醇的选择性大于97％。A liquid-phase furfural hydrogenation catalyst for producing furfuryl alcohol has components by weight percentage of 50-53% of CuO, 47-50% of Cr 2 O 3 and 0.08-0.15% of Pd. The catalyst and furfural are installed in the reactor so that the amount of the catalyst accounts for 3% of the weight of the furfural. The reaction conditions are temperature 180-200 DEG C and pressure 7.5-8.5MPa. The catalyst of the invention has higher activity, the conversion rate of furfural is greater than 99%, and the selectivity of furfuryl alcohol is greater than 97%.
Description
Technical field
The invention belongs to catalyzer and uses thereof, relate in particular to a kind of catalyzer that is used for preparing furancarbinol from liquid-phase furol hydrogenation and uses thereof.
Background technology
Furfuryl alcohol is a kind of important organic chemical industry's intermediate, is mainly used in the fine chemistry industry aspect, can make levulinic acid (having another name called oxysuccinic acid), the furane resin of various performances (as furfuryl resin, furans I, II type resin), furfuryl alcohol-Precondensed UreaFormaldehyde Resin and resol etc.; Be widely used in building, the foundary industry, particularly automotive industry.
The at present industrial furfuryl alcohol of producing all is to adopt furfural shortening method to produce.China is furfural big producing country, and in the furfural deep processed product, furfuryl alcohol is to be worth very high a kind of product.
Chinese patent ZL 91103132.4, the composition of " producing furfuryl alcohol thunder Buddhist nun's cobalt hydrogenation catalyst and method for making thereof " disclosed catalyzer: cobalt 35.1-46.5%, aluminium 40.2-60.7%, chromium 4.2-13.3%.Its activation method is used the distilled water cleaning catalyst then for to take out reactive aluminum with 20% caustic soda soln, and the pH value about 7 that makes scavenging solution is for extremely.120 ℃ of temperature of reaction, carry out preparing furancarbinol from liquid-phase furol hydrogenation under the condition of 1Mpa, transformation efficiency is greater than 99%.In this catalyst preparation process, need a large amount of cobalt metals, increased the expense of catalyzer; Thunder Buddhist nun cobalt catalyst belongs to the spontaneous combustion type in addition, need be kept in the ethanol, has increased the use difficulty.
Summary of the invention
The object of the present invention is to provide a kind of easy to usely, be used for catalyzer of preparing furancarbinol from liquid-phase furol hydrogenation and uses thereof.
Catalyzer each component weight percent of the present invention is:
CuO?50-53％ Cr
2O
3?47-50％ Pd?0.08-0.15％
Catalyzer of the present invention is to adopt precipitator method preparation, and concrete steps are as follows:
1. press the composition CuO 50-53% of catalyzer, Cr
2O
347-50%, Pd 0.08-0.15%, being mixed with concentration is the 1-2M metal salt solution;
2. with metal salt solution and alkaline precipitating agent, about 50 ℃ in temperature, mixing under stirring obtains precipitation, and churning time is 1 hour, aging 5 hours then;
3. throw out is through washing and filtering, 110-120 ℃ of drying 20 hours, and 330 ℃ of following roastings 4 hours, mills at last and promptly gets catalyzer.
Application of Catalyst of the present invention is that catalyzer and furfural are contained in the reactor, makes the amount of catalyzer account for 3% of furfural weight, and reaction conditions is temperature 180-200 ℃, pressure 7.5-8.5Mpa.
The present invention compared with prior art has following advantage:
Catalyst preparation process is simple, and is easy to use, and higher activity and selectivity are arranged, and the furfural transformation efficiency is greater than 99%, and the selectivity of furfuryl alcohol is greater than 97%.
Embodiment
Embodiment 1
(1) catalyst preparation process: take by weighing cupric nitrate 75.0g, ammonium chromate 50.0g, 1.0mg/ml palladium solution 4.5ml.Cupric nitrate, ammonium chromate are dissolved in respectively in about 500ml deionized water, are mixed with solution.Copper nitrate solution is slowly added ammonium chromate solution, under 50 ℃, constantly stir; And dropping ammonia solution, the pH value of solution is about about 6.5, mix to obtain precipitation, and then drip required palladium solution, aging 5hr, throw out be through washing and filtering, at 110 ℃ of dry 20hr, and at 330 ℃ of roasting 4hr.Mill to less than 120 purpose catalyst samples.
(2) reactivity worth:
Take by weighing 5g catalyzer (＜120 order) and 300ml furfural and pack in the high pressure stainless steel cauldron, steel cylinder hydrogen enters in the reactor by spinner-type flowmeter after the level pressure voltage stabilizing, 195 ℃ of temperature of reaction, under the pressure 7.5MPa condition, furfural transformation efficiency 99.1%, the selecting property 98.5% of furfuryl alcohol.
Embodiment 2
(1) catalyst preparation process:
Take by weighing cupric nitrate 76.5g, ammonium chromate 49.0g, 1.0mg/ml palladium solution 5.5ml, other is together
Embodiment 1.
(2) reactivity worth:
At 185 ℃, under the 8MPa condition, furfural transformation efficiency 99.4%, furfuryl alcohol selectivity 98.1%.
Embodiment 3
(1) catalyst preparation process:
Take by weighing cupric nitrate 78.0g, ammonium chromate 48.0g, 1.0mg/ml palladium solution 6.5ml, all the other are with embodiment 1.
(2) reactivity worth:
At 190 ℃, under the condition of 8.5Mpa, furfural transformation efficiency 99.7%, the selectivity 97.8% of furfuryl alcohol.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410012190 CN1562477A (en) | 2004-03-16 | 2004-03-16 | Catalyzer for preparing furfuryl alcohol through hydrogenation in liquid phase furfural |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410012190 CN1562477A (en) | 2004-03-16 | 2004-03-16 | Catalyzer for preparing furfuryl alcohol through hydrogenation in liquid phase furfural |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1562477A true CN1562477A (en) | 2005-01-12 |
Family
ID=34477929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410012190 Pending CN1562477A (en) | 2004-03-16 | 2004-03-16 | Catalyzer for preparing furfuryl alcohol through hydrogenation in liquid phase furfural |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1562477A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7425657B1 (en) * | 2007-06-06 | 2008-09-16 | Battelle Memorial Institute | Palladium catalyzed hydrogenation of bio-oils and organic compounds |
| CN100438976C (en) * | 2005-12-07 | 2008-12-03 | 南化集团研究院 | Catalyst for furfural gas-phase hydrogenation to furfuryl alcohol and preparation method thereof |
| CN106622327A (en) * | 2016-12-20 | 2017-05-10 | 中国科学院青岛生物能源与过程研究所 | A nitrogen-doped porous carbon-supported metal catalyst and its preparation method and use |
| CN104549318B (en) * | 2013-10-24 | 2018-01-23 | 中国石油化工股份有限公司 | The catalyst and preparation method of a kind of preparing furancarbinol from liquid-phase furol hydrogenation |
| CN109261182A (en) * | 2018-11-02 | 2019-01-25 | 湘潭大学 | A kind of preparation method of nitrogen-dopped activated carbon loaded Cu catalyst and its application in catalysis furfural hydrogenation |
| CN109718805A (en) * | 2017-10-27 | 2019-05-07 | 中国石油化工股份有限公司 | Furfural liquid phase hydrogenating catalyst and its method of application and preparing furancarbinol from liquid-phase furol hydrogenation |
| CN111097446A (en) * | 2018-10-25 | 2020-05-05 | 中国石油化工股份有限公司 | Catalyst for preparing furfuryl alcohol by furfural liquid phase hydrogenation, preparation method and application thereof, and method for preparing furfuryl alcohol by furfural liquid phase hydrogenation |
| CN112939904A (en) * | 2019-12-10 | 2021-06-11 | 中国科学院大连化学物理研究所 | Method for preparing furfuryl alcohol by catalyzing furfural hydrogenation with Pt-containing alloy catalyst |
-
2004
- 2004-03-16 CN CN 200410012190 patent/CN1562477A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100438976C (en) * | 2005-12-07 | 2008-12-03 | 南化集团研究院 | Catalyst for furfural gas-phase hydrogenation to furfuryl alcohol and preparation method thereof |
| US7425657B1 (en) * | 2007-06-06 | 2008-09-16 | Battelle Memorial Institute | Palladium catalyzed hydrogenation of bio-oils and organic compounds |
| US7956224B2 (en) | 2007-06-06 | 2011-06-07 | Battelle Memorial Institute | Palladium catalyzed hydrogenation of bio-oils and organic compounds |
| CN104549318B (en) * | 2013-10-24 | 2018-01-23 | 中国石油化工股份有限公司 | The catalyst and preparation method of a kind of preparing furancarbinol from liquid-phase furol hydrogenation |
| CN106622327A (en) * | 2016-12-20 | 2017-05-10 | 中国科学院青岛生物能源与过程研究所 | A nitrogen-doped porous carbon-supported metal catalyst and its preparation method and use |
| CN106622327B (en) * | 2016-12-20 | 2019-01-11 | 中国科学院青岛生物能源与过程研究所 | A kind of nitrogen-doped porous carbon-supported metal catalyst and its preparation method and use |
| CN109718805A (en) * | 2017-10-27 | 2019-05-07 | 中国石油化工股份有限公司 | Furfural liquid phase hydrogenating catalyst and its method of application and preparing furancarbinol from liquid-phase furol hydrogenation |
| CN111097446A (en) * | 2018-10-25 | 2020-05-05 | 中国石油化工股份有限公司 | Catalyst for preparing furfuryl alcohol by furfural liquid phase hydrogenation, preparation method and application thereof, and method for preparing furfuryl alcohol by furfural liquid phase hydrogenation |
| CN109261182A (en) * | 2018-11-02 | 2019-01-25 | 湘潭大学 | A kind of preparation method of nitrogen-dopped activated carbon loaded Cu catalyst and its application in catalysis furfural hydrogenation |
| CN109261182B (en) * | 2018-11-02 | 2021-08-03 | 湘潭大学 | A kind of preparation method of nitrogen-doped activated carbon supported Cu catalyst and its application in catalytic furfural hydrogenation |
| CN112939904A (en) * | 2019-12-10 | 2021-06-11 | 中国科学院大连化学物理研究所 | Method for preparing furfuryl alcohol by catalyzing furfural hydrogenation with Pt-containing alloy catalyst |
| CN112939904B (en) * | 2019-12-10 | 2023-01-03 | 中国科学院大连化学物理研究所 | Method for preparing furfuryl alcohol by catalyzing furfural hydrogenation with Pt-containing alloy catalyst |
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