CN102614883A - Environment-friendly 2-methyl furan catalyst and preparation method thereof - Google Patents
Environment-friendly 2-methyl furan catalyst and preparation method thereof Download PDFInfo
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- CN102614883A CN102614883A CN2012100406726A CN201210040672A CN102614883A CN 102614883 A CN102614883 A CN 102614883A CN 2012100406726 A CN2012100406726 A CN 2012100406726A CN 201210040672 A CN201210040672 A CN 201210040672A CN 102614883 A CN102614883 A CN 102614883A
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Abstract
The invention provides an environment-friendly 2-methyl furan catalyst and a preparation method thereof and relates to a hydrogenation catalyst and a preparation method thereof. The catalyst is prepared by a colloid precipitation method and the active component Cu is dispersed highly. The catalyst mainly comprises the following components as per percentage by weight: 15 to 50 percent of CuO and 40 to 80 percent of silicon oxide or aluminum oxide. The catalyst is applied to preparation of 2-methyl furan through furfural gas phase hydrogenation, wherein the conversion rate of the furfural is 100 percent and the selectivity of the 2-methyl furan reaches over 92 percent. By the colloid precipitation method, sol can be effectively bound with Cu and aid; the Cu can be dispersed on the surface of the carrier highly; and the catalyst has high activity and stability in the reaction of synthesizing the 2-methyl furan by hydrogenating the furfural. The catalyst applied to preparation of the 2-methyl furan by hydrogenating the furfural has simple components and does not comprise Cr so as to avoid the environmental pollution caused by pretreatment on the Cr-containing industrial catalyst and treatment on the waste catalyst.
Description
Technical field
The present invention relates to a kind of hydrogenation catalyst and preparation method thereof, particularly relate to a kind of environmentally friendly 2-methylfuran Catalysts and its preparation method.
Background technology
The 2-methylfuran is a kind of important Organic Chemicals, is widely used in aspects such as medicine, agricultural chemicals and fine chemistry industry.With it is that raw material can synthesize a series of organic chemicals, like pentadiene, pentanediol, acetylpropyl alcohol and ketone; In pharmaceuticals industry, the 2-methylfuran is used to produce Cobastab
1With antidysenteric chloroquine diphosphate, primaquine phosphate etc.Producing the 2-methylfuran in the industry all is to adopt the production of furfural catalytic hydrogenation, and the key of this process is the exploitation high performance catalyst.It mainly is the Cu-Cr series catalysts that the catalyst that uses is gone up in industry at present, and its price is very expensive.Russian Patent SU941366 has reported Cu0-Cr
2O
3/ graphite or aluminium oxide are catalyst, are 200-300 ℃ in reaction temperature, reaction pressure 0.005-0.3MPa and liquid air speed 0.25-0.5hr
-1The time, the yield of 2-methyl can reach 90%, but the accessory substance that produces is more, has increased the difficulty that post processing separates.Chinese patent CN1145274A has prepared the oxide catalyst that contains Cr with mixing method, and it consists of CuO 5%～15%, Cr
2O
30.5%～5%, Al
2O
380%～90%, 0.01%～2% at least a alkali metal and alkaline earth oxide (K
2O, Na
2O, CaO, BaO, MgO, suitable content 0.5%～1%), the oxide of 0.01%～2% at least a P of being selected from, Bi, Ce, Mo, Zn, B, Co (preferred range is 0.04%～1%).At normal pressure, 230～240 ℃ of reaction temperatures, liquid air speed 0.25～0.40 h
– 1Under the condition, lab scale turns round behind 1200 h continuously, and the furfural conversion ratio can reach 99%～100%, and 2-methylfuran selectivity reaches more than 95%, and yield can reach 92.5～94%.Chinese patent CN00120872.1, " being used for catalyst of preparing 2-methylfuran by gas-phase hydrogenation of furaldehyde and uses thereof ", disclosed catalysis consisted of: CuO 50-53%, Cr
2O
346-49%, NiO 0.2-1.1%.In reaction temperature is 230-250 ℃, and reaction pressure is lower than 0.06MPa, and furfural liquid air speed is 0.4-0.5hr-1, furfural conversion ratio 100%.2-methylfuran selectivity 95-97%.These catalyst all contain the extremely carcinogen Cr of poison, have not only brought injury to operating personnel aborning, and when the catalyst waste treatment, have caused the serious environmental pollution again.For this reason, researchers are actively making great efforts the efficient no Cr catalyst of exploitation.Chinese patent CN 101422731A " a kind of Catalysts and its preparation method of preparing 2-methylfuran by gas-phase hydrogenation of furaldehyde " has reported that component is CuO 18-22%, ZnO 3-7% and carrier A l
2O
3The no Cr catalyst of 73-77%.In reaction temperature is 230 degree, normal pressure, liquid air speed 0.4hr
-1Under the condition, the furfural conversion ratio is 100%.2-methylfuran selectivity is 91%-94%.Though this catalyst has provided higher 2-methylfuran selectivity, the less stable of catalyst.
Summary of the invention
The object of the present invention is to provide a kind of environmentally friendly 2-methylfuran Catalysts and its preparation method; This method furfural hydrogenation prepares 2-methylfuran catalyst; It forms simple; And, overcome the existing Cr industrial catalyst that contains and processed in earlier stage and the pollution of dead catalyst processing environment owing to do not contain Cr.
The objective of the invention is to realize through following technical scheme:
A kind of environmentally friendly 2-methylfuran catalyst, its said catalyst activity component CuO quality percentage composition is 15-50%, and the content of aluminium oxide is 40%-80%, and the quality percentage composition of silica is 40-80%, auxiliary agent Na
2O, K
2O, Sr
2The gross mass percentage composition of one or both of O, CaO, BaO and ZnO is 0-15%; Additive alkali metal or alkaline-earth metal are one or both among Na, K, Sr, Ca, Ba, the Zn; Wherein copper is active component, and alkali metal or alkaline-earth metal are auxiliary agent.
Described a kind of environmentally friendly 2-methylfuran catalyst, the mantoquita that it is described and the nitrate of auxiliary agent be in aluminium colloidal sol or in the Ludox, or the concentration in the sial mixed sols is 0.1-2mol/l, and precipitant solution concentration is 0.1-2mol/l.
Described a kind of environmentally friendly 2-methylfuran catalyst, its described copper salt, alkali metal or alkali salt are corresponding solubility nitrate.
A kind of environmentally friendly 2-methylfuran Preparation of catalysts method; Said method comprises following process: copper salt and alkali metal or alkali salt are dissolved in aluminium colloidal sol or Ludox, or in Ludox and the aluminium colloidal sol mixed sols, obtain the colloidal precipitation thing with the precipitating reagent reaction then; After treating that deposition is accomplished; Aging 1-4 hour,, make the oxidation state precursor of catalyst through filtration, washing, drying, moulding and roasting.
Described a kind of environmentally friendly 2-methylfuran Preparation of catalysts method; Wherein the Preparation of catalysts method is the colloidal precipitation method; The Ludox of salt or aluminium colloidal sol; Or the feed way of sial mixed sols solution and precipitating reagent reaction be positive addition, anti-addition or and add, the control precipitation temperature is 20-60 ℃, the pH value of deposition is controlled at 6-8.
Described a kind of environmentally friendly 2-methylfuran Preparation of catalysts method, wherein precipitating reagent is NaCO
3, (NH
4)
2CO
3, in NaOH or the ammoniacal liquor one or both; Wherein dry temperature is 100-120 ℃, and the temperature of roasting is 400-500 ℃.
This method is dissolved in Ludox or aluminium colloidal sol with copper salt, alkali metal or alkali salt; Or in the sial mixed sols aqueous solution; Obtain the colloidal precipitation thing with the precipitating reagent reaction then,, finally make the oxidation state precursor of catalyst then through super-dry and roasting in air.
Concrete reactions step is: by each components contents; One or more of required metal nitrate are dissolved in Ludox or aluminium colloidal sol; Or sial mixed sols solution; Then with precipitating reagent through feed way be positive addition, anti-addition or and add to react and obtain the colloidal precipitation thing, the control precipitation temperature is 20-60 ℃, the pH value of deposition is controlled at 6-8;
Wherein copper is active component, and its content 15-50%, alkali metal or alkaline-earth metal are auxiliary agent, and its content is 0-15%, and silica or alumina content are 40-80%.Wherein precipitating reagent is NaCO
3, (NH
4)
2CO
3, in NaOH or the ammoniacal liquor one or both; Gained be deposited in dry 12 h under the 100-120 ℃ of temperature conditions, then further under 400-500 ℃ of condition roasting 4-6 h promptly make catalyst.
Advantage of the present invention and effect are:
1. the present invention compares with traditional infusion process, adopts this catalyst of colloidal precipitation method preparation, and active component is scattered, stable performance.
2. catalyst of the present invention has high activity and high selectivity, and the furfural conversion ratio is 100%, and 2-methylfuran selectivity is more than 92%.
3. do not contain Cr in the catalytic component of the present invention, have the environmental protection characteristics.
4. catalyst furfural hydrogenation of the present invention prepares the stable performance of 2-methylfuran, shows that catalyst has the commercial Application characteristic.
The specific embodiment
Below in conjunction with embodiment the present invention is elaborated.
Embodiment 1With 30.6 gram nitrate trihydrate copper, 8.36 gram zinc nitrate hexahydrates are dissolved in the 100ml deionized water, join then in the 250ml aluminium colloidal sol.Getting 32 gram sodium carbonate is dissolved in the 200ml deionized water; The aluminium sol solution that under stirring condition, will dissolve nitrate mixes under 40 ℃ of conditions with aqueous sodium carbonate and obtains deposition; PH is 7.5, aging then 2h, and deposition is after filtering and washing; Drying is 12 hours under 110 ℃ of conditions, and 500 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 2With 24 gram nitrate trihydrate copper, 8.36 gram barium nitrates, 4.2 gram calcium nitrate are dissolved in the 100ml deionized water, join then in the 250ml aluminium colloidal sol.Getting 36 gram sodium carbonate is dissolved in the 200ml deionized water; The aluminium sol solution that under stirring condition, will dissolve nitrate mixes under 40 ℃ of conditions with aqueous sodium carbonate and obtains deposition; PH is 7.5, aging then 2h, and deposition is after filtering and washing; Drying is 12 hours under 110 ℃ of conditions, and 500 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 3With 72 gram nitrate trihydrate copper, 30 gram calcium nitrate, 8.2 gram zinc nitrates are dissolved in the 100ml deionized water, join then in the 600ml aluminium colloidal sol.Getting 50 gram NaOH is dissolved in the 500ml deionized water; The aluminium sol solution that under stirring condition, will dissolve nitrate mixes under 50 ℃ of conditions with sodium hydrate aqueous solution and obtains deposition; PH is 8 aging then 2h; Deposition is after filtering and washing, and drying is 12 hours under 110 ℃ of conditions, and 500 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 4With 72 gram nitrate trihydrate copper, 24 gram potassium nitrate, 8.2 gram calcium nitrate are dissolved in the 100ml deionized water, join then in the 600ml aluminium colloidal sol.Getting 120 gram sodium acid carbonates is dissolved in the 500ml deionized water; The silicon sol solution that under stirring condition, will dissolve nitrate mixes under 20 ℃ of conditions with aqueous sodium carbonate and obtains deposition; PH is 7, aging then 2h, and deposition is after filtering and washing; Drying is 12 hours under 110 ℃ of conditions, and 500 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 5With 144 gram nitrate trihydrate copper, 48 gram barium nitrates, 16.2 gram zinc nitrates are dissolved in the 200ml deionized water, join then in the 1500ml aluminium colloidal sol.Get 0.5mol/L ammonia spirit 700ml; The aluminium sol solution that under stirring condition, will dissolve nitrate and ammonia spirit mix under 20 ℃ of conditions that to obtain precipitating pH be 8; Aging then 2h; Deposition is after filtering and washing, and drying is 12 hours under 110 ℃ of conditions, and 400 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 6With 72 gram nitrate trihydrate copper, 30 gram calcium nitrate, 8.2 gram zinc nitrates are dissolved in the 100ml deionized water, join then in the 300ml Ludox.Getting 50 gram NaOH is dissolved in the 500ml deionized water; The silicon sol solution that under stirring condition, will dissolve nitrate mixes under 50 ℃ of conditions with sodium hydrate aqueous solution and obtains deposition; PH is 8 aging then 2h; Deposition is after filtering and washing, and drying is 12 hours under 110 ℃ of conditions, and 500 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 7With 72 gram nitrate trihydrate copper, 24 gram potassium nitrate, 8.2 gram calcium nitrate are dissolved in the 100ml deionized water, join then in the 300ml Ludox.Getting 120 gram sodium acid carbonates is dissolved in the 500ml deionized water; The silicon sol solution that under stirring condition, will dissolve nitrate mixes under 20 ℃ of conditions with aqueous sodium carbonate and obtains deposition; PH is 7, aging then 2h, and deposition is after filtering and washing; Drying is 12 hours under 110 ℃ of conditions, and 500 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 8With 144 gram nitrate trihydrate copper, 48 gram barium nitrates, 16.2 gram zinc nitrates are dissolved in the 200ml deionized water, join then in the 700ml Ludox.Get 0.5mol/L ammonia spirit 700ml; The silicon sol solution that under stirring condition, will dissolve nitrate and ammonia spirit mix under 20 ℃ of conditions that to obtain precipitating pH be 8; Aging then 2h; Deposition is after filtering and washing, and drying is 12 hours under 110 ℃ of conditions, and 400 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.
Embodiment 9With 144 gram nitrate trihydrate copper, 48 gram barium nitrates, 16.2 gram zinc nitrates, 36 grams, nine water aluminum nitrates are dissolved in the 200ml deionized water, join then in the 700ml Ludox.Get 0.5mol/L ammonia spirit 700ml; The silicon sol solution that under stirring condition, will dissolve nitrate and ammonia spirit mix under 20 ℃ of conditions that to obtain precipitating pH be 8; Aging then 2h; Deposition is after filtering and washing, and drying is 12 hours under 110 ℃ of conditions, and 400 ℃ of roastings made catalyst in 4 hours in Muffle furnace then.Catalytic performance is tested as follows:
The catalyst for preparing after mediating extrusion on the small-sized shaping of catalyst machine, is prepared the cylindricality particle of 3mm * 4mm.Getting the 30g cylindricality beaded catalyst internal diameter of packing into is in the stainless steel reaction pipe of 22mm, feeds H
2/ N
2Nitrogen and hydrogen mixture for 1:10; Close nitrogen in reduction under the 250 degree conditions after 4 hours; Feeding pure hydrogen and furfural reacts; Hydrogen is metered into vaporizer by mass flowmenter, and furfural is transported to vaporizer through measuring pump and is carried like reactor by hydrogen and reacts, and product is analyzed through gas-chromatography.
At normal pressure, reaction temperature is 220 ℃, and liquid air speed is that experimental result is as shown in table 1 under the 0.35h-1 condition.
Table 1 reaction result
Catalyst to instance 3 preparations carries out the single tube amplification test.In the stainless steel reaction pipe, pack into the cylindricality beaded catalyst of 1000 gram 3mm * 4mm through after the hydrogen nitrogen mixed gas reduction, carries out the furfural hydrogenation reaction; Hydrogen is controlled by mass flow controller, and furfural has by measuring pump control, at normal pressure; Reaction temperature is between 220-240 ℃, and liquid air speed is 0.2h
-1, in 1200 hours, the furfural conversion ratio is 100%, the dimethyl furan selectivity is between 92%-96%.This shows that this catalyst possesses the commercial Application performance.
Claims (6)
1. an environmentally friendly 2-methylfuran catalyst is characterized in that, said catalyst activity component CuO quality percentage composition is 15-50%, and the content of aluminium oxide is 40%-80%, and the quality percentage composition of silica is 40-80%, auxiliary agent Na
2O, K
2O, Sr
2The gross mass percentage composition of one or both of O, CaO, BaO and ZnO is 0-15%; Additive alkali metal or alkaline-earth metal are one or both among Na, K, Sr, Ca, Ba, the Zn; Wherein copper is active component, and alkali metal or alkaline-earth metal are auxiliary agent.
2. a kind of environmentally friendly 2-methylfuran catalyst according to claim 1; It is characterized in that; The described mantoquita and the nitrate of auxiliary agent is in aluminium colloidal sol or in the Ludox, or the concentration in the sial mixed sols is 0.1-2mol/l, and precipitant solution concentration is 0.1-2mol/l.
3. a kind of environmentally friendly 2-methylfuran catalyst according to claim 1 is characterized in that said wherein said copper salt, alkali metal or alkali salt are corresponding solubility nitrate.
4. environmentally friendly 2-methylfuran Preparation of catalysts method is characterized in that said method comprises following process: copper salt and alkali metal or alkali salt are dissolved in aluminium colloidal sol or Ludox; Or in Ludox and the aluminium colloidal sol mixed sols; Obtain the colloidal precipitation thing with the precipitating reagent reaction then, after waiting to precipitate completion, aging 1-4 hour; Through filtration, washing, drying, moulding and roasting, make the oxidation state precursor of catalyst.
5. a kind of environmentally friendly 2-methylfuran Preparation of catalysts method according to claim 4; It is characterized in that; Wherein the Preparation of catalysts method is the colloidal precipitation method, the Ludox of salt or aluminium colloidal sol, or the feed way of sial mixed sols solution and precipitating reagent reaction be positive addition, anti-addition or and add; The control precipitation temperature is 20-60 ℃, and the pH value of deposition is controlled at 6-8.
6. a kind of environmentally friendly 2-methylfuran Preparation of catalysts method according to claim 4 is characterized in that wherein precipitating reagent is NaCO
3, (NH
4)
2CO
3, in NaOH or the ammoniacal liquor one or both; Wherein dry temperature is 100-120 ℃, and the temperature of roasting is 400-500 ℃.
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| CN103007941A (en) * | 2012-12-27 | 2013-04-03 | 珠海凯美科技有限公司 | Catalyst used in process of preparing furfuryl alcohol by furfural through selective hydrogenation and preparation method of catalyst |
| CN103007942A (en) * | 2012-12-27 | 2013-04-03 | 山东迅达化工集团有限公司 | Catalyst for preparing 2-methyl furan by furfural hydrogenation and preparation method thereof |
| CN103028405A (en) * | 2012-12-27 | 2013-04-10 | 珠海凯美科技有限公司 | Catalyst for preparing 2-methyl furan through selective furfural hydrogenation and preparation method of catalyst |
| CN104383929A (en) * | 2014-11-18 | 2015-03-04 | 沈阳化工大学 | 2-methyl furan catalyst and preparation method thereof |
| CN105435800A (en) * | 2015-11-19 | 2016-03-30 | 中科合成油技术有限公司 | Catalyst used for preparing 2,5-methyl furan and preparation method thereof |
| CN105498787A (en) * | 2014-09-25 | 2016-04-20 | 中国石油化工股份有限公司 | Catalyst for producing 2-methylfuran through gas phase hydrogenation of furfural and preparation method of the catalyst |
| CN106902840A (en) * | 2015-12-22 | 2017-06-30 | 中国石油天然气股份有限公司 | A kind of catalyst for preparing 2-methylfuran by gas-phase hydrogenation of furaldehyde and preparation method thereof |
| CN108863995A (en) * | 2018-06-18 | 2018-11-23 | 苏州盖德精细材料有限公司 | The high-efficiency environment friendly preparation method of 2- methylfuran |
| CN109482183A (en) * | 2018-11-07 | 2019-03-19 | 沈阳化工大学 | A kind of effective furfural is converted into the preparation method of 2- methylfuran catalyst |
| CN109529835A (en) * | 2018-12-10 | 2019-03-29 | 沈阳化工大学 | A kind of furfural is converted into 2- methylfuran method for preparing catalyst |
| CN110180550A (en) * | 2019-04-04 | 2019-08-30 | 沈阳化工大学 | A kind of environmental protection furfural Efficient Conversion is the preparation method of 2- methylfuran catalyst |
| CN110961117A (en) * | 2019-12-06 | 2020-04-07 | 山西大学 | Cu-Mn-O-SiO2-Al2O3Preparation method and application of catalyst |
| CN114618491A (en) * | 2022-04-06 | 2022-06-14 | 北京石油化工学院 | Preparation method of copper-based catalyst and method for preparing alkanol by catalytic hydrogenation of copper-based catalyst |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103007941B (en) * | 2012-12-27 | 2015-05-06 | 珠海凯美科技有限公司 | Preparation method for catalyst used in process of preparing furfuryl alcohol by furfural through selective hydrogenation |
| CN103007942A (en) * | 2012-12-27 | 2013-04-03 | 山东迅达化工集团有限公司 | Catalyst for preparing 2-methyl furan by furfural hydrogenation and preparation method thereof |
| CN103028405A (en) * | 2012-12-27 | 2013-04-10 | 珠海凯美科技有限公司 | Catalyst for preparing 2-methyl furan through selective furfural hydrogenation and preparation method of catalyst |
| CN103007941A (en) * | 2012-12-27 | 2013-04-03 | 珠海凯美科技有限公司 | Catalyst used in process of preparing furfuryl alcohol by furfural through selective hydrogenation and preparation method of catalyst |
| CN105498787B (en) * | 2014-09-25 | 2018-01-23 | 中国石油化工股份有限公司 | A kind of methylfuran catalyst of preparation by furfural gas phase hydrogenation 2 and preparation method |
| CN105498787A (en) * | 2014-09-25 | 2016-04-20 | 中国石油化工股份有限公司 | Catalyst for producing 2-methylfuran through gas phase hydrogenation of furfural and preparation method of the catalyst |
| CN104383929A (en) * | 2014-11-18 | 2015-03-04 | 沈阳化工大学 | 2-methyl furan catalyst and preparation method thereof |
| CN105435800A (en) * | 2015-11-19 | 2016-03-30 | 中科合成油技术有限公司 | Catalyst used for preparing 2,5-methyl furan and preparation method thereof |
| CN106902840A (en) * | 2015-12-22 | 2017-06-30 | 中国石油天然气股份有限公司 | A kind of catalyst for preparing 2-methylfuran by gas-phase hydrogenation of furaldehyde and preparation method thereof |
| CN106902840B (en) * | 2015-12-22 | 2019-06-11 | 中国石油天然气股份有限公司 | A kind of catalyst and preparation method thereof for preparing 2-methylfuran by gas-phase hydrogenation of furaldehyde |
| CN108863995A (en) * | 2018-06-18 | 2018-11-23 | 苏州盖德精细材料有限公司 | The high-efficiency environment friendly preparation method of 2- methylfuran |
| CN109482183A (en) * | 2018-11-07 | 2019-03-19 | 沈阳化工大学 | A kind of effective furfural is converted into the preparation method of 2- methylfuran catalyst |
| CN109529835A (en) * | 2018-12-10 | 2019-03-29 | 沈阳化工大学 | A kind of furfural is converted into 2- methylfuran method for preparing catalyst |
| CN110180550A (en) * | 2019-04-04 | 2019-08-30 | 沈阳化工大学 | A kind of environmental protection furfural Efficient Conversion is the preparation method of 2- methylfuran catalyst |
| CN110961117A (en) * | 2019-12-06 | 2020-04-07 | 山西大学 | Cu-Mn-O-SiO2-Al2O3Preparation method and application of catalyst |
| CN114618491A (en) * | 2022-04-06 | 2022-06-14 | 北京石油化工学院 | Preparation method of copper-based catalyst and method for preparing alkanol by catalytic hydrogenation of copper-based catalyst |
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Application publication date: 20120801 |