CN109833884A - A kind of methyl glycollate hydrogenolysis prepares catalyst of ethyl alcohol and its preparation method and application - Google Patents
A kind of methyl glycollate hydrogenolysis prepares catalyst of ethyl alcohol and its preparation method and application Download PDFInfo
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- CN109833884A CN109833884A CN201711223439.0A CN201711223439A CN109833884A CN 109833884 A CN109833884 A CN 109833884A CN 201711223439 A CN201711223439 A CN 201711223439A CN 109833884 A CN109833884 A CN 109833884A
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Abstract
The present invention relates to the catalyst and its preparation method and application that a kind of methyl glycollate hydrogenolysis prepares ethyl alcohol, and the catalyst is by M-Cu/SiO2Composition, wherein M is one or more of Pt, Pd, Ir, and the molar ratio with Cu is 1:10~1:500；Wherein, Cu/SiO2It is prepared by ammonia still process method, M is introduced by the method for dipping.The catalyst can be at 200 DEG C -300 DEG C, Hydrogen Vapor Pressure 1-5MPa, and liquid air speed is 0.03h‑1‑0.5h‑1, hydrogen/methyl glycollate molar ratio is to convert ethyl alcohol, and 300 hours non-inactivations of catalyst continuously-running with high selectivity for methyl glycollate under the reaction condition of 50-500:1.
Description
Technical field
This patent is related to a kind of methyl glycollate hydrogenolysis and prepares catalyst of ethyl alcohol and its preparation method and application.
Technical background
Ethyl alcohol is a kind of public chemicals, is all widely used in numerous areas such as food, the energy, medicine, China is to second
The demand of alcohol is in annual ascendant trend, is up to 10,000,000 tons to demand of the year two thousand twenty China to ethyl alcohol is estimated.
The main method of industrial production ethyl alcohol has at present: biological fermentation process, synthesis gas preparation Ethanol Method.
Biological fermentation process: monosaccharide, then the effect in enzyme mainly are obtained under cellulase effect by celluloses such as stalks
Under obtain ethyl alcohol.Synthesis gas prepares Ethanol Method: can first prepare dimethyl oxalate by synthesis gas, then under high-temperature and high-pressure conditions
Dimethyl oxalate elder generation partial hydrogenation is set to obtain methyl glycollate, methyl glycollate adds hydrogen that ethylene glycol, last depth hydrogenolysis can be obtained
Ethyl alcohol can be prepared.
Document (J.Am.Chem.Soc., 2012,134:13922-13925), it was recently reported that Cu/ has been synthesized by ammonia still process method
SiO2Catalyst, dimethyl oxalate hydrogenolysis prepares ethyl alcohol at 280 DEG C, and ethanol yield can reach 83%, document (Nature
Communications, 2013,4:1-7) reporting Cu is dispersed in a page cupric silicate outer surface Cu@CuPSNTs type catalyst,
Ethanol yield can reach 91% at 280 DEG C.
Document (ACS Catal., 2014,4:3612-3620) reports the Cu/Al by self assembly high dispersive2O3
Catalyst, dimethyl oxalate hydrogenolysis prepares ethyl alcohol at 270 DEG C, and ethanol yield is 94.9% in liquid.
In from the reactions above, it can be seen that Cu base catalyst is a kind of effective catalysis dimethyl oxalate hydrogenolysis preparation second
The catalyst of alcohol, but the catalyst need to realize that energy consumption is larger at higher temperatures, and Cu catalyst is easy under the conditions of pyroreaction
It grows up inactivation.So seeking a kind of high activity and highly selective catalyst, it can be made to complete under relatively lower temp should
Reaction is the key that improve catalyst stability.
38-50% is cellulose in biomass, so being to solve biomass resource utilization for the Study on Transformation of cellulose
Committed step.In recent years, with the continuous development of biomass transformation technology, some catalysis skills for capableing of Efficient Conversion cellulose
Art is also applied and is given birth to.Document: (ChemSusChem., 2017,10:1390-1394) can be by cellulose using tungsten-based catalyst
One step converts to obtain methyl glycollate.The further hydrogenolysis of methyl glycollate is obtained into ethyl alcohol, and then one kind can be developed with fiber
Element is the efficient chemical catalysis technique that raw material prepares ethyl alcohol.
Summary of the invention
The present invention provides the catalyst and its preparation method and application that a kind of methyl glycollate hydrogenolysis prepares ethyl alcohol.
To achieve the above object, the technical solution of the present invention is as follows:
A kind of methyl glycollate hydrogenolysis prepares the catalyst of ethyl alcohol, and the group of catalyst becomes M-Cu/SiO2。
The M is one or more of precious metals pt, Pd, Ir, and content is the 0.01-1% of catalyst quality；
The molar ratio that the content of the Cu is 5-30%, M and the Cu of catalyst quality is 1:10-1:500.
The M-Cu/SiO2The preparation method comprises the following steps:
Catalyst first passes through ammonia still process method and obtains Cu/SiO2；M-Cu/SiO is synthesized by rear infusion process again2；
A) by Cu (NO3)2·6H2O is dissolved in deionized water, then SiO is added thereto2Colloidal sol, adjusting pH value with ammonium hydroxide is
10.0-12.0,60 DEG C -80 DEG C of water-bath ammonia still processs 2-5 hours, be filtered, washed, dry, then forged in 400 DEG C of -500 DEG C of Muffle furnaces
It burns 3-5 hours and obtains Cu/SiO2Catalyst；
B) Cu/SiO obtained in the precursor solution impregnation steps a) with M metal2, then in 350 DEG C of -400 DEG C of Muffles
It is calcined 1-3 hours in furnace, 3 hours obtained M-Cu/SiO is restored under 350 DEG C of hydrogen atmospheres2Catalyst.
The presoma of the metal M be one or both of chloride, nitrate, acetylacetonate, hydroxide with
On；Solvent used by the dipping is one or both of water, ethyl alcohol.
The methyl glycollate hydrogenolysis prepares the catalyst of ethyl alcohol for methyl glycollate catalytic hydrogenolysis ethanol synthesis.
The condition of the methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are quality
Concentration is 5-80% methyl glycollate methanol solution, and Hydrogen Vapor Pressure 1-5MPa, reaction temperature is 200 DEG C -300 DEG C, liquid-containing air
Fast 0.03h-1-0.5h-1, hydrogen/methyl glycollate molar ratio is 50-500:1.
Beneficial effects of the present invention:
Compared with prior art, which is the downstream product of cellulose, in M-Cu/SiO2Catalyst action
Under, 200 DEG C -300 DEG C, Hydrogen Vapor Pressure 1-5MPa, liquid air speed is 0.03h-1-0.5h-1, hydrogen/methyl glycollate molar ratio is
Under the reaction condition of 50-500:1, ethyl alcohol is converted by methyl glycollate is highly selective, ethanol yield is up to 70-80%, catalysis
It does not inactivate within agent continuous operation 300 hours.
Specific embodiment
Embodiment 1
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, then calcined 4 hours in 450 DEG C of Muffle furnaces
Obtain Cu/SiO2。
It b) is that 0.1% 4 ammino platinic hydroxide solution impregnates Cu/SiO by mass fraction2, then in 350 DEG C of Muffle furnaces
It calcines 3 hours, restores 3 hours obtained Pt-Cu/SiO under 350 DEG C of hydrogen atmospheres2, wherein Pt load capacity is 0.1%, Cu load capacity
It is 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 230 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Pt-Cu/SiO2Under the action of, ethanol yield is up to 76.7%.
Embodiment 2
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, calcined 4 hours in 450 DEG C of Muffle furnaces and obtain Cu/
SiO2。
It b) is that 0.1% 4 ammino palladium hydroxide solution impregnates Cu/SiO by mass fraction2, then in 350 DEG C of Muffle furnaces
It calcines 3 hours, restores 3 hours obtained Pd-Cu/SiO under 350 DEG C of hydrogen atmospheres2Catalyst, wherein Pd load capacity is 0.1%, Cu
Load capacity is 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 230 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Pd-Cu/SiO2Under the action of catalyst, ethanol yield is up to 70.5%.
Embodiment 3
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, calcined 4 hours in 450 DEG C of Muffle furnaces and obtain Cu/
SiO2。
It b) is 0.1%IrCl by mass fraction3The precursor solution of metal impregnates Cu/SiO2, then in 350 DEG C of Muffle furnaces
It is middle to calcine 3 hours, 3 hours obtained Ir-Cu/SiO are restored under 350 DEG C of hydrogen atmospheres2Catalyst, wherein Ir load capacity is 0.1%,
Cu load capacity is 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 230 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Ir-Cu/SiO2Under the action of catalyst, ethanol yield is up to 67.5%.
Embodiment 4
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, calcined 4 hours in 450 DEG C of Muffle furnaces and obtain Cu/
SiO2。
It b) is that 0.1% 4 ammino platinic hydroxide solution impregnates Cu/SiO by mass fraction2, then in 350 DEG C of Muffle furnaces
It calcines 3 hours, restores 3 hours obtained Pt-Cu/SiO under 350 DEG C of hydrogen atmospheres2Catalyst, wherein Pt load capacity is 0.06%,
Cu load capacity is 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 230 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Pt-Cu/SiO2Under the action of catalyst, ethanol yield is up to 36.2%.
Embodiment 5
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, calcined 4 hours in 450 DEG C of Muffle furnaces and obtain Cu/
SiO2。
It b) is that 0.1% 4 ammino platinic hydroxide solution impregnates Cu/SiO by mass fraction2, then in 350 DEG C of Muffle furnaces
It calcines 3 hours, restores 3 hours obtained Pt-Cu/SiO under 350 DEG C of hydrogen atmospheres2Catalyst, wherein Pt load capacity is 0.3%, Cu
Load capacity is 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 230 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Pt-Cu/SiO2Under the action of catalyst, ethanol yield is up to 46.5%.
Embodiment 6
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, calcined 4 hours in 450 DEG C of Muffle furnaces and obtain Cu/
SiO2。
It b) is that 0.1% 4 ammino platinic hydroxide solution impregnates Cu/SiO by mass fraction2, then in 350 DEG C of Muffle furnaces
It calcines 3 hours, restores 3 hours obtained Pt-Cu/SiO under 350 DEG C of hydrogen atmospheres2Catalyst, wherein Pt load capacity is 0.1%, Cu
Load capacity is 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 200 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Pt-Cu/SiO2Under the action of catalyst, ethanol yield is up to 3.7%.
Embodiment 7
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, calcined 4 hours in 450 DEG C of Muffle furnaces and obtain Cu/
SiO2。
It b) is that 0.1% 4 ammino platinic hydroxide solution impregnates Cu/SiO by mass fraction2, then in 350 DEG C of Muffle furnaces
It calcines 3 hours, restores 3 hours obtained Pt-Cu/SiO under 350 DEG C of hydrogen atmospheres2Catalyst, wherein Pt load capacity is 0.1%, Cu
Load capacity is 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 220 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Pt-Cu/SiO2Under the action of catalyst, ethanol yield is up to 19.4%.
Embodiment 8
A) by 1.0g Cu (NO3)2·6H2O is dissolved in 100mL deionized water, then SiO is added thereto2Colloidal sol uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, calcined 4 hours in 450 DEG C of Muffle furnaces and obtain Cu/
SiO2。
It b) is that 0.1% 4 ammino platinic hydroxide solution impregnates Cu/SiO by mass fraction2, then in 350 DEG C of Muffle furnaces
It calcines 3 hours, restores 3 hours obtained Pt-Cu/SiO under 350 DEG C of hydrogen atmospheres2Catalyst, wherein Pt load capacity is 0.1%,
Cu load capacity is 15%
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 240 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, and under the action of the reaction condition and Pt-Cu/SiO2 catalyst, ethanol yield is up to 68.8%.
Embodiment 9
1.0g Cu (NO3) 26H2O is dissolved in 100mL deionized water, then SiO2 colloidal sol is added thereto, uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, then calcined 4 hours in 450 DEG C of Muffle furnaces
After obtain Cu/SiO2, wherein Cu load capacity be 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 200 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Cu/SiO2Under the action of catalyst, ethanol yield 0.9%.
Embodiment 10
1.0g Cu (NO3) 26H2O is dissolved in 100mL deionized water, then SiO2 colloidal sol is added thereto, uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, then calcined 4 hours in 450 DEG C of Muffle furnaces
After obtain Cu/SiO2, wherein Cu load capacity be 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 220 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, in the reaction condition and Cu/SiO2Under the action of catalyst, ethanol yield 9.4%.
Embodiment 11
1.0g Cu (NO3) 26H2O is dissolved in 100mL deionized water, then SiO2 colloidal sol is added thereto, uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, then calcined 4 hours in 450 DEG C of Muffle furnaces
After obtain Cu/SiO2, wherein Cu load capacity be 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 250 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, under the action of the reaction condition and Cu/SiO2 catalyst, ethanol yield 45.7%.
Embodiment 12
1.0g Cu (NO3) 26H2O is dissolved in 100mL deionized water, then SiO2 colloidal sol is added thereto, uses ammonium hydroxide
Adjust pH value be 11.0,80 DEG C water-bath ammonia still process 4 hours, be filtered, washed, dry, then calcined 4 hours in 450 DEG C of Muffle furnaces
After obtain Cu/SiO2, wherein Cu load capacity be 15%.
The condition of methyl glycollate catalytic hydrogenolytic cleavage are as follows: fixed bed continuous reaction, reaction raw materials are that mass concentration is
50% methyl glycollate methanol solution, Hydrogen Vapor Pressure 1MPa, reaction temperature are 270 DEG C, liquid air speed 0.03h-1, hydrogen/second
Alkyd methyl esters molar ratio is 50, under the action of the reaction condition and Cu/SiO2 catalyst, ethanol yield 50.8%.
1 different catalysts of table prepare ethanol synthesis performance to methyl glycollate hydrogenolysis at a temperature of differential responses
As can be seen from Table 1, when the mass fraction of Pt is 0.1%, when reaction temperature is 230 DEG C, the yield of ethyl alcohol is most
Height can reach 76.7%, the M-Cu/SiO prepared by Pd and Ir2Its ethanol yield does not have Pt-Cu/SiO2It is high；With Cu/SiO2
Catalyst is compared, Pt-Cu/SiO2Catalyst makes reaction temperature drop to 230 DEG C from 270 DEG C, and the yield of ethyl alcohol is from 50.8%
It is increased to 76.7%；The addition of minute amount of noble metal Pt is more conducive to alkyd methyl esters hydrogenolysis and prepares ethyl alcohol.
Claims (6)
1. the catalyst that a kind of methyl glycollate hydrogenolysis prepares ethyl alcohol, it is characterised in that: the group of the catalyst becomes M-Cu/
SiO2。
2. the catalyst that methyl glycollate hydrogenolysis according to claim 1 prepares ethyl alcohol, it is characterised in that: the M is expensive
One or more of Pt metal, Pd, Ir, content are the 0.01-1% of catalyst quality；The content of the Cu is to urge
The molar ratio of 5-30%, M and the Cu of agent quality are 1:10-1:500.
3. a kind of methyl glycollate hydrogenolysis of any of claims 1 or 2 prepares the preparation method of the catalyst of ethyl alcohol, feature exists
In:
A) by Cu (NO3)2·6H2O is dissolved in deionized water, then SiO is added thereto2Colloidal sol, adjusting pH value with ammonium hydroxide is 10.0-
12.0,60-80 DEG C water-bath ammonia still process 2-5 hours, be filtered, washed, dry, then in 400 DEG C of -500 DEG C of Muffle furnaces calcine 3-5 it is small
When obtain Cu/SiO2；
B) Cu/SiO obtained in the precursor solution impregnation steps a) with M metal2, then forged in 350 DEG C of -400 DEG C of Muffle furnaces
It burns 1-3 hours, 3 hours obtained M-Cu/SiO is restored under 350 DEG C of hydrogen atmospheres2Catalyst.
4. the preparation method that methyl glycollate hydrogenolysis according to claim 3 prepares the catalyst of ethyl alcohol, it is characterised in that:
The presoma of the metal M is one or more of chloride, nitrate, acetylacetonate or hydroxide；It is described
Solvent used by impregnating is one or both of water, ethyl alcohol.
5. the application that a kind of methyl glycollate hydrogenolysis of any of claims 1 or 2 prepares the catalyst of ethyl alcohol, it is characterised in that:
The catalyst is used for methyl glycollate catalytic hydrogenolysis ethanol synthesis.
6. the application that methyl glycollate hydrogenolysis according to claim 5 prepares the catalyst of ethyl alcohol, it is characterised in that: ethyl alcohol
It is fixed bed continuous reaction that sour methyl esters hydrogenolysis, which prepares ethanol synthesis condition, and reaction raw materials are mass concentration 5-80% glycolic first
Ester methanol solution, Hydrogen Vapor Pressure 1-5MPa, reaction temperature are 200 DEG C -300 DEG C, liquid air speed 0.03h-1-0.5h-1, hydrogen/
Methyl glycollate molar ratio is 50-500:1.
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| CN110642954A (en) * | 2019-09-20 | 2020-01-03 | 万华化学集团股份有限公司 | Method for preparing cellulose acetate butyrate with high hydroxyl content |
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