CN107473936B - Method for preparing lower alkanol from diol compound - Google Patents
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- CN107473936B CN107473936B CN201710691071.4A CN201710691071A CN107473936B CN 107473936 B CN107473936 B CN 107473936B CN 201710691071 A CN201710691071 A CN 201710691071A CN 107473936 B CN107473936 B CN 107473936B
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Abstract
The invention belongs to the technical field of organic matter preparation, and discloses a method for preparing lower alkanol from diol compounds, which comprises the following steps: the diol compound and water are subjected to hydrothermal reaction under the action of a nano nickel catalyst, and the reaction is carried out for 6-24 hours at the reaction temperature of 160-220 ℃ to obtain the lower alkanol. The catalyst used in the invention is a nano nickel catalyst, the raw materials are easy to obtain, and the cost is low; the catalyst is simple to prepare and can be repeatedly used; the reaction system takes water as a solvent, and does not need to introduce hydrogen. The method has mild reaction conditions, low requirements on equipment, simple equipment and easy operation, only needs a sealed reaction kettle, has the yield of the corresponding lower alkanol (ethanol is prepared from 1, 2-propylene glycol) up to 65 percent, and has good industrial prospect.
Description
Technical Field
The invention belongs to the technical field of organic matter preparation, and particularly relates to a method for preparing lower alkanol from diol compounds.
Background
In recent years, the conversion of biomass derivative diol compounds (ethylene glycol, 1,2-propanediol, 1, 2-butanediol, etc.) into fuels and other high value-added chemicals by chemical or biological methods has been widely studied and developed worldwide. Among them, the conversion of glycols into lower alcohols (methanol, ethanol, butanol) is another trend of the conversion and utilization of such compounds, and is receiving attention. Since lower alcohols (methanol, ethanol, butanol) can be directly applied to power fuels, the synthesis route can not only improve the flammability of the biomass derivative, but also improve the application range of the biomass derivative. The diol compound contains carbon oxygen and carbon, wherein the carbon oxygen bond is easier to break, but the selective realization of the carbon bond breaking to prepare the lower alkanol has certain difficulty. Since nonpolar carbon-carbon bonds are thermodynamically very stable in the field of organic chemistry, their HOMO energy is too low, and LUMO energy is too high to be easily combined with a catalyst, carbon-carbon bonds are stabilized in many organic reactions, and thus, a diol compound produces a lower alkanol. At present, the main problems of carbon-carbon bond breakage are: the complexity of the reaction substrate does not have universality. The catalyst has complex synthesis, harsh reaction conditions and low selectivity to lower alcohols. There is also a significant problem in that the conversion of glycols to lower alcohols requires the introduction of large amounts of hydrogen and toxic chemical solvents.
In summary, the problems of the prior art are as follows: in the process of preparing lower alkanol from diol compounds, the used catalyst is complex to prepare, high-pressure hydrogen is introduced, and the catalyst has certain danger and uses toxic organic solvents; the selectivity is low in the process of synthesizing the lower alkanol, and the problems of easy formation of ether compounds, difficult operation process, high cost and the like exist.
Disclosure of Invention
In view of the problems of the prior art, the present invention provides a method for preparing a lower alkanol from a diol compound.
The present invention has been accomplished in this way by a process for producing a lower alkanol from a diol compound, which comprises charging the diol compound and water as raw materials without introducing hydrogen gas, using nano nickel as a catalyst, charging the diol compound, water and nano nickel into a high-pressure reactor, sealing the reactor under a saturated steam pressure of water (0.6 to 2.3Mpa) to cause a hydrothermal reaction, reacting the reaction mixture at 160 to 220 ℃ for 6 to 30 hours, cooling the reaction mixture, and filtering the reaction mixture to obtain a lower alkanol solution.
Further, the chemical reaction formula of the method for preparing the lower alkanol from the diol compound is as follows:
further, the diol compound is one of 1,2-propanediol, 1, 2-butanediol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 3-propanediol, and 1, 2-butadienol.
Further, the lower alkanol after the reaction is: 1,2-propanediol corresponds to ethanol; 1, 2-butanediol corresponds to n-propanol; the 1, 2-pentanediol corresponds to n-butanol; 1, 2-hexanediol corresponds to n-pentanol; 1, 3-propanediol corresponds to ethanol; 1, 2-butadienol corresponds to n-propanol.
Further, in the case where the diol compound and water are used as raw materials, the aqueous solution of the diol compound is: 25ml of 0.05mol/L aqueous solution of diol compound; the nano nickel is as follows: 0.05g to 0.5 g.
Further, the nano nickel catalyst is prepared by adopting a wet chemical reduction method, and the specific method comprises the following steps:
dissolving 4.27g of nickel chloride in 300ml of water, dropwise adding 100ml of 1mol of sodium borohydride aqueous solution under the nitrogen atmosphere, violently stirring for 3-5 h, washing with water for several times after the reaction is finished, and drying in a vacuum drying oven for 12h to obtain the nano nickel catalyst.
It is another object of the present invention to provide a lower alkanol produced by the above-mentioned method for producing a lower alkanol from a diol compound.
The invention also aims to provide a power fuel prepared by utilizing the lower alkanol.
The invention has the advantages and positive effects that:
the invention develops a new method, which effectively converts diol compounds into lower alcohols through selective carbon-carbon bond breakage by hydrothermal reaction under the condition of not using high-pressure hydrogen and using a simple amorphous nickel-based catalyst. Provides a new idea for the activation of carbon-carbon bonds in organic reactions, in particular for the breaking of carbon-carbon bonds.
The closest prior art to the present invention is published in ACS Catal.2012,2,1285-1289, entitled Partial Deoxygenation of 1, 2-general catalysis by Iridium center Complexes. Compared with the method, the method has the advantages that:
the catalyst used in the invention is a nano nickel catalyst, the raw materials are easy to obtain, and the cost is low; the catalyst is simple to prepare and can be repeatedly used; the reaction system takes water as a solvent, and does not need to introduce hydrogen. The method has mild reaction conditions, low requirements on equipment, simple equipment and easy operation, only needs a sealed reaction kettle, has the yield of the corresponding lower alkanol (ethanol is prepared from 1, 2-propylene glycol) up to 65 percent, and has good industrial prospect.
Drawings
FIG. 1 is a flow chart of a process for preparing a lower alkanol from a diol compound according to an embodiment of the present invention.
FIG. 2 is a mass spectrum of ethanol, a product of examples 1 and 18, provided by the present invention.
FIG. 3 is a mass spectrum of n-propanol, a product of examples 14 and 17, according to the present invention.
FIG. 4 is a mass spectrum of n-butanol as a product in example 15, which is provided by the present invention.
FIG. 5 is a mass spectrum of n-pentanol, a product of example 16, according to the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In the prior art, the preparation of the used catalyst is complex, high-pressure hydrogen is introduced, so that the catalyst has certain danger and toxic dioxane is used as a solvent; the synthesized n-propanol has the problems of easy formation of ether compounds, difficult operation process, high cost and the like.
Based on this theory, the present inventors have developed a novel process for efficiently converting glycols into lower alcohols by selective carbon-carbon bond cleavage under hydrothermal conditions using a simple amorphous nickel-based catalyst. Provides a new idea for the activation of carbon-carbon bonds in organic reactions, in particular for the breaking of carbon-carbon bonds.
The following detailed description of the principles of the invention is provided in connection with the accompanying drawings.
As shown in fig. 1, the method for preparing a lower alkanol from a diol compound according to an embodiment of the present invention includes:
s101: putting a certain amount of diol compound, a certain amount of water and nano nickel into a high-pressure reaction kettle, and uniformly mixing.
S102: and (3) sealing, reacting for 6-24 hours at 160-220 ℃, and cooling to obtain a lower alkanol solution.
In a preferred embodiment of the present invention, the diol compound is 1,2-propanediol, 1, 2-butanediol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 3-propanediol, or 1, 2-butadienol.
The main product after the reaction is 1, 2-propylene glycol corresponding to ethanol, 1, 2-butanediol corresponding to n-propanol, 1, 2-pentanediol corresponding to n-butanol, 1, 2-hexanediol corresponding to n-pentanol, 1, 3-propanediol corresponding to ethanol, and 1, 2-butadienol corresponding to n-propanol.
The nano nickel catalyst is prepared by adopting a wet chemical reduction method, and the specific method comprises the following steps:
dissolving 4.27g of nickel chloride in 300ml of water, dropwise adding 100ml of 1mol of sodium borohydride aqueous solution under the nitrogen atmosphere, violently stirring for 3-5 h, washing with water for several times after the reaction is finished, and drying in a vacuum drying oven for 12h to obtain the nano nickel catalyst.
As a preferable scheme of the embodiment of the invention, the preferable condition is that the reaction is carried out for 6-30 h at 160-220 ℃.
As a preferred embodiment of the present invention, the amount of the catalyst is preferably 0.05 to 0.5 g.
The application of the principles of the present invention will now be described in further detail with reference to specific embodiments.
Example 1
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). According to the concentration-peak area standard curve and the peak area of the product, the molar yield of ethanol in the product can be calculated to be 48%.
Example 2
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at 220 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 43%.
Example 3
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at 180 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 46%.
Example 4
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is closed, the reaction is carried out for 24 hours at 160 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). According to the concentration-peak area standard curve and the peak area of the product, the molar yield of ethanol in the product can be calculated to be 35%.
Example 5
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.05g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). According to the concentration-peak area standard curve and the peak area of the product, the molar yield of ethanol in the product can be calculated to be 15%.
Example 6
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.05g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 30 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). According to the concentration-peak area standard curve and the peak area of the product, the molar yield of the ethanol in the product can be calculated to be 20%.
Example 7
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.1g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 42%.
Example 8
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.3g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 47%.
Example 9
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.4g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 46%.
Example 10
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.5g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). According to the concentration-peak area standard curve and the peak area of the product, the molar yield of ethanol in the product can be calculated to be 45%.
Example 11
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.5g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 30 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 47%.
Example 12
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 6 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). According to the concentration-peak area standard curve and the peak area of the product, the molar yield of ethanol in the product can be calculated to be 5%.
Example 13
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 12 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 31%.
Example 14
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.5g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 18 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 43%.
Example 15
25mL of 0.05 mol/L1, 2-propylene glycol aqueous solution and 0.5g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 30 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of ethanol in the product was calculated to be 46%.
Example 16
Putting 25mL of 0.05 mol/L1, 2-butanediol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride into a high-pressure reaction kettle with the volume of 30mL, sealing the reaction kettle, reacting for 24 hours at 200 ℃, and cooling the reaction kettle to obtain a reaction solution to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of n-propanol in the product was calculated to be 42%.
Example 17
25mL of 0.05 mol/L1, 2-pentanediol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be measured.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of n-butanol in the product was calculated to be 50%.
Example 18
25mL of 0.05 mol/L1, 2-hexanediol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are placed in a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be measured.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of n-pentanol in the product can be calculated to be 50%.
Example 19
25mL of 0.05 mol/L1, 2-butadienol aqueous solution and 0.2g of nano nickel prepared by sodium borohydride reduction are placed into a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is sealed and then reacts for 24 hours at 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). From the concentration-peak area standard curve and the product peak area, the molar yield of n-propanol in the product was calculated to be 32%.
Example 20
25mL of 0.05 mol/L1, 3-propanediol aqueous solution and 0.2g of nano nickel prepared by reducing sodium borohydride are put into a high-pressure reaction kettle with the volume of 30mL, the reaction kettle is closed, the reaction is carried out for 24 hours at the temperature of 200 ℃, and after the reaction kettle is cooled, the reaction solution is to be tested.
The resulting solution was examined by gas chromatography-mass spectrometer (TRACE DSQ GC-MS). According to the concentration-peak area standard curve and the peak area of the product, the molar yield of ethanol in the product can be calculated to be 25%.
FIG. 2 is a mass spectrum of ethanol, a product of examples 1 and 18, provided by the present invention.
FIG. 3 is a mass spectrum of n-propanol, a product of examples 14 and 17, according to the present invention.
FIG. 4 is a mass spectrum of n-butanol as a product in example 15, which is provided by the present invention.
FIG. 5 is a mass spectrum of n-pentanol, a product of example 16, according to the present invention.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (5)
1. A process for producing a lower alkanol from a diol compound, comprising charging the diol compound, water and nano nickel into a high-pressure reactor using the diol compound and water as raw materials and nano nickel as a catalyst, sealing the reactor, carrying out a hydrothermal reaction, reacting the reaction product at 160 to 220 ℃ for 6 to 30 hours, cooling the reaction product, and filtering the reaction product to obtain a lower alkanol solution; the lower alkanol is ethanol, n-propanol, n-butanol or n-pentanol;
in the raw materials of the diol compound and water, the aqueous solution of the diol compound is as follows: 25ml of 0.05mol/L aqueous solution of diol compound; the nano nickel is as follows: 0.1g or 0.3-0.5 g.
2. The process for producing a lower alkanol from a diol compound according to claim 1, wherein the process for producing a lower alkanol from a diol compound has the chemical reaction formula:
3. the process for producing a lower alkanol from a diol compound according to claim 1,
the diol compound is one of 1, 2-propylene glycol, 1, 2-butanediol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 3-propylene glycol and 1, 2-butadienol.
4. The process for producing a lower alkanol from a diol compound according to any one of claims 1 to 3, wherein the lower alkanol after the reaction is: 1,2-propanediol corresponds to ethanol; 1, 2-butanediol corresponds to n-propanol; the 1, 2-pentanediol corresponds to n-butanol; 1, 2-hexanediol corresponds to n-pentanol; 1, 3-propanediol corresponds to ethanol; 1, 2-butadienol corresponds to n-propanol.
5. The method of claim 1, wherein the nano nickel catalyst is prepared by wet chemical reduction, and the method comprises:
dissolving 4.27g of nickel chloride in 300ml of water, dropwise adding 100ml of 1mol of sodium borohydride aqueous solution under the nitrogen atmosphere, violently stirring for 3-5 h, washing with water for several times after the reaction is finished, and drying in a vacuum drying oven for 12h to obtain the nano nickel catalyst.
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| CN108187674A (en) * | 2016-12-08 | 2018-06-22 | 中国科学院大连化学物理研究所 | Tantalum base catalyst and its application in the reaction of tetrahydrofurfuryl alcohol 1,5- pentanediols |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103288596A (en) * | 2012-02-27 | 2013-09-11 | 中国科学院大连化学物理研究所 | Method for preparing monohydric alcohol or dihydric alcohol through organic acid hydrogenation |
| CN103962570A (en) * | 2013-02-03 | 2014-08-06 | 宇辰新能源材料科技无锡有限公司 | Preparation method of nickel nanopowder |
| CN103193593A (en) * | 2013-03-08 | 2013-07-10 | 吉林大学 | Method for preparing n-butanol from ethanol by using hydrothermal technique |
| CN106866364A (en) * | 2015-12-12 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of method that 1,3- ring pentanediols are prepared by furfuryl alcohol |
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