CN112495434B - Novel method for preparing ethanol amide and preparation of catalyst thereof - Google Patents

Novel method for preparing ethanol amide and preparation of catalyst thereof Download PDF

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CN112495434B
CN112495434B CN202011531386.0A CN202011531386A CN112495434B CN 112495434 B CN112495434 B CN 112495434B CN 202011531386 A CN202011531386 A CN 202011531386A CN 112495434 B CN112495434 B CN 112495434B
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CN112495434A (en
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于富红
崔丽凤
周品
柏寄荣
周全法
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Changzhou Institute of Technology
Shandong Hualu Hengsheng Chemical Co Ltd
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    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
    • B01J31/0275—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 also containing elements or functional groups covered by B01J31/0201 - B01J31/0269
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/42—Platinum
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/464—Rhodium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/75—Cobalt
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/755—Nickel
    • B01J35/19—
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination

Abstract

The invention discloses a novel method for preparing ethanol amide and preparation of a catalyst thereof, belonging to the technical field of coal chemical industry and catalysts. The invention utilizes different precursors to prepare a high-activity metal catalyst by a high-temperature molten salt method, and simultaneously adds a liquid catalyst to form a solid-liquid mixed catalyst, and then takes an intermediate product methyl glycolate in the production process of preparing ethylene glycol from coal as an initial raw material to react with a primary amine compound under the action of the prepared catalyst to generate the ethanol amide. The method for preparing the ethanol amide provided by the invention is novel, the yield is higher, the prepared catalyst is unique, and high activity is shown in the reaction process.

Description

Novel method for preparing ethanol amide and preparation of catalyst thereof
Technical Field
The invention relates to a novel method for preparing ethanol amide and preparation of a catalyst thereof, belonging to the technical field of coal chemical industry and catalysts.
Background
With the increasingly perfect technology of preparing ethylene glycol from coal, the whole ethylene glycol industry faces the excess of productivity and the severe market competition due to the production of large-scale industrialized devices for preparing ethylene glycol from coal in China, and the development of downstream products of the ethylene glycol from coal is urgent. A large amount of intermediate ethyl glycolate can be produced in the industrial production process of preparing ethylene glycol from coal, and the downstream demand of utilizing the ethyl glycolate is a method for solving the surplus capacity of the ethylene glycol industry.
Ethanolamine is one of the most important products in amino alcohols, which is used as a key fine organic chemical raw material and comprises three isomers: monoethanolamine (MEA), Diethanolamine (DEA) and Triethanolamine (TEA). The monoethanolamine accounts for about 50% of the total output of the ethanolamine, is mainly used for the aspects of surfactants, synthetic detergents, polyurethane aids, air purifiers, textile aids, rubber processing aids, cosmetics and the like, the domestic demand for the monoethanolamine is continuously increased, and the output of the monoethanolamine has certain gaps compared with the demand.
The ethyl glycolate in the ethylene glycol production line with excess capacity is utilized to solve the problem of ethanolamine production with insufficient supply and demand, which means that the industry can flexibly mix ethyl glycolate and ethanolamine according to the market demand. Therefore, how to realize the synthesis route of the process is urgent. The glycolamide (hydroxyacetamide) can be used as an acylation reagent, and the glycolamide can be mainly hydrogenated to prepare the ethanolamine, so that the synthesis of the glycolamide by using the ethyl glycolate as a raw material for preparing the ethanolamine is a feasible process route. Meanwhile, the preparation and screening of the high-activity catalyst for assisting the high-efficiency ammonolysis of the ethyl glycolate to synthesize the glycolamide is also an urgent problem to be solved. Therefore, the development of the synthetic route of the ethanol amide and the exploration of the high-efficiency catalyst required by the synthetic route have important significance.
Disclosure of Invention
In order to overcome the defects in the prior art, a specific composite catalyst system for catalyzing amidation is developed, a novel synthesis route of the ethanol amide is constructed, a new development route for improving the ethanol with excessive upstream capacity is provided, and a new opportunity is provided for the production of the downstream ethanol amine.
The technical scheme of the invention is summarized as follows:
a first object of the present invention is to provide a method for preparing a solid-liquid composite catalyst for catalytic amidation, the method comprising the processes of:
putting a metal salt precursor, molten salt and a reducing agent into a reactor for calcining; after calcining and sintering, cooling to obtain a solid metal catalyst; then mixing the solid metal catalyst with the liquid catalyst to obtain a solid-liquid composite catalyst;
wherein, the liquid catalyst is selected from any one or more of the following: tetraethyl titanate, tetraisopropyl titanate, tetrabutyl titanate, isopropyl zirconate (also known as zirconium isopropoxide), and n-propyl zirconate (also known as zirconium n-propoxide).
In one embodiment of the present invention, the metal salt precursor includes at least one of nickel dichloride, cobalt dichloride, rhodium trichloride, platinum tetrachloride, and the like.
In one embodiment of the present invention, the molten salt includes at least one or more mixed molten salts of lithium chloride, sodium chloride, potassium chloride, aluminum chloride, magnesium chloride, zinc chloride, and the like.
In one embodiment of the invention, the reducing agent comprises at least one of lithium, sodium, potassium, magnesium, aluminum, zinc, and the like.
In one embodiment of the present invention, the temperature of the calcination is 300-700 ℃.
In one embodiment of the invention, the calcining comprises calcining with a closed autoclave or a tube furnace under the protection of inert gas.
In one embodiment of the present invention, the mass ratio of the solid metal catalyst to the liquid catalyst in the solid-liquid composite catalyst is (1 to 8): 10.
in one embodiment of the present invention, the means for mixing the solid metal catalyst with the liquid catalyst comprises at least one of ultrasound, high-speed stirring, and the like.
The second purpose of the invention is to provide a solid-liquid composite catalyst for catalyzing amidation by using the method.
The third purpose of the invention is to provide a method for preparing the ethanol amide, which utilizes the solid-liquid composite catalyst to carry out catalytic amidation reaction.
In one embodiment of the present invention, the reaction process of the method for preparing the ethanol amide is as follows:
Figure BDA0002852206090000021
wherein R is selected from H, C1-C6Straight or branched alkyl, aryl substituted C1-C6Straight or branched alkyl of (2), C1-C4A straight or branched alkyl group of (A) or an unsubstituted aryl group, C1-C4A straight or branched alkyl-substituted or unsubstituted heterocyclic aryl group of (a);
using methyl glycolate as a starting material, and reacting with a primary amine compound under the action of the solid-liquid composite catalyst to obtain the glycolamide.
In one embodiment of the invention, the starting material, methyl glycolate, is an intermediate product in the production process of ethylene glycol from coal.
In one embodiment of the present invention, the molar ratio of methyl glycolate to primary amine compound is (0.5-1.5): 1.
in one embodiment of the present invention, the solid-liquid composite catalyst is used in an amount of 2 to 8 wt% relative to methyl glycolate. Wherein, the solid metal catalyst in the solid-liquid composite catalyst accounts for 1 to 3 weight percent of the methyl glycolate, and the liquid catalyst accounts for 1 to 5 weight percent of the methyl glycolate.
In one embodiment of the invention, R is preferably selected from: H. c6-C10Aryl of (C)1-C6Alkyl and its derivatives, pyridyl, pyrimidinyl, furyl, morpholinyl, N-methylpiperazinyl, N-ethylpiperazinyl, tetrahydropyrrolyl.
In one embodiment of the present invention, R may further preferably: at least one of p-chlorophenyl, p-tolyl, p-fluorophenyl, p-trifluoromethylphenyl, p-ethylphenyl, p-propylphenyl, p-tert-butylphenyl, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, or cyclohexyl, and the like.
In one embodiment of the invention, the catalytic amidation reaction may be carried out in a reaction vessel using magnetic stirring. The reaction vessel comprises a three-neck flask and a stainless steel autoclave.
In one embodiment of the invention, the temperature at which the amidation reaction is catalyzed is 60 to 200 ℃.
Has the advantages that:
the novel solid-liquid composite catalyst is prepared in a specific mode, and the method is simple and convenient. The prepared solid-liquid composite catalyst is used for preparing the ethanolamide, can efficiently catalyze amidation of methyl glycolate and amino compounds, has good reaction activity, high yield and high purity (the purity of the methyl glycolate is more than 99 percent), and has simple process and strong industrial applicability. And moreover, the intermediate product in the coal-based chemical industry is used as a raw material, so that the high-efficiency utilization of the chemical intermediate product is realized, a new development route for improving the ethanol extract with excessive upstream capacity is provided, and a new opportunity is provided for the production of the downstream ethanolamine.
Drawings
FIG. 1 is a schematic diagram of the process for preparing the solid-liquid composite catalyst according to the present invention.
FIG. 2 is a scanning electron micrograph of a platinum-based solid catalyst obtained in example 1.
FIG. 3 is a schematic view of a reaction apparatus for reacting methyl glycolate with a primary amine compound in example 1.
FIG. 4 is a scanning electron micrograph of a cobalt-based solid catalyst obtained in example 2.
FIG. 5 is a scanning electron micrograph of a nickel-based solid catalyst obtained in example 3.
FIG. 6 is a scanning electron micrograph of a rhodium-based solid catalyst obtained in example 4.
Detailed Description
The "yield of ethanolamide" referred to is defined by the following formula:
the yield (%) of glycolamide is the amount of the reactant converted to glycolamide/the amount of methyl glycolate charged × 100%.
The preparation process of the solid-liquid composite catalyst is shown in figure 1.
Example 1
Preparing a solid-liquid composite catalyst:
uniformly mixing 20g of platinum tetrachloride, 10g of magnesium powder and 50g of sodium chloride, putting the mixture into a corundum porcelain boat, heating the mixture to 650 ℃ in a tubular furnace under the protection of argon, reacting for 3 hours, cooling, removing impurities by using dilute hydrochloric acid and deionized water, and obtaining a platinum-series solid catalyst (shown in figure 2); 5g of platinum solid catalyst and 10g of tetraethyl titanate liquid catalyst are mixed to prepare the corresponding solid-liquid composite catalyst.
Preparing the ethanol amide by using the obtained solid-liquid composite catalyst:
450g of methyl glycolate, 100g of urea and 15g of the obtained solid-liquid composite catalyst (5g of platinum-based solid catalyst-10 g of tetraethyl titanate liquid) were put into a three-necked flask, heated to 160 ℃ and reacted for 3 hours, and the reaction was carried out with stirring, as shown in FIG. 3. After the reaction is finished and cooled, the reaction product is filtered and analyzed, and the yield is calculated and 94% of the ethanol amide is obtained.
Example 2
Preparing a solid-liquid composite catalyst:
uniformly mixing 30g of cobalt dichloride, 8g of sodium and 50g of sodium chloride, putting the mixture into a corundum porcelain boat, heating the mixture to 600 ℃ in a tube furnace under the protection of argon, reacting for 3 hours, cooling, and washing with deionized water to remove impurities to obtain a cobalt-based solid catalyst, wherein the cobalt-based solid catalyst is shown in figure 4; 5g of cobalt-based solid catalyst and 10g of tetraethyl zirconate liquid catalyst are mixed to prepare the corresponding solid-liquid composite catalyst.
Preparing the ethanol amide by using the obtained solid-liquid composite catalyst:
450g of methyl glycolate, 100g of urea and 15g of the obtained solid-liquid composite catalyst (5g of cobalt-based solid catalyst-10 g of tetraethyl zirconate) were put into a three-necked flask, heated to 170 ℃ and reacted for 3 hours, followed by reaction with stirring. After the reaction was completed and cooled, the reaction mixture was filtered and analyzed to calculate the yield, which was 89% of ethanolamide.
Example 3
28g of nickel dichloride, 6g of lithium and 50g of lithium chloride are uniformly mixed and then put into a corundum porcelain boat, the mixture is heated to 500 ℃ in a tube furnace under the protection of argon, the reaction is carried out for 5 hours, and the mixture is cooled and washed by deionized water to remove impurities, so that the nickel-based solid catalyst is obtained, as shown in figure 5. 5g of a nickel-based solid catalyst and 10g of a tetraethyl zirconate liquid catalyst were charged into a three-necked flask.
450g of methyl glycolate and 100g of urea were put into a three-necked flask, heated to 180 ℃ and reacted for 3 hours with stirring. After the reaction was completed and cooled, the reaction mixture was filtered and analyzed to calculate the yield, i.e., the yield of the ethanolamide was 92%.
Example 4
Uniformly mixing 25g of rhodium trichloride, 5g of zinc powder and 50g of zinc chloride, putting the mixture into a corundum porcelain boat, heating the mixture to 450 ℃ in a tube furnace under the protection of argon, reacting for 8 hours, cooling, and washing away impurities by using dilute hydrochloric acid and deionized water to obtain the rhodium-based solid catalyst, wherein the rhodium-based solid catalyst is shown in figure 6. 5g of a rhodium-based solid catalyst and 10g of a zirconium isopropyl ester liquid catalyst were charged in a three-necked flask.
450g of methyl glycolate and 100g of urea were put into a three-necked flask, heated to 160 ℃ and reacted for 4 hours with stirring. After the reaction was completed and cooled, the reaction mixture was filtered and analyzed to calculate the yield, i.e., the yield of the ethanolamide was 91%.
Example 5
2g of the nickel-based solid catalyst prepared in example 6 and 5g of tetraethyl titanate liquid catalyst were charged into a three-necked flask.
200 g of methyl glycolate was added to a three-necked flask, and stirring was started, the temperature was raised to 100 ℃ and ammonia gas was introduced to react for 3 hours. After the reaction was completed and cooled, the reaction mixture was filtered and analyzed to calculate the yield, i.e., the yield of the ethanolamide was 93%.
Comparative example 1
Catalyst-free preparation of ethanolamide:
450g of methyl glycolate and 100g of urea were added to a three-necked flask, and the temperature was raised to 160 ℃ without adding a catalyst, followed by reaction for 3 hours with stirring. After the reaction was completed and cooled, the reaction mixture was filtered and analyzed to calculate the yield, i.e., the yield of the ethanolamide was 21%.
Comparative example 2
Preparing a solid metal catalyst:
uniformly mixing 20g of platinum tetrachloride, 10g of magnesium powder and 50g of sodium chloride, putting the mixture into a corundum porcelain boat, heating the mixture to 650 ℃ in a tubular furnace under the protection of argon, reacting for 3 hours, cooling, removing the mixture, and washing out impurities by using dilute hydrochloric acid and deionized water to obtain the platinum-based solid catalyst.
The pure application of the solid metal catalyst to prepare the ethanol amide:
450g of methyl glycolate, 100g of urea and 5g of a platinum-based solid catalyst were put into a three-necked flask, heated to 160 ℃ and reacted for 3 hours with stirring. After the reaction was completed and cooled, the reaction mixture was filtered and analyzed to calculate the yield, which was 62% of the ethanolamide yield.
Comparative example 3
Preparation of ethanolamide using a liquid catalyst alone:
10g of tetraethyl titanate liquid catalyst was charged into a three-neck flask. Then 450g of methyl glycolate and 100g of urea were added to the three-necked flask, and the mixture was heated to 160 ℃ to react for 3 hours, followed by reaction under stirring. After the reaction was completed and cooled, the reaction mixture was filtered and analyzed to calculate the yield, i.e., the yield of the ethanolamide was 83%.
The results of comparing the catalyst not added in comparative example 1, the single solid catalyst in comparative example 2, the single liquid catalyst in comparative example 3 and the solid-liquid composite catalyst in example 1 for preparing ethanol amide are shown in table 1.
TABLE 1 results of preparation of ethanolamide by different catalytic systems in example 1 and comparative examples 1 to 3
Figure BDA0002852206090000051
。

Claims (7)

1. A preparation method of a solid-liquid composite catalyst for catalytic amidation is characterized by comprising the following steps:
putting a metal salt precursor, molten salt and a reducing agent into a reactor for calcining; after calcining and sintering, cooling to obtain a solid metal catalyst; then mixing the solid metal catalyst with the liquid catalyst to obtain a solid-liquid composite catalyst;
wherein, the liquid catalyst is selected from any one or more of the following: tetraethyl titanate, tetraisopropyl titanate, tetrabutyl titanate, isopropyl zirconate, n-propyl zirconate;
the metal salt precursor comprises at least one of nickel dichloride, cobalt dichloride, rhodium trichloride and platinum tetrachloride;
the molten salt comprises at least one or more mixed molten salts of lithium chloride, sodium chloride, potassium chloride, aluminum chloride, magnesium chloride and zinc chloride;
the reducing agent comprises at least one of lithium, sodium, potassium, magnesium, aluminum and zinc;
the calcining temperature is 300-700 ℃; the calcination comprises calcination by using a closed high-temperature kettle or a tubular furnace under the protection of inert gas.
2. The method according to claim 1, wherein the mass ratio of the solid-liquid composite catalyst to the liquid catalyst is (1-8): 10;
the mixing mode of the solid metal catalyst and the liquid catalyst comprises at least one of ultrasound and high-speed stirring.
3. A solid-liquid composite catalyst for catalytic amidation prepared by the method of any one of claims 1-2.
4. A method for preparing ethanolamide, which comprises carrying out catalytic amidation reaction using the solid-liquid composite catalyst according to claim 3.
5. The method according to claim 4, wherein the reaction process of the method for preparing the ethanol amide is as follows:
Figure FDA0003169402440000011
wherein R is selected from H, C1-C6Straight or branched alkyl, aryl substituted C1-C6Straight or branched alkyl of (2), C1-C4A straight or branched alkyl group of (A) or an unsubstituted aryl group, C1-C4A straight or branched alkyl-substituted or unsubstituted heterocyclic aryl group of (a);
using methyl glycolate as a starting material, and reacting with a primary amine compound under the action of the solid-liquid composite catalyst to obtain the glycolamide.
6. The process according to claim 5, wherein the molar ratio of methyl glycolate to primary amine compound is (0.5-1.5): 1.
7. the method according to claim 5 or 6, wherein the amount of the solid-liquid composite catalyst used is 2 to 8 wt% relative to methyl glycolate.
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