CN116351467A - Composite catalyst for preparing dialkyl carbonate from dialkyl oxalate - Google Patents

Composite catalyst for preparing dialkyl carbonate from dialkyl oxalate Download PDF

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CN116351467A
CN116351467A CN202211533678.7A CN202211533678A CN116351467A CN 116351467 A CN116351467 A CN 116351467A CN 202211533678 A CN202211533678 A CN 202211533678A CN 116351467 A CN116351467 A CN 116351467A
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composite catalyst
dialkyl
carbonate
preparing
catalyst
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吴晓斌
汪俊
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Shanghai Xiechen New Material Technology 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
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
    • B01J31/0212—Alkoxylates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The application provides a composite catalyst for preparing dialkyl carbonate from dialkyl oxalate, wherein the composite catalyst is a composite organic salt of alkali metal and alkaline earth metal, and the ratio of the amount of the alkali metal to the amount of the alkaline earth metal is 50-99:1. Also provides a preparation method of the composite catalyst and a method for preparing dialkyl carbonate by applying the composite catalyst to dialkyl oxalate. The composite catalyst for preparing the dialkyl carbonate by using the dialkyl oxalate can directly obtain the mixed solution of the dialkyl carbonate with high purity.

Description

Composite catalyst for preparing dialkyl carbonate from dialkyl oxalate
Technical Field
The application relates to the technical field of chemical industry, in particular to a composite catalyst for preparing dialkyl carbonate from dialkyl oxalate.
Background
The dialkyl carbonate includes dimethyl carbonate, diethyl carbonate, methylethyl carbonate, and the like; is a good solvent and an important organic chemical raw material, is insoluble in water, and can be mixed with organic solvent alcohol, ester and the like in any proportion. Wherein, the dimethyl carbonate is an important organic chemical raw material, has wide application prospect in the fields of pesticides, medicines, plastics, dyes, paints, new materials and the like, and is known as a new foundation stone for organic synthesis in the 21 st century. DMC is low in toxicity, has excellent solubility, and can be used as a green solvent to replace freon, chloroform, benzene, xylene and the like; DMC structures contain carbonyl groups and can be used as carbonylation agents to replace phosgene which is a highly toxic and highly corrosive byproduct, and to synthesize carbonic acid derivatives, such as Polycarbonate (PC) and the like. The dimethyl carbonate has high oxygen content (53%), high octane number and low vapor pressure, and can be used as additive of gasoline or diesel oil.
The current methods for synthesizing dialkyl carbonates are: phosgene method, transesterification method, methanol oxidative carbonylation method, urea alcoholysis method, CO2 and methanol direct synthesis method, etc., wherein the industrial production mainly comprises phosgene method and transesterification method. The phosgene method is a traditional synthesis method, and uses highly toxic phosgene as a raw material, so that the safety is poor, the environment is polluted, and the generated byproduct HCl has high corrosiveness to equipment. The transesterification method uses ethylene carbonate or propylene carbonate and methanol to carry out transesterification reaction to generate dimethyl carbonate, the raw material supply depends on petroleum, and the generation cost is high.
The synthesis of dimethyl carbonate from CO and methyl nitrite at low temperature and low pressure was originally proposed by UBE in Japan and realized industrialization. The method has mild reaction conditions, part of reaction products can be recycled in the reaction, the reaction is carried out in a gas phase, no water is generated in the reaction, and the harm of water to the catalyst in the liquid phase method is avoided. With the increasing demand of DMC, the domestic research on catalyst and process for synthesizing dimethyl carbonate from CO and methyl nitrite is increasing. The catalyst for synthesizing dimethyl carbonate by gas-phase carbonyl of CO and methyl nitrite is Cu-Pd bimetallic Wacker type chlorine-containing catalyst prepared by taking active carbon, alumina, lithium aluminate spinel and the like as carriers. Chlorine-containing catalysts have good activity and high selectivity, but have the problems of poor stability, short service life, equipment corrosion and the like, and the root cause of the reduction of the catalyst activity is the loss of chloride ions on the catalyst. In order to improve the stability of the catalyst, it is most common practice to add a certain amount of chlorine-containing compounds, such as HCl or methyl chloroformate, to the feed gas. For example, US patent 5426209 discloses a catalyst which uses activated carbon as a carrier, palladium chloride as a main active component, copper chloride as an auxiliary agent, and the DMC space-time yield is optimally 725 g/(l×h) and can be stabilized for only 8h. U.S. patent 5688984 discloses a carrier for a catalyst for synthesizing dimethyl carbonate, namely lithium aluminate with a spinel structure, and the catalyst prepared by adopting the carrier has higher activity and selectivity, the selectivity of the catalyst reaches more than 95 percent based on CO and methyl nitrite, and the catalyst performance can be improved to different degrees by adding different auxiliary agents, but the service life of the catalyst is still shorter. From the data reported in the literature, it is known that even with continuous replenishment of HCl during the reaction, the activity of the catalyst decreases by 20% to 30% over the 100 hour reaction period. The catalyst has low activity and short service life, and greatly limits the industrial application of the catalyst.
Disclosure of Invention
The application provides a composite catalyst for preparing dialkyl carbonate from dialkyl oxalate, which aims to solve the problems of low activity and short service life of the existing catalyst.
In order to solve the technical problems, the application provides a composite catalyst for preparing dialkyl carbonate from dialkyl oxalate, wherein the composite catalyst is an alkali metal-alkaline earth metal composite organic salt, and the ratio of the amount of alkali metal to the amount of alkaline earth metal substances is 50-99:1.
Further, the alkali metal is one or more of lithium, sodium or potassium.
Further, the alkaline earth metal is one or more of lanthanum or cerium.
Further, the organic salt is an organic salt of methanol, ethanol, propanol or isobutanol.
The application also provides a preparation method of the composite catalyst, wherein the composite catalyst is used for preparing dialkyl carbonate from dialkyl oxalate, and comprises the following steps:
dissolving an alkali metal organic salt in absolute methanol or ethanol to obtain a first solution;
dissolving alkaline earth metal organic salt in absolute methanol or ethanol to obtain a second solution;
mixing the first solution and the second solution, heating and stirring, and completely refluxing the distilled substances to obtain a mixed suspension;
and filtering the mixed suspension to obtain the composite catalyst.
The application also provides a method for preparing dialkyl carbonate by using the composite catalyst, which adopts one or more of a kettle reactor, a tower reactor or a micro-channel reactor to contact the dialkyl oxalate with the composite catalyst, wherein the composite catalyst is a composite organic salt of alkali metal-alkaline earth metal, the reaction pressure is normal pressure-1.0 MPaG at the reaction temperature of 90-180 ℃, the mass ratio of the dialkyl oxalate to the composite catalyst is 5-20:1, and the transesterification reaction and decarbonylation reaction are carried out, and the reaction product is a mixed solution containing dimethyl carbonate, methyl ethyl carbonate and diethyl carbonate.
The technical scheme of the application at least comprises the following advantages: in the method, a composite catalyst is obtained by mixing and reacting organic alkali metal salt and organic alkaline earth metal salt for a period of time, and dialkyl oxalate raw materials can undergo transesterification and decarbonylation under the condition of continuous feeding to obtain a mixture of CO gas and dialkyl carbonate; the mixture containing dialkyl carbonate is subjected to extractive distillation to remove light components and alkyl alcohol, and unreacted dialkyl oxalate and heavy components are further removed, so that the mixed solution of dialkyl carbonate with high purity can be directly obtained, and the mixed solution can be used as a raw material for producing battery electrolyte.
Detailed Description
The following description of the embodiments in this application is provided for clarity and completeness, and it is apparent that the described embodiments are some, but not all, of the embodiments of this application. All other embodiments, which can be made by one of ordinary skill in the art based on the embodiments herein without making any inventive effort, are intended to be within the scope of the present application.
In addition, the technical features described below in the different embodiments of the present application may be combined with each other as long as they do not collide with each other.
The invention provides a composite catalyst for preparing dialkyl carbonate from dialkyl oxalate, which is a composite organic salt of alkali metal and alkaline earth metal, wherein the ratio of the amount of the alkali metal to the amount of the alkaline earth metal is 50-99:1.
Further, the alkali metal is one or more of lithium, sodium or potassium.
Further, the alkaline earth metal is one or more of lanthanum or cerium.
Further, the organic salt is an organic salt of methanol, ethanol, propanol or isobutanol.
The application also provides a preparation method of the composite catalyst, wherein the composite catalyst is used for preparing dialkyl carbonate from dialkyl oxalate, and comprises the following steps:
dissolving an alkali metal organic salt in absolute methanol or ethanol to obtain a first solution;
dissolving alkaline earth metal organic salt in absolute methanol or ethanol to obtain a second solution;
mixing the first solution and the second solution, heating and stirring, and completely refluxing the distilled substances to obtain a mixed suspension;
and filtering the mixed suspension to obtain the composite catalyst.
The application also provides a method for preparing dialkyl carbonate by using the composite catalyst, which adopts one or more of a kettle reactor, a tower reactor or a micro-channel reactor to contact the dialkyl oxalate with the composite catalyst, wherein the composite catalyst is a composite organic salt of alkali metal-alkaline earth metal, the reaction pressure is normal pressure-1.0 MPaG at the reaction temperature of 90-180 ℃, the mass ratio of the dialkyl oxalate to the composite catalyst is 5-20:1, and the transesterification reaction and decarbonylation reaction are carried out, and the reaction product is a mixed solution containing dimethyl carbonate, methyl ethyl carbonate and diethyl carbonate.
Example 1
1) Weighing 100g of lithium methoxide, and dissolving in 200ml of absolute ethyl alcohol;
2) Weighing 14.42g of lanthanum triethanolammonium, and dissolving in 100ml of absolute ethyl alcohol;
3) Mixing the above solutions, stirring at 60deg.C, and refluxing the above distilled liquid for 1 hr;
4) Cooling the suspension, filtering, and taking out the filtered clear liquid as a liquid catalyst A;
the catalyst obtained was determined to have an alkali metal to alkaline earth metal mass ratio of 50:1.
Comparative example 1
In accordance with the method of example 1, except that step 2) was not performed, comparative catalyst A1 was obtained.
Example 2
1) Weighing 100g of sodium methoxide, and dissolving in 200ml of anhydrous methanol;
2) Weighing 5.13g of lanthanum triethanolate, and dissolving in 90ml of absolute methanol and 10ml of absolute ethanol;
3) Mixing the above solutions, stirring at 60deg.C, and refluxing the above distilled liquid for 1 hr;
4) Cooling the suspension, filtering, and taking out the filtered clear liquid as a liquid catalyst B;
the catalyst obtained was determined to have an alkali metal to alkaline earth metal mass ratio of 99:1. The specific properties of the catalyst obtained are shown in Table 1.
Comparative example 2
In accordance with the method of example 2, except that step 2) was not performed, comparative catalyst B1 was obtained.
Example 3
1) Weighing 100g of potassium ethoxide, and dissolving in 200ml of absolute ethyl alcohol;
2) Weighing 7.92g of 2-methoxyethanol cerium, and dissolving in 100ml of absolute ethyl alcohol; the method comprises the steps of carrying out a first treatment on the surface of the
3) Mixing the above solutions, stirring at 60deg.C, and refluxing the above distilled liquid for 1 hr;
4) Cooling the suspension, filtering, and taking out the filtered clear liquid as a liquid catalyst C;
the catalyst obtained was determined to have an alkali metal to alkaline earth metal mass ratio of 66:1.
Example 4
1) 100g of sodium n-propoxide is weighed and dissolved in 150ml of absolute methanol and 50ml of absolute ethanol;
2) Weighing 6.67g of lanthanum triethanolammonium, and dissolving in 100ml of absolute methanol; the method comprises the steps of carrying out a first treatment on the surface of the
3) Mixing the above solutions, stirring at 60deg.C, and refluxing the above distilled liquid for 1 hr;
4) Cooling the suspension, filtering, and taking out the filtered clear liquid as a liquid catalyst D;
the catalyst obtained was determined to have an alkali metal to alkaline earth metal mass ratio of 50:1.
Example 5
1) Weighing 100g of lithium methoxide, weighing 100g of sodium ethoxide, and dissolving in 400ml of absolute ethyl alcohol;
2) 2-methoxyethanol cerium 21.08g is weighed and dissolved in 200ml absolute ethyl alcohol; the method comprises the steps of carrying out a first treatment on the surface of the
3) Mixing the above solutions, stirring at 60deg.C, and refluxing the above distilled liquid for 1 hr;
4) Cooling the suspension, filtering, and taking out the filtered clear liquid as a liquid catalyst E;
the catalyst obtained was determined to have an alkali metal to alkaline earth metal mass ratio of 85:1.
The catalysts obtained in examples 1-5 and comparative examples 1-2 were adjusted to the reaction process conditions for the reaction.
Test examples 1-5 and comparative examples 1-2
Table 1 shows the results of the reaction for ethylene glycol production with different catalysts, the catalysts prepared in preparation examples 1-5 and comparative examples 1-2 were placed in a kettle-type continuous flow reactor, absolute methanol or absolute ethanol was added to the reactor at a rate of 30-60ml/h, the catalyst was added at a rate of 10.0ml/h, dimethyl oxalate was added at a rate of 90-100 ml/h, the reaction temperature was 100-120℃and the reaction pressure was atmospheric pressure-0.2 MPa (G), and the dialkyl carbonate-containing product was collected after condensation. The solution is subjected to extractive distillation to remove light components and alkyl alcohol, and unreacted dialkyl oxalate and heavy components are further removed to obtain dialkyl carbonate mixed solution, and the separated alkyl alcohol and dialkyl oxalate are returned to the reactor for recycling. The reaction results are shown in Table 1.
TABLE 1
Figure SMS_1
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While nevertheless, obvious variations or modifications may be made to the embodiments described herein without departing from the scope of the invention.

Claims (6)

1. A composite catalyst for preparing dialkyl carbonate from dialkyl oxalate is characterized in that the composite catalyst is an alkali metal-alkaline earth metal composite organic salt, and the ratio of the amount of alkali metal to the amount of alkaline earth metal substances is 50-99:1.
2. The composite catalyst for preparing dialkyl carbonate from dialkyl oxalate according to claim 1, wherein the alkali metal is one or more of lithium, sodium or potassium.
3. The composite catalyst for preparing dialkyl carbonate from dialkyl oxalate according to claim 1, wherein the alkaline earth metal is one or more of lanthanum or cerium.
4. The composite catalyst for preparing dialkyl carbonate from dialkyl oxalate according to claim 1, wherein the organic salt is an organic salt of methanol, ethanol, propanol or isobutanol.
5. A method for preparing a composite catalyst for preparing dialkyl carbonate from dialkyl oxalate, comprising:
dissolving an alkali metal organic salt in absolute methanol or ethanol to obtain a first solution;
dissolving alkaline earth metal organic salt in absolute methanol or ethanol to obtain a second solution;
mixing the first solution and the second solution, heating and stirring, and completely refluxing the distilled substances to obtain a mixed suspension;
and filtering the mixed suspension to obtain the composite catalyst.
6. A method for preparing dialkyl carbonate by using a composite catalyst in dialkyl oxalate is characterized in that one or more of a kettle reactor, a tower reactor or a micro-channel reactor is adopted, dialkyl oxalate is used for contact with the composite catalyst, the composite catalyst is a composite organic salt of alkali metal-alkaline earth metal, the reaction temperature is 90-180 ℃, the reaction pressure is normal pressure-1.0 MPaG, the mass ratio of dialkyl oxalate to the composite catalyst is 5-20:1, and the transesterification reaction and decarbonylation reaction are carried out, wherein the reaction product is a mixed solution of dimethyl carbonate, methyl ethyl carbonate and diethyl carbonate.
CN202211533678.7A 2022-12-01 2022-12-01 Composite catalyst for preparing dialkyl carbonate from dialkyl oxalate Pending CN116351467A (en)

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CN111229218A (en) * 2020-01-10 2020-06-05 清华大学 Monoatomic palladium composite catalyst and preparation method and application thereof
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JPH0748319A (en) * 1992-11-20 1995-02-21 Chiyoda Corp Production of dialkyl carbonate
CA2122228A1 (en) * 1993-04-29 1994-10-30 Joerg-Dietrich Jentsch Process for preparing dialkyl carbonates
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CN106660933A (en) * 2014-09-05 2017-05-10 沙特基础工业全球技术有限公司 Method of melt polymerizing polycarbonate and the polycarbonate made therefrom
CN111229218A (en) * 2020-01-10 2020-06-05 清华大学 Monoatomic palladium composite catalyst and preparation method and application thereof
CN113181894A (en) * 2021-04-10 2021-07-30 张威 Catalytic system for catalyzing decarbonylation of dimethyl oxalate to directly generate dimethyl carbonate
CN114433081A (en) * 2022-02-25 2022-05-06 中国科学院福建物质结构研究所 Preparation method of catalyst for CO-production of carbonic ester and formic ester by synthesizing oxalate with CO

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