CN109134420B - Preparation method of cyclic carbonate - Google Patents

Preparation method of cyclic carbonate Download PDF

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CN109134420B
CN109134420B CN201811087291.7A CN201811087291A CN109134420B CN 109134420 B CN109134420 B CN 109134420B CN 201811087291 A CN201811087291 A CN 201811087291A CN 109134420 B CN109134420 B CN 109134420B
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group
cyclic carbonate
catalyst
independently selected
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CN109134420A (en
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成卫国
应挺
苏倩
董丽
张锁江
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Institute of Process Engineering of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates

Abstract

The invention provides a preparation method of cyclic carbonate, which comprises the following steps: catalyzing the synthesis of cyclic carbonates using a catalyst that is an aminoacrylic ionic liquid polymer heterogeneous catalyst; the cyclic carbonate prepared by the method has high selectivity and conversion rate, the purity of the obtained cyclic carbonate product can reach 99.9 mol%, and compared with the traditional method for preparing the cyclic carbonate, the ionic liquid polymer catalyst used in the invention has the advantages of more active sites, high catalytic efficiency, stability, difficulty in decomposition, simple preparation process, less addition amount, easiness in separation from a liquid phase and the like, and has high industrial application value.

Description

Preparation method of cyclic carbonate
Technical Field
The invention belongs to the field of green catalysis, and particularly relates to a preparation method of cyclic carbonate.
Background
Carbon dioxide is one of greenhouse gases, the efficient capture and conversion of the carbon dioxide are one of the research centers of numerous scholars at present, the carbon dioxide can obtain various high value-added compounds such as cyclic carbonate, dimethyl carbonate or isocyanate and the like through various synthesis means, wherein the cyclic carbonate can be used as an aprotic high-boiling-point polar solvent with very wide application, can be used as an electrolyte in a lithium ion battery and can also be used for synthesizing intermediates of medicines and fine chemicals, so the cyclic carbonate is synthesized by taking the carbon dioxide as a raw material through a green chemical means, and the technical problem which needs to be solved urgently in the chemical industry at present is solved.
Because the reactivity of carbon dioxide gas is poor, the preparation of cyclic carbonate by using carbon dioxide gas as a raw material in the chemical industry at present is mainly carried out under the reaction conditions of high temperature and high pressure and the presence of a catalyst, the catalyst is very important for the reaction of synthesizing the cyclic carbonate, the catalysts for synthesizing the cyclic carbonate reported at present can be divided into two types of homogeneous catalysts and heterogeneous catalysts, the homogeneous catalysts mainly refer to a homogeneous catalyst system consisting of Lewis acid and halogen ions and comprise quaternary ammonium salts, quaternary phosphonium salts, imidazole ionic liquids, Lewis acid metal complexes and the like, for example, CN108299375A discloses a method for preparing the cyclic carbonate by using a succinimide and halide combined catalyst, the synergistic effect of the succinimide and the halide is utilized, the reaction temperature is 25-90 ℃, and the reaction pressure is 0.1-1 MPa, the reaction time is 1-10 h, the yield of the obtained cyclic carbonate can reach more than 90%, however, the homogeneous catalyst is usually used in a large amount, and the problems that the separation is difficult in a post-treatment process after the reaction is finished, a solvent harmful to the environment is required to be used in the separation process, the industrial continuous reaction is difficult to apply, and the like need to be solved, so that the application prospect is not large.
Heterogeneous catalysts developed so far include quaternary phosphonium salt supported system catalysts, alkali metal salt supported catalysts, alkali modified ion exchange resin catalysts and the like, and heterogeneous catalysts such as supported metal catalysts and supported quaternary ammonium salt catalysts can solve the problems of difficult catalyst recovery and the like to a certain extent, however, the heterogeneous catalysts are generally low in activity, generally have the problems of large dosage, complex synthesis, short service life and the like in the reaction, so that the use cost is high, for example, CN101318949A discloses a method for catalytically synthesizing cyclic carbonates by using an immobilized ionic liquid catalyst, wherein a mesoporous molecular sieve is used as a carrier, the imidazole salt ionic liquid is loaded on the surface of the catalyst, the obtained catalyst can catalyze and synthesize cyclic carbonate at lower temperature and pressure, but the catalytic efficiency is lower, and the service life is shorter, CN103030623A discloses a composite catalyst consisting of a silica carrier loaded with metal silicate and a silica carrier grafted with alkyl silicate, the composite catalyst has higher catalytic efficiency and less addition when being used for catalyzing the reaction of ethylene oxide and carbon dioxide to prepare the cyclic carbonate, but the loading capacity of the used carrier is limited, and the service life of the obtained catalyst is still shorter.
In recent years, ionic liquid polymers have attracted extensive attention of researchers because of their advantages of no need of a carrier, no decomposition, long service life, many active sites, and the like, and the structures of which can be modified or modified by different groups, and thus have great potential for use as cyclic carbonate synthesis catalysts. Based on the prior art, the technical personnel in the field need to further try to utilize ionic liquid polymer, especially amino acrylic ionic liquid polymer, to be functionalized to be used as a heterogeneous cyclic carbonate synthesis catalyst, so that the catalyst has the advantages of being capable of efficiently catalytically synthesizing cyclic carbonate under the conditions of no solvent, high temperature and high pressure, prolonging the service life of the cyclic carbonate, and proving the potential of the heterogeneous catalyst in the industrial production of cyclic carbonate.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a method for efficiently and catalytically synthesizing cyclic carbonate under the conditions of no solvent, high temperature and high pressure, and proves the potential of a heterogeneous catalyst in the industrial production of cyclic carbonate.
To achieve the above object, one of the objects of the present invention is to provide a method for preparing a cyclic carbonate, the method comprising the steps of:
the synthesis of cyclic carbonates is catalyzed using a catalyst.
The catalyst comprises an ionic liquid polymer.
The ionic liquid polymer has a structure as shown in formula one:
Figure BDA0001803469360000031
wherein m and n are each independently selected from any natural number, and m + n.gtoreq.4, such as 5, 8, 12, 20, 40, 60, 100, 120, 150, 180, 200, 250, 300, or the like.
R1And R2Each independently selected from a hydrogen atom or any one of alkane groups, such as a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, or the like.
R3～R6Each independently selected from any one of the alkane groups, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or the like.
A1And A2Each independently selected from any alkylene group such as methylene, ethylene, propylene or butylene, and the like.
X1And X2Each independently selected from any compatible anion。
B1And B2Each independently selected from any one of an alkane group, a hydroxyl-terminated alkane group, a carboxyl-terminated alkane group or a sulfonate-terminated alkane group.
The invention utilizes the ionic liquid polymer as the catalyst to catalyze and synthesize the cyclic carbonate, utilizes the characteristic that the ionic liquid is rich in ions, is beneficial to stabilizing a reaction intermediate and reducing the activation energy of the reaction, and simultaneously, the characteristics of the polymer ensure that the ionic liquid can be used as a heterogeneous catalyst, thereby being beneficial to the separation of the catalyst and the reduction of the occurrence of side reactions and further improving the conversion rate of the cyclic carbonate synthesis reaction.
Preferably, the preparation method comprises the following steps:
the carbon dioxide and the compound containing the epoxy group are subjected to addition reaction under the catalysis of a catalyst to obtain cyclic carbonate.
Preferably, the reaction temperature of the addition reaction is 80 to 150 ℃, for example, 85 ℃, 90 ℃, 95 ℃, 100 ℃, 105 ℃, 115 ℃, 125 ℃, 135 ℃ or 145 ℃.
Preferably, the reaction pressure of the addition reaction is 1 to 5MPa, for example, 1.5MPa, 1.8MPa, 2.0MPa, 2.5MPa, 3.2MPa, 3.5MPa, 4.0MPa or 4.5 MPa.
Preferably, the reaction time of the addition reaction is 1 to 8 hours, such as 1.5 hours, 2 hours, 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours, 5 hours, 5.5 hours, 6 hours, 6.5 hours, 7 hours, 7.5 hours and the like.
Preferably, the particle size of the catalyst is 10-100 mm, for example, 12mm, 15mm, 20mm, 30mm, 40mm, 50mm, 60mm, 70mm, 80mm, 90mm or 95mm, and the like, and the suitable particle size of the catalyst is favorable for promoting the adsorption of carbon dioxide, thereby improving the conversion rate of carbon dioxide.
Preferably, the mass ratio of the catalyst to the epoxy group in the epoxy group-containing compound is 1:2 to 200, for example, 1:3, 1:5, 1:10, 1:20, 1:30, 1:50, 1:70, 1:90, 1:110, 1:130, 1:150, 1:170, or 1: 190.
Preferably, the compound containing an epoxy group is any one or a mixture of at least two of ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide, cyclohexene oxide or cyclopentane oxide.
Preferably, in the structure shown in the formula I, m + n is less than or equal to 136, and the catalytic efficiency is easily reduced due to the high polymerization degree.
Preferably, in the structure shown in formula I, R1And R2Each independently selected from a hydrogen atom or a methyl group.
Preferably, in the structure shown in formula I, R3～R6Each independently selected from any alkane group with the carbon number less than or equal to 4.
Preferably, in the structure shown in formula I, A1And A2Each independently selected from any one of alkylene groups with the carbon number less than or equal to 4.
Preferably, in the structure shown in formula I, A1And A2Each independently selected from ethylene or propylene.
Preferably, in the structure shown in formula I, X1And X2Each independently selected from any one of tetrafluoroborate, hexafluorophosphate, hydrogen sulfate, dihydrogen phosphate, nitrate, bis (trifluoromethanesulfonyl) imide, trifluoromethanesulfonate, hydroxide, fluoride, chloride or bromide.
Preferably, in the structure shown in formula I, B1And B2The number of carbon atoms in the group is 2-10.
Preferably, in the structure shown in formula I, B1And B2The groups are respectively and independently selected from any one of hydroxyethyl, hydroxypropyl, carboxyethyl or carboxypropyl, and in the catalytic reaction, the hydroxyl-containing B group can interact with epoxide through forming a hydrogen bond, so that the activation energy of the reaction is greatly reduced, and the reactant is promoted to be efficiently converted into a product.
Preferably, the preparation method comprises the following steps:
and (2) placing the compound containing the epoxy group and catalyst powder with the particle size of 10-1000 microns in a closed reaction kettle, uniformly mixing, maintaining the temperature of the reaction kettle within the range of 80-150 ℃, continuously introducing carbon dioxide gas into the reaction kettle, maintaining the pressure of a reaction system in the kettle within the range of 1-5 MPa, and performing addition reaction for 1-8 hours to obtain the cyclic carbonate.
The recitation of numerical ranges herein includes not only the above-recited numerical values, but also any numerical values between non-recited numerical ranges, and is not intended to be exhaustive or to limit the invention to the precise numerical values encompassed within the range for brevity and clarity.
Compared with the prior art, the invention has the beneficial effects that:
(1) the invention provides a novel amino acrylic ionic liquid polymer heterogeneous catalyst, which is used for catalyzing carbon dioxide to perform addition reaction with a compound containing an epoxy group to obtain cyclic carbonate, the cyclic carbonate prepared by the method has high selectivity and conversion rate, and the purity of the obtained cyclic carbonate product can reach 99.9 mol%.
(2) Compared with the traditional method for preparing cyclic carbonate, the ionic liquid polymer catalyst used in the invention has the advantages of more active sites, high catalytic efficiency, stability, difficult decomposition, simple preparation process, less addition amount, easy separation from a liquid phase and the like, and has higher industrial application value.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments.
The ionic liquid polymers used in the following examples and comparative examples are either commercially available or can be synthesized by themselves.
Illustratively, the ionic liquid polymer may be synthesized by:
step (1), adding a certain amount of dimethylaminoethyl methacrylate monomer and bromoethanol into a 100mL flask, stirring for 12h at 25 ℃ to react, repeatedly washing a reaction product for 3 times by using ethyl acetate after the reaction is finished, and then drying the reaction product in vacuum at 40 ℃ overnight to obtain a white powdery substance, namely an ionic liquid monomer;
and (2) adding 3g of the ionic liquid monomer synthesized in the step (1) and 30mL of a methanol and chloroform mixed solution into a 100mL flask, then adding an oil-soluble initiator Azobisisobutyronitrile (AIBN) with the mass of 0.3 wt% of the monomer, then carrying out free radical polymerization reaction on the mixed solution at 70 ℃ under a nitrogen atmosphere, after 24h of reaction, removing residual solvent by using a rotary evaporator, repeatedly washing the residual product for 3 times by using diethyl ether and acetone, finally carrying out vacuum drying at 40 ℃ overnight to obtain the ionic liquid polymer 1, and determining the stability.
The average degree of polymerization of the resulting ionic liquid polymer was 68 as determined by GPC measurement.
By increasing and changing the types of the polymerization monomers, replacing bromoethanol with other types of compounds or changing the adding amount of the initiator, the ionic liquid polymer with any structure and polymerization degree can be obtained by the technical personnel in the field.
In each example of the present invention, the yield of the product was quantitatively determined by gas chromatography model 6820GC-TCD, manufactured by Agilent.
Example 1
Placing 143mmol of propylene oxide and 300mg of ionic liquid polymer 1 powder with the particle size of 100mm in a 750mL closed reaction kettle, uniformly mixing, maintaining the temperature of the reaction kettle at 110 ℃, continuously introducing carbon dioxide gas into the reaction kettle, maintaining the pressure of a reaction system in the kettle at 2MPa, and performing addition reaction for 3 hours to obtain a product propylene carbonate, wherein the yield of the propylene carbonate is 99.8 mol%.
The ionic liquid polymer 1 has a structure as shown in compound 1:
Figure BDA0001803469360000071
example 2
The only difference from example 1 is that the ionic liquid polymer 1 was replaced with ionic liquid polymer 2.
Example 2 the product propylene carbonate was obtained in a yield of 99.6 mol%.
The ionic liquid polymer 2 has a structure shown as compound 2:
Figure BDA0001803469360000081
example 3
The only difference from example 1 is that the ionic liquid polymer 1 was replaced with ionic liquid polymer 3.
Example 3 the product propylene carbonate was obtained in a yield of 98.8 mol%.
The ionic liquid polymer 3 has a structure as shown in compound 3:
Figure BDA0001803469360000082
example 4
The only difference from example 1 is that the ionic liquid polymer 1 was replaced with ionic liquid polymer 4.
Example 4 gave propylene carbonate as a product in a yield of 99.6 mol%.
The ionic liquid polymer 4 has a structure as shown in compound 4:
Figure BDA0001803469360000091
example 5
The only difference from example 1 is that the particle size of the ionic liquid polymer 1 powder was 10 mm.
Example 5 gave propylene carbonate as a product in a yield of 99.9 mol%.
Example 6
The only difference from example 1 is that the ionic liquid polymer 1 powder was added in an amount of 30 mg.
Example 6 gave the product propylene carbonate in a yield of 99.2 mol%.
Example 7
The only difference from example 1 is that the temperature of the reaction kettle is controlled at 150 ℃, the pressure of the reaction system in the kettle is controlled at 4.4MPa, and the time of the addition reaction is 1 h.
Example 7 gave the product propylene carbonate in a yield of 99.5 mol%.
Example 8
The only difference from example 1 is that the temperature of the reaction kettle is controlled at 80 ℃, the pressure of the reaction system in the kettle is controlled at 1.2MPa, and the time of the addition reaction is 8 h.
Example 8 gave propylene carbonate as a product in a yield of 99.6 mol%.
Example 9
The only difference from example 1 is that the ionic liquid polymer 1 was replaced with ionic liquid polymer 5.
Example 9 gave the product propylene carbonate in a yield of 98.1 mol%.
The ionic liquid polymer 5 has a structure as shown in compound 5:
Figure BDA0001803469360000101
example 10
The only difference from example 1 is that the ionic liquid polymer 1 was replaced with ionic liquid polymer 6.
Example 10 gave the product propylene carbonate in a yield of 95.8 mol%.
The ionic liquid polymer 6 has a structure as shown in compound 6:
Figure BDA0001803469360000102
example 11
The only difference from example 1 is that the propylene oxide therein was replaced with the same molar amount of epichlorohydrin.
Example 11 gave a propylene carbonate product in a yield of 96.4 mol%.
Example 12
The only difference from example 1 is that the propylene oxide therein was replaced by the same molar amount of styrene oxide.
Example 12 gave styrene carbonate as a product in a yield of 93.9 mol%.
In conclusion, the invention provides a novel amino acrylic ionic liquid polymer heterogeneous catalyst, the cyclic carbonate is obtained by catalyzing carbon dioxide to perform addition reaction with a compound containing an epoxy group, the cyclic carbonate prepared by the method has higher selectivity and conversion rate, and the purity of the obtained cyclic carbonate product can reach 99.9 mol%.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention, and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. A preparation method of cyclic carbonate is characterized by comprising the following steps:
carrying out addition reaction on carbon dioxide and a compound containing an epoxy group under the catalysis of a catalyst to obtain cyclic carbonate;
the catalyst comprises an ionic liquid polymer;
the ionic liquid polymer has a structure as shown in formula one:
Figure FDA0002554155450000011
wherein m and n are independently selected from any natural number, m + n is more than or equal to 4, and m + n is less than or equal to 136;
R1and R2Each independently selected from a hydrogen atom or a methyl group;
R3～R6each independently selected from any alkane group with the carbon number less than or equal to 4;
A1and A2Each independently selected from any one alkylene group with the carbon number less than or equal to 4;
X1and X2Each independently selected from any one of tetrafluoroborate, hexafluorophosphate, hydrogen sulfate, dihydrogen phosphate, nitrate, bis (trifluoromethanesulfonyl) imide, trifluoromethanesulfonate, hydroxide, fluoride, chloride or bromide;
B1and B2Each independently selected from any one of an alkane group, a hydroxyl-terminated alkane group, a carboxyl-terminated alkane group or a sulfonate-terminated alkane group, and B1And B2The number of carbon atoms in the group is 2-10.
2. The method according to claim 1, wherein the reaction temperature of the addition reaction is 80 to 150 ℃.
3. The method according to claim 1, wherein the reaction pressure of the addition reaction is 1 to 5 MPa.
4. The preparation method according to claim 1, wherein the reaction time of the addition reaction is 1-8 hours.
5. The method according to claim 1, wherein the catalyst has a particle size of 10 to 100 mm.
6. The method according to claim 1, wherein the mass ratio of the catalyst to the epoxy group in the epoxy group-containing compound is 1:2 to 200.
7. The method according to claim 1, wherein the compound containing an epoxy group is any one or a mixture of at least two of ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide, cyclohexene oxide, or cyclopentane oxide.
8. The method according to claim 1, wherein in the structure represented by formula I, A is1And A2Each independently selected from ethylene or propylene.
9. The method according to claim 1, wherein in the structure represented by formula I, B is1And B2Each group is independently selected from any one of hydroxyethyl, hydroxypropyl, carboxyethyl or carboxypropyl.
10. The method according to any one of claims 1 to 9, wherein the method comprises the steps of:
and (2) placing the compound containing the epoxy group and catalyst powder with the particle size of 10-1000 microns in a closed reaction kettle, uniformly mixing, maintaining the temperature of the reaction kettle within the range of 80-150 ℃, continuously introducing carbon dioxide gas into the reaction kettle, maintaining the pressure of a reaction system in the kettle within the range of 1-5 MPa, and performing addition reaction for 1-8 hours to obtain the cyclic carbonate.
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CN112159386B (en) * 2020-09-16 2021-12-03 中国科学院过程工程研究所 Method for synthesizing cyclic carbonate by mild catalysis of ionic liquid crosslinked polymer
CN112341394B (en) * 2020-11-03 2023-01-06 中国科学院过程工程研究所 Method for preparing cyclic carbonate ester by catalysis of hydrogen bond donor functionalized polymeric ionic liquid
CN112250656B (en) * 2020-11-03 2022-06-17 中国科学院过程工程研究所 Method for catalytically synthesizing cyclic carbonate based on multi-active-center ionic liquid
CN112495431B (en) * 2020-11-24 2022-02-11 中国科学院过程工程研究所 Method for synthesizing cyclic carbonate by mild catalysis of multi-site ionic liquid
CN113185490A (en) * 2021-04-15 2021-07-30 西北大学 Carboxylic acid/metal halide composite catalytic CO2Method for preparing cyclic carbonate by cycloaddition with epoxide
CN114276322A (en) * 2022-01-06 2022-04-05 惠州市绿色能源与新材料研究院 Method for preparing cyclic carbonate by photo-initiated polymerization of ionic liquid material
CN115739179B (en) * 2022-11-01 2024-04-09 南京大学 Composite high-molecular catalyst and preparation method and application thereof

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