CN114835854A - Ionic liquid copolymer and method for preparing cyclic carbonate by using same - Google Patents
Ionic liquid copolymer and method for preparing cyclic carbonate by using same Download PDFInfo
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- CN114835854A CN114835854A CN202210653325.4A CN202210653325A CN114835854A CN 114835854 A CN114835854 A CN 114835854A CN 202210653325 A CN202210653325 A CN 202210653325A CN 114835854 A CN114835854 A CN 114835854A
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- ionic liquid
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 63
- 229920001577 copolymer Polymers 0.000 title claims abstract description 40
- 150000005676 cyclic carbonates Chemical class 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 25
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 14
- 150000002118 epoxides Chemical class 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 150000004693 imidazolium salts Chemical class 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 5
- 230000000996 additive effect Effects 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 7
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical group C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 claims description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical group C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 claims description 6
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 5
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 claims description 5
- JFDMLXYWGLECEY-UHFFFAOYSA-N 2-benzyloxirane Chemical compound C=1C=CC=CC=1CC1CO1 JFDMLXYWGLECEY-UHFFFAOYSA-N 0.000 claims description 5
- ANCUXNXTHQXICN-UHFFFAOYSA-N 2-prop-1-en-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(=C)C)=CC=C21 ANCUXNXTHQXICN-UHFFFAOYSA-N 0.000 claims description 5
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000007789 gas Substances 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 239000003546 flue gas Substances 0.000 abstract description 5
- 238000004064 recycling Methods 0.000 abstract description 3
- 238000002485 combustion reaction Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 alkali metal salts Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- GXBYFVGCMPJVJX-BYPYZUCNSA-N (2s)-2-ethenyloxirane Chemical compound C=C[C@H]1CO1 GXBYFVGCMPJVJX-BYPYZUCNSA-N 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 2
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UDSWRXKMHZVDEL-UHFFFAOYSA-N 1-(2-chloroethyl)-4-ethenylbenzene Chemical compound ClCCC1=CC=C(C=C)C=C1 UDSWRXKMHZVDEL-UHFFFAOYSA-N 0.000 description 1
- YNCPXBIZAPNQIJ-UHFFFAOYSA-N 1h-imidazole;sodium Chemical compound [Na].C1=CNC=N1 YNCPXBIZAPNQIJ-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 1
- AETJTBDBQRMLLQ-UHFFFAOYSA-N 4-chloro-5-methyl-1,3-dioxolan-2-one Chemical compound CC1OC(=O)OC1Cl AETJTBDBQRMLLQ-UHFFFAOYSA-N 0.000 description 1
- ZKOGUIGAVNCCKH-UHFFFAOYSA-N 4-phenyl-1,3-dioxolan-2-one Chemical compound O1C(=O)OCC1C1=CC=CC=C1 ZKOGUIGAVNCCKH-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- 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
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention relates to an ionic liquid copolymer, which is prepared by copolymerizing imidazolium salt containing hydroxyl, carboxyl or amino and rigid molecule containing unsaturated bonds. The ionic liquid copolymer has the advantages of simple structure, easy synthesis, good mechanical stability, high recycling degree and the like, is used as a heterogeneous catalyst for preparing cyclic carbonate by directly reacting low-concentration carbon dioxide and epoxide, does not need additional solvent and additive, has high catalytic activity and selectivity, avoids the steps of gas capture, purification and storage, reduces investment and operation cost, and is suitable for directly converting and utilizing flue gas after large-scale combustion.
Description
Technical Field
The invention relates to the technical field of clean catalysis and carbon resource chemical utilization, in particular to an ionic liquid copolymer and a method for preparing cyclic carbonate by using the same.
Background
Carbon dioxide is one of the main greenhouse gases and is a cheap, abundant and nontoxic C1 resource, so that the conversion of carbon dioxide into chemicals and organic fuels with high added values is one of the solutions for alleviating the greenhouse effect and the energy crisis. The reaction of carbon dioxide and epoxide has 100 atom percent of economy, and the obtained cyclic carbonate is a good polar solvent and a pharmaceutical chemical intermediate, and has been widely noticed and researched in recent years.
The common carbon dioxide cycloaddition reaction takes pure carbon dioxide as a gas source, and carries out compression and sealing treatment on mixed gas such as flue gas and the like after being trapped and purified, so that the process has high energy consumption, high operation cost and more operation steps, and the flue gas after being subjected to desulfurization and denitration treatment is directly used as the gas source to react with epoxide, thereby reducing the number of devices and lowering the investment cost. At present, alkali metal salts (Dalton T., 2019, 48, 7527), metal halides (Chinese J. Catal., 2018, 39, 997), ionic liquids (mol. Catal., 2020, 480, 110637, Chinese patent CN 112159387B), metal organic frameworks (Chinese patent CN 107096569) and the like are used as catalysts for the cycloaddition reaction of carbon dioxide, but the catalysts have the problems of high cost, use of cocatalysts, severe reaction conditions, low stability of a catalytic system, difficult regeneration and the like. Therefore, the method has important application value and sustainable development significance for developing a high-efficiency catalyst which is simple to prepare, low in cost, easy to recover and capable of being recycled and realizing direct catalytic conversion of low-concentration carbon dioxide and epoxide.
In view of the fact that ionic liquid has low vapor pressure, good thermal stability, adjustable physicochemical properties and excellent catalytic activity, the preparation of ionic liquid based multiphase catalysts through a specific method has become a research hotspot in recent years, one method is to utilize supported ionic liquid multiphase catalysts, such as imidazole ionic liquid modified metalloporphyrin compounds (chinese patent CN 106008448B), ionic liquid supported mineral substance multiphase catalysts (chinese patent CN 113117747A), hydroxyl functionalized ionic liquid supported catalysts (chinese patent CN 105772081A) and the like to realize the synthesis of cyclic carbonates, however, the used carriers generally have limited loading capacity and short catalyst life; still another way is to prepare ionic liquid polymers, such as polyurethane-based ionic liquid polymers (Green chem., 2013, 15, 1584), quaternary ammonium phosphate polyionic acid liquid (chinese patent CN 105367541B), amino acrylic ionic liquid polymers (chinese patent CN 109134420B), etc., and catalytically synthesize cyclic carbonates, however, some materials have the problems of poor rigidity, high dosage or poor stability, etc. On the other hand, the functionalized organic polymer has high adsorption capacity and affinity, and has good development prospect in the aspect of preparing cyclic carbonate by directly converting low-concentration carbon dioxide (Green chem, 2016, 18, 6493; Chinese patent CN 114014833A). In conclusion, the preparation of the functionalized ionic liquid copolymer with the rigid group is expected to realize the direct capture of low-concentration carbon dioxide in large-scale industrial flue gas and the preparation of the cyclic carbonate.
Disclosure of Invention
The invention aims to solve the technical problem of providing the ionic liquid copolymer which has the advantages of simple structure, good mechanical and chemical stability, easy regeneration and high recycling degree.
Another technical problem to be solved by the invention is to provide a method for preparing cyclic carbonate by using the ionic liquid copolymer.
In order to solve the above problems, the present invention provides an ionic liquid copolymer, which is characterized in that: the copolymer is prepared by copolymerizing imidazolium salt containing hydroxyl, carboxyl or amino and rigid molecules containing unsaturated bonds; the imidazolium salt is selected from one or more of functionalized ionic liquid monomers I-VI shown in the following structural formula:
in the formula: x — Is an anion of a functionalized ionic liquid monomer I-VI, and X is selected from Cl, Br, I and BF 4 、PF 6 One of (1); m = 1-6; n = 1-6; the unsaturated bond-containing rigid molecule is selected from styrene (CAS number: 100-42-5),α-methylstyrene (CAS number: 98-83-9), divinylbenzene (CAS number: 1321-74-0), 4-vinyl-1, 1 ' -biphenyl (CAS number: 2350-89-2), 4 ' -divinyl-1, 1 ' -biphenyl (CAS number: 4433-13-0), 2-naphthylethylene (CAS number: 827-54-3), 2-isopropenylnaphthalene (CAS number: 3710-23-4).
The functionalized ionic liquid monomer is I type and IV type, and X is one of Cl and Br.
The rigid molecules containing unsaturated bonds are styrene and divinylbenzene.
The method for preparing the cyclic carbonate by using the ionic liquid copolymer is characterized by comprising the following steps: using ionic liquid copolymer as CO 2 The trapping agent and the heterogeneous catalyst are used for realizing the reaction of low-concentration carbon dioxide and epoxide under the condition of no solvent and no additive to directly prepare the cyclic carbonate.
Said CO 2 The volume concentration is 3-50%.
The epoxides include ethylene oxide (CAS number: 75-21-8), propylene oxide (CAS number: 75-56-9), epichlorohydrin (CAS number: 106-89-8), 2-vinyl ethylene oxide (CAS number: 62249-80-3), 1, 2-butylene oxide (CAS number: 106-88-7), glycidyl ether (CAS number: 13236-02-7), (methoxymethyl) ethylene oxide (CAS number: 930-37-0), 1, 2-pentylene oxide (CAS number: 1003-14-1), cyclohexene oxide (CAS number: 286-20-4), styrene oxide (CAS number: 96-09-3), 2-benzyl ethylene oxide (CAS number: 4436-24-2).
The reaction conditions include that the pressure of mixed gas is 0.5-10 MPa, the reaction temperature is 60-180 ℃, the dosage of the catalyst is 0.1-10 wt% of epoxide, and the reaction time is 1-12 hours.
Compared with the prior art, the invention has the following advantages:
1. the ionic liquid copolymer is prepared by copolymerizing imidazolium salt containing hydroxyl, carboxyl or amino and rigid molecules containing unsaturated bonds, and has the advantages of simple structure, easiness in synthesis, good mechanical stability, high recycling degree and the like.
2. The ionic liquid copolymer prepared by the invention is used as a heterogeneous catalyst for preparing cyclic carbonate by directly reacting low-concentration carbon dioxide with epoxide without additional solvent and additive, has high catalytic activity and selectivity, has a yield of 60-99%, avoids the steps of gas capture, purification and storage, reduces investment and operation cost, and is suitable for direct conversion and utilization of flue gas after large-scale combustion.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 is an infrared spectrum characterization of ionic liquid copolymer 1-1 of the present invention.
FIG. 2 is a graph showing the cycle stability test of the ionic liquid copolymer 1-1 of the present invention.
Detailed Description
An ionic liquid copolymer is prepared by copolymerizing imidazolium salt containing hydroxyl, carboxyl or amino and rigid molecule containing unsaturated bond.
The imidazolium salt is selected from one or more of functionalized ionic liquid monomers I-VI shown in the following structural formula:
in the formula: x — Is an anion of a functionalized ionic liquid monomer I-VI, and X is selected from Cl, Br, I and BF 4 、PF 6 One of (1); m = 1-6; n =1~ 6. Preferably: i and IV, and X is one of Cl and Br.
The rigid molecule containing unsaturated bonds is selected from styrene (CAS number: 100-42-5),α-methylstyrene (CAS number: 98-83-9), divinylbenzene (CAS number: 1321-74-0), 4-vinyl-1, 1' -biphenyl (CCAS number: 2350-89-2), 4 '-divinyl-1, 1' -biphenyl (CAS No.: 4433-13-0), 2-naphthylethylene (CAS No.: 827-54-3), 2-isopropenylnaphthalene (CAS No.: 3710-23-4). Preferably: styrene and divinylbenzene.
The synthesis method of the ionic liquid copolymer comprises the following steps:
mixing a mixture of 1: 1.1-1: 1.2 heating and refluxing the 1-vinyl imidazole and halogenated alkyl alcohol (or halogenated alkyl acid or halogenated alkylamine) in an absolute ethyl alcohol or acetonitrile solvent at the temperature of 60-80 ℃ for 12-24 hours, and then carrying out reduced pressure distillation, solvent washing and drying to obtain the functionalized ionic liquid monomers I-III.
The functionalized ionic liquid monomers IV-VI are prepared by a two-step method: mixing a mixture of 1: 0.8: 0.9-1: 1.2: 1.1 reacting halogenated alkyl styrene with imidazole and sodium hydroxide (or potassium hydroxide) at high temperature (70-110 ℃) for 6-24 hours to obtain 1- (4-alkyl styrene) imidazole, and then heating and refluxing the 1- (4-alkyl styrene) imidazole and slightly excessive halogenated alkyl alcohol (or halogenated alkyl acid or halogenated alkylamine) in an absolute ethyl alcohol or acetonitrile solvent at 60-80 ℃ for 12-36 hours to obtain the functionalized ionic liquid monomer IV-VI.
And finally, at the temperature of 70-120 ℃, mixing the functionalized ionic liquid monomers I-VI and rigid molecules (styrene, divinyl benzene, 4-vinyl-1, 1 ' -biphenyl, 4 ' -divinyl-1, 1 ' -biphenyl, 2-naphthylethylene and the like) containing unsaturated bonds according to the weight ratio of 1: 0.5-1: 5, mixing the mixture with a free radical initiator azobisisobutyronitrile with the mass of 0.1-5% of the monomer in absolute ethyl alcohol (or toluene), stirring for 0.5-12 hours to obtain a mixed solution, and carrying out vacuum filtration and drying to obtain the ionic liquid copolymer.
A method for preparing cyclic carbonate by using an ionic liquid copolymer comprises the following steps:
simultaneously using the ionic liquid copolymer as CO with the volume concentration of 3-50% 2 The trapping agent and the heterogeneous catalyst react under the conditions of no solvent and no additive, wherein the reaction conditions are that the pressure of mixed gas is 0.5-10 MPa, the reaction temperature is 60-180 ℃, the dosage of the catalyst is 0.1-10 wt% of epoxide, and the reaction time is 1-12 hours, so that low-concentration carbon dioxide and epoxide are realizedThe cyclic carbonate is directly prepared by the reaction, and the yield is 60-99%.
Wherein: epoxides include, but are not limited to, ethylene oxide (CAS number: 75-21-8), propylene oxide (CAS number: 75-56-9), epichlorohydrin (CAS number: 106-89-8), 2-vinyloxirane (CAS number: 62249-80-3), 1, 2-butylene oxide (CAS number: 106-88-7), glycidyl ether (CAS number: 13236-02-7), (methoxymethyl) oxirane (CAS number: 930-37-0), 1, 2-pentylene oxide (CAS number: 1003-14-1), cyclohexene oxide (CAS number: 286-20-4), styrene oxide (CAS number: 96-09-3), 2-benzylethylene oxide (CAS number: 4436-24-2).
EXAMPLE 1 preparation of Ionic liquid copolymer 1-1
Mixing the components in a molar ratio of 1:1.1 heating and refluxing the 1-vinyl imidazole and bromoethanol in absolute ethanol at 60 ℃ for 12 hours, and obtaining bromo-1-hydroxyethyl-3-vinyl imidazolium salt after the reaction is finished by reduced pressure distillation, solvent washing and drying; then, bromo-1-hydroxyethyl-3-vinylimidazolium salt, equimolar styrene and 0.5% of free radical initiator azobisisobutyronitrile are added into toluene, mixed and stirred for 6 hours at 110 ℃ to obtain a mixed solvent, and then the mixed solvent is subjected to vacuum filtration and drying to obtain the ionic liquid copolymer 1-1, wherein the number average molecular weight is 8450.
The obtained ionic liquid copolymer 1-1 was subjected to infrared characterization as shown in FIG. 1. 3309 cm -1 Stretching vibration peak at-OH 3067 cm -1 The vicinity is a stretching vibration peak of C-H bond in cation of imidazole ring, 2924 cm -1 The infrared absorption peak is saturated C-H stretching vibration, 1645 cm -1 Nearby is a characteristic peak of infrared breathing of a benzene ring, 1551 cm -1 1443 cm for skeletal vibration of imidazole ring -1 The absorption peak of saturated carbon-hydrogen bond is near 1064 cm -1 Is the vibration peak of the C-O bond, and in conclusion, the monomer structure and the introduction of the styryl group in the ionic liquid copolymer can be seen.
EXAMPLE 2 preparation of Ionic liquid copolymer 4-2
The imidazole and sodium hydroxide are subjected to melt reaction for 6 hours at 110 ℃ in a molar ratio of 1:1.1 to obtain imidazole sodium salt, then p-chloroethylstyrene and acetonitrile solvent with 1.1 molar equivalent are added, the mixture is heated and refluxed for 12 hours at 80 ℃ to obtain 1-p-ethylstyrylimidazole, and then the mixture is heated and refluxed for 24 hours at 80 ℃ in the acetonitrile solvent with slightly excessive chloroacetic acid to obtain the functionalized ionic liquid 1-carboxymethyl-3-p-ethylstyrylimidazole chloride. And then adding the functionalized ionic liquid, divinylbenzene with the same molar equivalent weight and azodiisobutyronitrile as a free radical initiator with the mass of 0.8 percent of the monomer into toluene, mixing, stirring at 110 ℃ for 12 hours to obtain a mixed solvent, and then carrying out vacuum filtration and drying to obtain the ionic liquid copolymer 4-2 with the number average molecular mass of 10650.
Therefore, the invention can synthesize other types of ionic liquid copolymers in the same way by changing the types of the functionalized ionic liquid and the unsaturated bond-containing rigid molecule.
Example 3 Low CO 2 Synthesis of Cyclic carbonate at concentration:
2 mL of propylene oxide and 2 wt% of ionic liquid copolymer 1-1 were charged in a 100 mL reaction vessel, and 12 vol.% CO was charged 2 CO of 2 /N 2 And (3) controlling the temperature of the mixed gas to be 140 ℃ to react for 10 hours, cooling to room temperature, slowly releasing pressure, and determining the yield of the propylene carbonate by a gas chromatograph by taking dodecane as an internal standard method, wherein the yield is 99%.
Example 4 Low CO 2 Synthesis of Cyclic carbonate at concentration:
the process is as in example 3, and a charge of CO with a concentration of 12% by volume is made 2 CO of (2) 2 /N 2 The mixed gas is adjusted to 4 MPa, other conditions are unchanged, and the yield of the propylene carbonate is 84 percent.
Example 5 Low CO 2 Synthesis of Cyclic carbonate at concentration:
the process is as in example 3, and 20% by volume CO is introduced 2 CO of 2 /N 2 The mixed gas is adjusted to 4 MPa, other conditions are unchanged, and the yield of the propylene carbonate is 99 percent.
Example 6 Low CO 2 Synthesis of Cyclic carbonate at concentration:
the method is the same as example 3, the mass ratio of the ionic liquid copolymer 1-1 to the substrate propylene oxide is 1 wt%, other conditions are unchanged, and the yield of the propylene carbonate is 61%.
Example 7 Low CO 2 Synthesis of Cyclic carbonate at concentration:
the process is the same as example 3, the reaction temperature is 120 ℃, the other conditions are unchanged, and the yield of the propylene carbonate is 73%.
Example 8 Low CO 2 Synthesis of Cyclic carbonate at concentration:
the reaction time was 6 hours as in example 3, the other conditions were unchanged, and the yield of propylene carbonate was 78%.
Example 9 Low CO 2 Synthesis of Cyclic carbonate at concentration:
the method is the same as example 3, the catalyst is the ionic liquid copolymer 4-2 in example 2, other conditions are not changed, and the yield of the propylene carbonate is 95%.
Example 10 catalyst cycling test
The method is the same as example 3, the catalyst is recycled after being filtered and recovered, and the yield of the product propylene carbonate after 10 times of use is still higher than 95%, and is respectively 99%, 98%, 97%, 96% and 95% as shown in figure 2.
EXAMPLE 11 ethylene oxide reaction
The method is the same as example 3, the epoxypropane is replaced by the epoxyethane, the epoxyethane is added into the reaction kettle at low temperature, the reaction temperature is 120 ℃, other conditions are unchanged, and the yield of the ethylene carbonate is 99%.
Example 12 epichlorohydrin reaction
The method is the same as example 3, the epoxy chloropropane is replaced by the epoxy propane, other conditions are not changed, and the yield of the epoxy chloropropylene carbonate is 98 percent.
EXAMPLE 13 glycidyl Ether reaction
The procedure is as in example 3, replacing the propylene oxide with glycidyl ether, otherwise conditions are unchanged and the yield of glycerol carbonate is 95%.
EXAMPLE 14 styrene oxide reaction
The procedure is as in example 3, replacing propylene oxide with styrene oxide, otherwise unchanged, and giving a styrene carbonate yield of 95%.
Claims (7)
1. An ionic liquid copolymer characterized by: the copolymer is prepared by copolymerizing imidazolium salt containing hydroxyl, carboxyl or amino and rigid molecules containing unsaturated bonds; the imidazolium salt is selected from one or more of functionalized ionic liquid monomers I-VI shown in the following structural formula:
in the formula: x — Is an anion of a functionalized ionic liquid monomer I-VI, and X is selected from Cl, Br, I and BF 4 、PF 6 One of (1); m = 1-6; n = 1-6; the unsaturated bond-containing rigid molecule is selected from styrene,αOne or more of-methyl styrene, divinyl benzene, 4-vinyl-1, 1 ' -biphenyl, 4 ' -divinyl-1, 1 ' -biphenyl, 2-naphthylethylene and 2-isopropenyl naphthalene.
2. An ionic liquid copolymer according to claim 1 wherein: the functionalized ionic liquid monomer is I type and IV type, and X is one of Cl and Br.
3. An ionic liquid copolymer according to claim 1 wherein: the rigid molecules containing unsaturated bonds are styrene and divinylbenzene.
4. The method of claim 1 for preparing a cyclic carbonate using an ionic liquid copolymer, wherein: using ionic liquid copolymer as CO 2 The trapping agent and the heterogeneous catalyst are used for realizing the reaction of low-concentration carbon dioxide and epoxide under the condition of no solvent and no additive to directly prepare the cyclic carbonate.
5. The method for preparing a cyclic carbonate from an ionic liquid copolymer according to claim 4, wherein: what is needed isCO as described above 2 The volume concentration is 3-50%.
6. The method for preparing a cyclic carbonate from an ionic liquid copolymer according to claim 4, wherein: the epoxide includes ethylene oxide, propylene oxide, epichlorohydrin, 2-vinyl oxirane, 1, 2-butylene oxide, glycidyl ether, (methoxymethyl) ethylene oxide, 1, 2-cyclopentane oxide, cyclohexene oxide, styrene oxide, 2-benzyl oxirane.
7. The method for preparing a cyclic carbonate from an ionic liquid copolymer according to claim 4, wherein: the reaction conditions include that the pressure of mixed gas is 0.5-10 MPa, the reaction temperature is 60-180 ℃, the dosage of the catalyst is 0.1-10 wt% of epoxide, and the reaction time is 1-12 hours.
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