CN109867654B - 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 - Google Patents
一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 Download PDFInfo
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- CN109867654B CN109867654B CN201910121914.6A CN201910121914A CN109867654B CN 109867654 B CN109867654 B CN 109867654B CN 201910121914 A CN201910121914 A CN 201910121914A CN 109867654 B CN109867654 B CN 109867654B
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- Prior art keywords
- catalyst
- alkylene
- oxide
- triphenylphosphine
- carbon dioxide
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 34
- -1 alkylene carbonate Chemical compound 0.000 title claims abstract description 22
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 19
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 44
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 13
- 239000011701 zinc Substances 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 238000010438 heat treatment Methods 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 19
- 239000002243 precursor Substances 0.000 claims description 18
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 17
- 229960004889 salicylic acid Drugs 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000005086 pumping Methods 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 11
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical group OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 description 19
- 238000001816 cooling Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 6
- 239000011592 zinc chloride Substances 0.000 description 6
- 235000005074 zinc chloride Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229940102001 zinc bromide Drugs 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000005431 greenhouse gas Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- OIWSIWZBQPTDKI-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole;hydrobromide Chemical compound [Br-].CCCC[NH+]1CN(C)C=C1 OIWSIWZBQPTDKI-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- UYDGECQHZQNTQS-UHFFFAOYSA-N 2-amino-4,6-dimethylpyridine-3-carboxamide Chemical compound CC1=CC(C)=C(C(N)=O)C(N)=N1 UYDGECQHZQNTQS-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N o-cresotic acid Natural products CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UURPXOUNIIQPRT-UHFFFAOYSA-N tributyl-iodo-methyl-lambda5-phosphane Chemical compound CCCCP(C)(I)(CCCC)CCCC UURPXOUNIIQPRT-UHFFFAOYSA-N 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
-
- 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
-
- 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
- C07D317/38—Ethylene carbonate
-
- 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
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/26—Zinc
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
Claims (3)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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CN201910121914.6A CN109867654B (zh) | 2019-02-19 | 2019-02-19 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
PCT/CN2020/075759 WO2020169032A1 (zh) | 2019-02-19 | 2020-02-18 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
EP20758997.9A EP3805208A4 (en) | 2019-02-19 | 2020-02-18 | PROCESS FOR THE PREPARATION OF ALKYLENE CARBONATE FROM EPOXYALCANE AND CARBON DIOXIDE |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201910121914.6A CN109867654B (zh) | 2019-02-19 | 2019-02-19 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
Publications (2)
Publication Number | Publication Date |
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CN109867654A CN109867654A (zh) | 2019-06-11 |
CN109867654B true CN109867654B (zh) | 2021-06-29 |
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CN201910121914.6A Active CN109867654B (zh) | 2019-02-19 | 2019-02-19 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
Country Status (3)
Country | Link |
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EP (1) | EP3805208A4 (zh) |
CN (1) | CN109867654B (zh) |
WO (1) | WO2020169032A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109867654B (zh) * | 2019-02-19 | 2021-06-29 | 胜华新能源科技(东营)有限公司 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
CN115417850B (zh) * | 2022-10-21 | 2023-04-18 | 深圳新宙邦科技股份有限公司 | 含螺环状化合物催化剂在催化环氧化合物和二氧化碳反应中的应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1566110A (zh) * | 2003-07-03 | 2005-01-19 | 中国科学院兰州化学物理研究所 | 合成环状碳酸酯的方法 |
CN1566111A (zh) * | 2003-07-03 | 2005-01-19 | 中国科学院兰州化学物理研究所 | 环状碳酸酯的制备方法 |
CN101974024A (zh) * | 2010-09-06 | 2011-02-16 | 河北工业大学 | 一种Salen-金属络合物及其制备方法和应用 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2907771A (en) | 1957-12-05 | 1959-10-06 | Olin Mathieson | Ethylene carbonate |
PE20070477A1 (es) | 2005-08-02 | 2007-05-16 | Shell Int Research | Proceso para la preparacion de carbonatos de alquileno |
CN100478338C (zh) | 2006-12-27 | 2009-04-15 | 中国科学院过程工程研究所 | 一种制备环状碳酸酯的方法 |
JP5725019B2 (ja) * | 2010-04-28 | 2015-05-27 | 三菱化学株式会社 | アルキレンカーボネート及び/又はアルキレングリコールの製造方法 |
CN103028441B (zh) * | 2011-09-30 | 2014-10-15 | 中国石油化工股份有限公司 | 用于环氧乙烷和二氧化碳制备碳酸乙烯酯的催化剂 |
CN109867654B (zh) * | 2019-02-19 | 2021-06-29 | 胜华新能源科技(东营)有限公司 | 一种用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
CN109810091B (zh) * | 2019-02-19 | 2020-04-17 | 山东石大胜华化工集团股份有限公司 | 用于环氧烷烃和二氧化碳制备碳酸亚烷基酯的方法 |
-
2019
- 2019-02-19 CN CN201910121914.6A patent/CN109867654B/zh active Active
-
2020
- 2020-02-18 EP EP20758997.9A patent/EP3805208A4/en active Pending
- 2020-02-18 WO PCT/CN2020/075759 patent/WO2020169032A1/zh unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1566110A (zh) * | 2003-07-03 | 2005-01-19 | 中国科学院兰州化学物理研究所 | 合成环状碳酸酯的方法 |
CN1566111A (zh) * | 2003-07-03 | 2005-01-19 | 中国科学院兰州化学物理研究所 | 环状碳酸酯的制备方法 |
CN101974024A (zh) * | 2010-09-06 | 2011-02-16 | 河北工业大学 | 一种Salen-金属络合物及其制备方法和应用 |
Non-Patent Citations (2)
Title |
---|
Homogenous Dual-Ligand Zinc Complex Catalysts for Chemical Fixation of CO2 to Propylene Carbonate;Yan-Li Shi,et al.;《Catal Lett》;20151231;1673-1682 * |
锌(II)与2-甲基咪唑和水杨酸络合物的结构分析;林吟卿等;《分析测试通报》;19891231;51-54 * |
Also Published As
Publication number | Publication date |
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CN109867654A (zh) | 2019-06-11 |
EP3805208A4 (en) | 2021-09-15 |
WO2020169032A1 (zh) | 2020-08-27 |
EP3805208A1 (en) | 2021-04-14 |
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