CN101773858A - Preparation method of novel high-efficiency environmental-protection compound ion liquid catalyst used for synthesizing high-quality propene carbonate - Google Patents
Preparation method of novel high-efficiency environmental-protection compound ion liquid catalyst used for synthesizing high-quality propene carbonate Download PDFInfo
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- CN101773858A CN101773858A CN200910256077A CN200910256077A CN101773858A CN 101773858 A CN101773858 A CN 101773858A CN 200910256077 A CN200910256077 A CN 200910256077A CN 200910256077 A CN200910256077 A CN 200910256077A CN 101773858 A CN101773858 A CN 101773858A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 36
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000007788 liquid Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 6
- -1 compound ion Chemical class 0.000 claims abstract description 19
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000005309 metal halides Chemical class 0.000 claims abstract description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 8
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical class CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 4
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Chemical class CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000006837 decompression Effects 0.000 claims abstract description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000002608 ionic liquid Substances 0.000 claims description 17
- 239000002131 composite material Substances 0.000 claims description 10
- 239000001294 propane Substances 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 150000005676 cyclic carbonates Chemical group 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- 238000004062 sedimentation Methods 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 230000002779 inactivation Effects 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 238000006352 cycloaddition reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910003112 MgO-Al2O3 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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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
- Y02P20/141—Feedstock
Abstract
The invention relates to a preparation method of a novel high-efficiency environmental-protection compound ion liquid catalyst used for synthesizing high-quality propene carbonate. The invention has the technical scheme of comprising the following steps of: (1) reacting halogenated alkane and methylimidazole in a reaction kettle according to a proportion; (2) washing by using an ester compound, settling after stirring fully, and stratifying; (3) distilling off the unreacted halogenated alkane, the ester compound and light impurities under a decompression condition; (4) adding a metal halide catalysis aid to obtain a novel compound ion liquid catalyst; and (5) taking propylene oxide and carbon dioxide as raw materials and novel compound ion liquid as the catalyst, and synthesizing the propene carbonate. The invention has the advantages that the cost of the catalyst is low, the inactivation of the catalyst is slow, the service life is long, and the annual use cost is equivalent to 1/4 to 1/5 of that of a tetraethyl ammonium halide catalyst; and the activity of the catalyst is high, the reaction speed is high, the selectivity is high, and the yield of the propene carbonate can reach 97 to 98 percent.
Description
One, technical field:
The present invention relates to a kind of chemical industry preparation method, particularly a kind of preparation method who is used for the synthetic novel high-efficiency environment friendly compound ion liquid catalyst of high-quality propene carbonate.
Two, background technology:
Propene carbonate (PC) is a kind of high polar organic solvent of higher boiling of function admirable, is used widely in fields such as organic synthesis, cosmetics, gas separation, cell electrolyte and metal extractions.In recent years, many urea production producer heightens its demand used as decarburizer.The PC synthetic method mainly contains phosgenation, ester-interchange method, chlorine
Propyl alcohol method and expoxy propane (PO) and CO2 cycloaddition method etc.With PO and CO2 is that raw material cycloaddition system PC is a low pollution, eco-friendly route.The catalyst of having reported that is used for PO and CO2 cycloaddition has alkali, quaternary ammonium salt, slaine, complex and MgO, MgO-Al2O3, KI-ZnO, KI-crown ether and KI-polyethylene glycol etc.Although catalizer variety is various, but still exist catalyst activity not high, product yield is low, quality is low, severe reaction conditions, and environmental pollution is serious, problems such as product separation and catalyst recovery difficulty.
Ionic liquid is just receiving the concern of countries in the world catalysis circle and petroleum chemical enterprise circle as " cleaning " solvent and new catalyst system and catalyzing, the normal temperature ionic liquid is meant the molten salt system that is in a liquid state at normal temperatures, have excellent chemistry and heat endurance, multiple organic and inorganic compound of solubilized and metal complex etc., because ion liquid steam forces down, can under higher temperature, work,, reach the purpose of recycling so methods such as available distillation are separated ionic liquid with product.At present, abroad in reactions such as Friedel-Crafts, alkylation, isomerization, dimerizing olefins and catalytic hydrogenation, be applied, though more report is arranged in PO and CO2 cycloaddition reaction, but still do not realize industrialization.
Three, summary of the invention:
Purpose of the present invention is exactly the above-mentioned defective that exists at prior art, and a kind of preparation method who is used for the synthetic novel high-efficiency environment friendly compound ion liquid catalyst of high-quality propene carbonate is provided.
Its technical scheme is to comprise following technical process:
(1) halogenated alkane and methylimidazole are 1 according to mol ratio: (1-1.2) reacted 2-6 hour in 60-80 ℃ in reactor; (2) the aforesaid reaction vessel material is cleaned 2-3 time with ester type compound, fully stir back sedimentation layering; (3) above-mentioned layering material is steamed unreacted halogenated alkane, ester type compound and light impurity under decompression 5-20Kpa condition, promptly obtain high-purity ion liquid,, prevent ionic liquid crystallization at low temperatures to wherein adding a certain proportion of organic solvent; (4) in aforesaid reaction vessel, add a certain proportion of metal halide (MXn) cocatalyst, under 60-80 ℃ of condition, stirred 2-3 hour, promptly obtain the NEW TYPE OF COMPOSITE ionic-liquid catalyst; (5) be raw material with expoxy propane and carbon dioxide, certain density above-mentioned NEW TYPE OF COMPOSITE ionic liquid is a catalyst, gets final product synthesizing acrylic ester under uniform temperature, pressure.
Used ester type compound is ethyl acetate, dimethyl carbonate, methyl formate or isopropyl acetate etc. in the above-mentioned step (2).
Used organic solvent is a cyclic carbonate in the above-mentioned step (3), and added ratio is 50-200% (wt).
The metal halide and the ion liquid mass ratio that are added in the above-mentioned step (4) are 1: (4-8).
Described concentration in the above-mentioned step (5) is meant ionic liquid composite catalyst shared mass ratio 0.5-1.0% in reaction system, and temperature is meant 110-160 ℃, and pressure is meant 2.0-6.0Mpa.
The present invention compares with tetraethyl ammonium halide catalyst, and its beneficial effect is:
(1) the catalyst cost is low, and catalysqt deactivation is slow, and the life-span is long, from present operating position, but replenishes once half a year; Year use cost is equivalent to 1/4～1/5 of tetraethyl ammonium halide catalyst; (2) the catalyst activity height, reaction speed is fast, selectivity is high, can make the propene carbonate yield improve 1～2 percentage point, makes the propene carbonate yield reach 97～98%; (3) side reaction is few, propene carbonate product purity height, and colourity is low, and average chrominance＜5 can be applied to high-end science and technology; (4) the catalyst fusing point is low, boiling point is high, and is good with reaction system raw material compatibility, do not exist crystallization to separate out the phenomenon that causes blocking pipeline or equipment; (5) reaction condition is relatively gentleer, and temperature, moderate pressure can be saved energy and reduce the cost significantly; (6) catalyst does not efflux, and not only reduces labour intensity, and reduces environmental pollution, really accomplishes environmental protection.
Four, description of drawings:
Accompanying drawing 1 is the structural representation of novel composite catalyst preparation facilities of the present invention;
Among the last figure: charging aperture 1, drain 2, conduction oil outlet 3, conduction oil inlet 4, discharging opening 5, condensing water inlet 6, condensation-water drain 7, vacuum system 8, agitator 9, reactor 10.
Five, the specific embodiment:
With reference to accompanying drawing 1, the invention will be further described:
The present invention is 1 in molar ratio: methylimidazole (1-1.2) and halogenated alkane are by charging aperture 1, enter reactor 10, in 60-80 ℃ of reaction 2-6 hour, after reaction finishes, by charging aperture 1 a certain amount of dimethyl carbonate is squeezed into reactor 10, standing demix behind the stirring 1h, lower floor is an ionic liquid, the upper strata is dimethyl carbonate and unreacted halogenated alkane and light impurity, be evacuated to 5-20Kpa by vacuum system 8, with unreacted halogenated alkane, dimethyl carbonate and light impurity are extracted out, the charging aperture 1 that passes through that repeats is squeezed into reactor 10 for 2-3 time with a certain amount of dimethyl carbonate, light material is extracted out, can be obtained high-purity ion liquid after repeating 2-3 time.Inject in reactor 10 quite as the propene carbonate of ionic liquid 50-200% by charging aperture 1, fully stir 1-2h, obtaining propene carbonate, to make the ionic liquid of solvent stand-by.Metal halide (MXn) cocatalyst that adds in reactor 10, wherein metal halide and ion liquid mass ratio are 1: (4-8), stirred 2-3 hour under 60-80 ℃ of condition, obtain the NEW TYPE OF COMPOSITE ionic-liquid catalyst, can use.
Column bottoms pump by reactor 10, from discharging opening 5 the NEW TYPE OF COMPOSITE ionic-liquid catalyst is squeezed into the propene carbonate synthesizer, wherein the NEW TYPE OF COMPOSITE ionic-liquid catalyst is under concentration 0.5-1.0% (wt), temperature 110-160 ℃, the condition of pressure 2.0-6.0Mpa in system, promptly can expoxy propane and carbon dioxide be the raw material synthesizing acrylic ester, by evidence propyl alcohol method and expoxy propane (PO) conversion ratio is 99.43%, propene carbonate (PC) purity is 99.59%, colourity＜10, propene carbonate (PC) yield 98.64%.
Claims (5)
1. preparation method who is used for the synthetic novel high-efficiency environment friendly compound ion liquid catalyst of high-quality propene carbonate is characterized in that comprising following technical process:
(1) halogenated alkane and methylimidazole are 1 according to mol ratio: (1-1.2) reacted 2-6 hour in 60-80 ℃ in reactor;
(2) the aforesaid reaction vessel material is cleaned 2-3 time with ester type compound, fully stir back sedimentation layering;
(3) above-mentioned layering material is steamed unreacted halogenated alkane, ester type compound and light impurity under decompression 5-20Kpa condition, promptly obtain high-purity ion liquid,, prevent ionic liquid crystallization at low temperatures to wherein adding a certain proportion of organic solvent;
(4) in aforesaid reaction vessel, add a certain proportion of metal halide (MXn) cocatalyst, under 60-80 ℃ of condition, stirred 2-3 hour, promptly obtain the NEW TYPE OF COMPOSITE ionic-liquid catalyst;
(5) be raw material with expoxy propane and carbon dioxide, certain density above-mentioned NEW TYPE OF COMPOSITE ionic liquid is a catalyst, gets final product synthesizing acrylic ester under uniform temperature, pressure.
2. according to the described preparation method who is used for the synthetic novel high-efficiency environment friendly compound ion liquid catalyst of high-quality propene carbonate of claim 1, it is characterized in that: used ester type compound is ethyl acetate, dimethyl carbonate, methyl formate or isopropyl acetate etc. in the described step (2).
3. according to the described preparation method who is used for the synthetic novel high-efficiency environment friendly compound ion liquid catalyst of high-quality propene carbonate of claim 1, it is characterized in that: used organic solvent is a cyclic carbonate in the described step (3), and added ratio is 50-200% (wt).
4. according to the described preparation method who is used for the synthetic novel high-efficiency environment friendly compound ion liquid catalyst of high-quality propene carbonate of claim 1, it is characterized in that: the metal halide and the ion liquid mass ratio that are added in the described step (4) are 1: (4-8).
5. according to the described preparation method who is used for the synthetic novel high-efficiency environment friendly compound ion liquid catalyst of high-quality propene carbonate of claim 1, it is characterized in that: the described concentration in the described step (5) is meant ionic liquid composite catalyst shared mass ratio 0.5-1.0% in reaction system, temperature is meant 110-160 ℃, and pressure is meant 2.0-6.0Mpa.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650026A (en) * | 2014-11-21 | 2015-05-27 | 沈阳工业大学 | Method for preparing propylene carbonate |
| CN107413379A (en) * | 2017-04-28 | 2017-12-01 | 濮阳市宏源石油化工有限公司 | For alkyl carbonate and the catalyst and preparation method of aryl alcohol transesterification reaction |
| CN111957343A (en) * | 2020-08-25 | 2020-11-20 | 安徽金禾实业股份有限公司 | Ionic liquid loaded silicon dioxide and preparation method and application thereof |
| CN111978285A (en) * | 2020-08-10 | 2020-11-24 | 华东理工大学 | Method for preparing propylene (or ethylene) carbonate by amino functionalized composite ionic liquid |
| CN114437330A (en) * | 2022-02-14 | 2022-05-06 | 西北师范大学 | Catalyst system for copolymerization of cyclic monomer sequences and process for preparing block polyesters |
| CN115385888A (en) * | 2022-10-31 | 2022-11-25 | 山东海科新源材料科技股份有限公司 | Production device and method for synthesizing ethylene carbonate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1817878A (en) * | 2006-03-21 | 2006-08-16 | 中国科学院过程工程研究所 | Preparation of cyclic carbonic ester with high-activity catalyst |
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2009
- 2009-12-24 CN CN2009102560774A patent/CN101773858B/en active Active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650026A (en) * | 2014-11-21 | 2015-05-27 | 沈阳工业大学 | Method for preparing propylene carbonate |
| CN107413379A (en) * | 2017-04-28 | 2017-12-01 | 濮阳市宏源石油化工有限公司 | For alkyl carbonate and the catalyst and preparation method of aryl alcohol transesterification reaction |
| CN107413379B (en) * | 2017-04-28 | 2020-08-25 | 濮阳市宏源石油化工有限公司 | Catalyst for alkyl carbonate and aryl alcohol ester exchange reaction and preparation method thereof |
| CN111978285A (en) * | 2020-08-10 | 2020-11-24 | 华东理工大学 | Method for preparing propylene (or ethylene) carbonate by amino functionalized composite ionic liquid |
| CN111957343A (en) * | 2020-08-25 | 2020-11-20 | 安徽金禾实业股份有限公司 | Ionic liquid loaded silicon dioxide and preparation method and application thereof |
| CN111957343B (en) * | 2020-08-25 | 2022-12-30 | 安徽金禾实业股份有限公司 | Ionic liquid loaded silicon dioxide and preparation method and application thereof |
| CN114437330A (en) * | 2022-02-14 | 2022-05-06 | 西北师范大学 | Catalyst system for copolymerization of cyclic monomer sequences and process for preparing block polyesters |
| CN114437330B (en) * | 2022-02-14 | 2023-11-17 | 西北师范大学 | Catalyst system for copolymerization of cyclic monomer sequences and method for preparing block polyester |
| CN115385888A (en) * | 2022-10-31 | 2022-11-25 | 山东海科新源材料科技股份有限公司 | Production device and method for synthesizing ethylene carbonate |
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