CN1569805A - Method for synthesizing carbonic ethenyl (allyl) ester from carbon dioxide and epoxy ethane (propane) - Google Patents
Method for synthesizing carbonic ethenyl (allyl) ester from carbon dioxide and epoxy ethane (propane) Download PDFInfo
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- CN1569805A CN1569805A CN 03145914 CN03145914A CN1569805A CN 1569805 A CN1569805 A CN 1569805A CN 03145914 CN03145914 CN 03145914 CN 03145914 A CN03145914 A CN 03145914A CN 1569805 A CN1569805 A CN 1569805A
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 19
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000001569 carbon dioxide Substances 0.000 title abstract description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 title abstract description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title abstract 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 239000001294 propane Substances 0.000 title abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title abstract 2
- 230000002194 synthesizing effect Effects 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000002808 molecular sieve Substances 0.000 claims abstract description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 3
- -1 alkene ester Chemical class 0.000 claims description 29
- 238000001035 drying Methods 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 235000011089 carbon dioxide Nutrition 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 4
- 150000008045 alkali metal halides Chemical class 0.000 claims description 4
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229910052728 basic metal Inorganic materials 0.000 claims description 3
- 150000003818 basic metals Chemical class 0.000 claims description 3
- 238000007598 dipping method Methods 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000011949 solid catalyst Substances 0.000 abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 24
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 13
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 235000007715 potassium iodide Nutrition 0.000 description 8
- 229960004839 potassium iodide Drugs 0.000 description 8
- 230000009466 transformation Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- COLRBPHEBSHUAG-UHFFFAOYSA-L disodium bromide chloride Chemical compound [Na+].[Na+].[Cl-].[Br-] COLRBPHEBSHUAG-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention relates to a method for preparing carbonic ethenyl (allyl) ester by reacting carbon dioxide with epoxy ethane (propane), the reaction pressure is 3.0-7.0 MPa (gauge pressure), the reaction temperature is 100-200 ℃, a load type solid catalyst is adopted, the carrier is beta type molecular sieve, and the active component is halide of alkali metal or alkaline earth metal or the mixture of the alkali metal or alkaline earth metal. The method has the advantages of simple and economic catalyst preparation method, simple reaction process and 80-96% of ethylene oxide conversion rate; the selectivity is 90-98%.
Description
Technical field
The present invention relates to a kind ofly, prepare the method for ethylene (third) alkene ester, particularly prepare NSC 11801 by oxyethane and carbon dioxide reaction by epoxy second (third) alkane and carbon dioxide reaction.
Background technology
Ethylene (third) alkene ester is a kind of solvent of excellent property and the raw material of tensio-active agent, especially better to many polymkeric substance and dissolving resin effect, NSC 11801 also can be used as organic synthesis intermediate, raw material as synthetic Nifurazolidone, as water glass is slurry, the machining agent of fibre finish agent and other fiber etc.In addition, NSC 11801 also can be done the high tension battery electrolytic solution of high added value.
Before the present invention, the known method for preparing ethylene (third) alkene ester is to adopt alkali metal halide, alkaline earth metal halide, ammonium halide, Phosphorates phosphorus Halides.As U.S.Pat.No.4,881,555, U.S.Pat.No.4,931,571, catalyzer is organic tetravalence ammonium halide, organic tetravalence Phosphorates phosphorus Halides, organic halogenation sulphur and organic halogenation antimony among the Japanese Laid-Open Pat.No.7-206846; Japan Laid-Open Pat.No.9-067365 and No.8-059557 catalyzer are alkali metal halide and alkaline earth metal halide; U.S.Pat.No.2,773,070 employings contain tetravalence Phosphorates phosphorus Halides ion-exchange resin catalyst; U.S.Pat.No.4,233,221 adopt DOWEX and Amberlite ion-exchange resin catalyst; U.S.Pat.No.4,665,467 and U.S.Pat.No.5,283,356 adopt and contain the phthalocyanine of Co, Cr, Fe, Mn, Ni, Ti, V, Zr or the catalyzer of porphyrin; U.S.Pat.No.6,156,909 usefulness indium halide and lead halide are catalyzer; U.s.Pat.No.6,160,130 adopt the manganese halide catalyzer; U.S.Pat.No.6,258,962 adopt the solid carrier that contains alkaline-earth metal.In industrial production, adopt homogeneous catalyst long reaction time (above 5 hours), epoxy second (third) alkane transformation efficiency is low, and reaction process is high temperature (180 ℃) high pressure (10MPa) reactions.
In the prior art, use homogeneous catalyst carbonate synthesis second (third) alkene ester to have the problem of separating catalyst from product, thereby make catalyst loss.For example, a kind of method for preparing NSC 11801 by oxyethane and carbon dioxide reaction, use potassium iodide catalyst, because reaction produces the polyoxyethylene glycol by product, potassiumiodide is dissolved in the polyoxyethylene glycol, is difficult to separate, and potassiumiodide is separated with polyoxyethylene glycol as a result, need supplementary equipment therefore that potassiumiodide is told from polyoxyethylene glycol like this, increased expense.
Summary of the invention
The objective of the invention is to overcome the problem that prior art exists and provide a kind of employing solid catalyst to prepare the method for ethylene (third) alkene ester.
The invention provides a kind of method by carbonic acid gas and epoxy second (third) alkane prepared in reaction ethylene (third) alkene ester, reaction pressure is 3.0-7.0Mpa (gauge pressure), temperature of reaction 100-200 ℃, adopt the supported solid catalyzer, carrier is a beta molecular sieve, and active ingredient is the halogenide of basic metal or alkaline-earth metal or their mixture.
Alkali metal halide in present method is potassium halide or sodium halide, as Repone K, Potassium Bromide, potassiumiodide, sodium-chlor, Sodium Bromide, sodium iodide etc.; Alkaline earth metal halide is a magnesium halide, as magnesium chloride, magnesium bromide, magnesium iodide etc.The preferred potassiumiodide of active ingredient.
The preparation method of solid catalyst used in the present invention is: beta molecular sieve is joined in the solution of active substance that concentration is 10-70%, flooded 10-50 hour, filter, drying, be 20-50 hour time of drying; Drying temperature is 100-200 ℃.
For making reaction effect better, beta molecular sieve can be extruded into bar shaped or cloverleaf pattern.The preferred 30-60% of active substance solution concentration, the preferred 20-40 of dipping time hour, preferred 30-40 hour time of drying, the preferred 100-150 of drying temperature ℃.
The present invention adopts one or more fixed-bed reactor intermittences or carries out prepared in reaction ethylene (third) alkene ester continuously.In fixed-bed reactor, the upper and lower filling porcelain ring of beds, reactant carbonic acid gas and epoxy second (third) alkane enter and produce the minimum pressure drop in the reactor.
By epoxy second (third) alkane and carbon dioxide reaction, prepare the method for ethylene (third) alkene ester by the present invention, can continuous or discontinuous carrying out.Industrial, preferred operate continuously.
The mode that unattended operation carries out (continuous or discontinuous) keeps enough pressure so that molecular balance moves right.After reaction finishes, by conventional separation method (as distillation) NSC 11801 is separated, carbonic acid gas and a spot of oxyethane separate that the back is capable of circulation uses to reactor.
Reaction product is identified with vapor-phase chromatography.
The invention has the advantages that: the solid catalyst that adopts in the inventive method is for having pore structure carrier-beta molecular sieve, and active ingredient is basic metal or alkaline-earth metal, the method for preparing catalyst simple economy; By carbonic acid gas and epoxy second (third) alkane prepared in reaction ethylene (third) alkene ester, reaction process is simple, and the oxyethane transformation efficiency is 90-96%; Selectivity is 90-98%.
Embodiment
Content percentage ratio of the present invention is weight percentage.
Embodiment 1
It is in 40% the potassiumiodide 200g solution, to flood 30 hours that the beta molecular sieve 20g of cloverleaf pattern joins concentration, filters, drying, and be 30 hours time of drying; Drying temperature is 150 ℃, obtains solid catalyst.
In the 1L high-pressure reactor, add the NSC 11801 of 420g, the oxyethane of 40mL; The beta molecular sieve catalyzer is 17.7g, reaction is 2 hours under 140 ℃, 5.25MPa condition, cooling reactive system to 40 ℃, product analysis, ethylene oxide content is 2.40%, the content of NSC 11801 is 92.56%, and obtaining the oxyethane transformation efficiency is 95.45%; Selectivity is 91.95%.
Embodiment 2
Utilize the catalyzer among the embodiment 1, in reactor, add the NSC 11801 of 420g, the oxyethane of 40mL again; Reaction conditions is identical with embodiment 1, and product analysis, ethylene oxide content are 1.97%, ethylene carbonate content is 94.14%, and obtaining the oxyethane transformation efficiency is 96.22%; Selectivity is 93.95%.
Embodiment 3
Utilize the catalyzer among the embodiment 1, in reactor, add the NSC 11801 of 420g, the oxyethane of 40mL again; Reaction conditions is identical with embodiment 1, product analysis, and ethylene oxide content 3.31%, ethylene carbonate content are 92.47%, obtain oxyethane transformation efficiency 93.77%; Selectivity is 92.87%.
Embodiment 4
Adopting active ingredient is the beta molecular sieve catalyzer 15g of sodium iodide, the concentration of sodium iodide is 17%, identical among other condition and the embodiment 1, product analysis, ethylene oxide content 4.47%, ethylene carbonate content are 90.70%, obtaining the oxyethane transformation efficiency is 91.03%, and selectivity is 91.60%.
Embodiment 5
In the fixed-bed reactor of φ 32 * 2.5, contain excessive carbon dioxide and beta molecular sieve catalyzer 35g, the concentration of active ingredient potassiumiodide is 30%, the flow of oxyethane is 40mL/hr, join in the reactor after oxyethane and 5.0MPa carbonic acid gas be preheating to 120 ℃, reaction is 100 hours under 140 ℃, the condition of 5.0-6.0MPa, product is extraction after cooling off, analytical results, ethylene oxide content is 2.78%, ethylene carbonate content is 92.31%, the transformation efficiency of oxyethane is 94.74%, and selectivity is 92.23%.
Claims (6)
1. method by carbonic acid gas and epoxy second (third) alkane prepared in reaction ethylene (third) alkene ester, reaction pressure is 3.0-7.0Mpa (gauge pressure), temperature of reaction 100-200 ℃, adopt the supported solid catalyzer, carrier is a beta molecular sieve, and active ingredient is the halogenide of basic metal or alkaline-earth metal or their mixture.
2. according to the method for claim 1, it is characterized in that alkali metal halide wherein is potassium halide or sodium halide.
3. according to the method for claim 1, it is characterized in that alkaline earth metal halide wherein is a magnesium halide.
4. the supported solid Preparation of catalysts method of claim 1 is: beta molecular sieve is joined in the solution of active substance that concentration is 10-70%, flooded 10-50 hour, filter, drying, be 20-50 hour time of drying; Drying temperature is 100-200 ℃.
According to claim 4 method, it is characterized in that beta molecular sieve wherein being extruded into bar shaped or cloverleaf pattern.
6. according to the Preparation of catalysts method of claim 4, it is characterized in that wherein active substance solution concentration is that 30-60%, dipping time are that 20-40 hour, time of drying are that 30-40 hour, drying temperature are 100-150 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03145914 CN1569805A (en) | 2003-07-17 | 2003-07-17 | Method for synthesizing carbonic ethenyl (allyl) ester from carbon dioxide and epoxy ethane (propane) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03145914 CN1569805A (en) | 2003-07-17 | 2003-07-17 | Method for synthesizing carbonic ethenyl (allyl) ester from carbon dioxide and epoxy ethane (propane) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1569805A true CN1569805A (en) | 2005-01-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 03145914 Pending CN1569805A (en) | 2003-07-17 | 2003-07-17 | Method for synthesizing carbonic ethenyl (allyl) ester from carbon dioxide and epoxy ethane (propane) |
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| Country | Link |
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| CN (1) | CN1569805A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101613339B (en) * | 2009-07-27 | 2012-02-01 | 广西壮族自治区化工研究院 | Method for synthesizing ethylene carbonate and catalyst therefor |
| CN102731438A (en) * | 2012-06-18 | 2012-10-17 | 天津大学 | Absorption-rectification method and apparatus for separation of carbon dioxide-epoxypropane mixture |
| CN107915709A (en) * | 2016-10-08 | 2018-04-17 | 中国石油化工股份有限公司 | The method that ethylene oxide and carbon dioxide prepare ethylene carbonate |
| CN107915714A (en) * | 2016-10-08 | 2018-04-17 | 中国石油化工股份有限公司 | The method of synthesizing ethylene carbonate |
| CN107915712A (en) * | 2016-10-08 | 2018-04-17 | 中国石油化工股份有限公司 | It is used to prepare the method for ethylene carbonate |
| CN112876450A (en) * | 2021-01-19 | 2021-06-01 | 中科院过程工程研究所南京绿色制造产业创新研究院 | Preparation method and application of cyclic carbonate |
-
2003
- 2003-07-17 CN CN 03145914 patent/CN1569805A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101613339B (en) * | 2009-07-27 | 2012-02-01 | 广西壮族自治区化工研究院 | Method for synthesizing ethylene carbonate and catalyst therefor |
| CN102731438A (en) * | 2012-06-18 | 2012-10-17 | 天津大学 | Absorption-rectification method and apparatus for separation of carbon dioxide-epoxypropane mixture |
| CN102731438B (en) * | 2012-06-18 | 2014-05-07 | 天津大学 | Absorption-rectification method and apparatus for separation of carbon dioxide-epoxypropane mixture |
| CN107915709A (en) * | 2016-10-08 | 2018-04-17 | 中国石油化工股份有限公司 | The method that ethylene oxide and carbon dioxide prepare ethylene carbonate |
| CN107915714A (en) * | 2016-10-08 | 2018-04-17 | 中国石油化工股份有限公司 | The method of synthesizing ethylene carbonate |
| CN107915712A (en) * | 2016-10-08 | 2018-04-17 | 中国石油化工股份有限公司 | It is used to prepare the method for ethylene carbonate |
| CN107915712B (en) * | 2016-10-08 | 2020-01-03 | 中国石油化工股份有限公司 | Method for preparing ethylene carbonate |
| CN107915714B (en) * | 2016-10-08 | 2020-06-09 | 中国石油化工股份有限公司 | Method for synthesizing ethylene carbonate |
| CN112876450A (en) * | 2021-01-19 | 2021-06-01 | 中科院过程工程研究所南京绿色制造产业创新研究院 | Preparation method and application of cyclic carbonate |
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