CN102877086B - Method for preparing cyclic carbonate from olefin and carbon dioxide by electrochemical method - Google Patents
Method for preparing cyclic carbonate from olefin and carbon dioxide by electrochemical method Download PDFInfo
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Abstract
The invention discloses a method for preparing cyclic carbonate from olefin and carbon dioxide by an electrochemical method. By the method, the olefin and the carbon dioxide are used as raw materials, and an inert anode is used for converting the olefin and the carbon dioxide into the cyclic carbonate at a time through an electrochemical reaction at normal temperature and normal pressure in a diaphragm-free single chamber electrolytic tank. According to the method, the olefin and the carbon dioxide which are low in price and readily available are used as the raw materials, so that an oxidant and a catalyst are not required to be added additionally; a sacrificial metal anode is replaced by the inert anode, so that the problem of consumption performance of metal anodes is solved radically; and the method is mild in reaction condition, simple in process operation and low in production cost, has the characteristics of high selectivity, high yield, high efficiency, high economy and environment friendliness, is suitable for appreciation processing of olefin products in petrochemical industries and conversion utilization of the carbon dioxide serving as waste gas generated in petrifaction oil refineries, thermal power plants and other industries, and has economic and environment-friendly benefits.
Description
Technical field
The invention belongs to electrochemistry technical field of organic synthesis, relate to the preparation method of cyclic carbonate, be specifically related to a kind of method being raw material electrochemical production cyclic carbonate with alkene and carbonic acid gas.。
Background technology
Cyclic carbonate is the important chemical materials of a class, can be used as plasticising, spin solvent or the dispersion agent of water-soluble dye pigment and the extraction agent of alkene and aromatic hydrocarbons; Also can be used as the presoma of organic synthesis raw material and macromolecular material; Also can be used as the excellent medium of high tension battery and electrical condenser, in organic synthesis, petrochemical complex, textile industry and electronic industry extensive application.
The traditional synthesis of cyclic carbonate be with epoxy compounds and carbonic acid gas for raw material, realized by homogeneous catalysis or heterocatalysis cycloaddition reaction.Epoxy compounds price is relatively costly, and cause product cyclic carbonate cost higher, this constrains the large-scale industrial application of cyclic carbonate to a certain extent.Epoxy compounds can be obtained by alkene epoxidation, therefore with cheap and easy to get, that toxicity is less alkene fictitious hosts costly, epoxy compounds that toxicity is larger, with carbonic acid gas direct reaction synthesizing annular carbonate, can significantly reduce production cost, to environment also more friendly, have more industrial application value.
Adopt common thermochemical method, by alkene and the direct synthesizing annular carbonate of carbonic acid gas, actual experience two processes, namely first alkene be oxidized to epoxy compounds, then epoxy compounds and CO
2initial ring addition reaction forms target product cyclic carbonate.According to oxidant type, this synthetic route is divided into as Types Below:
(1) with hydrogen peroxide, organo-peroxide for oxygenant:
Sun Jianmin etc. [Sun Jianmin, Wang Lu, Wang Yali, etc. SCI. 2007,28 (3), 502] with ionic liquid/Bu
4nBr, Au/SiO
2-ZnBr
2/ Bu
4nBr is catalyzer, by vinylbenzene and CO
2synthesizing styrene cyclic carbonate ester, productive rate is 38 ~ 42%, also has the by product such as phenylacetic aldehyde, polymkeric substance to be formed.Chinese patent CN101602014B reports with carried by nano carbon fiber acetylacetonate nickel or vanadyl and ZnBr
2/ Bu
4nBr compound comes from different backgrounds and possess different abilities catalyst system, and catalysis obtains the vinylbenzene cyclic carbonate ester of yield 48 ~ 53%.Chinese patent CN 102127051A develops methyl ethyl diketone molybdenum match/ionic liquid or quaternary ammonium salt catalyst system, utilize the pattern of one pot of interval, stepwise reaction, obtain the target product of higher yields, but also exist that efficiency is low, energy consumption large, catalyzer costly waits not enough.The people such as Li [N. Eghbali, C. Li, Green. Chem., 2007,9,13] utilize N-bromosuccinimide or Br
-/ H
2o
2for styrene oxidation is bromohydrin intermediate by bromide reagent, then under the effect of 1,8-diazabicylo-dicyclo (5,4,0)-7-hendecene organic alkali (DBU), slough proton, generate active intermediate, nucleophilic attack carbonic acid gas obtains cyclic carbonate.
Above-mentioned prior art all adopts organo-peroxide that price is higher or hydrogen peroxide to be oxygenant, also relate to the catalyst system of complexity or costliness, oxidising process often needs excessive oxygenant, cause production cost high and easily generate a large amount of by product, these deficiencies govern the further application of this synthesis route.
(2) take oxygen as oxygenant:
From industrial application angle, with oxygen cheap and easy to get or atmospheric oxygen for oxygenant, have more actual application value.The research that the people such as Aresta [M. Aresta, E. Quaranta, J. Mol. Catal. A:Chem, 1987,41,355] are catalyzer expansion this respect with Rh title complex, metal oxide, but the productive rate of target product is lower than 10%.
Electrochemistry organic synthesis does not need to add poisonous or dangerous oxygenant or reductive agent, generally do not need the catalyzer additionally adding complex and expensive yet, but utilize the most clean reaction reagent " electronics ", oxygenant needed for original position produces or reductive agent, reactive intermediate etc., can realize the reaction that general chemistry method is difficult to carry out in a mild condition.Electrochemistry organic synthesis is described as eco-friendly green synthesis techniques, has vast potential for future development, is more and more subject to concern and the research of people.Compared with general chemistry synthetic method, electrochemical method for synthesizing is more economical, environmental friendliness more.Adopting the prior art of electrochemical method synthesizing annular carbonate, is all raw material with epoxy compounds, and adopts MAGNESIUM METAL or aluminium to be the electrochemical method of sacrificial anode.Sacrificial anode protection not only consumes a large amount of metallic substance, increases cost, and brings very large trouble to follow-up separating-purifying, and this is the bottleneck problem hindering the further industrial applications of the method.
Summary of the invention
The object of the invention is to the shortcoming overcoming prior art, a kind of method being raw material electrochemical production cyclic carbonate with alkene and carbonic acid gas is provided, with alkene and carbonic acid gas for raw material, adopt inert anode, without in barrier film single compartment electrolytic cell, electrochemical reaction is passed through under normal temperature and pressure, alkene and carbon dioxide conversion are cyclic carbonate by one step, without the need to additionally adding oxygenant and catalyzer, have efficient, economical, the feature of environmental protection, be suitable for increment processing and the refinery of petrochemical complex olefin product, the trans-utilization of the exhaust carbon dioxide that the industries such as fuel-burning power plant produce.
In order to achieve the above object, present invention employs following technical scheme:
With alkene and CO
2for the method for raw material electrochemical production cyclic carbonate, comprise the following steps: be equipped with inert anode, negative electrode without in barrier film single chamber high-pressure electrolysis pond, add conducting salt, electroanalysis solvent, olefin(e) compound successively, then to pass into carbonic acid gas to electrolyzer pressure be 0.1 ~ 5MPa, sealing; Then electrolytic reaction is carried out at normal temperatures; After having reacted, underpressure distillation, organic solvent extraction are carried out to electrolytic solution, obtains cyclic carbonate.
Described negative electrode is the alloy that is a kind of or wherein two or more composition in nickel, silver, copper, platinum, tin, titanium, iron, zinc, aluminium or chromium; Described inert anode is platinum or graphite.
Described conducting salt is one or more in the sodium salt of halogen, sylvite, inorganic ammonium salt or organic ammonium salt; Described halogen is chlorine, bromine or iodine.
Described electroanalysis solvent is
n,N-dimethyl formamide, acetonitrile, tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), dioxane or water.
Described olefin(e) compound is normal olefine or cyclic olefin.
The mol ratio of described carbonic acid gas and olefin(e) compound is (1.5 ~ 3): 1.
Described electrolytic reaction is carried out under continuous current or potentiostatic mode, when the olefin(e) compound of every mole passes into electricity
qwhen being 96500 ~ 482500 coulombs, stop electrolysis.Electrolysis time
twith the molar weight of olefin(e) compound and the strength of current of electrolysis
irelevant
,by
q=
i*tcalculate.
Described organic solvent is ether or ethyl acetate.
Principle of the present invention is shown below:
The present invention compared with prior art, has following advantage and beneficial effect:
(1) the present invention replaces sacrificial anode with inert anode, overcomes the consumptive problem of metal anode, fundamentally solves the bottleneck problem of electrochemical process synthesizing annular carbonate, has good industrial applications prospect;
(2) the present invention produces oxygenant, active intermediate by the electrochemical reaction original position of electrode, without the need to additionally adding oxygenant, catalyzer, thus efficiently avoid and use poisonous, dangerous or expensive oxygenant, it also avoid the tedious work preparing complicated catalyzer, reaction system is simply effective, the easy separating-purifying of product;
(3) the present invention uses alkene cheap and easy to get, carbonic acid gas for raw material, in room temperature, carbonic acid gas is synthesizing annular carbonate under the reaction conditions of 1 atmospheric gentleness, to avoid in traditional method use the severe condition of high temperature, high pressure, operation is easy, safety, easily realizes industrialization;
(4) target product selectivity high, almost do not have by product, productive rate high, substrate olefin is applied widely, and production cost is low, has very high industrial applications and is worth;
(5) this technique realizes effective trans-utilization of carbonic acid gas under lower material consumption, energy consumption, has economy, environmental protection double benefit.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but the scope of protection of present invention is not limited to this.
embodiment 1
Take Graphite Electrodes as anode, metallic nickel is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, DMSO), 1mmol vinylbenzene, 30mmol sodium-chlor, magnetic stir bar add 20mL dimethyl sulfoxide (DMSO) successively (to be called for short:, pass into carbon dioxide again to 0.1MPa, sealing; Under the pattern of continuous current, the direct current of logical 0.06A, electrolysis 3 hours under room temperature, stops energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product Styrene carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of Styrene carbonate is 93%.
embodiment 2
Take Graphite Electrodes as anode, stainless steel is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, adds 20mL successively
n,NdMF), 1mmol vinylbenzene, 20mmol ammonium chloride, magnetic stir bar-dimethyl formamide (is called for short:, then passes into carbon dioxide to 0.1MPa, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product Styrene carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of Styrene carbonate is 90%.
embodiment 3
Take Graphite Electrodes as anode, latten(-tin) (that is: Cu-Sn alloy) is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL DMF, 1mmol vinylbenzene, 20mmol Potassium Bromide, magnetic stir bar successively, pass into carbon dioxide again to 0.1MPa, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product Styrene carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of Styrene carbonate is 92%.
embodiment 4
Take Graphite Electrodes as anode, copper is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, adds 20mL tetrahydrofuran (THF), 1mmol vinylbenzene, 20mmol sodium iodide, magnetic stir bar successively, pass into carbon dioxide again to 0.1MPa, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product Styrene carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of Styrene carbonate is 85%.
embodiment 5
Take Graphite Electrodes as anode, metallic nickel is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL acetonitrile, 1mmol successively to chloro-styrene, 20mmol Sodium Bromide, magnetic stir bar, pass into carbon dioxide to 0.1MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product to chloro-styrene cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.Be 90% to the isolated yield of chloro-styrene cyclic carbonate.
embodiment 6
Take Graphite Electrodes as anode, metallic aluminium is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL dioxane, 1mmol successively to bromstyrol, 30mmol ammonium iodide, magnetic stir bar, pass into carbon dioxide to 0.1MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product to bromstyrol cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.Be 93% to the isolated yield of bromstyrol cyclic carbonate.
embodiment 7
Take Graphite Electrodes as anode, metal titanium is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL tetrahydrofuran (THF), 1mmol p-methylstyrene, 20mmol Tetrabutyl amonium bromide, magnetic stir bar successively, pass into carbon dioxide to 0.1MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product p-methylstyrene cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of p-methylstyrene cyclic carbonate is 92%.
embodiment 8
Take Graphite Electrodes as anode, metallic zinc is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 30mL DMSO, 10mmol vinylbenzene, 30mmol ammonium chloride, magnetic stir bar successively, pass into carbon dioxide to 1MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.16A, electrolysis 5 hours, stop energising; After electrolysis terminates, slowly bleed off unreacted carbonic acid gas, electrolytic solution under reduced pressure distills, be then extracted with ethyl acetate three times, after ethyl acetate volatilization, obtain target product.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of Styrene carbonate is 85%.
embodiment 9
Take platinum electrode as anode, metallic nickel is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL DMF, 1mmol successively to methoxy styrene, 30mmol tetrabutylammonium iodide, magnetic stir bar, pass into carbon dioxide to 0.1MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, be then extracted with ethyl acetate three times, after ethyl acetate volatilization, obtain target product to methoxy styrene cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.Be 86% to the isolated yield of methoxy styrene cyclic carbonate.
embodiment 10
Take platinum electrode as anode, metallic nickel is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL DMF, 1mmol pfluorostyrene, 20mmol tetrabutylammonium chloride, magnetic stir bar successively, pass into carbon dioxide to 0.1MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product pfluorostyrene cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of pfluorostyrene cyclic carbonate is 88%.
embodiment 11
Take Graphite Electrodes as anode, metal platinum is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL DMF, 1mmol 1-phenylbutene, 20mmol Repone K, magnetic stir bar successively, pass into carbon dioxide to 2.5MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product 1-phenylbutene cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of 1-phenylbutene cyclic carbonate is 84%.
embodiment 12
Take Graphite Electrodes as anode, metallic tin is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, add 20mL DMF, 1mmol tetrahydrobenzene, 30mmol potassiumiodide, magnetic stir bar successively, pass into carbon dioxide to 0.1MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product tetrahydrobenzene cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.The isolated yield of tetrahydrobenzene cyclic carbonate is 80%.
embodiment 13
Take Graphite Electrodes as anode, chromium metal is negative electrode, at 100mL with in teflon-lined stainless steel single chamber high-pressure electrolysis pond, adds 20mL DMF, 1mmol successively
α-naphthalene ethene, 30mmol brometo de amonio, magnetic stir bar, pass into carbon dioxide to 5MPa again, sealing; Under the pattern of continuous current, connect the direct current of 0.06A, electrolysis 3 hours under room temperature, stop energising; After electrolysis terminates, slowly bleed off unreacted carbon dioxide, electrolytic solution under reduced pressure distills, then use extracted with diethyl ether three times, after ether volatilization, obtain target product
α-naphthalene ethene cyclic carbonate.
The structure of products obtained therefrom by IR,
1h NMR,
13c NMR and GC-MS determines.
αthe isolated yield of-naphthalene ethene cyclic carbonate is 90%.
Claims (7)
1. with the method that alkene and carbonic acid gas are raw material electrochemical production cyclic carbonate, it is characterized in that, comprise the following steps: be equipped with inert anode, negative electrode without in barrier film single chamber high-pressure electrolysis pond, add conducting salt, electroanalysis solvent, olefin(e) compound successively, passing into carbonic acid gas to electrolyzer pressure is again 0.1 ~ 5MPa, sealing; Then electrolytic reaction is carried out at normal temperatures; After having reacted, underpressure distillation, organic solvent extraction are carried out to electrolytic solution, obtains cyclic carbonate;
Described electrolytic reaction is carried out under continuous current or potentiostatic mode, when to pass into electricity be 96500 ~ 48200 coulombs to the olefin(e) compound of every mole, stops electrolysis.
2. method according to claim 1, is characterized in that, described negative electrode is the alloy that is a kind of or wherein two or more composition in nickel, silver, copper, platinum, tin, titanium, iron, zinc, aluminium or chromium; Described inert anode is platinum or graphite.
3. method according to claim 2, is characterized in that, described conducting salt is one or more in the sodium salt of halogen, sylvite, inorganic ammonium salt or organic ammonium salt; Described halogen is chlorine, bromine or iodine.
4. method according to claim 3, is characterized in that, described electroanalysis solvent is DMF, acetonitrile, tetrahydrofuran (THF), dimethyl sulfoxide (DMSO) or dioxane.
5. method according to claim 4, is characterized in that, described olefin(e) compound is normal olefine or cyclic olefin.
6. according to the method one of Claims 1 to 5 Suo Shu, it is characterized in that, the mol ratio of described carbonic acid gas and olefin(e) compound is (1.5 ~ 3): 1.
7. method according to claim 6, is characterized in that, described organic solvent is ether or ethyl acetate.
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| CN103789789B (en) * | 2014-02-11 | 2016-06-29 | 华东师范大学 | Electrochemical synthesis has the method for optically active Styrene carbonate |
| CN104557886B (en) * | 2014-12-25 | 2018-01-05 | 华南理工大学 | The method of one kind synthesis (E) α (iodo alkylidene) cyclic carbonate |
| WO2018027322A1 (en) * | 2016-08-12 | 2018-02-15 | The Governing Council Of The University Of Toronto | Electrochemical carbon dioxide utilization |
| JP7327758B2 (en) * | 2019-10-29 | 2023-08-16 | 株式会社ダイセル | Method for producing epoxy compound |
| CN114214649B (en) * | 2022-01-13 | 2023-03-28 | 万华化学集团股份有限公司 | Preparation method of aliphatic diol |
| CN114737208B (en) * | 2022-05-13 | 2024-06-07 | 北京理工大学深圳汽车研究院(电动车辆国家工程实验室深圳研究院) | Synthetic method of organic carbonate |
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| EP0127003A1 (en) * | 1983-05-02 | 1984-12-05 | Union Carbide Corporation | Improved process for the production of alkene oxides |
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| 室温下电化学活化CO2与环氧化合物反应合成环碳酸脂;王颖等;《有机化学》;20071130;第27卷(第11期);第1397-1400页 * |
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| CN112111756B (en) * | 2020-08-31 | 2022-02-11 | 湖南工程学院 | Method for electrochemically synthesizing cyclic carbonate and application thereof |
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