CN102383142A - Synthetic method of glycerol carbonate - Google Patents

Synthetic method of glycerol carbonate Download PDF

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Publication number
CN102383142A
CN102383142A CN2011102619775A CN201110261977A CN102383142A CN 102383142 A CN102383142 A CN 102383142A CN 2011102619775 A CN2011102619775 A CN 2011102619775A CN 201110261977 A CN201110261977 A CN 201110261977A CN 102383142 A CN102383142 A CN 102383142A
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usp kosher
esterification
electrolyte
electrolytic solution
temperature
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王欢
朱美侠
吴腊霞
鲍少华
张贵荣
陆嘉星
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East China Normal University
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East China Normal University
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Abstract

The invention discloses a synthetic method of glycerol carbonate. The synthetic method is characterized in that: N,N-dimethylformamide is mixed with tetraethyl ammonium iodide and glycerol to obtain an electrolyte, the electrolyte is saturated with CO2 at normal pressure and is electrolyzed under conditions of a constant current, and the electrolyte is esterified and distillated to prepare glycerol carbonate. Compared with the prior art, the synthetic method of the invention, which has the advantages of simple technology, convenient operation, safety, cheap and easily available raw material, effective utilization of a greenhouse effect gas carbon dioxide, substantial reduction of atmospheric pollution, realization of the high efficiency conversion of glycerol, and alleviation of the increasingly exhausted energy problem and has a very significant meaning to the environment protection, is a technical route with a good industrial synthetic value.

Description

A kind of compound method of USP Kosher carbonic ether
Technical field
The present invention relates to the organic chemistry synthesis technical field, specifically a kind of compound method of USP Kosher carbonic ether.
Background technology
The USP Kosher carbonic ether, English name: glycerol carbonate, molecular formula C 4H 6O 4, molecular weight is 118.09, is a kind of colourless viscous liquid, boiling point is 137～140 ℃ of 0.5mm Hg (lit.), has pungency, is slightly soluble in water, ether, is dissolved in ester.The USP Kosher carbonic ether is a kind of applied range, relatively the multi-functional compounds of market outlook is arranged.The USP Kosher carbonic ether can be used as protonic solvent, the liquid membrane of separating carbon dioxide and nitrogen, the additive in the lithium cell; Also be important organic synthesis intermediate simultaneously, can polycarbonate synthesis, gather aminolipid; Because of having no side effect, have low toxicity, low vapo(u)rability, low catching fire and humidity-preserving type, also can be used for makeup and medical aspect etc.
At present, the preparation of relevant USP Kosher carbonic ether has following several method through retrieval:
Figure 2011102619775100002DEST_PATH_IMAGE002
, Maria J. Climent etc. are at Journal of Catalysis, and 2010,269; Be raw material with the USP Kosher among 140 – 149; With NSC 11801 under 35 ℃ temperature, and under catalyst action, obtain the USP Kosher carbonic ether; In this process; Cost is higher, and product separates comparatively difficulty, and the energy uses upward unreasonable.
Figure 2011102619775100002DEST_PATH_IMAGE004
, Yogesh Patel etc. are at Green Chemistry; 2009; 11, be raw material with the USP Kosher among the 1056-1060, under the temperature of diethyl carbonate and 100 ℃; And under catalyst action, obtain the USP Kosher carbonic ether.In this process, cost is higher, and temperature is higher, and product separates comparatively difficulty, and the energy uses upward unreasonable.
Figure DEST_PATH_IMAGE006
, Takumi Mizuno etc. is at Heteroatom Chemistry, 2010,21, be raw material with the USP Kosher among the 99-102, make it and CO, O 2Reaction is 16 hours under the effect of catalyzer, obtains the USP Kosher carbonic ether.In this process, the reaction times is long, has used toxic gas simultaneously, does not meet the requirement of Green Chemistry.
Figure DEST_PATH_IMAGE008
, Jimil George, wait A:Chemical at Journal of Molecular Catalysis, 2009,304, be raw material with the USP Kosher among the 1-7, with CO 2Reacted 4 hours in 80 ℃ in temperature under the pressure 3.5MPa, and under the effect of catalyzer, obtain the USP Kosher carbonic ether, in this reaction process, pressure is higher, and temperature is higher, and productive rate is lower, does not meet the requirement of Green Chemistry.
The problem that above public technology exists is all need under corresponding catalyzer, react; Its synthetic production cost is high, and complicated process of preparation is not easy to operate; Though the USP Kosher carbonic ether is unusual important chemical product; But in actual industrial production, do not find very satisfied preparation technology so far yet, up to now, the home and abroad is not seen the USP Kosher carbonic ether synthetic report of not only economy but also environmental protection as yet.
Summary of the invention
The compound method of a kind of USP Kosher carbonic ether that the objective of the invention is to be directed against the deficiency of prior art and provide, it adopts electrochemical synthetic technology, utilizes the synthetic USP Kosher carbonic ether of the by product USP Kosher of producing diesel oil; Technology is simple, equipment is few; Raw material is easy to get, and transformation efficiency is high, and cost is low; Free from environmental pollution, be a kind of synthetic operational path that is worth of industry that has very much.
The technical scheme that realizes the object of the invention is: a kind of compound method of USP Kosher carbonic ether; Be characterized in that this method is with N; Dinethylformamide mixes with tetraethyl ammonium iodide and USP Kosher; Under normal pressure behind the saturated carbonic acid gas with constant-current electrolysis, electrolytic solution through esterification, revolve steam the USP Kosher carbonic ether, concrete steps are following:
The preparation of a, electrolytic solution
With USP Kosher and tetraethyl ammonium iodide and N, dinethylformamide is pressed the 1:1:129 mixed in molar ratio, and putting into negative electrode is that copper electrode, anode are the electrolyzer of graphite rod;
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.07～10.01mA/cm 2The constant current density electrolysis, temperature is 0～25 ℃, the energising amount is every mole of USP Kosher 2.0～3.0F, F is a Faraday's number;
C, esterification
Above-mentioned electrolytic solution is mixed by the 50:6:15 volume ratio with Anhydrous potassium carbonate and methyl iodide; In temperature is 50～60 ℃, and stirring and refluxing was carried out esterification in 4～5 hours, and dripping hydrochloric acid neutralizes then; Make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure;
D, revolve steaming
Electrolytic solution after the above-mentioned esterification and ETHYLE ACETATE are pressed 1:1 volume ratio extraction three times; Merge the ester layer, then with the anhydrous magnesium sulfate after-filtration that dewaters, filtrating after vacuum rotary steam removes ETHYLE ACETATE the USP Kosher carbonic ether; The temperature of its vacuum rotary steam is 35 ℃, and pressure is 0.1MPa.
It is simple that the present invention compared with prior art has method, easy to operate, safe advantage, and raw material is to utilize the by product USP Kosher of producing diesel oil; Thereby it is cheap and easy to get; And the greenhouse gases carbonic acid gas carried out effective utilization, and significantly reduced topsoil, realize the efficient conversion of USP Kosher simultaneously; But also reduce the production cost of biofuel and the extension of industrial chain effectively; Having alleviated the exhausted day by day problem of the energy, environment protection is had very significant meaning, is a kind of synthetic operational path that is worth of industry that has very much.
Embodiment
Through following specific embodiment the present invention is done further detailed description.
Embodiment 1
The preparation of a, electrolytic solution
With 0.1M (0.0921g) USP Kosher and 0.1M (0.2572g) tetraethyl ammonium iodide and the analytically pure N of 10 mL; After dinethylformamide mixed, putting into the negative electrode was that copper electrode, anode are a Room type electrolyzer of graphite rod, and wherein: USP Kosher is a substrate; N; Dinethylformamide is 4 grades of solvents after the molecular sieve drying, and tetraethyl ammonium iodide is a supporting electrolyte, and tetraethyl ammonium iodide and USP Kosher are analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 8.37mA/cm 2Current density, temperature is 25 ℃, carries out constant-current electrolysis, the energising amount is 193C.
C, esterification
After electrochemical reaction finishes; Above-mentioned electrolytic solution is moved in the flask; And add 0.3g Anhydrous potassium carbonate and the analytically pure methyl iodide mixing of 0.3mL, and stirring and refluxing was carried out esterification in 5 hours under 60 ℃ of temperature, and reaction is cooled to room temperature with solution after finishing; Drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7.
D, revolve steaming
With the analytically pure ethyl acetate extraction in used for electrolyte 20mL * 3 after the above-mentioned esterification three times; Ester layer in the combining extraction liquid, the extraction liquid ester layer that merges with 5mL saturated nacl aqueous solution washing more once moves to the ester layer in the Erlenmeyer flask; And in Erlenmeyer flask, add 1 hour after-filtration of anhydrous magnesium sulfate drying of about 2.2g; To filtrate then and take off to analyse and remove behind the ETHYLE ACETATE to such an extent that product be the USP Kosher carbonic ether to 0.1MPa through rotatory evaporator vacuum rotary steam under 35 ℃ of temperature, its productive rate is 72%.
Embodiment 2
The preparation of a, electrolytic solution
With 0.1M (0.0921g) USP Kosher and 0.1M (0.2572g) tetraethyl ammonium iodide and the analytically pure N of 10 mL; After dinethylformamide mixed, putting into the negative electrode was that copper electrode, anode are a Room type electrolyzer of graphite rod, and wherein: USP Kosher is a substrate; N; Dinethylformamide is 4 grades of solvents after the molecular sieve drying, and tetraethyl ammonium iodide is a supporting electrolyte, tetraethyl ammonium iodide and USP Kosher analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 8.37mA/cm 2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 193C.
C, esterification
After electrochemical reaction finishes; Above-mentioned electrolytic solution is moved in the flask; And add 0.3g Anhydrous potassium carbonate, the analytically pure methyl iodide mixing of 0.3mL, and stirring and refluxing was carried out esterification in 5 hours under 60 ℃ of temperature, and reaction is cooled to room temperature with solution after finishing; Drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7.
D, revolve steaming
With the analytically pure ethyl acetate extraction in used for electrolyte 20mL * 3 after the above-mentioned esterification three times; Ester layer in the combining extraction liquid, the extraction liquid ester layer that merges with 5mL saturated nacl aqueous solution washing more once moves to the ester layer in the Erlenmeyer flask; And in Erlenmeyer flask, add 1 hour after-filtration of anhydrous magnesium sulfate drying of about 2.2g; To filtrate then through rotatory evaporator under 35 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ETHYLE ACETATE product USP Kosher carbonic ether, its productive rate is 40%.
Embodiment 3
The preparation of a, electrolytic solution
With 0.1M (0.0921g) USP Kosher and 0.1M (0.2572g) tetraethyl ammonium iodide and the analytically pure N of 10 mL; After dinethylformamide mixed, putting into the negative electrode was that copper electrode, anode are a Room type electrolyzer of graphite rod, and wherein: USP Kosher is a substrate; N; Dinethylformamide is 4 grades of solvents after the molecular sieve drying, and tetraethyl ammonium iodide is a supporting electrolyte, tetraethyl ammonium iodide and USP Kosher analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 10.01mA/cm 2Current density, temperature is 25 ℃, carries out constant-current electrolysis, the energising amount is 193C.
C, esterification
After electrochemical reaction finishes; Above-mentioned electrolytic solution is moved in the flask; And add 0.3g Anhydrous potassium carbonate, the analytically pure methyl iodide mixing of 0.3mL, and stirring and refluxing was carried out esterification in 5 hours under 60 ℃ of temperature, and reaction is cooled to room temperature with solution after finishing; Drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7.
D, revolve steaming
With the used for electrolyte 20mL after the above-mentioned esterification * 3 ethyl acetate extractions three times; Ester layer in the combining extraction liquid, the extraction liquid ester layer that merges with 5mL saturated nacl aqueous solution washing more once moves to the ester layer in the Erlenmeyer flask; And in Erlenmeyer flask, add 1 hour after-filtration of anhydrous magnesium sulfate drying of about 2.2g; To filtrate then through rotatory evaporator under 35 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ETHYLE ACETATE product USP Kosher carbonic ether, its productive rate is 66%.
Embodiment 4
The preparation of a, electrolytic solution
With 0.1M (0.0921g) USP Kosher and 0.1M (0.2572g) tetraethyl ammonium iodide and the analytically pure N of 10 mL; After dinethylformamide mixed, putting into the negative electrode was that copper electrode, anode are a Room type electrolyzer of graphite rod, and wherein: USP Kosher is a substrate; N; Dinethylformamide is 4 grades of solvents after the molecular sieve drying, and tetraethyl ammonium iodide is a supporting electrolyte, tetraethyl ammonium iodide and USP Kosher analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.07mA/cm 2Current density, temperature is 25 ℃, carries out constant-current electrolysis, the energising amount is 193C.
C, esterification
After electrochemical reaction finishes; Above-mentioned electrolytic solution is moved in the flask; And add 0.3g Anhydrous potassium carbonate, the analytically pure methyl iodide mixing of 0.3mL, and stirring and refluxing was carried out esterification in 5 hours under 60 ℃ of temperature, and reaction is cooled to room temperature with solution after finishing; Drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7.
D, revolve steaming
With the analytically pure ethyl acetate extraction in used for electrolyte 20mL * 3 after the above-mentioned esterification three times; Ester layer in the combining extraction liquid, the extraction liquid ester layer that merges with 5mL saturated nacl aqueous solution washing more once moves to the ester layer in the Erlenmeyer flask; And in Erlenmeyer flask, add 1 hour after-filtration of anhydrous magnesium sulfate drying of about 2.2g; To filtrate then through rotatory evaporator under 35 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ETHYLE ACETATE product USP Kosher carbonic ether, its productive rate is 50%.
Embodiment 5
The preparation of a, electrolytic solution
With 0.1M (0.0921g) USP Kosher and 0.1M (0.2572g) tetraethyl ammonium iodide and the analytically pure N of 10 mL; After dinethylformamide mixed, putting into the negative electrode was that copper electrode, anode are a Room type electrolyzer of graphite rod, and wherein: USP Kosher is a substrate; N; Dinethylformamide is 4 grades of solvents after the molecular sieve drying, and tetraethyl ammonium iodide is a supporting electrolyte, tetraethyl ammonium iodide and USP Kosher analytical pure.
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.07mA/cm 2Current density, temperature is 25 ℃, carries out constant-current electrolysis, the energising amount is 289C.
C, esterification
After electrochemical reaction finishes; Above-mentioned electrolytic solution is moved in the flask; And add 0.3g Anhydrous potassium carbonate, the analytically pure methyl iodide mixing of 0.3mL, and stirring and refluxing is 5 hours under 60 ℃ of temperature, and esterification is cooled to room temperature with solution after finishing; Drip 2M hydrochloric acid then and neutralize, make the electrolyte ph after the esterification be about 7.
D, revolve steaming
With the analytically pure ethyl acetate extraction in used for electrolyte 20mL * 3 after the above-mentioned esterification three times; Ester layer in the combining extraction liquid, the extraction liquid ester layer that merges with 5mL saturated nacl aqueous solution washing more once moves to the ester layer in the Erlenmeyer flask; And in Erlenmeyer flask, add 1 hour after-filtration of anhydrous magnesium sulfate drying of about 2.2g; To filtrate then through rotatory evaporator under 35 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ETHYLE ACETATE product USP Kosher carbonic ether, its productive rate is 28%.
More than each embodiment just the present invention is further specified, be not in order to restriction patent of the present invention, all be equivalence enforcement of the present invention, all should be contained within the claim scope of patent of the present invention.

Claims (1)

1. the compound method of a USP Kosher carbonic ether; It is characterized in that this method with N, dinethylformamide mixes with tetraethyl ammonium iodide and USP Kosher, under normal pressure behind the saturated carbonic acid gas with constant-current electrolysis; Electrolytic solution through esterification, revolve steam the USP Kosher carbonic ether, concrete steps are following:
The preparation of a, electrolytic solution
With USP Kosher and tetraethyl ammonium iodide and N, dinethylformamide is pressed the 1:1:129 mixed in molar ratio, and putting into negative electrode is that copper electrode, anode are the electrolyzer of graphite rod;
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 5.07～10.01mA/cm 2The constant current density electrolysis, its temperature is 0～25 ℃, the energising amount is every mole of USP Kosher 2.0～3.0F, F is a Faraday's number;
C, esterification
Above-mentioned electrolytic solution is mixed by the 50:6:15 volume ratio with Anhydrous potassium carbonate and methyl iodide; In temperature is 50～60 ℃, and stirring and refluxing was carried out esterification in 4～5 hours, and dripping hydrochloric acid neutralizes then; Make the electrolyte ph after the esterification be about 7, its methyl iodide is an analytical pure;
D, revolve steaming
Electrolytic solution after the above-mentioned esterification and ETHYLE ACETATE are pressed 1:1 volume ratio extraction three times; Merge the ester layer, then with the anhydrous magnesium sulfate after-filtration that dewaters, filtrating after vacuum rotary steam removes ETHYLE ACETATE the USP Kosher carbonic ether; The temperature of its vacuum rotary steam is 35 ℃, and pressure is 0.1MPa.
CN2011102619775A 2011-09-06 2011-09-06 Synthetic method of glycerol carbonate Pending CN102383142A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103789790A (en) * 2014-02-11 2014-05-14 华东师范大学 Method for asymmetric synthesis of styrene cyclic carbonate with optical activity
WO2018027322A1 (en) * 2016-08-12 2018-02-15 The Governing Council Of The University Of Toronto Electrochemical carbon dioxide utilization
CN114737208A (en) * 2022-05-13 2022-07-12 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
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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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103789790A (en) * 2014-02-11 2014-05-14 华东师范大学 Method for asymmetric synthesis of styrene cyclic carbonate with optical activity
CN103789790B (en) * 2014-02-11 2016-09-14 华东师范大学 Asymmetric synthesis has the method for optically active Styrene carbonate
WO2018027322A1 (en) * 2016-08-12 2018-02-15 The Governing Council Of The University Of Toronto Electrochemical carbon dioxide utilization
CN114737208A (en) * 2022-05-13 2022-07-12 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
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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Application publication date: 20120321