CN101591248A - A kind of synthetic method of methyl benzoate - Google Patents
A kind of synthetic method of methyl benzoate Download PDFInfo
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- CN101591248A CN101591248A CNA2009100535848A CN200910053584A CN101591248A CN 101591248 A CN101591248 A CN 101591248A CN A2009100535848 A CNA2009100535848 A CN A2009100535848A CN 200910053584 A CN200910053584 A CN 200910053584A CN 101591248 A CN101591248 A CN 101591248A
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- esterification
- electrolytic solution
- bromobenzene
- methyl benzoate
- dinethylformamide
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Abstract
The invention discloses a kind of synthetic method of methyl benzoate, characteristics be this method with N, dinethylformamide, tetraethyl ammonium iodide and bromobenzene mix, saturated CO under normal pressure
2The back is with constant-current electrolysis, electrolytic solution through esterification, after revolving steaming methyl benzoate.It is simple that the present invention compared with prior art has method; easy to operate, safety, raw material is easy to get, and cost is low; the productive rate height; advantage free from environmental pollution, and the greenhouse gases carbonic acid gas carried out effective utilization, not only save production cost; also significantly reduced topsoil; 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.
Description
Technical field
The present invention relates to the organic chemistry synthesis technical field, specifically a kind of electrochemical method for synthesizing of methyl benzoate.
Background technology
Methyl benzoate, English name are Methyl benzoate, are a kind of colourless oil liquids, and the intensive fragrance of a flower and cherry fragrance are arranged, fusing point-12.3 ℃, 199.6 ℃ of boiling points, 83 ℃ of flash-points, 505 ℃ of kindling temperatures, can be miscible with ether, be dissolved in methyl alcohol, ethanol, water insoluble and glycerine.The purposes of methyl benzoate is very extensive, is a kind of important fine chemical product, is used to prepare essence, also as solvent.
The synthetic method of methyl benzoate mainly contains at present:
(1), can obtain methyl benzoate by esterification, sterically hindered big just dying but in a single day esterification meets, for example benzoic phenyl ring.Therefore human basic catalyst NaOH is arranged, adopt Benzoyl chloride and methyl alcohol to react and prepare methyl benzoate.But this here method condition is relatively harsher, and the toxicity of methyl alcohol is high.
(2), Chinese patent CN10061706.9 (2007) puts into the reactor heated and stirred with methylcarbonate and methyl phenyl ketone, add catalyzer, be warmed up to 180 ~ 300 ℃, react after 2 ~ 10 hours, temperature of reaction is reduced to room temperature, separate making product, this technology shortcoming has been to use catalyzer, temperature of reaction height, time length etc.
(3), Chinese patent CN101402574 (2009) promotes carbonylation reaction synthesizing benzoic acids methyl esters by bromobenzene through light, this technology shortcoming has been to use catalyzer, has used toxic gas CO.
The synthetic technology of existing methyl benzoate exists complicated process of preparation, uses deleterious catalyzer, the production cost height, and also the purity of product, yield are all lower, and the intermediate instability of generation is apt to deteriorate, environment is had shortcomings such as pollution.
Summary of the invention
The synthetic method of a kind of methyl benzoate of providing at the deficiencies in the prior art is provided, and it adopts electrochemical synthetic technology, and equipment is simple, raw material is easy to get, and it is free from environmental pollution, the productive rate height, cost is low, is 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 synthetic method of methyl benzoate, characteristics be this method with N, dinethylformamide, tetraethyl ammonium iodide and bromobenzene mix, saturated CO under normal pressure
2The back is with constant-current electrolysis, electrolytic solution through esterification, after revolving steaming methyl benzoate, concrete steps are as follows:
The preparation of a, electrolytic solution
With bromobenzene, tetraethyl ammonium iodide and N, dinethylformamide is pressed 191: 200: 24780 mixed in molar ratio, and putting into negative electrode is that silver electrode, anode are the electrolyzer of magnesium rod;
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 2.27～5.67mAcm
-2Constant-current electrolysis, temperature are-10～20 ℃, and the energising amount is every mole of bromobenzene 1.5～3.5F, and F is a Faraday's number;
C, esterification
Above-mentioned electrolytic solution and Anhydrous potassium carbonate, methyl iodide are pressed 95: 217: 1180 mixed in molar ratio, wherein electrolytic solution with electrolysis before the amount of bromobenzene be benchmark, in temperature is 50 ℃ of stirring and refluxing 5 hours, remove N through revolving to steam then, dinethylformamide, dripping hydrochloric acid makes the electrolyte ph of esterification be about 7 again;
D, revolve steaming
The volume ratio of pressing 1: 1 with the electrolytic solution of ether and esterification extracts three times, wash with saturated nacl aqueous solution behind the combined ether layer, the volume ratio of saturated nacl aqueous solution and ether is 1: 6, then with the anhydrous magnesium sulfate after-filtration that dewaters, filtrate gets methyl benzoate after vacuum rotary steam removes ether, the temperature of vacuum rotary steam is 25 ℃, and pressure is 0.1MPa.
It is simple that the present invention compared with prior art has method; easy to operate, safety, raw material is easy to get, and cost is low; the productive rate height; advantage free from environmental pollution, and the greenhouse gases carbonic acid gas carried out effective utilization, not only save production cost; also significantly reduced topsoil; 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
The present invention is described in further detail by following specific embodiment.
Embodiment 1
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 4.54mAcm
-2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.87 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 73%.
Embodiment 2
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 2.27mAcm
-2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.87 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 56.3%.
Embodiment 3
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 5.67mAcm
-2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.87 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 54.7%.
Embodiment 4
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 4.54mAcm
-2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 2.39 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 78.2%.
Embodiment 5
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 4.55mAcm
-2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 1.43 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 55.0%.
Embodiment 6
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 4.54mAcm
-2Current density, temperature is 0 ℃, carries out constant-current electrolysis, the energising amount is 3.34 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 66.3%.
Embodiment 7
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 4.54mAcm
-2Current density, temperature is-10 ℃, carries out constant-current electrolysis, the energising amount is 2.39 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 65.4%.
Embodiment 8
The preparation of a, electrolytic solution
With 0.1mL bromobenzene, 0.2572g tetraethyl ammonium iodide, 10mLN, after dinethylformamide mixed, putting into the negative electrode was that silver electrode, anode are a Room type electrolyzer of magnesium rod, and wherein: bromobenzene is a substrate, and concentration is 0.95molL
-1N, dinethylformamide are solvent; Tetraethyl ammonium iodide is a supporting electrolyte, and concentration is 0.1molL
-1
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, and with 4.54mAcm
-2Current density, temperature is 20 ℃, carries out constant-current electrolysis, the energising amount is 2.39 * 10
-3F, F are Faraday's number, the electric weight of every mole of electronics of its expression, F=96485.309Cmol
-1
C, esterification
After electrochemical reaction finishes, above-mentioned electrolytic solution is moved in the flask, add 0.3g Anhydrous potassium carbonate, the mixing of 0.6mL methyl iodide, carried out esterification in 5 hours, remove N through revolving to steam then, behind the dinethylformamide, drip 2molL in 50 ℃ of following stirring and refluxing of temperature
-1Hydrochloric acid makes the electrolyte ph after the esterification be about 7;
D, revolve steaming
With the electrolytic solution of the above-mentioned esterification of 20mL extracted with diethyl ether three times, ether layer in the combining extraction liquid, the extraction liquid ether layer of usefulness 10mL saturated nacl aqueous solution washing merging once again, the ether layer is moved in the Erlenmeyer flask, and in Erlenmeyer flask, add the 3g anhydrous magnesium sulfate to remove the moisture in the extraction liquid, remove by filter anhydrous magnesium sulfate, with filtrate through rotatory evaporator under 25 ℃ of temperature vacuum rotary steam to 0.1MPa, take off analyse remove behind the ether the product methyl benzoate, productive rate is 40.2%.
More than each embodiment just the present invention will be further described, 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, a kind of synthetic method of methyl benzoate is characterized in that this method N, and dinethylformamide, tetraethyl ammonium iodide and bromobenzene mix, saturated CO under normal pressure
2The back with constant-current electrolysis, electrolytic solution through esterification, revolve steam methyl benzoate, concrete steps are as follows:
The preparation of a, electrolytic solution
With bromobenzene, tetraethyl ammonium iodide and N, dinethylformamide is pressed 191: 200: 24780 mixed in molar ratio, and putting into negative electrode is that silver electrode, anode are the electrolyzer of magnesium rod;
B, electrolysis
Under the normal pressure, in above-mentioned electrolyzer, feed carbonic acid gas to saturated, then with 2.27～5.67mAcm
-2Constant-current electrolysis, temperature are-10～20 ℃, and the energising amount is every mole of bromobenzene 1.5～3.5F, and F is a Faraday's number;
C, esterification
Above-mentioned electrolytic solution and Anhydrous potassium carbonate, methyl iodide are pressed 95: 217: 1180 mixed in molar ratio, wherein electrolytic solution with electrolysis before the amount of bromobenzene be benchmark, in temperature is 50 ℃ of stirring and refluxing 5 hours, remove N through revolving to steam then, dinethylformamide, dripping hydrochloric acid makes the electrolyte ph of esterification be about 7 again;
D, revolve steaming
Extract three times with the volume ratio of the electrolytic solution after ether and the esterification by 1: 1, wash with saturated nacl aqueous solution behind the combined ether layer, the volume ratio of saturated nacl aqueous solution and ether is 1: 6, then with the anhydrous magnesium sulfate after-filtration that dewaters, filtrate gets methyl benzoate after vacuum rotary steam removes ether, the temperature of vacuum rotary steam is 25 ℃, and pressure is 0.1MPa.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102383142A (en) * | 2011-09-06 | 2012-03-21 | 华东师范大学 | Synthetic method of glycerol carbonate |
| 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 |
| CN106245054A (en) * | 2016-09-05 | 2016-12-21 | 聊城大学 | A kind of synthetic method of 2 chloro benzoic ethers |
| CN107400898A (en) * | 2017-07-22 | 2017-11-28 | 聊城大学 | A kind of synthetic method of 2 pyridine carboxylic acid methyl esters |
-
2009
- 2009-06-23 CN CNA2009100535848A patent/CN101591248A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102383142A (en) * | 2011-09-06 | 2012-03-21 | 华东师范大学 | Synthetic method of glycerol carbonate |
| 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 |
| CN106245054A (en) * | 2016-09-05 | 2016-12-21 | 聊城大学 | A kind of synthetic method of 2 chloro benzoic ethers |
| CN107400898A (en) * | 2017-07-22 | 2017-11-28 | 聊城大学 | A kind of synthetic method of 2 pyridine carboxylic acid methyl esters |
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Application publication date: 20091202 |