Out of tank type electrochemical synthesizing method of p-methoxy phenylacetone

A kind of technology of methoxyphenylacetone and synthesis method, applied in the field of electrochemistry, can solve the problems of many operation steps, low yield, long synthesis route, etc., and achieve simple and easy-to-obtain reaction raw materials, simple and safe operation, and avoid pollution Effect

Inactive Publication Date: 2007-12-19
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] 1. British Patent No.1119612 uses peracetic acid to oxidize 1-(4-methoxyphenyl)propylene, and the oxidation product uses acidic substances such as ZnCl 2 After the reaction, p-methoxyphenylacetone is obtained. The disadvantage is that the yield in the acid treatment process is low, and the raw material peroxygen compound is easy to explode, and the operation must be extremely careful
[0005] 2. U.S. JACS, 77,700 (1955) uses 4-methoxyphenylacetonitrile to react with sodium ethoxide in ethyl acetate to obtain a precursor compound containing an acetyl group, which is then hydrolyzed to obtain p-methoxyphenylacetone. The disadvantage is Due to the use of sodium ethoxide, the entire reaction system must strictly remove water, and the yield of the hydrolysis step is low, and the preparation has to add the step of synthesizing the raw material 4-methoxyphenylacetonitrile, the synthesis route is long, and the operation steps are many
[0006] 3. U.S. Patent No. 4,638,094 utilizes 3-(4-methoxyphenyl)propene and alkyl nitrite to react, and simultaneously adds alcohol, palladium catalyst and amine or copper compound in the reaction system, and then carries out the above-mentioned product The final product is obtained by the hydrolysis reaction, and the yield is high, but the composition of the reaction system is complex and the catalyst is expensive
[0007] 4. French patent FR1,450,200 uses 4-methoxybenzaldehyde and α-chloropropionate to react under strong alkali conditions, and then the product is treated under strong acid conditions to obtain p-methoxyphenylacetone. The disadvantage is that the raw material 4 -Methoxybenzaldehyde and α-chloropropionate are expensive and difficult to obtain
[0008] 5. U.S. Patent No. 4,967,009 uses 2-(4-methoxyphenyl)propene and iodosobenzene diacetate to react in glacial acetic acid to obtain p-methoxyphenylacetone. The disadvantage is that the yield is low
[0009] At present, there is no report on the synthesis of p-methoxyphenylacetone by electrochemical method both at home and abroad

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In the second step, 20g acetic acid: the volume ratio of acetic anhydride is 1: acetic acid-: acetic anhydride solvent, 1g potassium acetate are supporting electrolyte and 5g lead acetate mix, reflux 6 hours under 80 ℃, obtain anolyte, inject institute Described anode compartment, 20g acetic acid: the volume ratio of acetic anhydride is 1: 1 acetic acid-: acetic anhydride solvent and 5g potassium acetate are supporting electrolyte mix, reflux 6 hours under 80 ℃, obtain catholyte, inject described cathode room;

[0035] In the third step, at 20°C, the current density is 5mA / cm 2 , power supply 5.4×10 -3 F, after stopping the electrolysis, add the electrolyte solution containing lead tetraacetate in the anode chamber to 0.4g anethole at normal pressure and 40°C, and react for 30 hours;

[0036] In the 4th step, under 100 ℃, hydrolyze for 10 hours, the addition of water is 20g, the consumption of diethyl ether is each 10g, H 2 SO 4 The concentration of the solution is ...

Embodiment 2

[0041] In the second step, 20g acetic acid: the volume ratio of acetic anhydride is 1: acetic acid-: acetic anhydride solvent, 3g potassium acetate are supporting electrolyte and 3g lead acetate mix, reflux 6 hours under 80 ℃, obtain anolyte, inject all Described anode chamber, all the other are with the second step of embodiment 1;

[0042] In the third step, at 40°C, the current density is 10mA / cm 2 , power supply 5.4×10 -3 F, after stopping the electrolysis, add the electrolyte solution containing lead tetraacetate in the anode chamber to 0.4g anethole at normal pressure and 60°C, and react for 20 hours;

[0043] In the fourth step, hydrolyze at 80°C for 7 hours, H 2 SO 4 The concentration of the solution is 40%;

[0044] In the fifth step, the product was obtained, p-methoxyphenylacetone 0.247g;

[0045] In the sixth step, lead acetate is recycled.

[0046] In the fifth step, the yield was 61.9%.

Embodiment 3

[0048] In the second step, 20g acetic acid: the volume ratio of acetic anhydride is 1: acetic acid-: acetic anhydride solvent, 5g potassium acetate are supporting electrolyte and 1g lead acetate mix, reflux 6 hours under 80 ℃, obtain anolyte, inject institute Described anode chamber, all the other are with the second step of embodiment 1;

[0049] In the third step, at 60°C, the current density is 15mA / cm 2 , power supply 5.4×10 -3 F, after stopping the electrolysis, add the electrolyte solution containing lead tetraacetate in the anode chamber to 0.4g anethole at normal pressure and 80°C, and react for 10 hours;

[0050] In the fourth step, hydrolysis at 60°C for 10 hours, H 2 SO 4The concentration of the solution is 60%;

[0051] In the fifth step, the product was obtained, p-methoxyphenylacetone 0.21g;

[0052] In the sixth step, lead acetate is recycled.

[0053] In the fifth step, the yield was 52.8%.

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Abstract

The invention discloses a tank-exterior electrochemistry composite technique of methoxylbenzyl-ketone that relates to electrochemistry technique field. Adopt Pt filament as positive pole and stainless fin as negative pole in bi-room electrolysis tank, acetic acid-acetic acid anhydride as disslovant, kalium acetate as electrolysis support, at certain temperature, lead acetate as reactor, electrolysis with constant electricity density acquiring lead tertraacetate, add all the obtained lead tertraacetate into anethole after the electrolysing is stopped and acquiring organic product after the reaction stops, hydrolytic decomposing with sulfuric acid , extract with diethyl ether and finally obtain the product acetone p-methoxybenzoate. The left lead acetate can be recycled after processing. The productivity of above technique is 52 to 62 percent. The invention has got advantages such as simple and easy reaction material, environmental reaction process, safe operation, high productivity and low cost, is a technique of high added value.

Description

technical field [0001] The invention relates to an out-of-tank electrochemical synthesis method of p-methoxyphenylacetone, which belongs to the technical field of electrochemistry. Background technique [0002] p-methoxyphenylacetone, molecular formula C 10 h 12 o 2 , with a boiling point of 266-268°C and a relative density of 1.067, it is an important synthetic intermediate for pesticides, medicines, especially synthetic antihypertensive drugs, antidepressants, etc., such as 4-methoxy-N-methyl prepared from it as an intermediate - Amphetamines are used as central nervous system stimulants in the treatment of narcolepsy and depression and are now widely used in Europe. [0003] Although p-methoxyphenylacetone is a very useful intermediate, a very satisfactory preparation process has not been found so far in actual industrial production. [0004] 1. British Patent No.1119612 uses peracetic acid to oxidize 1-(4-methoxyphenyl)propylene, and the oxidation product uses acidic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/02C25B3/23
Inventor 陆嘉星叶小鹤王欢张丽罗仪文
Owner EAST CHINA NORMAL UNIV
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