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: 2005-12-21
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
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  • 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, the volume ratio of 20g acetic acid: acetic anhydride is 1:1 acetic acid-: acetic anhydride solvent, 1g potassium acetate are supporting electrolyte and 5g lead acetate are mixed, refluxed at 80 DEG C for 6 hours to obtain anolyte, inject all Described anode chamber, 20g acetic acid: the volume ratio of acetic anhydride is the acetic acid of 1: 1: acetic anhydride solvent and 5g potassium acetate are supporting electrolyte mixing, reflux 6 hours at 80 DEG C, obtain catholyte, inject described cathode room;

[0035] In the third step, at 20°C, the current density is 5mA / cm 2 , the power is 5.4×10 -3 F. After stopping the electrolysis, at normal pressure and 40 ℃, the electrolyte solution containing lead tetraacetate in the anode chamber was added to 0.4 g of anethole, and the reaction was carried out for 30 hours;

[0036] In the fourth step, hydrolyzed at 100 ° C for 10 hours, the amount of water added is 20g, the amount of ether is 10g each time, ...

Embodiment 2

[0041] In the second step, the volume ratio of 20g acetic acid: acetic anhydride is 1:1 acetic acid-: acetic anhydride solvent, 3g potassium acetate are supporting electrolyte and 3g lead acetate are mixed, refluxed at 80 DEG C for 6 hours to obtain anolyte, injected into 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 , the power is 5.4×10 -3 F. After stopping the electrolysis, at normal pressure and 60 ℃, the electrolyte solution containing lead tetraacetate in the anode chamber was added to 0.4 g of anethole, and the reaction was carried out for 20 hours;

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

[0044] In the 5th step, obtain product, 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, the volume ratio of 20g acetic acid: acetic anhydride is 1:1 acetic acid-: acetic anhydride solvent, 5g potassium acetate are the supporting electrolyte and 1g lead acetate are mixed, refluxed at 80 ° C for 6 hours to obtain anolyte, injected into the 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 , the power is 5.4×10 -3F. After the electrolysis is stopped, the electrolyte solution containing lead tetraacetate in the anode chamber is added to 0.4 g of anethole under normal pressure and 80 ° C, and the reaction is carried out for 10 hours;

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

[0051] In the 5th step, obtain product, 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, and belongs to the technical field of electrochemistry. Background technique [0002] p-Methoxyphenylacetone, molecular formula C 10 H 12 O 2 , the boiling point is 266-268 °C, the relative density is 1.067, and it is an important synthetic intermediate for pesticides, medicines, especially the synthesis of hypotensive drugs, antidepressants, etc. -Amphetamine is used as a central nervous system stimulant in the treatment of narcolepsy and depression and is now widely used in Europe. [0003] Although p-methoxyphenylacetone is a very useful intermediate, a very satisfactory preparation process has not yet been found in actual industrial production. [0004] 1. British Patent No. 1119612 uses peracetic acid to oxidize 1-(4-methoxyphenyl)propene, and the oxidation product uses acidic substances such as ZnCl 2 After the reaction, p...

Claims

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Application Information

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