IP Library Granted Patent US 10,487,041
Granted Patent B2
US 10,487,041 · App. 16/330,775 · Granted Nov 26, 2019

Method for producing N-methyl-para-anisidine

Inventors: Alexandr Yurievich Frolov (Moscow, RU); Nikolay Grigorievich Belyakov (Moscow, RU)
Assignee: OBSCHESTVO S OGRANICHENNOI OTVETSTVENNOSTYU “IFOTOP”
C07C209/24C07C209/84C07C217/84
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Quick Facts
Patent No.
US 10,487,041
App. No.
16/330,775
Granted
Nov 26, 2019
Kind
B2
Abstract

The invention relates to chemical engineering processes, and more particularly to liquid-phase catalytic methods for producing, in the presence of hydrogen, alkylated para-anisidine for use as a chemical substance or as a gasoline additive for increasing the octane rating of a gasoline. The technical result of the claimed group of inventions is an increase in the yield of N-methyl-para-anisidine and a decrease in the yield of a dimethyl derivative. A method for producing N-methyl-para-anisidine in a liquid phase includes alkylating para-anisidine with formalin as they are separately, simultaneously fed into a mixer disposed in a reactor, directly upstream of a catalytic reduction zone, thus producing an intermediate azomethine, and subsequently reducing same on a hydrogenation catalyst at a temperature of 20-120° C. in an environment of hydrogen at elevated pressure, and then isolating the target product, N-methyl-para-anisidine.

Claims (8)

1. A method for producing N-methyl-para-anisidine in a liquid phase, comprising alkylating para-anisidine with formalin as they are separately, simultaneously fed into a mixer disposed in a reactor, directly upstream of a catalytic reduction zone, thus producing an intermediate azomethine-4-methoxy-(N-phenylmethanimine), and subsequently reducing said intermediate on a hydrogenation catalyst at a temperature of 20-120° C., in an environment of hydrogen at elevated pressure, and then separating the target product, N-methyl-para-anisidine, wherein para-anisidine is used in the form of a solution in a solvent selected from the group: ethanol, methanol, isopropanol.

2. The method according to claim 1 , wherein the alkylation is carried out in a batch mode.

3. The method according to claim 1 , wherein the alkylation is carried out on in a continuous mode.

4. The method according to claim 1 , wherein stabilizers are used during the alkylation in the form of tertiary aliphatic amines, wherein said stabilizers are used in the amount of 5-10 mol. % of the para-anisidine load.

5. The method according to claim 4 , wherein tertiary aliphatic amines are selected from the group: triethylamine, tetramethylethylenediamine, diisopropylethylamine, dimethylbenzylamine, diazabicyclooctane, tripropylamine, aqueous solution of trimethylamine.

6. The method according to claim 4 , wherein the stabilizer is introduced into the reactor during loading of the hydrogenation catalyst and/or during supply of para-anisidine.

7. The method according to claim 1 , wherein the hydrogenation catalyst is used in the form of a suspension or in the form of a fixed layer.

8. The method according to claim 1 , wherein the separation of N-methyl-para-anisidine is carried out by fractional distillation.

Assignments (2)
SECURITY INTEREST Recorded Jun 2, 2021
From: IFOTOP LIMITED LIABILITY COMPANY
To: LIMITED LIABILITY COMPANY OF COMMERCIAL BANK "ROSTFINANCE"
Reel/Frame 056409/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2019
From: FROLOV, ALEXANDR YURIEVICH; BELYAKOV, NIKOLAY GRIGORIEVICH
To: OBSCHESTVO S OGRANICHENNOI OTVETSTVENNOSTYU "IFOTOP"
Reel/Frame 050395/0296 →
Priority Claims (1)
RU 2016134238 · Sep 7, 2016 · national
Continuity (1)
Related Publication 20190241500A1 · Aug 8, 2019