IP Library Granted Patent US 10,647,657
Granted Patent B2
US 10,647,657 · App. 15/102,921 · Granted May 12, 2020

Purification of (meth)acrylic esters by membrane separation dehydration

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Quick Facts
Patent No.
US 10,647,657
App. No.
15/102,921
Granted
May 12, 2020
Kind
B2
Abstract

The invention relates to a method for producing alkyl (meth)acrylate comprising a linear or branched alkyl chain comprising 4 to 10 carbon atoms, by direct esterification of (meth)acrylic acid with a linear or branched alcohol comprising 4 to 10 carbon atoms in the presence of a catalyst, leading to formation of a reaction mixture comprising the desired ester, unreacted acid and alcohol, light by-products, and heavy by-products. The mixture undergoes purification treatment by separation means to obtain purified alkyl (meth)acrylate. The purification treatment comprises a step of membrane separation dehydration applied to at least one of the following: the stream subjected to the final distillation leading to the recovery of the purified (meth)acrylic ester, the aqueous stream originating from the settling out of the reaction mixture, or the stream resulting from the distillation of the light by-products present in the reaction mixture.

Claims (8)

1. A process for producing an alkyl (meth)acrylate or alkyl acrylate comprising a linear or branched alkyl chain comprising from 4 to 10 carbon atoms, by direct esterification of (meth)acrylic acid or acrylic acid with a linear or branched alcohol comprising from 4 to 10 carbon atoms in the presence of a catalyst, leading to the formation of a reaction mixture comprising an ester, unreacted acid and alcohol, light by-products and heavy by-products, which mixture is purified by separation to obtain purified alkyl (meth)acrylate or alkyl acrylate, said purification by separation comprising: i) a step of settling out the reaction mixture to produce an aqueous feed stream and an organic stream and ii) a step of treating the aqueous feed stream originating from settling out of the reaction mixture to membrane separation dehydration;

wherein the feed stream treated by membrane separation comprises from 80 to 99% by weight of water, less than 2% by weight of (meth)acrylic ester or acrylic ester and from 1 to 20% by weight of alcohol,

wherein said membrane consists of a hydrophobic polymeric membrane,

wherein said step of membrane separation dehydration is dehydration by pervaporation or vapor permeation at a temperature ranging from 50 to 100° C. and without dephlegmation, and

wherein a permeate is obtained having a lower water percentage by weight and a higher alcohol percentage by weight than that of the feed stream.

2. The process as claimed in claim 1 wherein the alcohol is selected from the group consisting of butanol, 2-ethylhexanol and 2-octanol.

3. The process as claimed in claim 1 wherein the acid is acrylic acid.

4. The process as claimed in claim 1 which is continuous, semi-continuous, or batch.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: TRETJAK, SERGE; MORELIERE, ANNE
To: ARKEMA FRANCE
Reel/Frame 040060/0202 →