Reclamation of noble products in a method for producing (meth)acrylic ester

Patent metadata

Field	Value
Publication number	US-10457630-B2
Application number	US-201615546074-A
Country	US
Kind code	B2
Filing date	Jan 28, 2016
Priority date	Feb 4, 2015
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

The invention relates to a method for producing a (meth)acrylic ester with improved productivity, by transesterfication of a light alkyl (meth)acrylate with a heavy alcohol. The method of the invention includes the recycling of noble products recovered after the thermal treatment of heavy fractions generated during the synthesis, said thermal treatment being carried out in the presence of a dialkyl phthalate, the alkyl chain of which corresponds to that of the light alkyl (meth)acrylate. The invention applies to the production of N,N-dimethyaminoethyl acrylate from ethyl acrylate.

First claim

The invention claimed is:

1. A process for recovering unreacted reagents and (meth)acrylic ester products from a heavy (meth)acrylic fraction generated during production of a (meth)acrylic ester by a continuous transesterification reaction of a light C 1 -C 4 alkyl (meth)acrylate with a heavy alcohol in the presence of a catalyst, the heavy fraction comprising at least unreacted reagents and (meth)acrylic ester products and Michael adducts resulting from addition reactions on the (meth)acrylic double bonds and also the catalyst, said process comprising heat treating said heavy fraction at a temperature sufficient to crack the Michael adducts into their constituent components, recovering unreacted reagents and (meth)acrylic ester products in the form of a distillate, and eliminating fluid final residue by means of a pump, wherein the heat treatment is carried out in the presence of at least one antifoulant and viscosity reducing agent which is a dialkyl phthalate, the alkyl chain of which corresponds to that of the light alkyl (meth)acrylate.

2. The process as claimed in claim 1 , wherein the light alkyl (meth)acrylate is methyl acrylate and the dialkyl phthalate is dimethyl phthalate.

3. The process as claimed in claim 1 , wherein the light alkyl (meth)acrylate is ethyl acrylate and the dialkyl phthalate is diethyl phthalate.

4. The process as claimed in claim 1 , wherein the light alkyl (meth)acrylate is butyl acrylate and the dialkyl phthalate is dibutyl phthalate.

5. The process as claimed in claim 1 wherein the dialkyl phthalate is added at a concentration ranging from 0.001% to 1% by weight into the heavy fraction to be treated.

6. The process as Claimed in claim 1 wherein the heavy alcohol is an aminoalcohol of formula (II):
HO-A-N(R′ 2 ) (R′ 3 )  (II)

in which
A is a linear or branched C 1 -C 5 alkylene radical,
R′ 2 and R′ 3 , which are identical to or different from one another, each represent a C 1 -C 4 alkyl radical.

7. The process as claimed in claim 6 , wherein the heavy alcohol is N,N-dimethylaminoethanol.

8. The process as claimed in claim 1 wherein the heavy alcohol is an alcohol of formula R 2 OH, in which R 2 represents a linear or branched C 5 -C 12 alkyl chain.

9. The process as claimed in claim 1 wherein at least a portion of the heavy fraction is recycled to the transesterification reaction, the other portion being subjected to said heat treatment.

10. The process as claimed in claim 1 wherein the heavy fraction is subjected beforehand to purification by passage over a film evaporator, at least a portion of the bottom stream from the film evaporator being recycled to the transesterification reaction, the other portion being subjected to said heat treatment.

11. process for producing a (meth)acrylic ester by a continuous transesterification reaction between a light C 1 -C 4 alkyl (meth)acrylate and a heavy alcohol, said process comprising at least the following steps:
a) subjecting a reaction mixture, comprising a light alkyl (meth)acrylate, a heavy alcohol, a transesterification catalyst and at least one polymerization inhibitor, to transesterification conditions in order to form i) a mixture of products comprising (meth)acrylic ester, unreacted light alkyl (meth)acrylate, and heavy alcohol, catalyst, polymerization inhibitors, Michael adducts resulting from addition reactions onto the (meth)acrylic double bonds, and heavy compounds; and ii) an azeotropic mixture of light alkyl (meth)acrylate/free light alcohol;
b) distilling the mixture i) of products in order to recover, at the top, a stream comprising (meth)acrylic ester and light products, a minority fraction of Michael adducts, heavy products and polymerization inhibitors, and which is substantially free of catalyst, and in order to leave, at the bottom, a heavy fraction comprising catalyst, polymerization inhibitors, Michael adducts and heavy compounds, with a minority fraction of (meth)acrylic ester and heavy alcohol and traces of light products;
c) purifying the top stream to obtain purified (meth)acrylic ester;
d) subjecting at least a portion of the heavy fraction to a process for recovering unreacted reagents and (meth)acrylic ester products in the form of a distillate as defined in claim 1 ;
e) recycling at least a portion of said distillate into at least one step chosen from the group consisting of step a) of reaction, step b) of distillation and step c) of purification;
f) optionally recycling the azeotropic mixture ii) formed in step a), to the light alkyl (meth)acrylate production unit;
g) optionally recycling at least a portion of the fluid final residue resulting from step d), to step a) of reaction;
h) incinerating the fluid final residue resulting from step d);
i) optionally recycling a portion of the heavy fraction to step a) of reaction.

12. The process as claimed in claim 11 , Wherein said heavy fraction is subjected beforehand to purification by passage over a film evaporator before step d).

13. The process as claimed in claim 12 , wherein a portion of the bottom stream from the film evaporator is recycled to step a) of reaction.

14. The process as claimed in claim 11 wherein step of purification c) is carried out using two distillation columns in series and at least a portion of the distillate resulting from step d) is recycled to the top of the first purification column.

15. The process as claimed in claim 11 wherein (meth)acrylic ester is N,N-dimethylaminoethyl acrylate resulting from the transesterification reaction between N,N-dimethylaminoethanol and ethyl acrylate, and step d) is carried out in the presence of diethyl phthalate.

Assignees

• Arkema France

Inventors

• Cabon Yves
• Dubut Fanny
• Riflade Benoit

Classifications

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07C213/10

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C213/06 Primary

  from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups · CPC title

• C08F20/18

  with acrylic or methacrylic acids · CPC title

• B01D3/143

  by two or more of a fractionation, separation or rectification step · CPC title