Process for recovering noble products in a process for producing dialkylaminoalkyl (meth) acrylates

Patent metadata

Field	Value
Publication number	US-9359287-B2
Application number	US-201214346802-A
Country	US
Kind code	B2
Filing date	Sep 11, 2012
Priority date	Sep 27, 2011
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

The invention relates to a process for recovery of noble products from heavy (meth)acrylic fractions generated during production of (meth)acrylic esters by transesterification, the heavy fractions comprising at least noble products and Michael adducts, the process comprising the steps of: (i) adding at least one antifouling agent and optionally a viscosity-reducing compound to the heavy fractions; (ii) submitting the mixture to temperature and distillation conditions sufficient to crack the Michael adducts into their components; and (iii) recovering the noble products in the form of a stream of distillate, and of a final residue that is sufficiently fluid to be transported by pump.

First claim

The invention claimed is:

1. A process for recovering noble products comprising dialkylaminoalkyl(meth)acrylate and an amino alcohol, starting from heavy (meth)acrylic fractions generated during the production of (meth)acrylic esters by transesterification, the heavy fractions comprising at least the noble products and Michael adducts resulting from reactions of addition on the (meth)acrylic double bonds, said process comprising the steps of:
(i) adding at least one antifouling agent and optionally a viscosity-reducing compound to the heavy fractions to form a mixture;
(ii) submitting the mixture to temperature and distillation conditions sufficient for cracking the Michael adducts into their constituent components without adding acid;
(iii) recovering the noble products in the form of a stream of distillate, and of a final residue that is sufficiently fluid to be transported by pump,
wherein the antifouling agent is a compound of formula (A):

in which:
R 1 represents a C 3 -C 30 alkyl radical, an aryl radical or an alkaryl radical, and these radicals can be interrupted or attached to the oxygen of the molecule by a chain —(OR 4 ) o —, where the R 4 each represent independently an ethylene, propylene or butylene chain and o is an integer from 0 to 50;
R 2 represents R 1 , a hydrogen atom or a counter-ion;
R 3 represents a hydrogen atom or a counter-ion.

2. The process of claim 1 , wherein the compounds of formula (A) are selected from those in which R 1 and R 2 each represent independently the radical

where p is an integer from 4 to 12, and q is an integer from 4 to 50, and R 3 represents a hydrogen atom or a counter-ion; and/or
those in which R 1 represents the radical

where r is an integer from 4 to 12, and s is an integer from 4 to 50, and R 2 and R 3 each represent independently a hydrogen atom or a counter-ion.

3. The process of claim 1 , wherein the antifouling agent is added in the range from 0.01 to 1 wt % to the heavy fraction to be treated.

4. The process of claim 1 , that wherein the conditions of cracking and of distillation comprise a temperature in the range from 100° C. to 250° C.

5. The process of claim 1 , wherein viscosity-reducing compound is introduced in an amount sufficient to render final residue from step (ii) pumpable.

6. The process of claim 1 , wherein a single compound acting as antifouling agent and viscosity-reducing agent is added in step (i).

7. The process of claim 1 , wherein the noble products comprise N,N dimethylaminoethyl acrylate and N,N dimethylaminoethanol.

8. A process for manufacturing a dialkylaminoalkyl(meth)acrylate of formula (I):
H 2 C═C(R′ i )-C(O)—O-A-N(R′ 2 )(R′ 3 )  (I)

in which:
R′i is a hydrogen atom or a methyl radical
A is a linear or branched C 1 -C 5 alkylene radical
R′ 2 and R′ 3 , which may be identical or different, each represent a C 1 -C 4 alkyl radical, by transesterification reaction between an amino alcohol of formula (II):
HO-A-N(R′ 2 )(R′ 3 )  (II)

in which A, R′ 2 and R′ 3 are as defined above,

and a light alkyl(meth)acrylate of formula (III):
CH 2 ═C(R′ i )-COOR′ 4   (III)

in which R′i is as defined above and R′ 4 represents the methyl or ethyl radical;

said process being a transesterification reaction comprising the following steps:
a) submitting a mixture comprising a compound of formula (III), an amino alcohol of formula (II), a transesterification catalyst, and at least one polymerization inhibitor, to transesterification to form a mixture comprising (meth)acrylic ester (I), the unreacted compounds (II) and (III), the catalyst, the polymerization inhibitor, Michael adducts resulting from reactions of addition on the (meth)acrylic double bonds, and other heavy compounds;
b) distilling the mixture of products to recover, at the top, an overhead stream comprising a major fraction of the required (meth)acrylic ester (I) and light products, comprising a minor fraction of Michael adducts and heavy products, but free or substantially free from catalyst, and leaving, at the bottom, a heavy fraction comprising the catalyst, the polymerization inhibitor, the Michael adducts and the heavy compounds, with a minor fraction of the required (meth)acrylic ester (I) and amino alcohol and traces of light products;
c) purifying the overhead stream, giving the purified dialkylaminoalkyl(meth)acrylate (I);
d) submitting at least a proportion of the heavy fraction to a process for recovery of noble products comprising dialkylaminoalkyl(meth)acrylate and an amino alcohol comprising the steps of: (i) adding at least one antifouling agent and optionally a viscosity-reducing compound; (ii) submitting the mixture to a temperature and distillation conditions sufficient for cracking the Michael adducts into their constituent components without the addition of acid; (iii) recovering the noble products in the form of a stream of distillate, and of a final residue that is sufficiently fluid to be transported by pump;
e) recycling, to the purification step c), at least a proportion of said stream of distillate comprising at least one compound selected from (meth)acrylic ester (I), amino alcohol (II) or alkyl(meth)acrylate (III);
f) disposing the final residue,
wherein the antifouling agent is a compound of formula (A):

in which:
R 1 represents a C 3 -C 30 alkyl radical, an aryl radical or an alkaryl radical, and these radicals can be interrupted or attached to the oxygen of the molecule by a chain —(OR 4 ) o —, where the R 4 each represent independently an ethylene, propylene or butylene chain and o is an integer from 0 to 50;
R 2 represents R 1 , a hydrogen atom or a counter-ion;
R 3 represents a hydrogen atom or a counter-ion,
added in the range from 0.1 to 1 wt %, to the distillation residue.

9. The process of claim 8 , wherein the purification step c) is carried out by two distillation columns in series and wherein at least a proportion of said stream of distillate from step d) is recycled to the top of the first purification column.

10. The process of claim 8 wherein the heavy fraction comprising the catalyst, the polymerization inhibitor, the Michael adducts and the heavy compounds, with a minor fraction of the required (meth)acrylic ester (1) and the amino alcohol and traces of light compounds, is first submitted to purification by passage through a film evaporator prior to step d).

11. The process of claim 8 , wherein the conditions of cracking and of distillation comprise a temperature in the range from 100° C. to 250° C.

12. The process of claim 8 , wherein the viscosity-reducing compound is introduced in sufficient amount so that the final residue from step (ii) is pumpable.

13. The process of claim 9 , wherein the dialkylaminoalkyl(meth)acrylate is N,N-dimethylaminoethyl acrylate.

Assignees

• Paul Jean-Michel
• Levray Andre
• Arkema France

Inventors

• Paul Jean-Michel
• Levray Andre

Classifications

• C07C219/20

  the carbon skeleton being unsaturated · CPC title

• C07C213/06

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

• C07C213/10

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

• C07C215/08

  with only one hydroxy group and one amino group bound to the carbon skeleton · CPC title

• C07C227/40 Primary

  Separation; Purification · CPC title