Process for producing (meth)acrylic esters

Patent metadata

Field	Value
Publication number	US-10752573-B2
Application number	US-201716466791-A
Country	US
Kind code	B2
Filing date	Dec 7, 2017
Priority date	Dec 8, 2016
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

This invention relates to a process for the continuous production of a (meth)acrylic ester by transesterification reaction between a C1-C4 light alkyl (meth)acrylate, with a heavy alcohol in the presence of a catalyst, characterised in that the flows feeding the reactor are introduced through a static mixer placed on a recirculation loop of the reactor. The use of a static mixer improves the selectivity of the reaction and consequently the overall productivity of (meth)acrylic ester synthesis process.

First claim

The invention claimed is:

1. A process for continuous production of a (meth)acrylic ester, said process comprising a homogeneous transesterification reaction between a light alkyl (meth)acrylate selected from the group consisting of methyl (meth)acrylate, methyl acrylate, ethyl (meth)acrylate and ethyl acrylate, with a heavy alcohol in the presence of a homogeneous transesterification catalyst and polymermization inhibitor using a reactor comprising a static mixer, a reactor reboiler, and a recirculation loop for carrying reagents, catalyst, and recycled flows which joins an outlet of the reactor to an inlet of the reactor through the reboiler, wherein all flows feeding the reactor are introduced through the static mixer which is a pipe element with propellers or baffles or other obstacles to increase turbulence, placed on the recirculation loop, and upstream or downstream of the reactor reboiler, such that a combined flow of reagents, catalyst, and recycled flows passes through the static mixer before entering the reactor.

2. The process according to claim 1 wherein the heavy alcohol is a linear or branched, primary or secondary alcohol comprising between 4 and 12 carbon atoms, optionally comprising at least one nitrogen atom.

3. The process according to claim 1 wherein the heavy alcohol is an amino alcohol of formula (II):
HO-A-N(R′ 2 )(R′ 3 )  (II)

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

4. The process according to claim 1 wherein the heavy alcohol is N,N-dimethylaminoethanol (DMAE), N,N-diethylaminoethanol, or N,N-dimethylaminopropanol.

5. The process according to claim 1 wherein the heavy alcohol is a primary or secondary alcohol of formula R 2 OH wherein R 2 represents a C 4 -C 12 linear or branched alkyl chain.

6. The process according to claim 1 wherein the heavy alcohol is 2-ethyl hexanol, 2-octanol or 2-propyl heptanol.

7. A process for the continuous production of a (meth)acrylic ester by a homogeneous transesterification reaction between a light alkyl (meth)acrylate selected from the group consisting of methyl (meth)acrylate, methyl acrylate, ethyl (meth)acrylate, and ethyl acrylate with a heavy alcohol in the presence of a homogeneous transesterification catalyst and polymerization inhibitor,
said method comprising at least the following steps:
a) feeding a reactor with the light alkyl (meth) acrylate, the heavy alcohol, the transesterification catalyst, and at least one polymerization inhibitor, and subjecting the reaction mixture to transesterification conditions to form:
i) a product mixture comprising the (meth) acrylic ester formed, the light alkyl (meth)acrylate and the unreacted heavy alcohol, the catalyst, the polymerization inhibitors and heavy by-products; and
ii) an azeotropic mixture of the light alkyl (meth)acrylate and the light alcohol released from the light alkyl(meth)acrylate during transesterification;

b) distilling, in a first distillation column, the product mixture i) of step a), and separating at the top, a stream consisting essentially of the desired (meth) acrylic ester and light products, and at the bottom, a heavy fraction comprising the catalyst, the polymerization inhibitors and heavy by-products;
c) purifying said overhead stream with at least a second distillation column, to obtain a purified (meth)acrylic ester, and a light product stream which is recycled to the reaction;
d) passing at least a portion of said heavy bottoms fraction to a film evaporator and separating traces of light compounds therefrom, wherein said light compounds are then recycled to the feed of the first distillation column, and the heavy residue is removed;
e) optionally recycling at least a portion of said heavy bottoms fraction of the first distillation column or the heavy residue formed in step d) to the reactor;
f) optionally recycling the azeotropic mixture ii) formed in step a), to a unit for producing light alkyl (meth) acrylate;
g) optional thermal cracking of at least a portion of said heavy bottoms fraction of the first distillation column, or heavy residue formed in step d);

wherein the reactor comprises a static mixer, a reactor reboiler, and a recirculation loop for carrying reagents, catalyst, and recycled flows which joins an outlet of the reactor to an inlet of the reactor through the reboiler,
wherein all flows feeding the reactor described in steps a) and e) pass through a static mixer which is a pipe element with propellers or baffles or other obstacles to increase turbulence, placed on the recirculation loop of the reactor, such that a combined flow of reagents, catalyst, and recycled flows passes through the static mixer before feeding into the reactor.

8. The process according to claim 7 , wherein the (meth) acrylic ester is N,N-dimethylaminoethyl acrylate, the light alkyl (meth)acrylate is ethyl acrylate and the heavy alcohol is N,N-dimethylaminoethanol.

Assignees

• Arkema France

Inventors

• Dubut Fanny
• Esch Marc
• Graire Coralie
• Riflade Benoit

Classifications

• B01F25/43141

  composed of consecutive sections of helical formed elements · CPC title

• B01F25/53

  in which the mixture is discharged from and reintroduced into a receptacle through a recirculation tube, into which an additional component is introduced · CPC title

• C07C219/08

  having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton · 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