Process for producing alkyl acrylate

Patent metadata

Field	Value
Publication number	US-10000439-B2
Application number	US-201314650906-A
Country	US
Kind code	B2
Filing date	Dec 16, 2013
Priority date	Dec 17, 2012
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

Abstract

The invention relates to the production of alkyl acrylate according to a continuous transesterification process. In one embodiment the process of the invention uses a simple column to purify a reaction mixture of acryl acrylate in one step yielding alkyl acrylate with a purity of greater than 99.8%.

First claim

The invention claimed is:

1. A process for the continuous production of alkyl acrylates, by a transesterification reaction between a light alkyl acrylate and a heavy alcohol in the presence of at least one catalyst and at least one polymerization inhibitor, said transesterification reaction represented by the reaction:
H 2 C═CHCOOR 1 +R 2 OH⇄H 2 C═CHCOOR 2 +R 1 OH

wherein R 1 is a methyl or ethyl group, R 2 is a linear or branched alkyl group having 4 to 9 carbon atoms, and optionally comprising a nitrogen atom,
carrying out said reaction in a reactor coupled to a distillation column from which an azeotropic mixture comprising light alkyl acrylate and light alcohol generated by the transesterification reaction is drawn off,
sending a crude reaction product comprising unreacted reactants, formed reaction products, catalyst(s) and polymerization inhibitor(s) to a single distillation column which is a simple column lacking a vertical divided wall and under reduced pressure for distillation, whereby the distillation yields:
at a top portion, a stream of light products consisting essentially of residual alcohols R 2 OH and R 1 OH and unreacted reactant H 2 C═CHCOOR 1 , which is recycled to the reactor,
in a bottom portion, product H 2 C═CHCOOR 2 which is drawn off laterally in a gas phase,
at a bottom, a stream of heavy reaction products comprising the catalyst(s), the polymerization inhibitor(s) and H 2 C═CHCOOR 2 which is recycled in part to the reactor;
such that said process produces said alkyl acrylates have a purity greater than 99.8%.

2. The process as claimed in claim 1 , wherein the single distillation column processing the crude reaction product is a simple column containing distillation plates with or without downcomers, or containing packing of random or structured type, optionally with recentering plates for the distribution of liquid, able to operate at pressures below atmospheric pressure.

3. The process as claimed in claim 1 wherein the alcohol R 2 OH is selected from the group consisting of 2-octanol, 2-ethylhexanol and N,N-dimethylaminoethanol.

4. The process as claimed in claim 3 wherein the alcohol is 2-octanol.

5. The process as claimed in claim 1 wherein the transesterification catalyst is an alkyl titanate of formula Ti(OR 1 ) 4 or Ti(OR 2 ) 4 in solution in the alcohol R 1 OH and/or R 2 OH.

6. The process as claimed in claim 1 wherein R 1 is an ethyl group.

7. The process as claimed in claim 1 wherein the catalyst is present in an amount of 5×10 −4 to 5×10 −2 mol per mole of R 2 OH.

8. The process as claimed in claim 1 wherein compound H 2 C═CHCOOR 1 and the compound R 2 OH have a molar ratio between 1 and 3.

9. The process as claimed in claim 1 wherein the transesterification reaction is carried out at a pressure between 350 mmHg (0.47×10 5 Pa) and atmospheric pressure, and at a temperature between 90° C. and 150° C.

10. The process as claimed in claim 1 for the manufacture of 2-octyl acrylate, using ethyl titanate and/or 2-octyl titanate in 2-octanol as the catalyst.

Assignees

• Arkema France

Inventors

• Riondel Alain F
• Graire Coralie
• Esch Marc
• Levray Andre

Classifications

• C07C213/06 Primary

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

• C07C67/54

  by distillation · CPC title

• C07C67/03 Primary

  by reacting an ester group with a hydroxy group · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title