Method for the production of 2-octyl acrylate by means of transesterification

Patent metadata

Field	Value
Publication number	US-9296679-B2
Application number	US-201314370228-A
Country	US
Kind code	B2
Filing date	Jan 14, 2013
Priority date	Jan 23, 2012
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

The invention relates to the production of 2-octyl acrylate of high purity and in good yield, that includes the recycling of economically upgradable products, such as un-reacted reactants and catalyst. The process uses ethyl titanate in solution in 2-octanol or 2-octyl titanate as a tranesterification catalyst and employs a purification train comprising only two distillation columns.

First claim

The invention claimed is:

1. A process for the continuous production of 2-octyl acrylate by a transesterification reaction between a light alcohol acrylate and 2-octanol using an alkyl titanate as transesterification catalyst and at least one polymerization inhibitor, an azeotropic mixture comprising light alcohol acrylate and light alcohol generated by the transesterification reaction being withdrawn continuously during the reaction, a crude reaction mixture being subjected to a purification treatment comprising two distillation columns, in order to obtain, on the one hand, substantially pure 2-octyl acrylate and, on the other hand, unreacted 2-octanol and light alcohol acrylate compounds and also the catalyst all for recycle, wherein the process further comprises the steps of:
choosing the catalyst from the group consisting of ethyl titanate in solution in 2-octanol and 2-octyl titanate;
sending the crude reaction mixture comprising 2-octyl acrylate with, as light products, unreacted 2-octanol and light alcohol acrylate and, as heavy products, catalyst, polymerization inhibitor and also heavy reaction products to a first distillation column (B) having a top and a bottom and under reduced pressure for distillation in said first column (B), to obtain:
at the top, a top stream consisting essentially of unreacted 2-octanol, light alcohol acrylate, and a minor fraction of 2-octyl acrylate, and
at the bottom, a bottom stream comprising 2-octyl acrylate, catalyst, polymerization inhibitor and heavy reaction products, and traces of light compounds; then

sending the bottom stream from the first distillation column (B) to a second distillation column (C) having a top and bottom and under reduced pressure, for distillation to obtain:
at the top, substantially pure 2-octyl acrylate; and
at the bottom, catalyst, the polymerization inhibitor and heavy reaction products, and 2-octyl acrylate;

recycling the bottom stream from the second distillation column (C) to the reaction, at least in part.

2. The process as claimed in claim 1 , wherein the catalyst is 2-octyl titanate.

3. The process as claimed in claim 1 wherein the catalyst is used in a proportion of 5×10 −4 to 5×10 −2 mol per mole of 2-octanol.

4. The process as claimed in claim 1 wherein the reaction is carried out starting from ethyl acrylate.

5. The process as claimed in claim 1 wherein the light alcohol acrylate/2-octanol molar ratio ranges from 1 to 3.

6. The process as claimed in claim 1 wherein the transesterification reaction is carried out at a pressure of between 500 mmHg (0.67×10 5 Pa) and atmospheric pressure (10 5 Pa) and at a temperature ranging from 90° C. to 130° C.

7. The process as claimed in claim 1 wherein the light alcohol acrylate is ethyl acrylate of renewable origin.

Assignees

• Arkema France

Inventors

• Riondel Alain
• Graire Coralie
• Esch Marc

Classifications

• 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

• B01J2219/00006

  Large-scale industrial plants · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title