Process for preparing heonone (meth)acrylate

Patent metadata

Field	Value
Publication number	US-9695136-B2
Application number	US-201514953854-A
Country	US
Kind code	B2
Filing date	Nov 30, 2015
Priority date	Dec 1, 2014
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

A process for preparing heonone (meth)acrylate by transesterification of alkyl (meth)acrylate with heonone.

First claim

The invention claimed is:

1. A process for preparing heonone (meth)acrylate by transesterification of alkyl (meth)acrylate with heonone, which comprises the steps:
(i) reaction of alkyl (meth)acrylate with heonone in the presence of a catalyst comprising titanium(IV) or zirconium(IV) and a stabilizer in the presence of an entrainer which forms an azeotrope with the alcohol produced from the alkyl (meth)acrylate,
(ii) continuous removal by distillation of the azeotrope of entrainer and alcohol, with steps (i) and (ii) being carried out simultaneously until heonone has essentially completely reacted,
(iii) addition of water to the product mixture comprising heonone (meth)acrylate obtained in steps (i) and (ii) and removal of the hydrolyzate of the catalyst comprising titanium(IV) or zirconium(IV) by filtration,
(iv) distillation of unreacted alkyl (meth)acrylate and entrainer from the product mixture, and
(v) distillation of water from the product mixture,
with step (iv) also being able to be carried out before step (iii) and steps (iv) and (v) also being able to be carried out in a distillation step,
wherein steps (i) and (ii) are carried out in the presence of an inorganic or organic acid.

2. The process according to claim 1 , wherein the entrainer is the alkyl (meth)acrylate.

3. The process according to claim 1 , wherein the entrainer is a separate solvent different from alkyl (meth)acrylate.

4. The process according to claim 3 , wherein the entrainer is selected from the group consisting of n-heptane and cyclohexane.

5. The process according to claim 1 , wherein steps (iv) and (v) are carried out in a joint distillation step.

6. The process according to claim 1 , wherein the alkyl (meth)acrylate is methyl or ethyl (meth)acrylate.

7. The process according to claim 1 , wherein the catalyst comprises titanium(IV) tetraisopropoxide.

8. The process according to claim 1 , wherein the stabilizer is methylhydroquinone.

9. The process according to claim 1 , wherein the alcohol is separated off from the azeotrope of entrainer and alcohol, distilled off in step (ii), by scrubbing with water and the entrainer is recirculated to the reaction vessel.

10. The process according to claim 1 , wherein a heonone (meth)acrylate having a by-product content of <2% by weight is obtained after step (v).

Assignees

• Basf Se

Inventors

• Misske Andrea
• Fleischhaker Friederike
• Fleckenstein Christoph
• Kaller Martin
• Stengel Ulrik
• Blanchot Mathieu
• Nair Ritesh

Classifications

• C07D263/38

  attached in position 2 · CPC title

• C07D263/22 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms · CPC title