Process for preparing isosorbide ethoxylate di(meth)acrylate

Patent metadata

Field	Value
Publication number	US-9562054-B2
Application number	US-201615051974-A
Country	US
Kind code	B2
Filing date	Feb 24, 2016
Priority date	Feb 26, 2015
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

A process for preparing isosorbide ethoxylate di(meth)acrylate by transesterifying alkyl (meth)acrylate with isosorbide ethoxylate, comprising the steps of:
(i) ethoxylating isosorbide to give isosorbide ethoxylate, (ii) reacting alkyl (meth)acrylate with isosorbide ethoxylate in the presence of potassium phosphate as catalyst and a stabilizer and in the presence of an azeotroping agent which forms an azeotrope with the alcohol bound in the alkyl (meth)acrylate, (iii) continuously distilling off the azeotrope of azeotroping agent and alcohol, wherein steps (ii) and (iii) are conducted simultaneously until the isosorbide ethoxylate has been essentially fully converted, (iv) removing the catalyst from the product mixture comprising isosorbide ethoxylate di(meth)acrylate, (v) distilling unconverted alkyl (meth)acrylate and azeotroping agent out of the product mixture.

First claim

The invention claimed is:

1. A process for preparing isosorbide ethoxylate di(meth)acrylate by transesterifying alkyl (meth)acrylate with isosorbide ethoxylate, the process comprising:
(i) ethoxylating isosorbide to obtain isosorbide ethoxylate,
(ii) reacting alkyl (meth)acrylate with isosorbide ethoxylate in the presence of potassium phosphate as a catalyst and a stabilizer and in the presence of an azeotroping agent which forms an azeotrope with alcohol bound in the alkyl (meth)acrylate,
(iii) continuously distilling off the azeotrope of the azeotroping agent and alcohol, wherein (ii) and (iii) are conducted simultaneously until the isosorbide ethoxylate has been essentially fully converted,
(iv) removing the catalyst from a product mixture comprising isosorbide ethoxylate di(meth)acrylate, and
(v) distilling unconverted alkyl (meth)acrylate and the azeotroping agent out of the product mixture.

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

3. The process according to claim 1 , wherein the azeotroping agent is a separate solvent other than alkyl (meth)acrylate.

4. The process according to claim 3 , wherein the azeotroping agent is at least one agent selected from the group consisting of n-heptane and cyclohexane.

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

6. The process according to claim 1 , wherein the stabilizer is hydroquinone monomethyl ether.

7. The process according to claim 1 , wherein the alcohol is removed from the azeotrope of an entraining agent and alcohol distilled off in (iii) by washing with water and the azeotroping agent is recycled into a reaction vessel.

8. The process according to claim 1 , wherein, after (v), an isosorbide ethoxylate di(meth)acrylate having a content of secondary components of <4% by weight is obtained.

9. The process according to claim 8 , wherein, after (v), an isosorbide ethoxylate di(meth)acrylate having a content of secondary components of <2% by weight is obtained.

Assignees

• Basf Se

Inventors

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

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C09J4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C09K8/44

  containing organic binders only · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C09K8/426

  for plugging · CPC title