Process for preparing isosorbide di(meth)acrylate

Patent metadata

Field	Value
Publication number	US-2016251371-A1
Application number	US-201615054506-A
Country	US
Kind code	A1
Filing date	Feb 26, 2016
Priority date	Feb 26, 2015
Publication date	Sep 1, 2016
Grant date	—

Abstract

A process for preparing isosorbide di(meth)acrylate by transesterifying alkyl (meth)acrylate with isosorbide, comprising the steps of:
(i) reacting alkyl (meth)acrylate with isosorbide in the presence of a catalyst comprising titanium(IV) or zirconium(IV) and a stabilizer in the presence of an azeotroping agent which forms an azeotrope with the alcohol bound in the alkyl (meth)acrylate, (ii) continuously distilling off the azeotrope of azeotroping agent and alcohol, wherein steps (i) and (ii) are conducted simultaneously until the isosorbide has been essentially fully converted, (iii) adding water to the product mixture which comprises isosorbide (meth)acrylate and is obtained in steps (i) and (ii) and removing the hydrolyzate of the catalyst comprising titanium(IV) or zirconium(IV), (iv) distilling unconverted alkyl (meth)acrylate and azeotroping agent out of the product mixture, (v) distilling off water from the product mixture,

wherein step (iv) can also be conducted before step (iii) and steps (iv) and (v) can also be conducted in one distillation step.

First claim

1 . A process for preparing an isosorbide di(meth)acrylate by transesterifying an alkyl (meth)acrylate with isosorbide, comprising:
(i) reacting an alkyl (meth)acrylate with isosorbide in the presence of a catalyst comprising titanium(IV) or zirconium(IV) and a stabilizer in the presence of an azeotroping agent which forms an azeotrope with alcohol bound in the alkyl (meth)acrylate, (ii) continuously distilling off the azeotrope of azeotroping agent and alcohol, wherein (i) and (ii) are conducted simultaneously until isosorbide has been essentially fully converted, to obtain a product mixture comprising an isosorbide (meth)acrylate, (iii) adding water to the product mixture comprising the isosorbide (meth)acrylate obtained in (ii) and removing a hydrolyzate of the catalyst comprising titanium(IV) or zirconium (IV), (iv) distilling unconverted alkyl (meth)acrylate and azeotroping agent out of the product mixture comprising the isosorbide (meth)acrylate, and (v) distilling water out of the product mixture comprising the isosorbide (meth)acrylate, wherein (iv) can be conducted before and (iv) and (v) can be conducted in one distillation operation.

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 the alkyl (meth)acrylate.

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

5 . The process according to claim 1 , wherein (iv) and (v) are conducted in a combined 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( 1 V) tetraisopropoxide.

8 . The process according to claim 1 , wherein the stabilizer is selected from the group consisting of hydroquinone monomethyl ether and PTZ.

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

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

11 . A resin component comprising the isosorbide di(meth)acrylate.

12 . The resin component according to claim 11 , suitable for use as a two-pack adhesive composition that is a plugging compound for securing an anchoring structure in a drillhole.

13 . A resin component comprising eth acrylate, , wherein the isosorbide di(meth)acrylate has been prepared by the process according to claim 1 .

Assignees

• Basf Se

Inventors

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

Classifications

• C07C35/24

  the condensed ring system containing five carbon atoms · 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

• C07C67/03

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

• C07C61/20

  having a carboxyl group bound to a five-membered ring · CPC title

• C07C67/02

  by interreacting ester groups, i.e. transesterification · CPC title