# US 10,370,383 B2 · Process for preparing isosorbide di(meth)acrylate > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,370,383 B2 - Document ID: US10370383B2 - Status: Granted - Kind: B2 - Application number: 15/054,506 - Filed: 2016-02-26 - Published: 2016-09-01 - Granted: 2019-08-06 - Earliest claimed: 2015-02-26 - Assignees: BASF SE - Applicants: BASF SE - Inventors: Andrea Misske; Friederike Fleischhaker; Christoph Fleckenstein; Martin Kaller; Ritesh Nair; Ulrik Stengel; Mathieu Blanchot - Web page: https://patentgrep.com/patent/US10370383B2 ## CPC - C07D 493/04: Ortho-condensed systems - C08F 22/20: Esters containing oxygen in addition to the carboxy oxygen - C09J 4/00: 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} - C09K 8/426: {for plugging} - C09K 8/44: containing organic binders only - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## 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. ## Claims ### 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 (iii), and (iv) and (v) can be conducted in one distillation operation. ### Claim 2 (depends on 1) The process according to claim 1, wherein the azeotroping agent is the alkyl (meth)acrylate. ### Claim 3 (depends on 1) The process according to claim 1, wherein the azeotroping agent is a separate solvent other than the alkyl (meth)acrylate. ### Claim 4 (depends on 3) The process according to claim 3, wherein the azeotroping agent is selected from the group consisting of n-heptane and cyclohexane. ### Claim 5 (depends on 1) The process according to claim 1, wherein (iv) and (v) are conducted in a combined distillation step. ### Claim 6 (depends on 1) The process according to claim 1, wherein the alkyl (meth)acrylate is methyl or ethyl (meth)acrylate. ### Claim 7 (depends on 1) The process according to claim 1, wherein the catalyst comprises titanium(IV) tetraisopropoxide. ### Claim 8 (depends on 1) The process according to claim 1, wherein the stabilizer is selected from the group consisting of hydroquinone monomethyl ether and PTZ. ### Claim 9 (depends on 1) 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. ### Claim 10 (depends on 1) 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. ### Claim 11 A two-pack adhesive composition for a chemical securing technology, comprising: (i) a synthetic resin having a viscosity at 23° C. between 100 and 10,000 mPa·s, comprising isosorbide di(meth)acrylate, and (ii) a hardener for the synthetic resin. ### Claim 12 (depends on 11) The two-pack adhesive composition of claim 11, wherein the synthetic resin has a viscosity at 23° C. between 200 and 2000 mPa·s. ### Claim 13 (depends on 11) The two-pack adhesive composition of claim 11, wherein the synthetic resin has a viscosity at 23° C. between 500 and 1500 mPa·s. ### Claim 14 (depends on 11) The two-pack adhesive composition of claim 11, wherein the synthetic resin further comprises from 2 to 20% by weight of a further curable resin selected from the group consisting of polyester resins, vinyl ester resins, bismaleimide resins, and epoxy resins. ### Claim 15 (depends on 11) The two-pack adhesive composition of claim 11, wherein the synthetic resin further comprises from 2 to 20% by weight of an impact modifier selected from the group consisting of polyamides, polyesters, and rubbers.