# US 2008/0188601 A1 · Mixture of Diisononyl Esters of 1,2-Cyclohexanedicarboxylic Acid, Method For the Production Thereof and Use of These Mextures > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2008/0188601 A1 - Document ID: US20080188601A1 - Status: Published application - Kind: A1 - Application number: 11/911,691 - Filed: 2006-04-27 - Published: 2008-08-07 - Earliest claimed: 2005-06-22 - Assignees: Oxeno Olefinchemie GmbH - Inventors: Michael Grass; Arne Lang - Web page: https://patentgrep.com/patent/US20080188601A1 ## CPC - C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds - C07C 67/303: by hydrogenation of unsaturated carbon-to-carbon bonds - C07C 69/75: of acids with a six-membered ring - C08K 5/12: of cyclic polycarboxylic acids - C07C 2601/14: The ring being saturated - Y02P 20/582: Recycling of unreacted starting or intermediate materials - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract The present invention relates to a mixture of diisononyl esters of 1,2-cyclohexanedicarboxylic acid, wherein the isononyl radicals of the diisononyl esters present in the mixture have a degree of branching of from 1.2 to 2.0, to a process for its preparation and to the use of such mixtures. ## Claims ### Claim 1 A mixture of diisononyl esters of 1,2-cyclohexanedicarboxylic acid, wherein the isononyl radicals of the diisononyl esters present in the mixture have a degree of branching of from 1.2 to 2.0. ### Claim 2 (depends on 1) The mixture as claimed in claim 1, wherein nonyl alcohols obtained by hydrolysis of the diisononyl esters contain less than 10 mol % of 3,5,5-trimethylhexanol. ### Claim 3 (depends on 1) The mixture as claimed in claim 1, wherein the diisononyl esters of 1,2-cyclohexanedicarboxylic acid are obtained by hydrogenating diisononyl phthalates. ### Claim 4 (depends on 3) The mixture as claimed in claim 3, wherein the hydrogenation of the diisononyl phthalates is carried out over a catalyst which comprises at least one metal from transition group VIII, optionally together with at least one metal of transition group II, III, IV, V and/or VI of the periodic table. ### Claim 5 (depends on 1) The mixture as claimed in claim 1, wherein the diisononyl esters of 1,2-cyclohexanedicarboxylic acid are obtained by transesterifying esters of 1,2-cyclohexanedicarboxylic acid with a mixture of isomeric nonanols. ### Claim 6 (depends on 1) The mixture as claimed in claim 1, wherein the diisononyl esters of 1,2-cyclohexanedicarboxylic acid are obtained by esterifying 1,2-cyclohexanedicarboxylic acid or an acid derivative especially the anhydride with a mixture of isomeric nonanols. ### Claim 7 A process for preparing mixtures of diisononyl esters of 1,2-cyclohexanedicarboxylic acid from a mixture of isomeric nonanols which has a degree of branching of from 1.2 to 2.0 in the preparation of the diisononyl esters comprising reacting the mixture of isomeric nonanols with phthalic acid or phthalic anhydride in an esterification step to give diisononyl phthalates and subsequently ring-hydrogenating said diisononyl phthalates. ### Claim 8 (depends on 7) The process as claimed in claim 7, wherein mixtures of isomeric nonanols which contain less than 10 mol % of 3,5,5-trimethylhexanol are used. ### Claim 9 (canceled) ### Claim 10 (depends on 7) The process as claimed in claim 7, wherein the hydrogenation of the diisononyl phthalates is carried out over a catalyst which comprises at least one metal from transition group VIII, optionally together with at least one metal of transition group II, III, IV, V and/or VI of the periodic table. ### Claim 11 (depends on 7) The process as claimed in claim 7, wherein alkyl esters of 1,2-cyclohexanedicarboxylic acid whose alkyl radicals have from 1 to 9 carbon atoms are reacted with the mixture of isomeric nonanols in a transesterification. ### Claim 12 (depends on 7) The process as claimed in claim 7, wherein 1,2-cyclohexanedicarboxylic acid or a corresponding acid derivative is esterified with the mixture of isomeric nonanols. ### Claim 13 (depends on 7) The process as claimed in claim 7, wherein a dicarboxylic acid or a corresponding acid derivative which is obtained by a process which includes a Diels-Alder reaction step is reacted with the mixture of isomeric nonanols. ### Claim 14 (depends on 7) The process as claimed in claim 7, wherein the mixture of isomeric nonanols used is a mixture which is obtainable by hydroformylation and subsequent or simultaneous hydrogenation of a mixture of isomeric octenes, the mixture of isomeric octenes being obtained by contacting a hydrocarbon mixture which comprises butenes and has a content of isobutene of less than 20% by weight based on the butenes present with a catalyst comprising nickel oxide. ### Claim 15 (depends on 14) The process as claimed in claim 14, wherein the hydrocarbon mixture comprising butenes has a content of isobutene between 0.01 and 1% by weight based on the butenes present. ### Claim 16 (depends on 7) The process as claimed in claim 7, wherein the mixture of isomeric nonanols is a mixture which is obtainable by oligomerization of olefins over a solid acidic catalyst. ### Claim 17 (depends on 7) The process as claimed in claim 7, wherein the mixture of isomeric nonanols is a mixture which is obtained by mixing isomerically pure nonanols and/or fractions of a plurality of isomeric nonanols. ### Claim 18 (canceled) ### Claim 19 (depends on 1) A process for preparing a mixture as claimed in claim 1, comprising: obtaining the mixture of diisononyl esters of 1,2-cyclohexanedicarboxylic acid by mixing mixtures of diisononyl esters of 1,2-cyclohexanedicarboxylic acid which have different degrees of branching with regard to the isononyl radicals. ### Claim 20 (depends on 1) A process of obtaining a mixture comprising mixing the mixture as claimed in claim 1 with paints, inks or coatings, plastisols, adhesives or adhesive components, sealants, plasticizers in plastics or plastic components, solvents, lubricant oil components and assistants in metal processing. ### Claim 21 (depends on 20) The process as claimed in claim 20, wherein the plastic is PVC. ### Claim 22 (depends on 20) The process as claimed in claim 20, wherein the plastisol is a PVC plastisol. ### Claim 23 (depends on 1) A plasticized PVC comprising PVC and from 5 to 120 parts by mass of a mixture as claimed in claim 1 per 100 parts by mass of PVC. ### Claim 24 (depends on 1) A plastisol comprising PVC and from 5 to 120 parts by mass of a mixture as claimed in claim 1 per 100 parts by mass of PVC.