# US 9,434,675 B2 · Method for producing isononanoic acid esters, starting from 2-ethyl hexanol > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,434,675 B2 - Document ID: US9434675B2 - Status: Granted - Kind: B2 - Application number: 14/413,550 - Filed: 2013-06-18 - Published: 2015-06-11 - Granted: 2016-09-06 - Earliest claimed: 2012-07-13 - Assignees: Oxga GmbH - Applicants: Oxea GmbH - Inventors: Guido D. Frey; Matthias Eisenacher; Kristina Kockrick; Heinz Strutz - Web page: https://patentgrep.com/patent/US9434675B2 ## CPC - C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds - C07C 1/24: by elimination of water - C07C 29/48: by oxidation reactions with formation of hydroxy groups - C07C 45/50: by oxo-reactions - C07C 51/235: of —CHO groups or primary alcohol groups - C08K 5/103: with polyalcohols - C10M 129/70: of monocarboxylic acids - C10M 129/74: of polyhydroxy compounds - C07C 2521/04: Alumina - C08K 5/10: Esters; Ether-esters - C10M 2207/281: of (cyclo)aliphatic monocarboxylic acids - C10M 2207/283: of polyhydroxy compounds - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) ## Abstract A Process for preparing carboxylic esters of a mixture of structurally branched C9 monocarboxylic acids proceeding from 2-ethylhexanol is characterized in that (a) 2-ethylhexanol is dehydrated to an octene mixture in the presence of a catalyst; (b) the octene mixture obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give a mixture of isomeric isononanals; (c) the mixture of isomeric isononanals obtained in step b) is oxidized to a mixture of structurally branched C9 monocarboxylic acids; and (d) the mixture of structurally branched C9 monocarboxylic acids obtained in step c) is reacted with alcohols to give carboxylic esters. ## Claims ### Claim 1 A process for preparing carboxylic esters of a mixture of structurally branched C9 monocarboxylic acids proceeding from 2-ethylhexanol, wherein (a) 2-ethylhexanol is dehydrated to an octene mixture in the presence of a catalyst; (b) the octene mixture obtained in step a) is reacted in the presence of a transition metal compound of group VIII of the periodic table of the elements with carbon monoxide and hydrogen to give a mixture of isomeric isononanals; (c) the mixture of isomeric isononanals obtained in step b) is oxidized to a mixture of structurally branched C9 monocarboxylic acids; and (d) the mixture of structurally branched C9 monocarboxylic acids obtained in step c) is reacted with alcohols to give carboxylic esters. ### Claim 2 (depends on 1) The process according to claim 1, wherein the catalyst used in step a) is alumina, nickel precipitated on alumina, or phosphoric acid precipitated on silica or alumina. ### Claim 3 (depends on 1) The process according to claim 1, wherein 2-ethylhexanol is dehydrated in the gas phase in step a). ### Claim 4 (depends on 1) The process according to claim 1, wherein the transition metal compound of group VIII of the periodic table of the elements used in step b) is a cobalt or rhodium compound. ### Claim 5 (depends on 1) The process according to claim 1, wherein the reaction in step b) is performed in the absence of complex-forming organophosphorous compounds. ### Claim 6 (depends on 1) The process according to claim 1, wherein the mixture of isomeric isononanals obtained in step b) is distilled. ### Claim 7 (depends on 1) The process according to claim 1, wherein the oxidation in step c) is effected in the presence of alkali metal or alkaline earth metal carboxylates. ### Claim 8 (depends on 7) The process according to claim 7, wherein the alkali metal or alkaline earth metal carboxylate used is lithium isononanoate, potassium isononanoate, sodium isononanoate, calcium isononanoate or barium isononanoate. ### Claim 9 (depends on 1) The process according to claim 1, wherein the mixture of isomeric isononanals is oxidized in the liquid phase in step c). ### Claim 10 (depends on 1) The process according to claim 1, wherein the mixture of isomeric isononanals is oxidized in step c) with oxygen or oxygen-containing gases provided to the mixture of structurally branched C9 monocarboxylic acids. ### Claim 11 (depends on 1) The process according to claim 1, wherein the reaction in step d) is performed in the presence of an adsorbent. ### Claim 12 (depends on 1) The process according to claim 1, wherein the reaction in step d) is performed in the presence of a catalyst. ### Claim 13 (depends on 1) The process according to claim 1, wherein the alcohols converted in step d) are of the general formula (I) R(OH)n (I) in which R is an aliphatic, cycloaliphatic or aromatic hydrocarbyl radical having 1 to 20 carbon atoms, and n is an integer from 1 to 8. ### Claim 14 (depends on 1) The process according to claim 1, wherein the alcohols converted in step d) are of the general formula (II) H—(—O—[—CR1R2—]m—)o—OH (II) in which R1 and R2 are each independently hydrogen or an alkyl radical having 1 to 5 carbon atoms, or a hydroxyalkyl radical having 1 to 5 carbon atoms, m is a number from 1 to 10, and o is an integer from 2 to 15. ### Claim 15 (depends on 1) The process according to claim 1, wherein the alcohol used in step d) is glycidyl alcohol. ### Claim 16 (depends on 2) The process according to claim 2, wherein 2-ethylhexanol is dehydrated in the gas phase in step a). ### Claim 17 (depends on 2) The process according to claim 2, wherein the transition metal compound of group VIII of the periodic table of the elements used in step b) is a cobalt or rhodium compound.