# US 7,408,085 B2 · Rapid cost effective method for the synthesis of TPD-type arylamines > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,408,085 B2 - Document ID: US7408085B2 - Status: Granted - Kind: B2 - Application number: 11/563,937 - Filed: 2006-11-28 - Published: 2008-05-29 - Granted: 2008-08-05 - Earliest claimed: 2006-11-28 - Assignees: Xerox Corporation - Inventors: Timothy P. Bender; Jennifer A. Coggan; Gregory McGuire; Leanne Dawn Murphy; Alan Edward John Toth - Web page: https://patentgrep.com/patent/US7408085B2 ## CPC - C07C 209/10: with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A process for forming a tetra(aryl)-biphenyldiamine compound, including reacting a dibromobiphenyl compound and a diarylamine compound in the presence of a palladium ligated catalyst and a base. ## Claims ### Claim 1 A process for forming a tetra(aryl)-biphenyldiamine compound, comprising: reacting a dibromobiphenyl compound and a diarylamine compound in the presence of a palladium ligated catalyst and a base, wherein the palladium ligated catalyst is a palladium acetate ligated with a molecule given by structural formula (I): wherein: each X individually represents either CH2 or an oxygen atom; Y1, Y2, Y3, and Y4 each individually represent a substituted or unsubstituted, straight or branched, alkyl, alkenyl, or alkynyl group, having from 1 to about 10 carbon atoms; and Y5 represents hydrogen, a substituted or unsubstituted alkyl group, or an aryl group. ### Claim 2 (depends on 1) The process according to claim 1, wherein the dibromobiphenyl compound is a 4,4′-dibromobiphenyl compound. ### Claim 3 (depends on 1) The process according to claim 1, wherein the molecule given by structural formula (I) is 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane. ### Claim 4 (depends on 1) The process according to claim 1, wherein Y1, Y2, Y3, and Y4 each individually represent a substituted or unsubstituted, straight or branched, alkyl, alkenyl, or alkynyl group, having from 1 to about 6 carbon atoms. ### Claim 5 (depends on 1) The process according to claim 1, wherein Y1, Y2, Y3, Y4 each individually represent a substituted or unsubstituted, straight branched, alkyl, alkenyl, or alkynyl group, having from 1 to about 3 carbon atoms. ### Claim 6 (depends on 1) The process according to claim 1, wherein the dibromobiphenyl compound, the diarylamine compound, and the tetra(aryl)-biphenyldiamine compound are represented as follows: wherein: R1, R2, R3, R4, R5, R6, R7, and R8, which can be the same or different, are selected from the group consisting of a hydrogen, a halogen, an alkyl group having from 1 to about 20 carbon atoms, a hydrocarbon radical having from 1 to about 20 carbon atoms, an aryl group, an aryl group substituted by one or more alkyl groups, an alkyl group containing a heteroatom and having from 1 to about 20 carbon atoms, a hydrocarbon radical containing a heteroatom and having from 1 to about 20 carbon atoms, an aryl group containing a heteroatom, and an aryl group containing a heteroatom substituted by one or more alkyl groups; and Ar1 and Ar2, which can be the same or different, are selected from the group consisting of substituted or unsubstituted aromatic components, and substituted or unsubstituted aryl groups having from 2 to about 15 conjugate bonded or fused benzene rings; wherein a substituent on the aryl groups Ar1 and Ar2 is selected from the group consisting of hydrogen, a halogen, an alkyl group having from 1 to about 20 carbon atoms, a hydrocarbon radical having from 1 to about 20 carbon atoms, an aryl group, an aryl group substituted by one or more alkyl groups, an alkyl group containing a heteroatom and having from 1 to about 20 carbon atoms, a hydrocarbon radical containing a heteroatom and having from 1 to about 20 carbon atoms, an aryl group containing a heteroatom, and an aryl group containing a heteroatom substituted by one or more alkyl groups. ### Claim 7 (depends on 1) The process according to claim 1, wherein the diarylamine compound is di-p-toylamine, and the tetra(aryl)-biphenyldiamine compound is N,N,N′,N′-tetra-p-tolylbiphenyl-4,4′-diamine. ### Claim 8 (depends on 1) The process according to claim 1, wherein the process is conducted in batch mode. ### Claim 9 (depends on 1) The process according to claim 1, wherein the process is conducted in continuous mode. ### Claim 10 (depends on 1) The process according to claim 1, wherein the process is carried out in a time of from about 30 minutes to about 5 hours. ### Claim 11 (depends on 1) The process according to claim 1, wherein the process is carried out in a solvent. ### Claim 12 (depends on 11) The process according to claim 11, wherein the solvent is toluene. ### Claim 13 (depends on 1) The process according to claim 1, wherein the process is carried out under an inert atmosphere. ### Claim 14 (depends on 1) The process according to claim 1, wherein the base is represented by a general formula MOR, where: O is oxygen; M is a metal selected from the group consisting of potassium, sodium, lithium, calcium, magnesium; and R is a hydrogen or a straight or branched alkyl group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups. ### Claim 15 (depends on 1) The process according to claim 1, wherein the base is potassium tert-butoxide. ### Claim 16 (depends on 1) The process according to claim 1, wherein the base is sodium t-pentoxide. ### Claim 17 (depends on 1) The process according to claim 1, wherein the base is sodium t-butoxide. ### Claim 18 A process for forming N,N,N′,N′-tetra-p-tolylbiphenyl-4,4′-diamine, comprising reacting 4,4-dibromobiphenyl and di-p-toylamine in the presence of a palladium ligated catalyst, wherein the catalyst comprises a palladium acetate ligated with 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane and sodium t-pentoxide base.