[미국특허]
Alkyl aromatic hydroalkylation for the production of plastisizers
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08K-005/00
C08K-005/101
C08K-005/12
출원번호
US-0751835
(2013-01-28)
등록번호
US-8829093
(2014-09-09)
발명자
/ 주소
Dakka, Jihad
DeCaul, Lorenzo C.
Costello, Christine A.
Mozeleski, Edmund J.
Osterrieth, Pierre J.
Smirnova, Diana S.
Zushma, Stephen
Godwin, Allen D.
출원인 / 주소
ExxonMobil Chemical Patents Inc.
인용정보
피인용 횟수 :
17인용 특허 :
8
초록▼
Provided are compounds of the following: wherein R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is the residue of a C4 to C14 OXO-alcohol. Also provided are processes for making the compounds and plasticized polymer compositions
Provided are compounds of the following: wherein R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is the residue of a C4 to C14 OXO-alcohol. Also provided are processes for making the compounds and plasticized polymer compositions containing said compounds.
대표청구항▼
1. Compounds of the formula wherein R1 is a saturated or unsaturated cyclic hydrocarbon substituted with an alkyl and/or an OXO-ester, and R2 is a hydrocarbon residue of a C4 to C14 OXO-alcohol. 2. The compounds of claim 1, wherein R1 is located at the ortho-, meta- or para-position. 3. The compoun
1. Compounds of the formula wherein R1 is a saturated or unsaturated cyclic hydrocarbon substituted with an alkyl and/or an OXO-ester, and R2 is a hydrocarbon residue of a C4 to C14 OXO-alcohol. 2. The compounds of claim 1, wherein R1 is located at the ortho-, meta- or para-position. 3. The compounds of claim 1, wherein R1 is phenyl located at the para-position. 4. The compounds of claim 3, wherein R1 is an alkyl and/or an OXO-ester-substituted phenyl at the ortho-, meta-, or para-position. 5. The compounds of claim 1, wherein R1 is an alkyl and/or an OXO-ester-substituted cyclohexyl at the ortho-, meta-, or para-position. 6. The compounds of claim 1, wherein R2 is the hydrocarbon residue of a C5 to C10 OXO-alcohol averaging from 0.2 to 5.0 branches per residue. 7. The compounds of claim 1, wherein the hydrocarbon residue averages from 0.05 to 0.4 branches per residue at the alcoholic beta carbon. 8. Compounds of the formula: wherein R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is a hydrocarbon residue of a C4 t C14 OXO-alcohol, wherein the hydrocarbon residue averages at least 1.3 to 5.0 methyl branches per residue. 9. The compounds of claim 1, wherein the hydrocarbon residue averages from 0.35 to 1.5 pendant methyl branches per residue. 10. The compounds of claim 1, which are represented by the formula: 11. The compounds of claim 1, which are represented by the formula: 12. The compounds of claim 1, which are represented by the formula: wherein R2 is C9H19, C10H21 or C13H27. 13. The compounds of claim 1, which are represented by the formula: wherein R2 is C9H19, C10H21, or C13H27. 14. The compounds of claim 1, which are represented by a mixture of the following at any ratio: wherein R2 is C9H19, C10H21, or C13H27. 15. A compound represented by the formula: wherein R2=C9H19, C10H21, or C13H27. 16. A mixture of the compounds of claim 15 at any ratio. 17. A compound represented by the formula: wherein R2=C9H19, C10H21, or C13H27. 18. A compound represented by the formula: wherein R2=C9H19 or C10H21, or C13H27. 19. A compound represented by the formula: wherein R2=C9H19, C10H21, or C13H27. 20. A mixture of the compounds represented by the formulae below at any ratio: wherein R2=C9H19, C10H21, or C13H27. 21. A compound represented by the formula: wherein R2=C9H19, C10H21, or C13H27. 22. A compound represented by the formula: wherein R2=C9H19, C10H21, or C13H27. 23. A compound represented by the formula: wherein R2=C9H19, C10H21, or C13H27. 24. A mixture of the compounds represented below at any ratio: wherein R2=C9H19, C10H21, or C13H27. 25. A composition comprising a mixture of the compounds of claims 20 and 24 at any ratio. 26. A process for making compounds of the formula: wherein R1 is a cyclic hydrocarbon substituted with an alkyl and/or an OXO-ester, and R2 is a hydrocarbon residue of a C4 to C14 OXO-alcohol, comprising the steps of: reacting benzene or alkylated benzene under conditions appropriate to form alkylated biphenyl;optionally alkylating biphenyl to form said alkylated biphenyl;oxidizing the alkyl group(s) on said alkylated biphenyl to form at least one acid group; andreacting said acid group(s) with an OXO-alcohol under esterification conditions to form said compounds. 27. The process of claim 26, wherein said reacting step is conducted with benzene, and said optional alkylating step is conducted with an alcohol. 28. The process of claim 27, wherein said alcohol is methanol and said alkylating step is conducted in the presence of an acid catalyst. 29. The process of claim 26, wherein said reacting step is conducted with benzene, further comprising the steps of: hydroalkylating benzene by reacting benzene in the presence of H2 to hydrogenate one mole of said benzene to form cyclohexene,alkylating benzene with said cyclohexene to form cyclohexylbenzene; dehydrogenating said cyclohexylbenzene to form biphenyl; andalkylating one or both aromatic moieties of said biphenyl to form said alkylated biphenyl. 30. The process of claim 29, wherein said hydroalkylating step is conducted in the presence of a hydrogenation catalyst, said alkylating step is conducted with an alkylation catalyst, and said dehydrogenating step is conducted with a dehydrogenation catalyst. 31. The process of claim 30, wherein said hydrogenation catalyst is selected from the group consisting of platinum, palladium, ruthenium, nickel, zinc, tin, cobalt, or a combination of these metals, said alkylation catalyst is selected from the group consisting of Zeolite, mixed metal oxides and said dehydrogenation catalyst is selected from the group consisting of platinum, pladium, Ru, Rh, nickel, zinc, tin, cobalt and combinations thereof. 32. The process of claim 26, wherein said reacting step is conducted with benzene in the presence of oxygen and an oxidative coupling catalyst, forming biphenyl, further comprising the step of: alkylating one or both aromatic moieties of said biphenyl to form said alkylated biphenyl. 33. The process of claim 32, wherein said alkylating step is conducted with an alkylation catalyst. 34. The process of claim 26, wherein the reacting step is conducted with toluene, further comprising the steps of: reacting toluene in the presence of H2 and a hydrogenation catalyst to form methyl cyclohexene,reacting said methyl cyclohexene with toluene in the presence of an alkylation catalyst to form dimethyl cyclohexylbenzene; anddehydrogenating said dimethyl cyclohexylbenzene in the presence of a dehydrogenation catalyst to form the alkylated biphenyl, which is dimethyl-biphenyl. 35. A polymer composition comprising a thermoplastic polymer and at least one plasticizer of the formula: wherein R1 is a saturated and unsaturated cyclic hydrocarbon substituted with an alkyl and/or an OXO-ester, and R2 is a hydrocarbon residue of a C4 to C14 OXO-alcohol. 36. The polymer composition of claim 35, wherein the thermoplastic polymer is selected from the group consisting of vinyl chloride resins, polyesters, polyurethanes, ethylene-vinyl acetate copolymer, rubbers, poly(meth)acrylics and combinations thereof. 37. The polymer composition of claim 35, wherein the thermoplastic polymer is polyvinylchloride. 38. Compounds of the formula wherein R1 is a saturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is a hydrocarbon residue of a C4 to C14 OXO-alcohol. 39. The compound of claim 1, where R2 contains mixed alkyl isomer residues of C4 to C13 OXO-alcohols. 40. The compound of claim 1, where R1 contains mixed alkyl isomer residues of C4 to C13 OXO-alcohols.
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de Smit, Emiel; Sangar, Neeraj; Salciccioli, Michael; Dakka, Jihad M.; DeCaul, Lorenzo C.; Helton, Terry E.; Weigel, Scott J., Hydroalkylation catalyst and process for use thereof.
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