Substituted naphthalenes as feedstock for plasticizer production
AssigneeExxonMobil Research and Engineering Company
InventorsJihad Mohammed Dakka, Edmund John Mozeleski, Lisa Saunders Baugh, Stephen Zushma
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Abstract
Provided are compounds and processes of making compounds of the formula: wherein x=4 to 8, R is H, C1 to C4 alkyl, —C(O)OR1 or —OC(O)R1, y=4 to 8, R′ is H, C1 to C4 alkyl, and at least one R′ is —C(O)OR1 or —OC(O)R1, wherein R1 is a branched C4 to C14 alkyl, and their use in polymer compositions.
Claims30
Compounds of the formula:
- wherein x=4 to 8, R is H, C1 to C4 alkyl, —C(O)OR1 or —OC(O)R1, y=4 to 8, R′ is H, C1 to C4 alkyl, and at least one R′ is —C(O)OR1 or —OC(O)R1, wherein R1 is a branched C4 to C14 alkyl.
A process for making compounds of the formula:
- wherein x=4 to 8, R is H, C1 to C4 alkyl, —C(O)OR1 or —C(O)OR1, y=4 to 8, R′ is H, C1 to C4 alkyl, and at least one R′ is —C(O)OR1, wherein R1 is a branched C4 to C14 alkyl, comprising:
- reacting an optionally-alkylated naphthalene under conditions appropriate to form an optionally alkyl-substituted naphthoic acid;
- reacting said acid group with an OXO-alcohol under esterification conditions to form optionally-alkylated naphthoic acid esters;
- and
- optionally hydrogenating said optionally-alkylated naphthoic acid esters.
A process for making compounds of the formula:
- wherein x=4 to 8, R is H, C1 to C4 alkyl, —C(O)OR1 or —OC(O)R1, y=4 to 8, R′ is H, C1 to C4 alkyl, and at least one R′ is —C(O)OR1, wherein R1 is a branched C4 to C14 alkyl, comprising:
- selectively hydrogenating an optionally-alkylated naphthalene to form an optionally-alkylated dihydronaphthalene;
- hydroformylating the optionally-alkylated dihydronaphthalene to form a corresponding aldehyde;
- oxidizing the aldehyde to form a corresponding acid;
- and
- esterifying the acid.
A process for making compounds of the formula:
- wherein x=4 to 8, R is H, C1 to C4 alkyl, —C(O)OR1 or —OC(O)R1, y=4 to 8, R′ is H, C1 to C4 alkyl, and at least one R′ is —OC(O)R1, wherein R1 is a branched C4 to C14 alkyl, comprising:
- hydroxylation of an optionally-alkylated naphthalene with hydroperoxide to form an optionally-alkylated naphthol, or hydration of an optionally-alkylated dihydronaphthalene to form an optionally-alkylated tetrahydronaphthalenol, or oxidative decarboxylation of an optionally-alkylated naphthoic acid to form an optionally-alkylated naphthol;
- esterifying the optionally-alkylated naphthol or optionally-alkylated tetrahydronaphthalenol with C4 to C14 alkanoic acid;
- and
- optionally hydrogenating said optionally-alkylated naphthol.
A polymer composition comprising a thermoplastic polymer and at least one plasticizer of the formula:
- wherein x=4 to 8, R is H, C1 to C4 alkyl, —C(O)OR1 or —OC(O)R1, y=4 to 8, R′ is H, C1 to C4 alkyl, and at least one R′ is —CO2R1 or —OC(O)R1, wherein R1 is a branched C4 to C14 alkyl.
Dependencies are inferred from the claim text.