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US 7,208,545 B1Granted
Selected cyclohexane -1,3-and -1,4-dicarboxylic acid esters
AssigneeBASF SE
InventorsMelanie Brunner, Lucien Thil, Boris Breitscheidel
Life of this patent
Estimating the term…
Abstract
Selected cyclohexane-1,3- and -1,4-dicarboxylic acid esters are described, as is their use as plasticizers in plastics and their preparation by hydrogenation of the corresponding isophthalic or terephthalic esters by bringing one or more of these isophthalic or terephthalic esters into contact with a hydrogen-containing gas in the presence of a catalyst which comprises, as active metal, at least one metal of the 8th transition group of the Periodic Table on its own or together with at least one metal of the 1st or 7th transition group of the Periodic Table, applied to a support, which comprises using a support having micropores.
Claims25
A cyclohexane-1,3- or -1,4-dicarboxylic acid ester selected from the group consisting of
- cyclohexane-1,3-dicarboxylic acid dinonyl ester;
- cyclohexane-1,3-dicarboxylic acid diisodecyl ester;
- cyclohexane-1,3-dicarboxylic acid diundecyl ester;
- cyclohexane-1,3-dicarboxylic acid didodecyl ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethyl-2-methylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,2,2-trimethylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(2-ethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(4-methylpentyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,3-dimethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,1-diethylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethyl-1-methylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis[2-methyl-1-(1-methylethyl)propyl] ester;
- cyclohexane-1,3-dicarboxylic acid bis(2,2-dimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis[3-methyl-1-(2-methylpropyl)butyl] ester;
- cyclohexane-1,3-dicarboxylic acid bis(3,3,5-trimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(2-ethyl-1,1-dimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid 1-heptyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[2-ethylbutyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-heptyl-3-[1,2,2-trimethylpropyl] ester;
- cyclohexane-1,3-dicarboxylic acid 1-dimethylbutyl-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[1-ethylbutyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[1-ethyl-2-methylpropyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-decyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-hexyl-3-[2-methyl-1-(1-methylethyl)propyl] ester;
- cyclohexane-1,3-dicarboxylic acid 1-dodecyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-nonyl-3-octyl ester;
- cyclohexane-1,4-dicarboxylic acid diisobutyl ester;
- cyclohexane-1,4-dicarboxylic acid dipentyl ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid diheptyl ester;
- cyclohexane-1,4-dicarboxylic acid diisooctyl ester;
- cyclohexane-1,4-dicarboxylic acid dinonyl ester;
- cyclohexane-1,4-dicarboxylic acid diisononyl ester;
- cyclohexane-1,4-dicarboxylic acid diundecyl ester;
- cyclohexane-1,4-dicarboxylic acid didodecyl ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylpropyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1,1-dimethylpropyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(3-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-ethylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(4-methylpentyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis[2-methyl-1-(1-methylethyl)propyl] ester;
- 2-methylcyclohexane-1,4-dicarboxylic acid bis(2-ethylhexyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylheptyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-ethyl-4-methylpentyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-methylheptyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1,1,3,3-tetramethylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(7-methyloctyl) ester;
- the cyclohexane-1,4-dicarboxylic acid bis(8-methylnonyl) ester;
- cyclohexane-1,4-dicarboxylic acid 1-[8-methylnonyl]-4-octyl ester;
- cyclohexane-1,4-dicarboxylic acid 1-decyl-4-octyl ester.
49 more elements
A process for producing a cyclohexane-1,3- or -1,4-dicarboxylic acid ester or mixtures thereof by hydrogenating an isophthalic or terephthalic ester selected from the group consisting of
- diheptyl isophthalate with CAS No. 4654-17-5;
- diisooctyl isophthalate with CAS No. 71850-11-8;
- dinonyl isophthalate with CAS No. 4654-19-7;
- diisodecyl isophthalate with CAS No. 52284-35-2;
- diundecyl isophthalate with CAS No. 18699-46-2;
- didodecyl isophthalate with CAS No. 18699-47-3;
- bis(1-ethyl-2-methylpropyl) isophthalate with CAS No. 16639391-29-3;
- bis(1-ethylbutyl) isophthalate with CAS No. 166391-28-2;
- bis(1,2,2-trimethylpropyl) isophthalide with CAS No. 166391-27-1;
- bis(2-ethylbutyl) isophthalate with CAS No. 166391-25-9;
- bis(4-methylpentyl) isophthalate with CAS No. 159375-22-1;
- bis(1,3-dimethylbutyl) isophthalate with CAS No. 166391-26-0;
- bis(1,1-diethylpropyl) isophthalate with CAS No. 123095-15-8;
- bis(1-ethyl-1-methylpropyl) isophthalate with CAS No. 145530-74-1;
- bis[2-methyl-1-(1-methylethyl)propyl] isophthalate with CAS No. 166391-48-6;
- bis(2,2-dimethylhexyl) isophthalate with CAS No. 17673-11-9;
- bis[3-methyl-1-(2-methylpropyl)butyl] isophthalate with CAS No. 127474-92-4;
- bis(3,3,5-trimethylhexyl) isophthalate with CAS No. 208527-97-3;
- bis(2-ethyl-1,1-dimethylhexyl) isophthalate with CAS No. 123892-24-0;
- 1-heptyl-3-hexyl isophthalate with CAS No. 166391-30-6;
- 1-[2-ethylbutyl]-3-heptyl isophthalate with CAS No. 166391-41-9;
- 1-heptyl-3-[1,2,2-trimethylpropyl] isophthalate with CAS No. 166391-43-1;
- 1-dimethylbutyl-3-heptyl isophthalate with CAS No. 166391-42-0;
- 1-[1-ethylbutyl]-3-heptyl isophthalate with CAS No. 166391-44-2;
- 1-[1-ethyl-2-methylpropyl]-3-heptyl isophthalate with CAS No. 166391-45-3;
- 1-decyl-3-hexyl isophthalate with CAS No. 154064-19-4;
- 1-hexyl-3-[2-methyl-1-(1-methylethyl)propyl] isophthalate with CAS No. 166391-46-4;
- 1-dodecyl-3-hexyl isophthalate with CAS No. 154147-75-8;
- 1-nonyl-3-octyl isophthalate with CAS No. 154147-74-7;
- diisobutyl terephthalate with Chemical Abstracts Registry number 18699-48-4;
- dipentyl terephthalate with CAS No. 1818-95-7;
- bis(1-methylbutyl) terephthalate with CAS No. 75151-02-9;
- diheptyl terephthalate with CAS No. 4654-25-5;
- diisooctyl terephthalate with CAS No. 27937-24-2;
- dinonyl terephthalate with CAS No. 4654-27-7;
- diisononyl terephthalate with CAS No. 59802-05-0;
- diisodecyl terephthalate with CAS No. 52114-72-8;
- diundecyl terephthalate with CAS No. 111204-04-7;
- didodecyl terephthalate with CAS No. 18749-84-3;
- bis(1-methylpropyl) terephthalate with CAS No. 64445-74-5;
- bis(1,1-dimethylpropyl) terephthalate with CAS No. 117769-96-7;
- bis(2-methylbutyl) terephthalate with CAS No. 75151-04-1;
- bis(3-methylbutyl) terephthalate with CAS No. 18699-49-5;
- bis(1-ethylbutyl) terephthalate with CAS No. 166391-32-8;
- bis(4-methylpentyl) terephthalate with CAS No. 159375-21-0;
- bis[2-methyl-1-(1-methylethyl)propyl] terephthalate with CAS No. 166391-33-9;
- bis(2-ethylhexyl) 2-methylterephthalate with CAS No. 51248-916;
- bis(1-methylheptyl) terephthalate with CAS No. 87321-19.5;
- bis(2-ethyl-4-methylpentyl) terephthalate with CAS No. 59726-62-4;
- bis(2-methylheptyl) terephthalate with CAS No. 83789-07-5;
- bis(1,1,3,3-tetramethylbutyl) terephthalate with CAS No. 90062-47-0;
- bis(7-methyloctyl) terephthalate with CAS No. 129951-1-42-4;
- bis(8-methylnonyl) terephthalate with CAS No. 129951-40-2;
- 1-[8-methylnonyl]-4-octyl terephthalate with CAS No. 129951-39-9;
- 1-decyl-4-octyl terephthalate with CAS No. 129951-41-3;
- or mixtures thereof by bringing one or more of said isophthalic or terephthalic esters into contact with a hydrogen-containing gas in the presence of a catalyst which comprises, as active metal, ruthenium applied to a support, said support having macro-pores.
53 more elements
A method for imparting flexibility, workability or stretchability to a plastic composition, said method comprising adding to the composition a cyclohexane-1,3- or 1,4-dicarboxylic acid ester selected from the group consisting of
- cyclohexane-1,3-dicarboxylic acid dinonyl ester;
- cyclohexane-1,3-dicarboxylic acid diisodecyl ester;
- cyclohexane-1,3-dicarboxylic acid diundecyl ester;
- cyclohexane-1,3-dicarboxylic acid didodecyl ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethyl-2-methylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,2,2-trimethylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(2-ethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(4-methylpentyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,3-dimethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,1-diethylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethyl-1-methylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis[2-methyl-1-(1-methylethyl)propyl] ester;
- cyclohexane-1,3-dicarboxylic acid bis(2,2-dimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis[3-methyl-1-(2-methylpropyl)butyl] ester;
- cyclohexane-1,3-dicarboxylic acid bis(3,3,5-trimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(2-ethyl-1,1-dimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid 1-heptyl-3-hexyl ester
- cyclohexane-1,3-dicarboxylic acid 1-[2-ethylbutyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-heptyl-3-[1,2,2-trimethylpropyl] ester;
- cyclohexane-1,3-dicarboxylic acid 1-dimethylbutyl-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[1-ethylbutyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[1-ethyl-2-methylpropyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-decyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-hexyl-3-[2-methyl-1-(1-methylethyl)propyl] ester;
- cyclohexane-1,3-dicarboxylic acid 1-dodecyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-nonyl-3-octyl ester;
- cyclohexane-1,4-dicarboxylic acid diisobutyl ester;
- cyclohexane-1,4-dicarboxylic acid dipentyl ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid diheptyl ester;
- cyclohexane-1,4-dicarboxylic acid diisooctyl ester;
- cyclohexane-1,4-dicarboxylic acid dinonyl ester;
- cyclohexane-1,4-dicarboxylic acid diisononyl ester;
- cyclohexane-1,4-dicarboxylic acid diisodecyl ester;
- cyclohexane-1,4-dicarboxylic acid diundecyl ester;
- cyclohexane-1,4-dicarboxylic acid didodecyl ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylpropyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1,1-dimethylpropyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(3-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-ethylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(4-methylpentyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis[2-methyl-1-(1-methylethyl)propyl] ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-ethylhexyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylheptyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-ethyl-4-methylpentyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-methylheptyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1,1,3,3-tetramethylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(7-methyloctyl) ester;
- the cyclohexane-1,4-dicarboxylic acid bis(8-methylnonyl) ester;
- cyclohexane-1,4-dicarboxylic acid 1-[8-methylnonyl]-4-octyl ester;
- cyclohexane-1,4-dicarboxylic acid 1-decyl-4-octyl ester.
50 more elements
A plastic composition comprising a cyclohexane-1,3- or 1,4-dicarboxylic acid ester selected from the group consisting of
- cyclohexane-1,3-dicarboxylic acid dinonyl ester;
- cyclohexane-1,3-dicarboxylic acid diusooctyl ester;
- cyclohexane-1,3-dicarboxylic acid diundecyl ester;
- cyclohexane-1,3-dicarboxylic acid didodecyl ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethyl-2-methylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethylbutyl ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,2,2-trimethylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(2-ethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(4-methylpentyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,3-dimethylbutyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1,1-diethylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(1-ethyl-1-methylpropyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis[2-methyl-1-(1-methylethyl )propyl] ester;
- cyclohexane-1,3-dicarboxylic acid bis(2,2-dimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis[3-methyl-1-(2-methylpropyl)butyl] ester;
- cyclohexane-1,3-dicarboxylic acid bis(3,3,5-trimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid bis(2-ethyl-1,1-dimethylhexyl) ester;
- cyclohexane-1,3-dicarboxylic acid 1-heptyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[2-ethylbutyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-heptyl-3-[1,2,2-trimethylpropyl] ester;
- cyclohexane-1,3-dicarboxylic acid 1-dimethylbityl-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[1-ethylbutyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-[1-ethyl-2-methylpropyl]-3-heptyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-decyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-hexyl-3-[2-methyl-1-(1-methylethyl)propyl] ester;
- cyclohexane-1,3-dicarboxylic acid 1-dodecyl-3-hexyl ester;
- cyclohexane-1,3-dicarboxylic acid 1-nonly-3-octyl ester;
- cyclohexane-1,4-dicarboxylic acid diisobutyl ester;
- cyclohexane-1,4-dicarboxylic acid dipentyl ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid diheptyl ester;
- cyclohexane-1,4-dicarboxylic acid diisooctyl ester;
- cyclohexane-1,4-dicarboxylic acid dinonyl ester;
- cyclohexane-1,4-dicarboxylic acid diisononyl ester;
- cyclohexane-1,4-dicarboxylic acid diisodecyl ester;
- cyclohexane-1,4-dicarboxylic acid diundecyl ester;
- cyclohexane-1,4-dicarboxylic acid didodecyl ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylpropyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1,1-dimethylpropyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(3-methylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-ethylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(4-methylpentyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis[2-methyl-1-(1-methylethyl)propyl] ester;
- 2-methylcyclohexane-1,4-dicarboxylic acid bis(2-ethylhexyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1-methylheptyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-ethyl-4-methylpentyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(2-methylheptyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(1,1,3,3-tetramethylbutyl) ester;
- cyclohexane-1,4-dicarboxylic acid bis(7-methyloctyl) ester;
- the cyclohexane-1,4-dicarboxylic acid bis(8-methylnonyl) ester;
- cyclohexane-1,4-dicarboxylic acid 1-[8-methylnonyl]-4-octyl ester;
- cyclohexane-1,4-dicarboxylic acid 1-decyl-4-octyl ester.
50 more elements
Dependencies are inferred from the claim text.