Methyl-substituted biphenyl compounds, their production and their use in the manufacture of plasticizers
US-9688602-B2 · Jun 27, 2017 · US
US10322979B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10322979-B2 |
| Application number | US-201815886115-A |
| Country | US |
| Kind code | B2 |
| Filing date | Feb 1, 2018 |
| Priority date | Feb 1, 2017 |
| Publication date | Jun 18, 2019 |
| Grant date | Jun 18, 2019 |
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A process for separating dimethyl biphenyl (DMBP) isomers, including contacting a mixture of 3,3′-DMBP, 3,4′-DMBP and 4,4′-DMBP in a first solvent with a 12-member ring zeolite exchanged with potassium or barium, or combinations thereof, and adsorbing the 3,3′-DMBP onto the 12-member ring zeolite, such as by passing the mixture through at least one packed bed of the potassium and/or barium exchanged 12-member ring zeolite.
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The invention claimed is: 1. A process for separating 3,3′-dimethyl biphenyl (DMBP) isomers from a mixture of 3,3′-DMBP, 3,4′-DMBP and 4,4′-DMBP isomers, the process comprising contacting the mixture with a 12-member ring zeolite exchanged with potassium or barium, or combinations thereof, wherein the 3,3′-DMBP isomer is more strongly adsorbed onto the 12-member ring than the 3-4′-DMBP and 4,4′-DMBP isomers. 2. The process of claim 1 , wherein the 12-member ring zeolite is exchanged with potassium. 3. The process of claim 1 , wherein the 12-member ring zeolite is exchanged with barium. 4. The process of claim 2 , wherein the 12-member ring zeolite is one of zeolite X (K—X) or zeolite Y (K—Y). 5. The process of claim 1 , wherein the 12-member ring zeolite is one of barium and potassium-exchanged zeolite X (BaK—X) or barium and potassium-exchanged zeolite Y (BaK—Y). 6. The process of claim 1 , wherein the isomer mixture is contained in a solvent which does not adsorb onto the 12-member ring zeolite. 7. A process for separating 3,3′-dimethyl biphenyl (DMBP) isomers from a mixture of 3,3′-DMBP, 3,4′-DMBP and 4,4′-DMBP isomers, the process comprising passing the mixture in a first solvent through at least one packed bed of 12-member ring zeolite exchanged with potassium or barium, or combinations thereof, wherein the 3,3′-DMBP is more strongly adsorbed onto the 12-member ring zeolite than the 3,4′-DMBP and 4,4′-DMBP isomers. 8. The process of claim 7 , wherein the 12-member ring zeolite is exchanged with potassium. 9. The process of claim 7 , wherein the 12-member ring zeolite is exchanged with barium. 10. The process of claim 7 , wherein the 12-member ring zeolite is one of zeolite X (K—X) or zeolite Y (K—Y). 11. The process of claim 7 , wherein the 12-member ring zeolite is one of barium and potassium-exchanged zeolite X (BaK—X) or barium and potassium-exchanged zeolite Y (BaK—Y). 12. The process of claim 7 , wherein the first solvent does not adsorb onto the 12-member ring zeolite. 13. The process of claim 7 , wherein the packed bed of 12-member ring zeolite is in a chromatographic column and the packed bed has an inlet and an outlet. 14. The process of claim 13 , further comprising collecting a raffinate mixture of 3,4′-DMBP and 4,4′-DMBP isomers at the outlet of the packed bed substantially before the 3,3′-DMBP isomer reaches the outlet of the packed bed. 15. The process of claim 14 , further comprising passing the raffinate mixture through multiple chromatographic columns containing packed beds of 12-member ring zeolite in a simulated moving bed separation system. 16. The process of claim 7 , further comprising desorbing the 3,3′-DMBP from the 12-member ring zeolite with a second solvent.
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