Method for reducing methylbenzofuran levels in high purity phenol

• US 6,388,144 B1
• Filed: 06/15/2001
• Issued: 05/14/2002
• Est. Priority Date: 06/15/2001
• Status: Expired due to Term

• Current Assignee: AdvanSix Resins & Chemicals, LLC (Advansix Inc.)
• Original Assignee: Sunoco, Inc. (Energy Transfer Operating, L.P.)
• Inventors: Wijesekera, Tilak P., Keenan, Scott R.
• Primary Examiner(s): SIEGEL, ALAN M
• Application Number:
  US09/882,447
• Time in Patent Office: 333 Days
• Field of Search: 568/754, 568/749, 568/758
• US Class Current: 568/754
• CPC Class Codes: C07C 37/685 Processes comprising at least two steps in series
• CPC Class Codes: C07C 37/82 by solid-liquid treatment; by chemisorption
• CPC Class Codes: C07C 37/86 by treatment giving rise to a chemical modification chemisorption C07C37/82
• CPC Class Codes: C07C 39/04 Phenol

Abstract

A process for treating phenol with a strong acid ion exchange resin to reduce the level of methylbenzofuran is provided. The process is capable of being carried out at elevated temperatures for extended periods, such that cooling of the phenol from distillation temperatures prior to the resin treatment is not required. The process can reduce or eliminate the substantial costs associated with conventional processes that require cooling and re-heating the phenol.

Claims

1. A continuous process for the reduction of methylbenzofuran impurities in a phenol stream, the process comprising the steps of;

treating the phenol stream containing methylbenzofuran impurities to reduce the level of acetol in the phenol,

passing the phenol stream through fixed bed containing a strong acid aromatic sulfonic acid resin at an operating temperature above about 130°

C.,

at a rate below about 12 bed volumes per hour to reduce the level of methylbenzofuran by conversion to higher boiling compounds; and

distilling the phenol to separate phenol from higher boiling compounds.

2. A process according to claim 1, wherein the phenol is contacted with a strong acid ion exchange resin at a temperature above about 150°

C.

3. A process according to claim 1, wherein the phenol is treated to reduce the level of acetol to less than 1 ppm.

4. A process according to claim 1, wherein the phenol is treated with an amine to reduce the level of acetol.

5. A process according to claim 4, wherein the level of methylbenzofuran is reduced by about 80% or more.

6. A process according to claim 5, wherein the level of methylbenzofuran is reduced to about 10 ppm or less.

7. A process according to claim 6, wherein the level of methylbenzofuran is reduced to about 3 ppm or less.

8. A process according to claim 1, wherein the phenol is contacted with the strong acid ion exchange resin at a rate below about 8 bed volumes per hour.

9. A continuous process for the reduction of methylbenzofuran impurities in phenol stream, the process comprising;

treating the phenol stream with an amine to reduce the level of acetol in the phenol, then

passing the phenol stream through fixed bed containing a strong acid aromatic sulfonic acid resin at an operating temperature above about 150°

C.,

at a rate below about 12 bed volumes per hour,

wherein the level of methylbenzofuran is reduced by about 80% or more.

10. A process according to claim 9, further comprising treating the phenol with an amine to reduce the level of acetol in the phenol to less than 1 ppm, then

passing the phenol through a fixed resin bed containing an aromatic sulfonic acid resin at a rate below about 8 bed volumes per hour,

wherein the level of methylbenzofuran is reduced to about 10 ppm or less.

11. A process according to claim 10, wherein the level of methylbenzofuran