# US 10,308,579 B2 · Method of bisphenol manufacture

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- Number: US 10,308,579 B2
- Document ID: US10308579B2
- Status: Granted
- Kind: B2
- Application number: 15/759,919
- Filed: 2016-12-06
- Published: 2018-09-20
- Granted: 2019-06-04
- Earliest claimed: 2015-12-11
- Assignees: Sabic Global Technologies B.V.
- Applicants: SABIC Global Technologies B.V.
- Inventors: Satish Chandra Pandey; Gaurav Mediratta; Alvaro Carrillo
- Web page: https://patentgrep.com/patent/US10308579B2

## CPC

- C07C 37/20: using aldehydes or ketones
- C07C 39/16: Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
- H01M 10/052: Li-accumulators
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 10/0565: Polymeric materials, e.g. gel-type or solid-type
- H01M 10/0587: of accumulators having only wound construction elements, i.e. wound positive electrodes, wound negative electrodes and wound separators
- H01M 10/613: Cooling or keeping cold
- H01M 10/6551: Surfaces specially adapted for heat dissipation or radiation, e.g. fins or coatings
- C07C 2527/03: Acids of sulfur other than sulfhydric acid or sulfuric acid, e.g. halosulfonic acids
- H01M 2300/0065: Solid electrolytes
- Y02E 60/10: Energy storage using batteries
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- Y02T 10/70: Energy storage systems for electromobility, e.g. batteries
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02T: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION

## Abstract

An improved method of manufacture of a bisphenol comprises heating a monohydric phenol to a first temperature sufficient to melt the monohydric phenol; adding a carbonyl compound to 2.0-3.0 molar equivalents, based on the moles of carbonyl compound, of the monohydric phenol in the presence of catalytic amounts of an organosulfonic acid catalyst and a reaction promoter at a second temperature sufficient to maintain unreacted monohydric phenol in a molten state; increasing the temperature to a third temperature higher than the second temperature, and mixing for a time sufficient to produce the bisphenol in a yield of 80 to 100%, based on the amount of carbonyl compound; wherein mineral acids, Lewis acids, and ion exchange resins are not used. The method is applicable to the manufacture of 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, a useful intermediate for the manufacture of bi-functional poly(phenylene ether)s.

## Claims

### Claim 1

A method of manufacture of a bisphenol of chemical structure:
wherein each R1 is independently selected from the group consisting of hydrogen, halogen, methoxy, and C1-12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl; each R2 is independently selected from the group consisting of hydrogen, halogen, and C1-12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, and each R3 is independently selected from the group consisting of hydrogen, halogen, and C1-11 hydrocarbyl, the method comprising:
heating a monohydric phenol of chemical structure:
wherein R1 and R2 are as defined above, to a first temperature sufficient to melt the monohydric phenol;
adding a carbonyl compound of chemical structure:
wherein R3 is as defined above, to 2.0 to 2.5 molar equivalents, based on the moles of carbonyl compound, of the monohydric phenol in the presence of catalytic amounts of an organosulfonic acid catalyst and a reaction promoter at a second temperature sufficient to maintain unreacted monohydric phenol in a molten state;
increasing the temperature to a third temperature higher than the second temperature, and mixing for a time sufficient to produce the bisphenol in a yield of 80 to 100%, based on the amount of carbonyl compound;
wherein mineral acids, Lewis acids, and ion exchange resins are not used.

### Claim 2 (depends on 1)

The method of claim 1, wherein the monohydric phenol is selected from phenol, 2-methylphenol, 2,6-dimethylphenol, 2,3,6-trimethylphenol, 2-methyl-6-phenylphenol, and combinations thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein the carbonyl compound is formaldehyde, a C2-12 aldehyde, or C3-12 ketone.

### Claim 4 (depends on 1)

The method of claim 1, wherein the carbonyl compound is selected from formaldehyde, acetaldehyde, acetone, cyclohexanone, and combinations thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the organosulfonic acid catalyst is selected from dodecylbenzene sulfonic acid, ethylbenzene sulfonic acid, butylnaphthalene sulfonic acid, and combinations thereof.

### Claim 6 (depends on 1)

The method of claim 1, wherein the reaction promoter is selected from 3-mercaptopropionic acid (3-MPA), 4-mercaptobutyric acid, 2-mercaptoisobutryric acid, 3-mercaptoisobutyric acid, and combinations thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein the carbonyl compound is added below a surface of molten monohydric phenol.

### Claim 8 (depends on 1)

The method of claim 1, wherein the organosulfonic acid catalyst is added simultaneously with the carbonyl compound, but as a separate stream.

### Claim 9 (depends on 1)

The method of claim 1, wherein the organosulfonic acid comprises, based on the moles of carbonyl compound, 0.05 to 0.4 molar equivalent of dodecylbenzene sulfonic acid and the reaction promoter comprises 0.03 to 0.2 molar equivalent of 3-mercaptopropionic acid.

### Claim 10 (depends on 1)

The method of claim 1, wherein each occurrence of R1 and R3 is methyl, and each occurrence of R2 is hydrogen.

### Claim 11 (depends on 1)

The method of claim 1, wherein the bisphenol is of chemical structure:
and
wherein the method comprises:
addition of acetone to 2.0 to 2.5 molar equivalents of 2,6-dimethylphenol in the presence of catalytic amounts of an organosulfonic acid catalyst and a reaction promoter at a second temperature of 40 to 50° C.; and
increasing the temperature to a third temperature of 70 to 80° C. and mixing.

### Claim 12 (depends on 11)

The method of claim 11, wherein the adding is done for 3 to 6 hours; and
the mixing is done for 18 to 36 hours.