US4277327A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Treatment of phenol-containing feed streams
Assignee: ExxonMobil Technology and Engineering Co
•
Filing: 1979-11-19
•
Granted: 1981-07-07
•
Expires: 1999-11-19
Abstract
Abstract Phenol-containing streams are treated by an oxygen-alkylation process to convert substantially all of the phenol groups to ether groups. The oxygen-alkylation process comprises contacting the phenol-containing stream, preferably a coal liquid, with (a) a basic solution comprising one or more oxides or hydroxides of a metal selected from the group consisting of alkali and alkaline-earth metals; and (b) an alkylating agent represented by the formula RX where R is a C1 to C18 alkyl, allyl, cycloalkyl, haloalkyl, benzyl or arylalkyl group provided X is located on the alkyl portion of the compound and X is sulfate or a halide selected from the group consisting of chlorine, bromine and iodine.
Inventors
- 👤 Richard H. Schlosberg
- 👤 Martin L. Gorbaty
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 06:44
CPC Classifications
C; C10; C10G; C10G29/00; C10G29/20; C10G29/205; C07; C07C; C07C41/00; C07C41/01; C07C41/16
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
136 words
A process for improving the properties of coal liquids by oxygen-alkylation comprising contacting the coal liquid at a temperature less than about 100° C. with: (a) an aqueous base solution comprised of an alkali or alkaline-earth metal oxide or hydroxide or mixtures thereof, wherein the base solution is capable of removing the acidic protons of the phenolic and carboxylic functionality of the coal liquid and forming the corresponding metal phenate salt; and (b) one or more alkylating agents represented by the formula RX where R is a C 1 to about C 18 group selected from the group consisting of alkyl, allyl, cycloalkyl, haloalkyl, benzyl and arylalkyl, provided X is located on the alkyl portion of the alkylating agent and X is sulfate or a halide selected from the group consisting of chlorine, bromine and iodine.
Claim 2
Dependent Claim
136 words
A process for improving the properties of coal liquids by oxygen-alkylation comprising contacting the coal liquid at a temperature less than about 100° C. with: (a) an aqueous base solution comprised of an alkali or alkaline-earth metal oxide or hydroxide or mixtures thereof, wherein the base solution is capable of removing the acidic protons of the phenolic and carboxylic functionality of the coal liquid and forming the corresponding metal phenate salt; and (b) one or more alkylating agents represented by the formula RX where R is a C 1 to about C 18 group selected from the group consisting of alkyl, allyl, cycloalkyl, haloalkyl, benzyl and arylalkyl, provided X is located on the alkyl portion of the alkylating agent and X is sulfate or a halide selected from the group consisting of chlorine, bromine and iodine.
Claim 3
Dependent Claim
23 words
The process of claim 1 wherein the base solution is a hydroxide selected from the group consisting of alkali metals, calcium and barium.
Claim 4
Dependent Claim
21 words
The process of claim 1 wherein the alkylating agent is a C 1 to C 4 alkyl sulfate or alkyl halide.
Claim 5
Dependent Claim
23 words
The process of claim 3 wherein the alkylating agent is selected from the group consisting of methyl chloride, methyl iodide, and dimethyl sulfate.
Claim 6
Dependent Claim
23 words
The process of claim 4 wherein the base solution is a hydroxide selected from the group consisting of alkali metals, calcium and barium.
Claim 7
Dependent Claim
23 words
The process of claim 1 wherein at least twice the stoichiometric amount of base to phenolic content of the coal liquid is employed.
Claim 8
Dependent Claim
136 words
A process for improving the properties of a phenol-containing stream by oxygen-alkylation comprising contacting the stream at a temperature less than about 100° C. with: (a) an aqueous base solution comprised of an alkali or alkaline-earth metal oxide or hydroxide or mixtures thereof, wherein the base solution is capable of removing the acidic protons of the phenolic and carboxylic functionality of the stream and forming the corresponding metal phenate salt; and (b) one or more alkylating agents represented by the formula RX where R is a C 1 to about C 18 group selected from the group consisting of alkyl, allyl, cycloalkyl, haloalkyl, benzyl and arylalkyl, provided X is located on the alkyl portion of the alkylating agent and X is a sulfate or a halide selected from the group consisting of chlorine, bromine and iodine.
Claim 9
Dependent Claim
136 words
A process for improving the properties of a phenol-containing stream by oxygen-alkylation comprising contacting the stream at a temperature less than about 100° C. with: (a) an aqueous base solution comprised of an alkali or alkaline-earth metal oxide or hydroxide or mixtures thereof, wherein the base solution is capable of removing the acidic protons of the phenolic and carboxylic functionality of the stream and forming the corresponding metal phenate salt; and (b) one or more alkylating agents represented by the formula RX where R is a C 1 to about C 18 group selected from the group consisting of alkyl, allyl, cycloalkyl, haloalkyl, benzyl and arylalkyl, provided X is located on the alkyl portion of the alkylating agent and X is a sulfate or a halide selected from the group consisting of chlorine, bromine and iodine.
Claim 10
Dependent Claim
23 words
The process of claim 7 wherein the base solution is a hydroxide selected from the group consisting of alkali metals, calcium and barium.
Claim 11
Dependent Claim
21 words
The process of claim 7 wherein the alkylating agent is a C 1 to C 4 alkyl sulfate or alkyl halide.
Claim 12
Dependent Claim
23 words
The process of claim 9 wherein the alkylating agent is selected from the group consisting of methyl chloride, methyl iodide and dimethyl sulfate.
Claim 13
Dependent Claim
23 words
The process of claim 10 wherein the base solution is a hydroxide selected from the group consisting of alkali metals, calcium and barium.
Claim 14
Dependent Claim
22 words
The process of claim 7 wherein at least twice the stoichiometric amount of base to phenolic content of the stream is employed.
Claim 15
Dependent Claim
13 words
The process of claim 7 wherein the phenol-containing stream is a waste-water stream.
References Cited (Backward Citations)
US1819687A
Cited
US1801901A
Cited
GB494450A
Cited
FR838900A
Cited
US3617513A
Cited
US3671422A
Cited
US3928171A
Cited
BE866064A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-07-06 | 1985-01-05 | 1985-07-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-06 | 1989-01-05 | 1989-07-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-06 | 1993-01-05 | 1993-07-07 | $7700.00 | Window Closed / Lapsed |