US4277326A
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US
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Oxygen alkylation of phenol-containing hydrocarbonaceous streams
Assignee: ExxonMobil Technology and Engineering Co
•
Filing: 1979-11-19
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Granted: 1981-07-07
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Expires: 1999-11-19
Abstract
Abstract Process for improving properties of phenol-containing hydrocarbonaceous streams such as a coal liquid by contacting stream with (a) a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of multivalent metals capable of forming hydroxy metal phenates with the phenols of the stream; and (b) one or more alkylating agents represented by the formula RX where R is a C1 to C18 group selected from the group consisting of alkyl, allyl, cycloalkyl, haloalkyl, benzyl, and arylalkyl, provided X is located on the alkyl portions of the alkylating agent and X is sulfate or a halide.
Inventors
- 👤 Richard H. Schlosberg
- 👤 Charles G. Scouten
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 05:14
CPC Classifications
C; C10; C10G; C10G29/00; C10G29/20; C10G29/205; C07; C07C; C07C41/00; C07C41/01; C07C41/16
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
134 words
A process for improving the properties of phenol-containing coal liquids by oxygen-alkylation which process comprises contacting the coal liquid with: (a) a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of one or more multivalent metals capable of forming hydroxy metal phenates with phenols of the coal liquid, wherein said contacting is performed at temperatures lower than the decomposition temperature of the hydroxy metal phenates; 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
134 words
A process for improving the properties of phenol-containing coal liquids by oxygen-alkylation which process comprises contacting the coal liquid with: (a) a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of one or more multivalent metals capable of forming hydroxy metal phenates with phenols of the coal liquid, wherein said contacting is performed at temperatures lower than the decomposition temperature of the hydroxy metal phenates; 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 multivalent metal is selected from the group consisting of Ca, Ba, Sr and Ni +++ .
Claim 4
Dependent Claim
13 words
The process of claim 1 wherein the multivalent metal composition is a hydroxide.
Claim 5
Dependent Claim
13 words
The process of claim 3 wherein the multivalent metal composition is calcium hydroxide.
Claim 6
Dependent Claim
23 words
The process of claim 1 wherein the coal liquid contains a stoichiometric amount of water to hydrolyze any multivalent metal oxides to hydroxides.
Claim 7
Dependent Claim
21 words
The process of claim 1 wherein the alkylating agent is a C 1 to C 4 alkyl halide or alkyl sulfate.
Claim 8
Dependent Claim
25 words
The process of claim 6 wherein the alkylating agent is selected from the group consisting of methyl chloride, methyl bromide, methyl iodide, and dimethyl sulfate.
Claim 9
Dependent Claim
21 words
The process of claim 2 wherein the alkylating agent is a C 1 to C 4 alkyl halide or alkyl sulfate.
Claim 10
Dependent Claim
134 words
A process for improving the properties of phenol-containing hydrocarbonaceous streams by oxygen-alkylation, the process which comprises contacting the stream with: (a) a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of one or more multivalent metals capable of forming hydroxy metal phenates with the phenols of the stream, wherein said contacting is performed at temperatures lower than the decomposition temperature of the hydroxy metal phenates; 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 11
Dependent Claim
134 words
A process for improving the properties of phenol-containing hydrocarbonaceous streams by oxygen-alkylation, the process which comprises contacting the stream with: (a) a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of one or more multivalent metals capable of forming hydroxy metal phenates with the phenols of the stream, wherein said contacting is performed at temperatures lower than the decomposition temperature of the hydroxy metal phenates; 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 12
Dependent Claim
23 words
The process of claim 9 wherein the multivalent metal is selected from the group consisting of Ca, Ba, Sr and Ni +++ .
Claim 13
Dependent Claim
13 words
The process of claim 9 wherein the multivalent metal composition is a hydroxide.
Claim 14
Dependent Claim
13 words
The process of claim 11 wherein the multivalent metal composition is calcium hydroxide.
Claim 15
Dependent Claim
22 words
The process of claim 9 wherein the stream contains a stoichiometric amount of water to hydrolyze any multivalent metal oxides to hydroxides.
Claim 16
Dependent Claim
21 words
The process of claim 9 wherein the alkylating agent is a C 1 to C 4 alkyl halide or alkyl sulfate.
Claim 17
Dependent Claim
25 words
The process of claim 14 wherein the alkylating agent is selected from the group consisting of methyl chloride, methyl bromide, methyl iodide and dimethyl sulfate.
Claim 18
Dependent Claim
21 words
The process of claim 10 wherein the alkylating agent is a C 1 to C 4 alkyl halide or alkyl sulfate.
Claim 19
Dependent Claim
145 words
A process for improving the properties of phenol-containing hydrocarbonaceous streams by oxygen-alkylation which process comprises: (a) contacting the stream with a multivalent metal composition selected from the group consisting of one or more multivalent metals capable of forming hydroxy metal phenates with the phenols of the stream, wherein said contacting is performed at temperatures lower than the decomposition temperature of the hydroxy metal phenates; (b) separating the hydroxy metal phenates from the treated stream; (c) reacting the hydroxy metal phenate with 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 20
Dependent Claim
145 words
A process for improving the properties of phenol-containing hydrocarbonaceous streams by oxygen-alkylation which process comprises: (a) contacting the stream with a multivalent metal composition selected from the group consisting of one or more multivalent metals capable of forming hydroxy metal phenates with the phenols of the stream, wherein said contacting is performed at temperatures lower than the decomposition temperature of the hydroxy metal phenates; (b) separating the hydroxy metal phenates from the treated stream; (c) reacting the hydroxy metal phenate with 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 21
Dependent Claim
23 words
The process of claim 17 wherein the multivalent metal is selected from the group consisting of Ca, Br, Sr and Ni +++ .
Claim 22
Dependent Claim
13 words
The process of claim 17 wherein the multivalent metal composition is a hydrxide.
Claim 23
Dependent Claim
13 words
The process of claim 19 wherein the multivalent metal composition is calcium hydroxide.
Claim 24
Dependent Claim
22 words
The process of claim 17 wherein the stream contains a stoichiometric amount of water to hydrolyze any multivalent metal oxides by hydroxides.
Claim 25
Dependent Claim
21 words
The process of claim 17 wherein the alkylating agent is a C 1 to C 4 alkyl halide or alkyl sulfate.
Claim 26
Dependent Claim
25 words
The process of claim 22 wherein the alkylating agent is selected from the group consisting of methyl chloride, methyl bromide, methyl iodide and dimethyl sulfate.
Claim 27
Dependent Claim
21 words
The process of claim 18 wherein the alkylating agent is a C 1 to C 4 alkyl halide or alkyl sulfate.
Claim 28
Dependent Claim
18 words
The process of claim 17 wherein the hydroxy metal phenate is dried before reacting with the alkylating agent.
Claim 29
Dependent Claim
23 words
The process of claim 17 wherein the hydroxy metal phenate is reacted with the alkylating agent in the presence of a polar solvent.
Claim 30
Dependent Claim
21 words
The process of claim 26 wherein the polar solvent is selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N,N,N,N-tetramethylurea, and N-methylpyrrolidone.
Claim 31
Dependent Claim
27 words
The process of claim 17 wherein the separation of the hydroxy metal phenates is done by concentrating the phenates in a minor portion of the feed stream.
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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 |