EP0034649A2
Expired / Lapsed
EP
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Alkoxylation of phenolic compounds
Assignee: ConocoPhillips Co
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Filing: 1980-10-15
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Granted: —
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Expires: 2000-10-15
Abstract
Abstract Cresylic acid ethoxylation is catalyzed by basic compounds and salts of alkaline earth metals. Ethoxylates from such reactions have narrow ethylene oxide distributions, lower pour points and lower by-products as compared to alkali base catalyzed ethoxylation. Suitable catalysts include strontium-containing and barium-containing materials. The catalyst also includes co-catalyst combinations using these materials with one or more promoters including polyols, amines, amides, carboxylic acids and phenols. The co-catalyst combinations can be preformed prior to introduction into the reaction mixture.
Inventors
- 👤 Kang Yang
- 👤 Gerald Lee Nield
- 👤 Paul Howard Washecheck
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-29 16:41
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/02; B01J31/0234; B01J31/0235; B01J31/0245; B01J31/0247; B01J23/00; B01J23/02; B01J31/0201; B01J31/0202; B01J31/0205; B01J31/0207; B01J31/0208; B01J31/0237; B01J31/04; B01J31/26; C; C07; C07C; C07C41/00; C07C41/01; C07C41/02; C07C41/03; B01J2231/00; B01J2231/40; B01J2231/48
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
114 words
A method for the alkoxylation of cresylic acid containing from about 6 to about 36 carbon atoms comprising carrying out said alkoxylation in the presence of basic barium-containing and strontium-containing materials wherein the cresylic acids are a phenolic compound or a mixture of phenolic compounds having the general formula wherein R 1 , R 2 , R 3 , R 4 , and RS are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, substituted aryl groups, halogen, hydroxyl, nitro, ether, or carbonyl and wherein in addition the R-designated groups can contain one or more functionalities selected from the group consisting-of halogen, ether, nitro, carboxyl, carbonyl, amine, amide, or hydroxyl.
Claim 2
Independent Claim
114 words
A method for the alkoxylation of cresylic acid containing from about 6 to about 36 carbon atoms comprising carrying out said alkoxylation in the presence of basic barium-containing and strontium-containing materials wherein the cresylic acids are a phenolic compound or a mixture of phenolic compounds having the general formula wherein R 1 , R 2 , R 3 , R 4 , and RS are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, substituted aryl groups, halogen, hydroxyl, nitro, ether, or carbonyl and wherein in addition the R-designated groups can contain one or more functionalities selected from the group consisting-of halogen, ether, nitro, carboxyl, carbonyl, amine, amide, or hydroxyl.
Claim 3
Dependent Claim
153 words
A method as described in claim 1 wherein in addition an effective amount of a catalyst promoter or mixture of catalyst promoters is used, wherein the catalyst promoter is selected from the group consisting of a) polyols containing a total of from 2 to 30 carbon atoms and having a boiling point above 100°C; b) aldehydes and ketones containing a total of from 2 to 30 carbon atoms and having a boiling point above 100°C; c) amides containing a total of from 1 to 30 carbon atoms and having a boiling point above 100°C; d) amines containing a total of from 1 to 30 carbon atoms and having a boiling point above 100°C; - e) organic acids containing a total of from 1 to 30 carbon atoms and having a boiling point of 100°C; f) phenols containing a total of from 6 to 30 carbon atoms and having a boiling point above 100°C.
Claim 4
Dependent Claim
431 words
A method as described in claim 2 wherein a) the polyol promoters contain 2 or more hydroxyl containing groups of the general formula wherein R 1 , R 2 , and R 3 are, independently, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or hydrogen and wherein the R-designated groups in addition can contain one or more functional groups selected from the group consisting of ether, amine, carboxyl, halogen, nitro, carbonyl, and amide; ' b) the aldehyde and ketone promoters contain one or more carbonyl containing groups of the general formula wherein R 1 , and R 2 are, independently, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups, or hydrogen, and wherein the R-designated groups in addition can contain one or more functional groups selected from the group consisting of hydroxyl, ether, carboxyl, carbonyl, amine, nitro or halogen; c) the primary, secondary or tertiary amide promoters contain one or more amide containing groups of the general formula wherein R l , R 2 1 and R 3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups or aryl groups and wherein the R-designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, ether, carboxyl, carbonyl, amine, nitro or halogen; d) the primary, secondary or tertiary amine promoters contain one or more amine containing groups of the general formula wherein R 1 , R 2 , and R 3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, or aryl groups, and wherein the R - designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, ether, carbonyl, halogen, carboxyl, nitro, or amide; e) the organic acid promoters contaip one or more carboxylic acid containing group of the general formula wherein R 1 is a hydrogen, linear or branched acyclic group, alicylic group, cyclic group, or aryl group and wherein R can in addition contain one or more functional groups selected from the group consisting of carbonyl, hydroxyl, halogen, ether, nitro, amine, or amide; f) the phenol promoters have one or more functional groups of the general formula wherein R 1 , R 2 , R 3 , R4, and R 5 are, independently, hydrogen, halogen, hydroxyl, nitro, ether, or carbonyl, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or substituted aryl groups wherein in addition the R-designated groups can contain one or more functional groups selected from the group consisting of halogen, ether, nitro, carboxyl, carbonyl, amine, amide, or hydroxyl.
Claim 5
Dependent Claim
22 words
A method as described in claim 3 wherein the alkoxylation is carried out using ethylene oxide, propylene oxide, or mixtures of these.
Claim 6
Dependent Claim
42 words
A method as described in claim 4 wherein the catalyst is selected from the group consisting of strontium metal, strontium hydride, strontium hydroxide, hydrated strontium hydroxide, strontium oxide, barium metal, barium hydride, barium hydroxide, hydrated barium hydroxide, barium oxide or mixtures thereof.
Claim 7
Dependent Claim
27 words
A method as described in claim 5 wherein the reaction is carried out at a pressure of u p to about 100 pounds per square inch gauge.
Claim 8
Dependent Claim
41 words
A method as described in claim 6 wherein ethylene oxide, propylene oxide or mixtures thereof are used as the alkoxylation agent and a mole adduct ratio ranges from about 20 weight percent to about 80 weight percent of the alkoxylated product.
Claim 9
Dependent Claim
38 words
A method as described in claim 7 wherein the barium or strontium-containing catalyst or mixture thereof is present in an amount of from about 0.05 to about 5.0% by weight based upon the cresylic acid to be reacted.
Claim 10
Dependent Claim
14 words
A method as described in claim 2 when carried out in a continuous reaction.
Claim 11
Independent Claim
521 words
A method of preparing an alkoxylation catalyst for the alkoxylation of cresylic acids containing from 6 to 36 carbon atoms with an alkoxylating agent selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide, said catalyst comprising a metal compound selected from the group consisting of strontium metal, strontium hydride, strontium oxide, strontium hydroxide, hydrated strontium hydroxide, barium metal, barium hydride, barium oxide, barium hydroxide and hydrated barium hydroxide preformed with a promoter or promoters selected from the group consisting of a) polyols containing 2 or more hydroxyl containing groups of the general formula wherein R l , R 21 and R 3 are, independently, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or hydrogen and wherein the R-designated groups in addition can contain one or more functional groups selected from the group consisting of ether, amine; carboxyl, halogen, nitro, carbonyl, and amide; b) aldehydes and ketones containing one or more carbonyl containing groups of the general formula wherein R 1 , and R 2 are, independently, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or hydrogen, and wherein the R-designated groups in addition can contain one or more functional groups selected from the group consisting of hydroxyl, ether, carboxyl, carbonyl, amine, nitro or halogen; c ) primary, secondary or tertiary amides containing one or more amide containing groups of the general formula wherein R1 , R2 , and R 3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups or aryl groups and wherein the R-designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, ether, carboxyl, carbonyl, amine, nitro or halogen; d) primary, secondary or tertiary amines containing one or more amine containing groups of the general formula wherein R l , R 2 , and R 3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, or aryl groups, and wherein the R-designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, ether, carbonyl, halogen, carboxyl, nitro, or amide; e) organic acids containing one or more carboxylic acid containing group of the general formula wherein R 1 is a hydrogen, linear or branched acyclic group, alicyclic group, cyclic group, or aryl group and wherein R can in addition, contain one or more functional groups selected from the group consisting of carbonyl, hydroxyl, halogen, ether, nitro, amine, or amide; f) phenols having one or more functional groups of the general formula wherein R l , R 2 , R 3 , R 4 , and R 5 are, independently, hydrogen, halogen, hydroxyl, nitro, ether, or carbonyl, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or substituted aryl groups wherein in addition the R-designated groups can contain one or more .unctional groups selected from the group consisting of halogen, ether, nitro, carboxyl, carbonyl, amine, amide, or hydroxyl, the method comprising heating a metal component with one or more promoters at a temperature up to 175°C for an effective period of time and recovering the preformed catalyst.
Claim 12
Independent Claim
521 words
A method of preparing an alkoxylation catalyst for the alkoxylation of cresylic acids containing from 6 to 36 carbon atoms with an alkoxylating agent selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide, said catalyst comprising a metal compound selected from the group consisting of strontium metal, strontium hydride, strontium oxide, strontium hydroxide, hydrated strontium hydroxide, barium metal, barium hydride, barium oxide, barium hydroxide and hydrated barium hydroxide preformed with a promoter or promoters selected from the group consisting of a) polyols containing 2 or more hydroxyl containing groups of the general formula wherein R l , R 21 and R 3 are, independently, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or hydrogen and wherein the R-designated groups in addition can contain one or more functional groups selected from the group consisting of ether, amine; carboxyl, halogen, nitro, carbonyl, and amide; b) aldehydes and ketones containing one or more carbonyl containing groups of the general formula wherein R 1 , and R 2 are, independently, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or hydrogen, and wherein the R-designated groups in addition can contain one or more functional groups selected from the group consisting of hydroxyl, ether, carboxyl, carbonyl, amine, nitro or halogen; c ) primary, secondary or tertiary amides containing one or more amide containing groups of the general formula wherein R1 , R2 , and R 3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups or aryl groups and wherein the R-designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, ether, carboxyl, carbonyl, amine, nitro or halogen; d) primary, secondary or tertiary amines containing one or more amine containing groups of the general formula wherein R l , R 2 , and R 3 are, independently, hydrogen, linear or branched acyclic groups, alicyclic groups, cyclic groups, or aryl groups, and wherein the R-designated groups can in addition contain one or more functional groups selected from the group consisting of hydroxyl, ether, carbonyl, halogen, carboxyl, nitro, or amide; e) organic acids containing one or more carboxylic acid containing group of the general formula wherein R 1 is a hydrogen, linear or branched acyclic group, alicyclic group, cyclic group, or aryl group and wherein R can in addition, contain one or more functional groups selected from the group consisting of carbonyl, hydroxyl, halogen, ether, nitro, amine, or amide; f) phenols having one or more functional groups of the general formula wherein R l , R 2 , R 3 , R 4 , and R 5 are, independently, hydrogen, halogen, hydroxyl, nitro, ether, or carbonyl, linear or branched acyclic groups, alicyclic groups, cyclic groups, aryl groups or substituted aryl groups wherein in addition the R-designated groups can contain one or more .unctional groups selected from the group consisting of halogen, ether, nitro, carboxyl, carbonyl, amine, amide, or hydroxyl, the method comprising heating a metal component with one or more promoters at a temperature up to 175°C for an effective period of time and recovering the preformed catalyst.
Claim 13
Dependent Claim
22 words
A method as described in claim 10 wherein the metal compound is contacted with the promoter in the presence of a solvent.
Claim 14
Dependent Claim
20 words
A method as described in claim 2 wherein the promoter is an alcohol having a pKa of less than 17.
Claim 15
Dependent Claim
27 words
A method as described in claim 12'wherein the alcohol is selected from the group consisting of triphenylmethanol, trichloroethanol, trifluoroethanol, 2-nitroethanol, 2-chloroethanol, 2,2-dichloroethanol, 2-methoxyethanol, 2-chlorocyclohexanol, and ortho-chlorobenzyl alcohol.
References Cited (Backward Citations)
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