Bridged phenol metal salt-halo carboxylic acid condensate additives for fuels
AssigneeThe Lubrizol Corporation
InventorThomas Frier Steckel
Life of this patent
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Abstract
Compositions made by reacting (I) a metal phenoxide salt of a bridged phenol of 2 to about 20 phenol groups and (II) a carboxylic acid reagent containing from one to three carboxyl-based groups and a halogen-substituted hydrocarbon-based aliphatic or alicyclic group containing a halogen atom are useful as additives for lubricants and normally liquid fuels. Analogous thiophenoxide-based compositions are similarly useful. These compositions can also be used as intermediates for the preparation of other useful additive compositions through their reaction with alcohols, amino compounds, reactive small ring heterocycles and basically reacting metal compounds.
Claims16
A normally liquid fuel composition comprising a major amount of a normally liquid fuel and about 1-10,000 parts per million parts by weight of fuel of a product made by reacting (I) at least one phenoxide metal salt of a bridged phenol having (a) at least 2 and up to about 20 phenolic moieties or thiophenol analogs thereof and (b) at least 1 and up to about 19 bridging linkages independently selected from the group consisting of covalent carbon-to-carbon signel bonds, ether linkages, sulfide linkages, polysulfide linkages of two to six sulfur atoms, sulfinyl linkages, sulfonyl linkages, methylene linkages, alkylene linkages, di(lower alkyl)methylene linkages, lower alkylene ether linkages, lower alkylene sulfide linkages, lower alkylene polysulfide linkages of two to six sulfur atoms, amino linkages, polyamino linkages and mixtures of said divalent bridging linkages with (II) at least one carboxylic acid reagent having 1 to about 3 Cox groups and a halogen-substituted hydrocarbon aliphatic or alicyclic group the ratio of equivalents of acid reagent to equivalents of phenoxide ranging between about 1:5 to about 5:1, wherein each Cox independently represents a member selected from the group consisting of a carboxylate of a Group IA metal, a carboxylic ester of a lower alkanol, a carboxamide of lower alkyl monoamines or ammonia, and a carboxylate of a lower alkyl monoamine or ammonia.
A normally liquid fuel composition comprising a major amount of a normally liquid fuel and about 1-10,000 parts per million parts by weight of fuel of a product made by reacting (I) at least one phenoxide metal salt of a bridged phenol of the general formula ##STR13## wherein n, n' and n" are each independently integers of 1-3;
- R, R' and R" are each independently aliphatic hydrocarbon groups of one to about 300 carbon atoms each;
- m, m' and m" are each independently integers of 0-3;
- N is an integer of 0-20 and each X is a divalent bridging linkage selected from the group consisting of covalent carbon-to-carbon single bonds, ether linkages, sulfide linkages, polysulfide linkages of two to six sulfur atoms, sulfinyl linkages, sulfonyl linkages, methylene linkages, alkylene linkages, di(lower alkyl)methylene linkages, lower alkylene ether linkages, lower alkylene sulfide linkages, lower alkylene polysulfide linkages of two to six sulfur atoms, amino linkages, polyamino linkages and mixtures of said divalent bridging linkages, with (II) at least one carboxylic acid reagent of the formula
- A--(Cox).sub.1-3
- wherein A represents a hydrocarbon aliphatic or alicyclic group containing at least one halogen atom and 1 to about 20 carbon atoms, each Cox independently representing a member selected from the group consisting of a carboxylate of a Group IA metal, a carboxylic ester of a lower alkanol, a carboxamide of lower alkyl monoamines or ammonia, and a carboxylate of a lower alkyl monoamine or ammonia, the ratio of equivalents of acid reagent to equivalents of phenoxide ranging between about 1:5 to about 5:1.
A normally liquid fuel composition comprising a major amount of a normally liquid fuel and about 1-10,000 parts per million parts by weight of fuel of a second product made by reacting at least one polyamine, higher polyhydric alcohol or mixture thereof with a first product made by reacting (I) at least one phenoxide metal salt of a bridged phenol of the general formula ##STR14## wherein n, n' and n" are each independently integers of 1-3;
- R, R' and R" are each independently aliphatic hydrocarbon groups of one to about 300 carbon atoms each;
- m, m' and m" are each independently integers of 0-3;
- N is an integer of 0-20 and each X is a divalent bridging linkage selected from the group consisting of covalent carbon-to-carbon single bonds, ether linkages, sulfide linkages, polysulfide linkages of two to six sulfur atoms, sulfinyl linkages, sulfonyl linkages, methylene linkages, alkylene linkages, di(lower alkyl)methylene linkages, lower alkylene ether linkages, lower alkylene sulfide linkages, lower alkylene polysulfide linkages of two to six sulfur atoms, amino linkages, polyamino linkages and mixtures of said divalent bridging linkages, with (II) at least one carboxylic acid reagent of the formula
- A--(Cox).sub.1-3
- wherein A represents a hydrocarbon aliphatic or alicyclic group containing at least one halogen atom and 1 to about 20 carbon atoms, each Cox independently representing a member selected from the group consisting of a carboxylate of a Group IA metal, a carboxylic ester of a lower alkanol, a carboxamide of lower alkyl monoamines or ammonia, and a carboxylate of a lower alkylmonoamine or ammonia, the ratio of equivalents of acid reagent to equivalents of phenoxide ranging between about 1:5 to about 5:1.
A normally liquid fuel composition comprising a major amount of a normally liquid fuel and about 1-10,000 parts per million parts by weight of fuel of an overbased, metal carboxylate made by reacting at least one basically reacting Group IIA oxide, hydroxide or alkoxide of a lower alkanol in the presence of a promoter and an acidic reagent with a product made by reacting (I) at least one phenoxide metal salt of a bridged phenol having (a) at least 2 and up to about 20 phenolic moieties or thiophenol analogs thereof and (b) at least 1 and up to about 19 bridging linkages independently selected from the group consisting of covalent carbon-to-carbon single bonds, ether linkages, sulfide linkages, polysulfide linkages of two to six sulfur atoms, sulfinyl linkages, sulfonyl linkages, methylene linkages, alkylene linkages, di(lower alkyl)methylene linkages, lower alkylene ether linkages, lower alkylene sulfide linkages, lower alkylene polysulfide linkages of two to six sulfur atoms, amino linkages, polyamino linkages and mixtures of said divalent bridging linkages with (II) at least one carboxylic acid reagent having 1 to about 3 Cox groups and a halogen-substituted hydrocarbon aliphatic or alicyclic group the ratio of equivalents of acid reagent to equivalents of phenoxide ranging between about 1:5 to about 5:1, wherein each Cox independently represents a member selected from the group consisting of a carboxylate of a Group IA metal, a carboxylic ester of a lower alkanol, a carboxamide of lower alkyl monoamines or ammonia, and a carboxylate of a lower alkyl monoamine or ammonia.
Dependencies are inferred from the claim text.