Patent US4347148A successfully refreshed from Google Patents.
US4347148A
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US
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Full and lubricant compositions containing nitro phenols
Assignee: Lubrizol Corp
•
Filing: 1979-11-19
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Granted: 1982-08-31
•
Expires: 1999-11-19
Abstract
Abstract Nitro phenols of the general formula ##STR1## wherein R is an aliphatic substituent of at least about 40 carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants and intermediates to such additives. These nitro phenols can be conveniently prepared by nitrating appropriate phenols. Typically nitro phenols are formed by nitration of alkyl phenols having an alkyl group of at least about 50 carbon atoms.
Inventors
- 👤 Kirk E. Davis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 06:21
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/096; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/61; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/42; C08; C08F; C08F8/00; C08F8/44; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/23; C10L1/231; C10L1/234; C10L1/238; C10M; C10M133/00; C10M133/52; C10M2203/00; C10M2203/02; C10M2203/022; C10M2203/024; C10M2203/04; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/024; C10M2205/026; C10M2205/028; C10M2207/00; C10M2207/04; C10M2207/044; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/34; C10M2207/40; C10M2207/402; C10M2207/404; C10M2209/00; C10M2209/02; C10M2209/10; C10M2209/103; C10M2209/104; C10M2209/105; C10M2209/109; C10M2209/11; C10M2209/111; C10M2211/00; C10M2211/06; C10M2213/00; C10M2213/02; C10M2213/06; C10M2213/062; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/08; C10M2215/082; C10M2215/20; C10M2215/202; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/02; C10M2219/024; C10M2219/04; C10M2219/044; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/06; C10M2223/061; C10M2223/065; C10M2227/00; C10M2227/02; C10M2227/04; C10M2229/00; C10M2229/04; C10M2229/042; C10M2229/045; C10M2229/046; C10M2229/047; C10M2229/048; C10M2229/05; C10N; C10N2040/00; C10N2040/02; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/06; C10N2040/08; C10N2040/20; C10N2040/25; C10N2040/251; C10N2040/252; C10N2040/253; C10N2040/255; C10N2040/26; C10N2040/28
Claims Analysis
Total Claims: 83
Claim 1
Independent Claim
125 words
A nitro phenol of the formula ##STR18## wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one -OH substituent attached directly to Ar; b and c are each independently integers of 1 up to three times the number of aromatic nuclei in Ar with the sum b+c not exceeding the number of unsatisfied valences in Ar, a is one and Ar is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, halo, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents and combinations of said optional substituents.
Claim 2
Dependent Claim
125 words
A nitro phenol of the formula ##STR18## wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one -OH substituent attached directly to Ar; b and c are each independently integers of 1 up to three times the number of aromatic nuclei in Ar with the sum b+c not exceeding the number of unsatisfied valences in Ar, a is one and Ar is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, halo, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents and combinations of said optional substituents.
Claim 3
Dependent Claim
20 words
A nitro phenol as claimed in claim 1 wherein R has an average of up to about 500 carbon atoms.
Claim 4
Dependent Claim
15 words
A nitro phenol as claimed in claim 2 wherein R is a purely hydrocarbyl substituent.
Claim 5
Dependent Claim
14 words
A nitro phenol as claimed in claim 3 wherein R is alkyl or alkenyl.
Claim 6
Dependent Claim
23 words
A nitro phenol as claimed in claim 1 wherein R is a substituent of at least about 50 to about 300 carbon atoms.
Claim 7
Dependent Claim
19 words
A nitro phenol as claimed in claim 5 wherein R is made from homopolymerized or interpolymerized C 2-10 olefins.
Claim 8
Dependent Claim
24 words
A nitro phenol as claimed in claim 6 wherein said olefins are selected from the group consisting of C 2-10 l-olefins and mixtures thereof.
Claim 9
Dependent Claim
24 words
A nitro phenol as claimed in claim 6 wherein said l-olefins are selected from the group consisting of ethylene, propylene, butylenes, and mixtures thereof.
Claim 10
Dependent Claim
15 words
A nitro phenol as claimed in claim 1 wherein b and c are each 1.
Claim 11
Dependent Claim
19 words
A nitro phenol as claimed in claim 4 wherein R is derived from homopolymerized or interpolymerized C 2-10 l-olefins.
Claim 12
Dependent Claim
24 words
A nitro phenol as claimed in claim 10 wherein said l-olefins are selected from the group consisting of ethylene, propylene, butylenes, and mixtures thereof.
Claim 13
Dependent Claim
82 words
A nitro phenol of the formula ##STR19## wherein R' is an aliphatic substituent having an average of from about 40 to about 500 carbon atoms in a position para to a hydroxyl group; R'" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents; and z is 0 or 1.
Claim 14
Dependent Claim
82 words
A nitro phenol of the formula ##STR19## wherein R' is an aliphatic substituent having an average of from about 40 to about 500 carbon atoms in a position para to a hydroxyl group; R'" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents; and z is 0 or 1.
Claim 15
Dependent Claim
23 words
A nitro phenol as claimed in claim 12 wherein R' is hydrocarbyl and contains at least about 50 to about 300 carbon atoms.
Claim 16
Dependent Claim
16 words
A nitro phenol as claimed in claim 13 wherein R' is an alkenyl or alkyl group.
Claim 17
Dependent Claim
12 words
A nitro phenol as claimed in claim 12 wherein z is zero.
Claim 18
Dependent Claim
23 words
A nitro phenol as claimed in claim 15 wherein R' contains an average of at least about 50 to about 300 carbon atoms.
Claim 19
Dependent Claim
21 words
A nitro phenol as claimed in claim 12 wherein R' is a substituent derived from homopolymerized or interpolymerized C 2-10 olefins.
Claim 20
Dependent Claim
26 words
A nitro phenol as claimed in claim 17 wherein said C 2-10 olefins are selected from the group consisting of C 2-10 l-olefins and mixtures thereof.
Claim 21
Dependent Claim
24 words
A nitro phenol as claimed in claim 18 wherein said l-olefins are selected from the group consisting of ethylene, propylene, butylenes, and mixtures thereof.
Claim 22
Dependent Claim
97 words
A nitro phenol of the formula ##STR20## wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one --OH substituent attached directly to Ar; b and c are each independently integers of 1 up to three times the number of aromatic nuclei in Ar with the sum b+c not exceeding the number of unsatisfied valences in Ar, a is one and Ar is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl or halo or combinations of said optional substituents.
Claim 23
Dependent Claim
97 words
A nitro phenol of the formula ##STR20## wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one --OH substituent attached directly to Ar; b and c are each independently integers of 1 up to three times the number of aromatic nuclei in Ar with the sum b+c not exceeding the number of unsatisfied valences in Ar, a is one and Ar is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl or halo or combinations of said optional substituents.
Claim 24
Dependent Claim
20 words
A nitro phenol as claimed in claim 20 wherein R has an average of up to about 500 carbon atoms.
Claim 25
Dependent Claim
15 words
A nitro phenol as claimed in claim 21 wherein R is a purely hydrocarbyl substituent.
Claim 26
Dependent Claim
14 words
A nitro phenol as claimed in claim 22 wherein R is alkyl or alkenyl.
Claim 27
Dependent Claim
23 words
A nitro phenol as claimed in claim 20 wherein R is a substituent of at least about 50 to about 300 carbon atoms.
Claim 28
Dependent Claim
19 words
A nitro phenol as claimed in claim 24 wherein R is made from homopolymerized or interpolymerized C 2-10 olefins.
Claim 29
Dependent Claim
24 words
A nitro phenol as claimed in claim 25 wherein said olefins are selected from the group consisting of C 2-10 l-olefins and mixtures thereof.
Claim 30
Dependent Claim
24 words
A nitro phenol as claimed in claim 25 wherein said l-olefins are selected from the group consisting of ethylene, propylene, butylenes, and mixtures thereof.
Claim 31
Dependent Claim
15 words
A nitro phenol as claimed in claim 20 wherein b and c are each 1.
Claim 32
Dependent Claim
33 words
A nitro phenol as claimed in claim 60 wherein R is a substituent having an average of at least about 40 carbon atoms and is derived from homopolymerized or interpolymerized C 2-10 l-olefins.
Claim 33
Dependent Claim
24 words
A nitro phenol as claimed in claim 29 wherein said l-olefins are selected from the group consisting of ethylene, propylene, butylenes, and mixtures thereof.
Claim 34
Dependent Claim
53 words
A nitro phenol of the formula ##STR21## wherein R' is an aliphatic substituent having an average of from about 40 to about 500 carbon atoms in a position para to a hydroxyl group; R'" is a member selected from the group consisting of lower alkyl or halo; and z is 0 or 1.
Claim 35
Dependent Claim
53 words
A nitro phenol of the formula ##STR21## wherein R' is an aliphatic substituent having an average of from about 40 to about 500 carbon atoms in a position para to a hydroxyl group; R'" is a member selected from the group consisting of lower alkyl or halo; and z is 0 or 1.
Claim 36
Dependent Claim
23 words
A nitro phenol as claimed in claim 31 wherein R' is hydrocarbyl and contains at least about 50 to about 300 carbon atoms.
Claim 37
Dependent Claim
16 words
A nitro phenol as claimed in claim 32 wherein R' is an alkenyl or alkyl group.
Claim 38
Dependent Claim
12 words
A nitro phenol as claimed in claim 31 wherein z is zero.
Claim 39
Dependent Claim
23 words
A nitro phenol as claimed in claim 34 wherein R' contains an average of at least about 50 to about 300 carbon atoms.
Claim 40
Dependent Claim
21 words
A nitro phenol as claimed in claim 31 wherein R' is a substituent derived from homopolymerized or interpolymerized C 2-10 olefins.
Claim 41
Dependent Claim
26 words
A nitro phenol as claimed in claim 36 wherein said C 2-10 olefins are selected from the group consisting of C 2-10 l-olefins and mixtures thereof.
Claim 42
Dependent Claim
24 words
A nitro phenol as claimed in claim 37 wherein said l-olefins are selected from the group consisting of ethylene, propylene, butylenes, and mixtures thereof.
Claim 43
Dependent Claim
121 words
A nitrated phenol made by nitrating with at least one nitrating agent at least one phenol of the formula (R).sub.a Ar'(OH).sub.c wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one --OH substituent attached directly to Ar'; c is one up to three times the number of aromatic nuclei in Ar', a is one and Ar' is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, halo, nitro, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents and combinations of said optional substituents.
Claim 44
Dependent Claim
121 words
A nitrated phenol made by nitrating with at least one nitrating agent at least one phenol of the formula (R).sub.a Ar'(OH).sub.c wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one --OH substituent attached directly to Ar'; c is one up to three times the number of aromatic nuclei in Ar', a is one and Ar' is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, halo, nitro, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents and combinations of said optional substituents.
Claim 45
Dependent Claim
20 words
A nitrated phenol as claimed in claim 39 wherein R has an average of up to about 500 carbon atoms.
Claim 46
Dependent Claim
58 words
A nitrated phenol as claimed in claim 39 wherein the nitrating agent is selected from the group consisting of nitric acid, No 2 , N 2 O 3 , N 2 O 4 , N 2 O 5 , NO 2 Cl, mixtures of alkali and alkaline earth metal nitrates with mineral acids, alkanoyl nitrates and mixtures thereof.
Claim 47
Dependent Claim
23 words
A nitrated phenol as claimed in claim 40 wherein R is hydrocarbyl and contains at least about 50 to about 300 carbon atoms.
Claim 48
Dependent Claim
22 words
A nitrated phenol as claimed in claim 32 wherein R is derived from homopolymerized or interpolymerized C 2-10 olefins and mixtures thereof.
Claim 49
Dependent Claim
15 words
A nitrated phenol as claimed in claim 43 wherein the nitrating agent is nitric acid.
Claim 50
Dependent Claim
14 words
A nitrated phenol as claimed in claim 44 wherein there are zero optional substituents.
Claim 51
Dependent Claim
90 words
A nitrated phenol made by nitrating with a nitrating agent at least one compound of the formula ##STR22## wherein R' is an aliphatic substituent having from about 40 to about 500 carbon atoms in a position para to the hydroxyl group; R'" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents; and z is 0 or 1.
Claim 52
Dependent Claim
90 words
A nitrated phenol made by nitrating with a nitrating agent at least one compound of the formula ##STR22## wherein R' is an aliphatic substituent having from about 40 to about 500 carbon atoms in a position para to the hydroxyl group; R'" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo, carboxy, carboxy ester of mono- and dihydric C 1-7 alkanols and carboxamide wherein the amide nitrogen can have up to 1 or 2 C 1-7 alkyl substituents; and z is 0 or 1.
Claim 53
Dependent Claim
22 words
A nitrated phenol as claimed in claim 46 wherein R' is derived from polymerized butylenes and mixtures thereof and z is zero.
Claim 54
Dependent Claim
34 words
A nitrated phenol as claimed in claim 46 wherein R' is an alkyl or alkenyl group derived from a homopolymerized or interpolymerized C 2-10 1-mono-olefin and contains about 50 to about 300 carbon atoms.
Claim 55
Dependent Claim
93 words
A nitrated phenol made by nitrating with at least one nitrating agent and at least one phenol of the formula (R).sub.a Ar'(OH).sub.c wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one --OH substituent attached directly to Ar'; c is 1 up to three times the number of aromatic nuclei in Ar', a is one and Ar' is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl or halo or combinations of said optional substituents.
Claim 56
Dependent Claim
93 words
A nitrated phenol made by nitrating with at least one nitrating agent and at least one phenol of the formula (R).sub.a Ar'(OH).sub.c wherein R is an aliphatic substituent of at least about 40 carbon atoms; R is para to at least one --OH substituent attached directly to Ar'; c is 1 up to three times the number of aromatic nuclei in Ar', a is one and Ar' is a benzene moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl or halo or combinations of said optional substituents.
Claim 57
Dependent Claim
20 words
A nitrated phenol as claimed in claim 49 wherein R has an average of up to about 500 carbon atoms.
Claim 58
Dependent Claim
58 words
A nitrated phenol as claimed in claim 49 wherein the nitrating agent is selected from the group consisting of nitric acid, NO 2 , N 2 O 3 , N 2 O 4 , N 2 O 5 , NO 2 Cl, mixtures of alkali and alkaline earth metal nitrates with mineral acids, alkanoyl nitrates and mixtures thereof.
Claim 59
Dependent Claim
23 words
A nitrated phenol as claimed in claim 50 wherein R is hydrocarbyl and contains at least about 50 to about 300 carbon atoms.
Claim 60
Dependent Claim
22 words
A nitrated phenol as claimed in claim 52 wherein R is derived from homopolymerized or interpolymerized C 2-10 olefins and mixtures thereof.
Claim 61
Dependent Claim
15 words
A nitrated phenol as claimed in claim 53 wherein the nitrating agent is nitric acid.
Claim 62
Dependent Claim
14 words
A nitrated phenol as claimed in claim 54 wherein there are zero optional substituents.
Claim 63
Dependent Claim
59 words
A nitrated phenol made by nitrating with a nitrating agent at least one compound of the formula ##STR23## wherein R' is an aliphatic substituent having from about 40 to about 500 carbon atoms in a position para to the hydroxyl group; R'" is a member selected from the group consisting of lower alkyl; and z is 0 or 1.
Claim 64
Dependent Claim
59 words
A nitrated phenol made by nitrating with a nitrating agent at least one compound of the formula ##STR23## wherein R' is an aliphatic substituent having from about 40 to about 500 carbon atoms in a position para to the hydroxyl group; R'" is a member selected from the group consisting of lower alkyl; and z is 0 or 1.
Claim 65
Dependent Claim
22 words
A nitrated phenol as claimed in claim 56 wherein R' is derived from polymerized butylenes and mixtures thereof and z is zero.
Claim 66
Dependent Claim
34 words
A nitrated phenol as claimed in claim 56 wherein R' is an alkyl or alkenyl group derived from a homopolymerized or interpolymerized C 2-10 1-mono-olefin and contains about 50 to about 300 carbon atoms.
Claim 67
Dependent Claim
33 words
A fuel or lubricant composition comprising a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of the nitro phenol claimed in claim 1.
Claim 68
Dependent Claim
33 words
A fuel or lubricant composition containing a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of the nitro phenol claimed in claim 12.
Claim 69
Dependent Claim
33 words
A fuel or lubricant composition containing a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of the nitro phenol claimed in claim 19.
Claim 70
Dependent Claim
33 words
A fuel or lubricant composition containing a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of the nitrated phenol claimed in claim 39.
Claim 71
Dependent Claim
33 words
A fuel or lubricant composition containing a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of the nitrated phenol claimed in claim 46.
Claim 72
Dependent Claim
33 words
A fuel or lubricant composition containing a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of the nitrated phenol claimed in claim 48.
Claim 73
Dependent Claim
7 words
A lubricant as claimed in claim 59.
Claim 74
Dependent Claim
7 words
A lubricant as claimed in claim 60.
Claim 75
Dependent Claim
7 words
A lubricant as claimed in claim 61.
Claim 76
Dependent Claim
7 words
A lubricant as claimed in claim 62.
Claim 77
Dependent Claim
7 words
A lubricant as claimed in claim 63.
Claim 78
Dependent Claim
7 words
A lubricant as claimed in claim 64.
Claim 79
Dependent Claim
26 words
A concentrate for treating lubricating oils or normally liquid fuels comprising a substantially inert solvent/diluent and at least one nitro phenol as claimed in claim 1.
Claim 80
Dependent Claim
26 words
A concentrate for treating lubricating oils or normally liquid fuels comprising a substantially inert solvent/diluent and at least one nitro phenol as claimed in claim 12.
Claim 81
Dependent Claim
26 words
A concentrate for treating lubricating oils or normally liquid fuels comprising a substantially inert solvent/diluent and at least one nitro phenol as claimed in claim 19.
Claim 82
Dependent Claim
26 words
A concentrate for treating lubricating oils or normally liquid fuels comprising a substantially inert solvent/diluent and at least one nitrated phenol as claimed in claim 39.
Claim 83
Dependent Claim
26 words
A concentrate for treating lubricating oils or normally liquid fuels comprising a substantially inert solvent/diluent and at least one nitrated phenol as claimed in claim 46.
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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) | 1985-08-30 | 1986-03-01 | 1986-08-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-30 | 1990-03-01 | 1990-08-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-30 | 1994-03-01 | 1994-08-31 | $7700.00 | Window Closed / Lapsed |