US2665253A - Mineral oil containing 1, 2-dialkoxy benzene as an oxidation inhibitor - Google Patents
Mineral oil containing 1, 2-dialkoxy benzene as an oxidation inhibitor Download PDFInfo
- Publication number
- US2665253A US2665253A US170021A US17002150A US2665253A US 2665253 A US2665253 A US 2665253A US 170021 A US170021 A US 170021A US 17002150 A US17002150 A US 17002150A US 2665253 A US2665253 A US 2665253A
- Authority
- US
- United States
- Prior art keywords
- benzene
- oil
- dialkoxy
- temperature conditions
- lubricating oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims description 38
- 230000003647 oxidation Effects 0.000 title description 16
- 238000007254 oxidation reaction Methods 0.000 title description 16
- 239000003112 inhibitor Substances 0.000 title description 13
- 239000002480 mineral oil Substances 0.000 title description 3
- 235000010446 mineral oil Nutrition 0.000 title description 3
- 239000010688 mineral lubricating oil Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 18
- 239000010687 lubricating oil Substances 0.000 description 12
- QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 150000001555 benzenes Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- GHKFGRVGAQYZNT-UHFFFAOYSA-N 1,2-dibutoxybenzene Chemical compound CCCCOC1=CC=CC=C1OCCCC GHKFGRVGAQYZNT-UHFFFAOYSA-N 0.000 description 1
- WFCGYXCDJFSUTO-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound C(C)OC1=C(C=CC=C1)OCC.C(C)OC1=C(C=CC=C1)OCC WFCGYXCDJFSUTO-UHFFFAOYSA-N 0.000 description 1
- XYJBIADAEAEWNG-UHFFFAOYSA-N 1,2-dipentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1OCCCCC XYJBIADAEAEWNG-UHFFFAOYSA-N 0.000 description 1
- MLSPENRYOBVDKN-UHFFFAOYSA-N 2,6-ditert-butyl-1-methylcyclohexa-2,4-dien-1-ol Chemical compound CC(C)(C)C1C=CC=C(C(C)(C)C)C1(C)O MLSPENRYOBVDKN-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006388 chemical passivation reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- Thisxinvention relates to mineral oil inhibited
- Many oxidation inhibitors have been proposedfor lubricating oil.
- certain alkylated phenols particularly tertiary-butyl-substituted phenols, such as 2,6-ditertiary butyl-4- methylphenol.
- Such alkylated phenols are generally eifective to inhibit oxidative deterioration of lubricating oil under ordinary conditions of use.
- Certain types of lubricating oil are used under unusually severe temperature: conditions, e. g. 250-450 F.; and oxidation inhibitors which are suitable at ordinary temperature conditions of use, e. g. 100-250 F., are frequently much less efiective and therefore unsuitable when used in such lubricating oil under such severe temperature conditions.
- Lubricating oil suitable for use under severe temperature conditions is required to have certain general specifications. For example, it must have relatively high flash point (A. S. T. M. D9246), e. g. 350 F. or above, and preferably above the highest temperature to which the oil is to be subjected; otherwise the oil will be too volatile for effective use under severe temperature conditions.
- relatively high flash point A. S. T. M. D9246
- Lubricating oil for certain specific applications involving severe temperature conditions must have additional specifications.
- lubricating oil for use in automotive fluid couplings where temperatures of about 400 F. must be withstood, are generally required to have an S. U. viscosity at 100 F. within the approximate range 170-190, and an S. U. viscosity at 210 F. not substantially less than 45.
- the present invention relates to the inhibition against oxidation of such lubricating oil and other lubricating oil suitable for use under severe temperature conditions.
- 1,2-dialkoxy benzenes oxidation inhibitor dation inhibitor for wherein the. alkoxy groupseach contain1-9' carbon. atoms are effective oxidation inhibitorsv for lubricatingv oil. used under severe temperature conditions.
- The. term 1,2-dialkoxy benzene is intended to indicatea substituted benzene having twoalkoxy substituents on adjacent carbon atoms of I the ring, butno hydroxy substituents.
- Preferred 1,2.-dialkoxy benzenes for use according to the inventionv are those wherein the alkoxy groups contain 24Sv carbon atoms.
- Oxidation inhibitors for use according to they invention should be substantially non-volatile at the. temperature atwhich the oil is used, i. e., they should have normal boiling points higher than the temperature of use of the oil.
- 1,,2-dialkoxy benzenes have high enough normaliboilingpointsfor almost all severe temperature uses ordinarily. encountered.
- Catechol diethyl ether (1,2-diethoxy benzene) is particularly advantageous for use according to the. invention; for it, hasbeen found that although catechol diethyl ether is generally inferior to at least one, widely used alkylated phenol of v the prior art as an oxioil under ordinary temperature conditions of. use, catechol diethyl ether is on the other hand distinctly superior to that same alkylated phenol oxidation inhibitor as an inhibitor for oil under severe temperature conditions of use.
- the amount of 1,2-dialkoxy benzene used in a given amount of lubricating oil will vary according to the degree of oxidation inhibition desired. Generally, satisfactory results are obtained with 0.01-2.00 weight percent of 1,2-dialkoxy benzene.
- the oil tested in this example was a solventrefined, dewaxed, acid-treated, and clay-treated distillate from mixed-base crude petroleum, the distillate having an S. U. viscosity at 10 F. of about 185 seconds, a viscosity index of about 90, and a flash point above 350 F.
- Two samples of such oil were tested for oxidation stability under severe temperature conditions by subjecting each to a temperature of 400 F. in an oven for hours, air being passed through the sample during this period at the rate of two bubbles per second. Before and after the oxidation period, the amount of naphtha-insoluble material in each sample and the S. U. viscosity at 210 F. of each sample were determined.
- Sample No. 1 contained one weight percent of 2,6-ditertiary butyllemethyl phenol as oxidation inhibitor, and sample'No. 2 contained one weight Percent In- Percent Increase in crease in Sample No. Naphtha- S. U. Vis- Insoluble cosity at Materials 210 F.
- lubricating oil inhibited with 2,6-ditertiary butyl-i-methyl phenol generally undergoes less oxidative deterioration under ordinary temperature conditions of use than does the same oil inhibited with catechol diethyl ether.
- an oil having properties generally like those of the oil tested in the example above, but having S. U. viscosity at 100 F. of about 160 was found to be more stable in the turbine oil oxidation stability test (A.S.T.M. D943-4'7T) which is conducted at 203 F., when inhibited with 2,6-ditertiary butyl-4-methyl phe- 1101 than when inhibited with catechol diethyl ether.
- 1,2-diethoxy benzene is used as an example of a 1,2- dialkoxy benzene
- similar results may be obtained when other 1,2-dialkoxy benzenes are used wherein the alkoxy groups contain 1-9- carbon atoms, e. g. 1,2-dimethoxy benzene, 1,2-dibutoxy benzene, 1,2-diamoxy benzene, etc.
- the two alkoxy groups contain the same number of carbon atoms; this is not strictly necessary, however, and generally satisfactory results may be obtained when using 1,2-dialkoxy benzenes such as l-ethoxy-Z-methoxy benzene, l-propoxy-2-methoxy benzene, l-butoxy-4-butyl-2-methoxy benzene, i-hexyloxy-2-methoxy benzene, etc.
- 1,2-dialkoxy benzenes such as l-ethoxy-Z-methoxy benzene, l-propoxy-2-methoxy benzene, l-butoxy-4-butyl-2-methoxy benzene, i-hexyloxy-2-methoxy benzene, etc.
- a composition comprising: a major proportion of mineral lubricating oil suitable for use under severe temperature conditions; and a minor proportion constituting an oxidationinhibiting quantity of a 1,2-dialkoxy benzene wherein the alkoxy groups contain 1-9 carbon atoms.
- composition according to claim 1 wherein said oil has a flash point of at least about 350 F.
- composition according to claim 1 wherein the weight percent of said 1,2-dialkoxy benzene in the composition is about 0.01-2.00%.
- composition according to claim 1 wherein said 1,2-dialkoxy benzene is 1,2-diethoxy benzene.
- the method of lubricating metal parts which comprises: contacting such parts with mineral lubricating oil at a temperature within the range from 250 F. to 450 F., said oil containing a minor proportion constituting an oxidation inhibiting quantity of a 1,2-dialkoxy benzene wherein the alkoxy groups contain 1-9 carbon atoms.
- a composition consisting essentially of a major proportion of mineral lubricating oil suitable for use under severe temperature conditions; and a minor proportion constituting an oxidation-inhibiting quantity of a 1,2-dialkoxy benzene wherein the alkoxy groups contain 1-9 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Jan. 5, 1954 MINERAL OIL CONT BENZENE ASfANO AINING- LZ-DIA-LKOXY-I XIDATION INHIBITOR William C. Hollibaugh, Springfield, Pa., assignor to Sun Oil. Company,
poration ofNcw-Jersey Philadelphia, .Pa.,. a. cor- No Drawing. Application June-23,1950; Serial No. 170,021-
6 Claims.
Thisxinvention relates to mineral oil inhibited Many oxidation inhibitors have been proposedfor lubricating oil. Among the best such inhibitors that have been proposed are certain alkylated phenols, particularly tertiary-butyl-substituted phenols, such as 2,6-ditertiary butyl-4- methylphenol. Such alkylated phenols are generally eifective to inhibit oxidative deterioration of lubricating oil under ordinary conditions of use.
Certain types of lubricating oil, however,- are used under unusually severe temperature: conditions, e. g. 250-450 F.; and oxidation inhibitors which are suitable at ordinary temperature conditions of use, e. g. 100-250 F., are frequently much less efiective and therefore unsuitable when used in such lubricating oil under such severe temperature conditions.
Lubricating oil suitable for use under severe temperature conditions is required to have certain general specifications. For example, it must have relatively high flash point (A. S. T. M. D9246), e. g. 350 F. or above, and preferably above the highest temperature to which the oil is to be subjected; otherwise the oil will be too volatile for effective use under severe temperature conditions.
Lubricating oil for certain specific applications involving severe temperature conditions must have additional specifications. For example, lubricating oil for use in automotive fluid couplings, where temperatures of about 400 F. must be withstood, are generally required to have an S. U. viscosity at 100 F. within the approximate range 170-190, and an S. U. viscosity at 210 F. not substantially less than 45. The present invention relates to the inhibition against oxidation of such lubricating oil and other lubricating oil suitable for use under severe temperature conditions.
I have discovered that 1,2-dialkoxy benzenes oxidation inhibitor. dation inhibitor for wherein the. alkoxy groupseach contain1-9' carbon. atoms are effective oxidation inhibitorsv for lubricatingv oil. used under severe temperature conditions. The. term 1,2-dialkoxy benzene, is intended to indicatea substituted benzene having twoalkoxy substituents on adjacent carbon atoms of I the ring, butno hydroxy substituents. Preferred 1,2.-dialkoxy benzenes for use according to the inventionv are those wherein the alkoxy groups contain 24Sv carbon atoms.
Oxidation inhibitors for use according to they invention should be substantially non-volatile at the. temperature atwhich the oil is used, i. e., they should have normal boiling points higher than the temperature of use of the oil. Generally 1,,2-dialkoxy benzenes have high enough normaliboilingpointsfor almost all severe temperature uses ordinarily. encountered.
Catechol diethyl ether (1,2-diethoxy benzene) is particularly advantageous for use according to the. invention; for it, hasbeen found that although catechol diethyl ether is generally inferior to at least one, widely used alkylated phenol of v the prior art as an oxioil under ordinary temperature conditions of. use, catechol diethyl ether is on the other hand distinctly superior to that same alkylated phenol oxidation inhibitor as an inhibitor for oil under severe temperature conditions of use.
The amount of 1,2-dialkoxy benzene used in a given amount of lubricating oil will vary according to the degree of oxidation inhibition desired. Generally, satisfactory results are obtained with 0.01-2.00 weight percent of 1,2-dialkoxy benzene.
The following example illustrates the invention:
The oil tested in this example was a solventrefined, dewaxed, acid-treated, and clay-treated distillate from mixed-base crude petroleum, the distillate having an S. U. viscosity at 10 F. of about 185 seconds, a viscosity index of about 90, and a flash point above 350 F. Two samples of such oil were tested for oxidation stability under severe temperature conditions by subjecting each to a temperature of 400 F. in an oven for hours, air being passed through the sample during this period at the rate of two bubbles per second. Before and after the oxidation period, the amount of naphtha-insoluble material in each sample and the S. U. viscosity at 210 F. of each sample were determined.
Sample No. 1 contained one weight percent of 2,6-ditertiary butyllemethyl phenol as oxidation inhibitor, and sample'No. 2 contained one weight Percent In- Percent Increase in crease in Sample No. Naphtha- S. U. Vis- Insoluble cosity at Materials 210 F.
The above results show that lubricating oil inhibited with 2,6-ditertiary buty1-4-methyl phenol undergoes greater oxidative deterioration under severe temperature conditions than does the same oil inhibited with catechol diethyl ether.
On the other hand, lubricating oil inhibited with 2,6-ditertiary butyl-i-methyl phenol generally undergoes less oxidative deterioration under ordinary temperature conditions of use than does the same oil inhibited with catechol diethyl ether. For example, an oil having properties generally like those of the oil tested in the example above, but having S. U. viscosity at 100 F. of about 160, was found to be more stable in the turbine oil oxidation stability test (A.S.T.M. D943-4'7T) which is conducted at 203 F., when inhibited with 2,6-ditertiary butyl-4-methyl phe- 1101 than when inhibited with catechol diethyl ether. I
Thus, it is seen that the efiectiveness of lubrieating oil oxidation inhibitors depends on the conditions to which the oil is subjected during use, and that catechol diethyl ether gives superior results in oil used under severe temperature conditions, as compared with a prior art oxidation inhibitor, such as 2,6-ditertiary butyllmethyl phenol.
Although in the preceding example, 1,2-diethoxy benzene is used as an example of a 1,2- dialkoxy benzene, similar results may be obtained when other 1,2-dialkoxy benzenes are used wherein the alkoxy groups contain 1-9- carbon atoms, e. g. 1,2-dimethoxy benzene, 1,2-dibutoxy benzene, 1,2-diamoxy benzene, etc. It is generally preferred that the two alkoxy groups contain the same number of carbon atoms; this is not strictly necessary, however, and generally satisfactory results may be obtained when using 1,2-dialkoxy benzenes such as l-ethoxy-Z-methoxy benzene, l-propoxy-2-methoxy benzene, l-butoxy-4-butyl-2-methoxy benzene, i-hexyloxy-2-methoxy benzene, etc.
I claim:
1. A composition comprising: a major proportion of mineral lubricating oil suitable for use under severe temperature conditions; and a minor proportion constituting an oxidationinhibiting quantity of a 1,2-dialkoxy benzene wherein the alkoxy groups contain 1-9 carbon atoms.
2. Composition according to claim 1 wherein said oil has a flash point of at least about 350 F.
3. Composition according to claim 1 wherein the weight percent of said 1,2-dialkoxy benzene in the composition is about 0.01-2.00%.
4. Composition according to claim 1 wherein said 1,2-dialkoxy benzene is 1,2-diethoxy benzene.
5. The method of lubricating metal parts which comprises: contacting such parts with mineral lubricating oil at a temperature within the range from 250 F. to 450 F., said oil containing a minor proportion constituting an oxidation inhibiting quantity of a 1,2-dialkoxy benzene wherein the alkoxy groups contain 1-9 carbon atoms.
6. A composition consisting essentially of a major proportion of mineral lubricating oil suitable for use under severe temperature conditions; and a minor proportion constituting an oxidation-inhibiting quantity of a 1,2-dialkoxy benzene wherein the alkoxy groups contain 1-9 carbon atoms.
WILLIAM C. HOLLIBAUGI-L References Cited in the file of this patentv UNITED STATES PATENTS Number Name Date Re. 23,239 ,Rosenwald June 6, 1950 2,067,960 Werntz Jan. 19, 1937 2,362,516 Wasson Nov. 14, 194
Claims (1)
1. A COMPOSITION COMPRISING: A MAJOR PROPORTION OF MINERAL LUBRICATING OIL SUITABLE FOR USE UNDER SEVERE TEMPERATURE CONDITIONS: AND A MINOR PROPORTION CONSTITUTING AN OXIDATIONINHIBITING QUANTITY OF A 1,2-DIALKOXY BENZENE WHEREIN THE ALKOXY GROUPS CONTAIN 1-9 CARBON ATOMS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US170021A US2665253A (en) | 1950-06-23 | 1950-06-23 | Mineral oil containing 1, 2-dialkoxy benzene as an oxidation inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US170021A US2665253A (en) | 1950-06-23 | 1950-06-23 | Mineral oil containing 1, 2-dialkoxy benzene as an oxidation inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2665253A true US2665253A (en) | 1954-01-05 |
Family
ID=22618205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US170021A Expired - Lifetime US2665253A (en) | 1950-06-23 | 1950-06-23 | Mineral oil containing 1, 2-dialkoxy benzene as an oxidation inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2665253A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1126055B (en) * | 1958-03-14 | 1962-03-22 | Basf Ag | Mineral oil based lubricants |
| US3095378A (en) * | 1958-06-18 | 1963-06-25 | Texaco Inc | Novel anti-oxidant additive and oxidation resistant lubricant composition |
| US3112273A (en) * | 1960-10-05 | 1963-11-26 | Mertwoy Abraham | Oxidatively auto-inhibitive compounds |
| WO2015162137A1 (en) * | 2014-04-25 | 2015-10-29 | Total Marketing Services | Use of a lubricant composition for reducing knocking |
| US10323204B2 (en) | 2013-10-25 | 2019-06-18 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
| US10323203B2 (en) | 2013-10-25 | 2019-06-18 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2067960A (en) * | 1937-01-19 | Ethers of dihydric phenols | ||
| US2362516A (en) * | 1942-05-02 | 1944-11-14 | Standard Oil Dev Co | Antioxidant |
| USRE23239E (en) * | 1950-06-06 | Inhibitor for gasoline |
-
1950
- 1950-06-23 US US170021A patent/US2665253A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2067960A (en) * | 1937-01-19 | Ethers of dihydric phenols | ||
| USRE23239E (en) * | 1950-06-06 | Inhibitor for gasoline | ||
| US2362516A (en) * | 1942-05-02 | 1944-11-14 | Standard Oil Dev Co | Antioxidant |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1126055B (en) * | 1958-03-14 | 1962-03-22 | Basf Ag | Mineral oil based lubricants |
| US3095378A (en) * | 1958-06-18 | 1963-06-25 | Texaco Inc | Novel anti-oxidant additive and oxidation resistant lubricant composition |
| US3112273A (en) * | 1960-10-05 | 1963-11-26 | Mertwoy Abraham | Oxidatively auto-inhibitive compounds |
| US10323204B2 (en) | 2013-10-25 | 2019-06-18 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
| US10323203B2 (en) | 2013-10-25 | 2019-06-18 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
| WO2015162137A1 (en) * | 2014-04-25 | 2015-10-29 | Total Marketing Services | Use of a lubricant composition for reducing knocking |
| FR3020377A1 (en) * | 2014-04-25 | 2015-10-30 | Total Marketing Services | LUBRICATING COMPOSITION COMPRISING ANTI-CLIQUETIS COMPOUND |
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