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 PDF

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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
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United States
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benzene
oil
dialkoxy
temperature conditions
lubricating oil
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US170021A
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William C Hollibaugh
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Sunoco Inc
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Sun Oil Co
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    • 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.

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.
US170021A 1950-06-23 1950-06-23 Mineral oil containing 1, 2-dialkoxy benzene as an oxidation inhibitor Expired - Lifetime US2665253A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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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