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US2285752A - Anticorrosive - Google Patents

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US2285752A
US2285752A US366148A US36614840A US2285752A US 2285752 A US2285752 A US 2285752A US 366148 A US366148 A US 366148A US 36614840 A US36614840 A US 36614840A US 2285752 A US2285752 A US 2285752A
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phenyl
corrosiveness
alpha
ethers
naphthyl
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US366148A
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Paul R Van Ess
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Shell Development Co
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Shell Development Co
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    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16Paraffin waxes; Petrolatum, e.g. slack wax
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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    • C10N2060/04Oxidation, e.g. ozonisation

Definitions

  • This invention deals with the use of alpha naphthyl ethers as addition agents to hydrocarbon oils and other organic substances. I have discovered that the presence of these compounds in suitable amounts reduces or inhibits the corrosiveness toward metallic surfaces of such hydrocarbon oils and other organic substances as possess this objectionable property.
  • corrosiveness of organic substances may be inherent in their chemical structure or composition, or may be induced by oxidation. Either type of corrosiveness may be reduced, and in many instances be completely inhibited.
  • Suitable alpha naphthyl ethers are particularly the symmetrical dialpha naphthyl ether, the phenyl and alkyl phenyl alpha naphthyl ethers, such as tolyl, xylyl, trimethyl phenyl, tetramethyl phenyl, methyl ethyl phenyl, n-propyl phenyl, isopropyl phenyl, primary, secondary and tertiary butyl or amyl phenyl, ditertiary butyl phenyl, methyl ditertiary butyl phenyl, tritertiary butyl phenyl, ditertiary amyl phenyl, methyl ditertiary amyl phenyl, tritertiary amyl phenyl, etc., alpha naphthyl ethers; and alkyl or aralkyl alpha naphthyl ethers, such as
  • beta naphthyl ethers and particularly the dibeta naphthyl ether, have very little inhibiting properties, and in some instances have been found to aggravate corrosiveness of substances to which they are added.
  • the alpha naphthyl ethers of this invention are thermally quite stable, and therefore are useful as addition agent -to a large number of substances which are in need of improvement with regard to reduction of corrosiveness. may be added to gasolines, kerosenes, diesel fuels, lubricants, electrical oils, or to non-hydrocarbon substances such as fats, fatty acids. soaps, naphthenate driers, essential oils. extracts of pyrethrum, or other insecticides which lose their potency on exposure to air. etc. Of particular interest is the use of the alpha naphthyl ethers in lubricating oils containing corrosion-inducing amounts, e.
  • oil-soluble detergents such as salts of polyvalent metals, more particularly of Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co, Cu.
  • organic acids such as fatty acids, fatty acids having attached aromatic radicals as phenyl, hydroxy phenyl, benzyl, benzal, etc., radicals; naphthenic acids, acids obtained from natural waxes as montan wax, carnauba wax. candelilla wax, etc., acids obtained by oxidation of paraflin wax, acids obtained by hydrolysis of rosin oil or tall oil, alkyl- Thus they.
  • the amounts of the ethers to be added varies somewhat depending upon the original corrosiveness or upon the tendency of the substance to increase in corrosiveness during storage or use or both. Thus, while lubricating oils and the like may require the use of amounts in excess of .2%
  • the alpha-naphthyl ethers As against alpha-naphthol, beta-naphthol, and many phenolic inhibitors, the alpha-naphthyl ethers have the advantage of being color stable in the presence of alkali.
  • Many compounded lubricating oils for internal combustion engines contain alkaline detergents, and in the presence of free alkali the naphthols in particular turn to weird hues, as purple, green or blue.
  • Mineral oil 0. 20 Mineral nil+2. 5% calcium petroleum sulfonate 5. 7 Mineral oil+2.5% calcium petroleum sulfonato+l% (ii-alpha naphthyl ether O. ()9 Mineral oil+2.5% calcium petroleum sulfonate+1% di-beta naphthyl other l0. 0
  • a non-corrosive lubricating oil composition 4. The composition of claim 3 wherein said small amount is between .1 96-5% 5.
  • a non-corrosive lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount 01' phenyl alpha naphthyl ether.
  • a non-corroslve-lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount of (ii-alpha naphthyl ether.

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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 June 9, 1942 ANTICORROSIVE Paul R. Van Ess, Berkeley, Calif., assignor to Shell Development Company, San Francisco, Calif., a corporation of Delaware No Drawing. Application November 18, 1940,
Serial No. 366,148
7 Claims.
This invention deals with the use of alpha naphthyl ethers as addition agents to hydrocarbon oils and other organic substances. I have discovered that the presence of these compounds in suitable amounts reduces or inhibits the corrosiveness toward metallic surfaces of such hydrocarbon oils and other organic substances as possess this objectionable property.
corrosiveness of organic substances may be inherent in their chemical structure or composition, or may be induced by oxidation. Either type of corrosiveness may be reduced, and in many instances be completely inhibited.
Suitable alpha naphthyl ethers are particularly the symmetrical dialpha naphthyl ether, the phenyl and alkyl phenyl alpha naphthyl ethers, such as tolyl, xylyl, trimethyl phenyl, tetramethyl phenyl, methyl ethyl phenyl, n-propyl phenyl, isopropyl phenyl, primary, secondary and tertiary butyl or amyl phenyl, ditertiary butyl phenyl, methyl ditertiary butyl phenyl, tritertiary butyl phenyl, ditertiary amyl phenyl, methyl ditertiary amyl phenyl, tritertiary amyl phenyl, etc., alpha naphthyl ethers; and alkyl or aralkyl alpha naphthyl ethers, such as methyl, ethyl, n-propyl, isopropyl, primary, secondary or tertiary butyl, primary, secondary or tertiary amyl, hexyl, benzyl, etc., alpha naphthyl ethers. If desired, the aromatic nucleus or nuclei, e. g., the naphthyl radical, may contain one or several alkyl radicals.
, It is of interest to note that the corresponding beta naphthyl ethers, and particularly the dibeta naphthyl ether, have very little inhibiting properties, and in some instances have been found to aggravate corrosiveness of substances to which they are added.
The alpha naphthyl ethers of this invention are thermally quite stable, and therefore are useful as addition agent -to a large number of substances which are in need of improvement with regard to reduction of corrosiveness. may be added to gasolines, kerosenes, diesel fuels, lubricants, electrical oils, or to non-hydrocarbon substances such as fats, fatty acids. soaps, naphthenate driers, essential oils. extracts of pyrethrum, or other insecticides which lose their potency on exposure to air. etc. Of particular interest is the use of the alpha naphthyl ethers in lubricating oils containing corrosion-inducing amounts, e. g., from about .1 of oil-soluble detergents such as salts of polyvalent metals, more particularly of Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co, Cu. with organic acids such as fatty acids, fatty acids having attached aromatic radicals as phenyl, hydroxy phenyl, benzyl, benzal, etc., radicals; naphthenic acids, acids obtained from natural waxes as montan wax, carnauba wax. candelilla wax, etc., acids obtained by oxidation of paraflin wax, acids obtained by hydrolysis of rosin oil or tall oil, alkyl- Thus they.
ated benzoic, hydroxy benzoic, naphthoic, etc., acids, sulfonic acids, such as so-called mahogany acids, etc. It is known that these soaps cause lubricating oils to become more or less corrosive, particularly to alloy bearings, such as copperlead, cadmium-silver, cadmium-nickel, etc.
The amounts of the ethers to be added varies somewhat depending upon the original corrosiveness or upon the tendency of the substance to increase in corrosiveness during storage or use or both. Thus, while lubricating oils and the like may require the use of amounts in excess of .2%
and up to 5 to 10% to insure continued non-corrosiveness, particularly if such lubricating oils should contain corrosive addition compounds, smaller amounts usually are suflicient to inhibit cases of slight corrosiveness as is normal for example in gasolines, kerosenes, etc. in which amounts varying from .001% to 1% are normally sufilcient.
As against alpha-naphthol, beta-naphthol, and many phenolic inhibitors, the alpha-naphthyl ethers have the advantage of being color stable in the presence of alkali. Many compounded lubricating oils for internal combustion engines contain alkaline detergents, and in the presence of free alkali the naphthols in particular turn to weird hues, as purple, green or blue.
The following example further illustrates my invention:
Samples of lubricating oils were subjected to a thrust-bearing corrosion test to determine their corrosiveness. In this test, a hardened steel disc The bearings reported below consisted of copper-lead alloy. The oils tested were of the type of anti-ringsticking diesel lubricating oil consisting of a 55 V. I. mineral lubricating oil S. A. E. 30 and containing a detergent soap which caused the oil to be quite corrosive. For comparison, the corrosiveness of the straight mineral oil is also shown:
Bearing loss, on mgJsq. cm.
Mineral oil 0. 20 Mineral nil+2. 5% calcium petroleum sulfonate 5. 7 Mineral oil+2.5% calcium petroleum sulfonato+l% (ii-alpha naphthyl ether O. ()9 Mineral oil+2.5% calcium petroleum sulfonate+1% di-beta naphthyl other l0. 0
I claim as my invention: 1. A non-corrosive lubricating oil composition 4. The composition of claim 3 wherein said small amount is between .1 96-5% 5. A non-corrosive lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount 01' phenyl alpha naphthyl ether.
6. A non-corrosive lubricating oil composition of claim 3 in which the ethers are present in amounts ranging from .001% to 10%.
7. A non-corroslve-lubricating oil composition comprising a lubricating oil which normally causes corrosion containing dissolved a small amount of (ii-alpha naphthyl ether.
PAUL R. VAN ESS.
US366148A 1940-11-18 1940-11-18 Anticorrosive Expired - Lifetime US2285752A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2438468A (en) * 1942-12-31 1948-03-23 Standard Oil Dev Co Oil composition
US2449025A (en) * 1943-07-21 1948-09-07 Atlantic Refining Co Rust-inhibiting lubricant
US2453690A (en) * 1944-10-23 1948-11-16 Ulrie B Bray Process of producing polyvalentmetal hydrocarbon sulfonate
US2485861A (en) * 1945-10-01 1949-10-25 Sumner E Campbell Lubricating oil
US2501731A (en) * 1946-10-14 1950-03-28 Union Oil Co Modified lubricating oil
US2677618A (en) * 1950-10-21 1954-05-04 Standard Oil Co Rust preventive compositions
US4304707A (en) * 1979-03-12 1981-12-08 Ici Americas Inc. Rust inhibiting coating compositions
US4889614A (en) * 1989-05-09 1989-12-26 Betz Laboratories, Inc. Methods for retarding coke formation during pyrolytic hydrocarbon processing

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2438468A (en) * 1942-12-31 1948-03-23 Standard Oil Dev Co Oil composition
US2449025A (en) * 1943-07-21 1948-09-07 Atlantic Refining Co Rust-inhibiting lubricant
US2453690A (en) * 1944-10-23 1948-11-16 Ulrie B Bray Process of producing polyvalentmetal hydrocarbon sulfonate
US2485861A (en) * 1945-10-01 1949-10-25 Sumner E Campbell Lubricating oil
US2501731A (en) * 1946-10-14 1950-03-28 Union Oil Co Modified lubricating oil
US2677618A (en) * 1950-10-21 1954-05-04 Standard Oil Co Rust preventive compositions
US4304707A (en) * 1979-03-12 1981-12-08 Ici Americas Inc. Rust inhibiting coating compositions
US4889614A (en) * 1989-05-09 1989-12-26 Betz Laboratories, Inc. Methods for retarding coke formation during pyrolytic hydrocarbon processing

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