US3039961A - Non-corrosive lubricating compositions - Google Patents

Non-corrosive lubricating compositions Download PDF

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Publication number
US3039961A
US3039961A US811802A US81180259A US3039961A US 3039961 A US3039961 A US 3039961A US 811802 A US811802 A US 811802A US 81180259 A US81180259 A US 81180259A US 3039961 A US3039961 A US 3039961A
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Prior art keywords
mercapto
oxazoline
oil
test
weight
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US811802A
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Robert J Harker
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Commercial Solvents Corp
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Commercial Solvents Corp
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring

Definitions

  • My invention relates to non-corrosive lubricating compositions. More particularly, it relates to non-corrosive lubricating compositions comprising a mercapto oxazoline having the following structural formula R2 R. H l 6 C where R is a member selected from the group consisting of CH QH Ol-l, and C H and R is a member selected from the group consisting of CH OH, CH and H.
  • hydrocarbon lubricating oils are susceptible to harmful oxidation.
  • the degree of susceptibility depends on the process used for refinement and the degree to which readily oxidizable substances are removed.
  • a satisfactory refined lubricating oil can be obtained by refining a crude hydrocarbon oil in the presence of sulfuric acid and treating the refined oil with various compositions; among them silica gel, natural clay, activated charcoal and A101
  • Such a lubricating oil tends to form acidic substances when subjected to oxidizing conditions. These acidic substances are undesirable and have a corrosive effect upon the metals with which the lubricating oil comes in contact during lubrication. This factor not only shortens the useful life of the lubricating composition, but causes the deterioration of much expensive machinery.
  • a suitable noncorrosive lubricating composition minimizes the corrosive etfect of oxidation products upon the metals with which a lubricant comes in contact during lubrication and forms a continuous film upon metal surfaces which will resist breakage over extended periods of time even though continuously exposed to the oxidation products normally formed in a lubricating oil.
  • a highly satisfactory noncorrosive lubricant which will form a protective film on metal surfaces, said film being resistant to breakage by oxidation products over an extended period of time, can be prepared by adding a mercapto oxazo-line having the following structural formula where R is a member selected from the group consisting of CH CH OH, and C l-I and R is a member selected from the group consisting of CH CH OH, and H, to a lubricating oil.
  • Examples of the above-described mercapto oxazolines which are operative in my invention are Z-mercapto 4 hydroxymethylt-methyl 2 oxazoline, 2 mercapto 4,4 dimethyl 2 oxazoline, Z-mercapto- 4,4 dihydroxymethyl 2 oxazoline, 2-mercapto-4- 3,039,61 Patented June 19, 1962 ethyl 2 oxazoline, Z-mercapto-4-ethyl-4-hydroxymethyl- 2-oxazoline, etc.
  • the mercapto oxazolines can be added to the desired lubricant in amounts of from about 0.2 to 10% by weight of the lubricating oil. However, I prefer to use from about 0.5 to 2% by weight of the mercapto oxazolines.
  • the corrosiveness of the lubricant can be tested by means of various devices.
  • One of these devices is the Underwood oxidation test apparatus.
  • the Underwood oxidation test apparatus comprises essential-ly an oil sump containing an electric heater, a gear pump driven by a A horsepowerelectric motor, a tube containing four orifices, a connecting means connecting the oil sump. and the tube, a 30 mesh wire screen positioned between the orifices and the oil sump, and a rectangular box containing all of the aforementioned, except the connecting means and the gear pump.
  • the apparatus is fitted with several control attachments, such as an adjustable thermostatic control attached'to a thermocouple for maintaining the desired temperature of the oil, a pressure gauge, a by-pass valve for adjustment to the desired pressure and a control switch for the electric immersion heaters.
  • the Underwood oxidation test is conducted by charging the desired amount of the test oil containing a suitable oxidation accelerator into the apparatus, placing two copper-lead bearings backed with a copper strip in position opposite the orifices, starting the pump and regulating the temperature and pressure.
  • the test can be conducted for any prescribed length of time after which the bearings are cleaned and weighed.
  • the amount of corrosion produced by a lubricating composition containing an oxidation accelerator can be compared to the amount of corrosion produced by a lubricating composition tested under the same conditions containing an oxidation accelerator and a corrosion inhibitor.
  • the oil base which can be used to prepare the noncorrosive lubricating composition of my invention is preferably a hydrocarbon lubricating oil which will not readily decompose over extended periods of time.
  • the hydrocarbon oil used in preparing the non-corrosive lubricants of my invention can also contain constituents to improve the pour point, etc. Materials used in the art for these purposes which are compatible with the hydrocarbon oil will be found to be useful in the non-corrosive lubricant of my invention.
  • Example I 2,500 mls. lOf test lubricant containing Kendall SAE No. 10 oil and 0.01% by weight Fe O as iron naphthenate was charged to the Underwood oxidation apparatus. Two previously weighed copper-lead bearing balls were fixed in position opposite the orifices. The heaters were turned to a temperature of 325 F. and the pressure was regulated to 10 p.s.i. The test was continued for 10 hours, after which the balls were cleaned by a special solvent consisting of equal parts of denatured alcohol, toluene and ethyl acetate and weighed to determine the weight loss due to corrosion. The table below shows the results of the test and shows the amount of corrosion produced by the lubricating composition containing an I oxidation accelerator.
  • Test 1 Test 2 Weight before test/gins 41. 9021 41. 9520 Weight alter test/gms -u 41. 7585 41. 0063 Weight loss 0. 1436 0. 1457 Percent weight loss I 0. 342 0. 347
  • Example I 2,500 mls. of test lubricant containing Kendall SAE No. 10 oil,'0.0l% Fe o as iron naphthenate by weight and 1% by weight 2-mercapto-4-hydroxymethyl-4-methyl- 2-oxazoline was charged to the Underwood apparatus, The Underwood oxidation test was performed as described in Example I. The table below shows the results of the test and shows the amount of corrosion produced by a lubricating composition containing an oxidation accelerator and a corrosion inhibitor.
  • a lubricating composition consisting essentially of a hydrocarbon lubricating oil and from about 0.2% to 10% by weight on the weight of the hydrocarbon lubri- 4 eating oil of a mercapto oxazoline having the following general formula where R is a member selected from the group consisting of CH CH OH and C H and R is a member selected from the group consisting of CH CH OH and H.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)

Description

- 3,039,961 NON-CORROSIVE LUBRICATING COMPOSITIONS Robert J. Harker, Terre Haute, Ind, assignor to Commercial Solvents Corporation, New York, N.Y., a corporation of Maryland No Drawing. Filed May 8, 1959, Ser. No. 811,802 Claims. ((31. 252-475) My invention relates to non-corrosive lubricating compositions. More particularly, it relates to non-corrosive lubricating compositions comprising a mercapto oxazoline having the following structural formula R2 R. H l 6 C where R is a member selected from the group consisting of CH QH Ol-l, and C H and R is a member selected from the group consisting of CH OH, CH and H.
It is well known to the art that substantially all hydrocarbon lubricating oils are susceptible to harmful oxidation. The degree of susceptibility depends on the process used for refinement and the degree to which readily oxidizable substances are removed. A satisfactory refined lubricating oil can be obtained by refining a crude hydrocarbon oil in the presence of sulfuric acid and treating the refined oil with various compositions; among them silica gel, natural clay, activated charcoal and A101 Such a lubricating oil, however, tends to form acidic substances when subjected to oxidizing conditions. These acidic substances are undesirable and have a corrosive effect upon the metals with which the lubricating oil comes in contact during lubrication. This factor not only shortens the useful life of the lubricating composition, but causes the deterioration of much expensive machinery.
Generally, a suitable noncorrosive lubricating composition minimizes the corrosive etfect of oxidation products upon the metals with which a lubricant comes in contact during lubrication and forms a continuous film upon metal surfaces which will resist breakage over extended periods of time even though continuously exposed to the oxidation products normally formed in a lubricating oil.
I have now discovered that a highly satisfactory noncorrosive lubricant which will form a protective film on metal surfaces, said film being resistant to breakage by oxidation products over an extended period of time, can be prepared by adding a mercapto oxazo-line having the following structural formula where R is a member selected from the group consisting of CH CH OH, and C l-I and R is a member selected from the group consisting of CH CH OH, and H, to a lubricating oil. Examples of the above-described mercapto oxazolines which are operative in my invention are Z-mercapto 4 hydroxymethylt-methyl 2 oxazoline, 2 mercapto 4,4 dimethyl 2 oxazoline, Z-mercapto- 4,4 dihydroxymethyl 2 oxazoline, 2-mercapto-4- 3,039,61 Patented June 19, 1962 ethyl 2 oxazoline, Z-mercapto-4-ethyl-4-hydroxymethyl- 2-oxazoline, etc.
In accordance with my invention, the mercapto oxazolines can be added to the desired lubricant in amounts of from about 0.2 to 10% by weight of the lubricating oil. However, I prefer to use from about 0.5 to 2% by weight of the mercapto oxazolines.
The corrosiveness of the lubricant can be tested by means of various devices. One of these devices is the Underwood oxidation test apparatus.
The Underwood oxidation test apparatus comprises essential-ly an oil sump containing an electric heater, a gear pump driven by a A horsepowerelectric motor, a tube containing four orifices, a connecting means connecting the oil sump. and the tube, a 30 mesh wire screen positioned between the orifices and the oil sump, and a rectangular box containing all of the aforementioned, except the connecting means and the gear pump. The apparatus is fitted with several control attachments, such as an adjustable thermostatic control attached'to a thermocouple for maintaining the desired temperature of the oil, a pressure gauge, a by-pass valve for adjustment to the desired pressure and a control switch for the electric immersion heaters.
The Underwood oxidation test is conducted by charging the desired amount of the test oil containing a suitable oxidation accelerator into the apparatus, placing two copper-lead bearings backed with a copper strip in position opposite the orifices, starting the pump and regulating the temperature and pressure. The test can be conducted for any prescribed length of time after which the bearings are cleaned and weighed. By calculating the loss in weight of the bearings the amount of corrosion produced by a lubricating composition containing an oxidation accelerator can be compared to the amount of corrosion produced by a lubricating composition tested under the same conditions containing an oxidation accelerator and a corrosion inhibitor.
The oil base which can be used to prepare the noncorrosive lubricating composition of my invention is preferably a hydrocarbon lubricating oil which will not readily decompose over extended periods of time. The hydrocarbon oil used in preparing the non-corrosive lubricants of my invention can also contain constituents to improve the pour point, etc. Materials used in the art for these purposes which are compatible with the hydrocarbon oil will be found to be useful in the non-corrosive lubricant of my invention.
The following examples are set. out to illustrate my invention. It is not intended that the invention be limited to the materials, procedures and proportions set out therein. Various equivalents of my invention will obviously occur to those skilled in the art and I intend to include such equivalents within the scope of my invention.
Example I 2,500 mls. lOf test lubricant containing Kendall SAE No. 10 oil and 0.01% by weight Fe O as iron naphthenate was charged to the Underwood oxidation apparatus. Two previously weighed copper-lead bearing balls were fixed in position opposite the orifices. The heaters were turned to a temperature of 325 F. and the pressure was regulated to 10 p.s.i. The test was continued for 10 hours, after which the balls were cleaned by a special solvent consisting of equal parts of denatured alcohol, toluene and ethyl acetate and weighed to determine the weight loss due to corrosion. The table below shows the results of the test and shows the amount of corrosion produced by the lubricating composition containing an I oxidation accelerator.
Test 1 Test 2 Weight before test/gins 41. 9021 41. 9520 Weight alter test/gms -u 41. 7585 41. 0063 Weight loss 0. 1436 0. 1457 Percent weight loss I 0. 342 0. 347
Example I] 2,500 mls. of test lubricant containing Kendall SAE No. 10 oil,'0.0l% Fe o as iron naphthenate by weight and 1% by weight 2-mercapto-4-hydroxymethyl-4-methyl- 2-oxazoline was charged to the Underwood apparatus, The Underwood oxidation test was performed as described in Example I. The table below shows the results of the test and shows the amount of corrosion produced by a lubricating composition containing an oxidation accelerator and a corrosion inhibitor.
Now having described my invention, What I claim is: l. A lubricating composition consisting essentially of a hydrocarbon lubricating oil and from about 0.2% to 10% by weight on the weight of the hydrocarbon lubri- 4 eating oil of a mercapto oxazoline having the following general formula where R is a member selected from the group consisting of CH CH OH and C H and R is a member selected from the group consisting of CH CH OH and H.
2. The lubricating composition of claim 1 wherein the mercapto oxazoline is present in amounts of from about 0.5% to about 2% by weight.
3. The lubricating composition of claim 1 wherein the mercapto oxazoline is 2-mercapto-4-hydroxyl-4 methyl-2- oxazoline.
4. The lubricating composition of claim 1 wherein the mercapto oxazoline is 2 mercapto 4,4 dimethyl-Z- oxazoline.
5. The lubricating composition of claim 1 wherein the mercapto oxazoline is 2-mercapto-4,4-dihydroxymethyl- 2-oxazoline.
References Cited in the file of this patent UNITED STATES PATENTS 2,206,152 Bennett July 2, 1940 2,348,917 Mathes May 16, 1944 2,364,399 Williams et al. Dec. 5, 1944 2,776,977 DAmico Jan. 8, 1957 2,860,962 Bluestone Nov. 18, 1958 2,953,573 Bluestone Sept. 20, 1960

Claims (1)

1. A LUBRICATING COMPOSITION CONSISTING ESSENTIALLY OF A HYDROCARBON LUBRICATING OIL AND FROM ABOUT 0.2% TO 10% BY WEIGHT ON THE WEIGTH OF THE HYDROCARBON LUBRICATING OIL OF A MERCAPTO OXAZOLINE HAVING THE FOLLOWING GENERAL FORMULA
US811802A 1959-05-08 1959-05-08 Non-corrosive lubricating compositions Expired - Lifetime US3039961A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4263153A (en) * 1979-10-11 1981-04-21 Exxon Research & Engineering Co. Oxazoline containing dispersants stabilized against oxidation with sulfur and fuels and lubricants containing same
US4292184A (en) * 1979-03-26 1981-09-29 Exxon Research & Engineering Co. Thio-bis-(hydrocarbon-bisoxazolines) as oleaginous additives for lubricants and fuels
US4491524A (en) * 1982-09-30 1985-01-01 Exxon Research & Engineering Co. Lubricating additive for drilling muds

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2206152A (en) * 1936-01-15 1940-07-02 Mid Continent Petroleum Corp Process of sulpnurizing oils
US2348917A (en) * 1940-10-04 1944-05-16 Goodrich Co B F Process for the manufacture of mercaptothiazolines
US2364399A (en) * 1939-07-07 1944-12-05 Du Pont Production of 2-mercapto-thiazoline
US2776977A (en) * 1955-04-18 1957-01-08 Monsanto Chemicals Halogen substituted unsaturated azolyl ethers
US2860962A (en) * 1954-03-29 1958-11-18 Diamond Alkali Co Method of defoliating plants
US2953573A (en) * 1957-01-23 1960-09-20 Diamond Alkali Co Certain thiazolidine-thione alkhalides and process

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2206152A (en) * 1936-01-15 1940-07-02 Mid Continent Petroleum Corp Process of sulpnurizing oils
US2364399A (en) * 1939-07-07 1944-12-05 Du Pont Production of 2-mercapto-thiazoline
US2348917A (en) * 1940-10-04 1944-05-16 Goodrich Co B F Process for the manufacture of mercaptothiazolines
US2860962A (en) * 1954-03-29 1958-11-18 Diamond Alkali Co Method of defoliating plants
US2776977A (en) * 1955-04-18 1957-01-08 Monsanto Chemicals Halogen substituted unsaturated azolyl ethers
US2953573A (en) * 1957-01-23 1960-09-20 Diamond Alkali Co Certain thiazolidine-thione alkhalides and process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4292184A (en) * 1979-03-26 1981-09-29 Exxon Research & Engineering Co. Thio-bis-(hydrocarbon-bisoxazolines) as oleaginous additives for lubricants and fuels
US4263153A (en) * 1979-10-11 1981-04-21 Exxon Research & Engineering Co. Oxazoline containing dispersants stabilized against oxidation with sulfur and fuels and lubricants containing same
US4491524A (en) * 1982-09-30 1985-01-01 Exxon Research & Engineering Co. Lubricating additive for drilling muds

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