US2476696A - Mineral oil composition - Google Patents

Mineral oil composition Download PDF

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Publication number
US2476696A
US2476696A US633045A US63304545A US2476696A US 2476696 A US2476696 A US 2476696A US 633045 A US633045 A US 633045A US 63304545 A US63304545 A US 63304545A US 2476696 A US2476696 A US 2476696A
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Prior art keywords
oil
ether
hydrogenated cardanol
hydrogenated
oils
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US633045A
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Caplan Solomon
Peter L Rosamilia
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Harvel Corp
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Harvel Corp
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Priority to US633045A priority Critical patent/US2476696A/en
Priority to GB21506/47A priority patent/GB643489A/en
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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
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix 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
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2040/135—Steam engines or turbines
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to improving hydrocar- L bon oils and particularly the hydrocarbon mineral oils known as petroleum oils.
  • the invention is directed to improving a mineral hydrocarbon oil by adding thereto an ether of hydrogenated cardanol.
  • the petroleum oils with which this invention is concerned are the crude or refined petroleum oils as well as those fractions thereof which have flash points no lower than 250 F.
  • the oils, whether crude or refined petroleum oils or fractions thereof and having ilash points above 250 F. find particular application in the arts of lubrication and electrical insulation. It has long been recognized that these oils sludge when employed in these fields, as .motor oils, turbine oils, aviation oils, Diesel oils, transformer oils and the like.
  • One of the main purposes of this invention is to eifect'ively reduce sludging by incorporating a quantity of an ether of hydrogenated cardanol into a mineral hydrocarbon oil Whose flash point is no lower than 250 F.
  • the sludging of said oils may be retarded and in many cases completely inhibited by adding thereto a quantity of an ether of hydrogenated cardanol.
  • the ratio by weight of said ether of hydrogenated cardanol to said 011 may be as low as 1 to 200 and may be between about 1 to 200 and 2 to 100 although it is also possible to employ these components in the ratio of about 1 to 1000 and to 100.
  • Hydrogenated cardanol may be prepared in a number of diiierent ways. Ordinarily it may be produced by recovering a particular distillate of hydrogenated cashew nut shell liquid.
  • the cashew nut shell liquid employed as one of the starting ingredients may be the raw cashew nut shell liquid obtained either by the solvent extraction of said liquid from said nuts by using a hot cashew nut shell liquid bath as set forth in the S. patent to E. R. Hughes, No. 2,058,456 of October 27, 1936. It is preferable to first treat the raw cashew nut shell liquid with a small amount of an acidic agent to remove therefrom any naturally occurring metals as set forth in the patents to Harvey et al., Nos.
  • the so treated cashew nut shell liquid has long been known as treated cashew nut shell liquid.
  • This treated cashew nut shell liquid is subjected to hydrogenation treatment in order to completely hydrogenate only the unsaturated side chains of the various phenols therein. This hydrogenation may be accomplished by following the method set forth in U. S. patent to S. Caplan, No. 2,181,119 of November 28, 1939. Then after only the unsaturated side chains of the various phenols in said cashew nut shell liquid have been completely hydrogenated or saturated with hydrogen, this hydrogenated cashew nut shell liquid is subjected to distillation under low pressure conditions.
  • distillate It may be distilled at a vapor temperature of 600 F. and at 30 mm. of Hg pressure. Distillation is continued under these conditions until the distillate recovered is between about 50% to by weight of the hydrogenated cashew nut shell liquid subjected to this distillation.
  • This recovered distillate is hydrogenated 'cardanol and is a waxy. solid at room temperature, consists essentially of a compound having a boiling point of approximately 227 C.-235 C. at 5 mm. of Hg pressure having the following general formula:
  • the ethers of hydrogenated cardanol employed in the practice of this invention are those ethers in which the hydrogen atom of the OH group of the hydrogenated cardanol is replaced by an organic radicle or substituent.
  • This substituent may be'either aliphatic, aromatic or a combination of both and is preferably a hydrocarbon radicle, examples of which are methyl, ethyl, amyl, ben'zyl, lauryl, tertiary butyl, etc.
  • the hydrocarbon radicle be a primary, secondary or tertiary alkyl radicle.
  • ethers may be produced in the manner set forth in the patent to S. Caplan, No. 2,181,119 of November 28, 1939. Generally, they may be produced by heating a mixture of approximately 300 grams of hydrogenated cardanol, 45 grams of NaOH in grams of water and a molecular equivalent of a halide or sulphate of the organic radicle which is to replace the hydrogen of the CH of hydrogenated cardanol. The mass is maintained at a temperature of about 100 C. until the reaction mixture is practically neutral and until a sample which is dehydrated and neutralized is substantially insoluble in three volumes of alcohol. After the reaction has been consummated, the ether is separated from the remainder of the reaction mass. By following this general procedure the various ethers of hydrogenated cardanol may be readily and easily produced.
  • the beakers containing the solution of petroleum oil and the benzyl, amyl or ethyl ethers of hydrogenated cardanol were examined and the oil containing Number the benzyl ether of hydrogenated cardanol as well as the 011 containing the amyl ether of hydrogenated cardanol showed greatly reduced sludging measuring about 25 of that of the control sample whereas the oil containing the ethyl ether of hydrogenated cardanol was found to be clear and showed no evidence whatever of sludging.
  • the various greases may be made by heat dissolving or dispersing a soap, such as sodium stearate, aluminum stearate or the like in said combination of mineral oil and an ether of hydrogenated cardanol and then cooling said mass.

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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 July 19, 1949 UNITED STATES TENT OFFICE v MINERAL OIL COMPOSITION Solomon Caplan, New York, N. Y., and Peter L. Rosamilia, Newark, N. 3., assignors to The Harvel Corporation, a corporation of New Jersey No Drawing. Application December 5, 1945, Serial No. 633,045
Claims. 1
This invention relates to improving hydrocar- L bon oils and particularly the hydrocarbon mineral oils known as petroleum oils. In its more specific aspect the invention is directed to improving a mineral hydrocarbon oil by adding thereto an ether of hydrogenated cardanol.
The petroleum oils with which this invention is concerned are the crude or refined petroleum oils as well as those fractions thereof which have flash points no lower than 250 F. The oils, whether crude or refined petroleum oils or fractions thereof and having ilash points above 250 F. find particular application in the arts of lubrication and electrical insulation. It has long been recognized that these oils sludge when employed in these fields, as .motor oils, turbine oils, aviation oils, Diesel oils, transformer oils and the like. One of the main purposes of this invention is to eifect'ively reduce sludging by incorporating a quantity of an ether of hydrogenated cardanol into a mineral hydrocarbon oil Whose flash point is no lower than 250 F.
In the course of our experimentations with this problem, we have discovered that the sludging of said oils may be retarded and in many cases completely inhibited by adding thereto a quantity of an ether of hydrogenated cardanol. For most purposes the ratio by weight of said ether of hydrogenated cardanol to said 011 may be as low as 1 to 200 and may be between about 1 to 200 and 2 to 100 although it is also possible to employ these components in the ratio of about 1 to 1000 and to 100.
Hydrogenated cardanol may be prepared in a number of diiierent ways. Ordinarily it may be produced by recovering a particular distillate of hydrogenated cashew nut shell liquid. The cashew nut shell liquid employed as one of the starting ingredients may be the raw cashew nut shell liquid obtained either by the solvent extraction of said liquid from said nuts by using a hot cashew nut shell liquid bath as set forth in the S. patent to E. R. Hughes, No. 2,058,456 of October 27, 1936. It is preferable to first treat the raw cashew nut shell liquid with a small amount of an acidic agent to remove therefrom any naturally occurring metals as set forth in the patents to Harvey et al., Nos. 2,128,247 of August 30, 1938, and 2,067,919 of January 19, 1937. The so treated cashew nut shell liquid has long been known as treated cashew nut shell liquid. This treated cashew nut shell liquid is subjected to hydrogenation treatment in order to completely hydrogenate only the unsaturated side chains of the various phenols therein. This hydrogenation may be accomplished by following the method set forth in U. S. patent to S. Caplan, No. 2,181,119 of November 28, 1939. Then after only the unsaturated side chains of the various phenols in said cashew nut shell liquid have been completely hydrogenated or saturated with hydrogen, this hydrogenated cashew nut shell liquid is subjected to distillation under low pressure conditions. It may be distilled at a vapor temperature of 600 F. and at 30 mm. of Hg pressure. Distillation is continued under these conditions until the distillate recovered is between about 50% to by weight of the hydrogenated cashew nut shell liquid subjected to this distillation. This recovered distillate is hydrogenated 'cardanol and is a waxy. solid at room temperature, consists essentially of a compound having a boiling point of approximately 227 C.-235 C. at 5 mm. of Hg pressure having the following general formula:
The ethers of hydrogenated cardanol employed in the practice of this invention are those ethers in which the hydrogen atom of the OH group of the hydrogenated cardanol is replaced by an organic radicle or substituent. This substituent may be'either aliphatic, aromatic or a combination of both and is preferably a hydrocarbon radicle, examples of which are methyl, ethyl, amyl, ben'zyl, lauryl, tertiary butyl, etc. Of these We prefer that the hydrocarbon radicle be a primary, secondary or tertiary alkyl radicle.
These ethers may be produced in the manner set forth in the patent to S. Caplan, No. 2,181,119 of November 28, 1939. Generally, they may be produced by heating a mixture of approximately 300 grams of hydrogenated cardanol, 45 grams of NaOH in grams of water and a molecular equivalent of a halide or sulphate of the organic radicle which is to replace the hydrogen of the CH of hydrogenated cardanol. The mass is maintained at a temperature of about 100 C. until the reaction mixture is practically neutral and until a sample which is dehydrated and neutralized is substantially insoluble in three volumes of alcohol. After the reaction has been consummated, the ether is separated from the remainder of the reaction mass. By following this general procedure the various ethers of hydrogenated cardanol may be readily and easily produced.
The following specific comparative tests indi- 3 cate the effectiveness of the ethers of hydrogenated cardanol as sludge inhibitors in petroleum oils.
Into each of four 400 cc. beakers was poured 200 grams of a petroleum oil known on the market as Wemco C and having a flash point above 260 F. and generally employed as a transformer oil. At this time the oil was: clear and free of sludge. To the oil in only three of said beakers were added respectively 4 grams of the benzyl ether of hydrogenated cardanol, the amyl ether of hydrogenated cardanol and the ethyl ether of hydrogenated cardanol, which was stirred therein whereupon solution took place. Then all four of these beakers together with their contents were placed in an oven at 300 F. for a period of 96 hours. At the end of this period they were removed from the oven and the following results were obtained: The control beaker containing only the petroleum oil was examined and the oil therein was cloudy and turbid and a clearly visible sludgy mass or precipitate had deposited out'on the bottom of the beaker. The beaker containing the solution of petroleum oil and the ethyl ether of hydrogenated cardanol showed a greatly reduced sludging measuring about 25% of that of the control whereas the oil in the beakers containing the benzyl or amyl ether of hydrogenated cardanol was examined and found to be clear and showed no evidence of sludging. At the end of this 96 hour period, the power factor of the contents of each of said four beakers was determined and it was found that the power factor of each of said ether-hydrocarbon oil solutions was no greater than that of the oil itself.
'Into'each of four 400 cc. beakers was poured 200 grams of a petroleum oil known on the market as Havoline No. 10-free of additives and having a flash point between 540 EL-600 F. and generally known and employed as a motor lubricating oil. At this time the oil was clear and free of sludge. To the oil in only three of said beakers were added respectively 4 grams of benzyl ether of hydrogenated cardanol, amyl ether of hydrogenated cardanol, and ethyl ether of hydrogenated cardanol, which were stirred therein whereupon solution took place. Then all four of these beakers together with their contents were placed in an oven at 300 F. for a period of 168 hours. At the end of this period they were removed from the oven and the following results were obtained: The control beaker containing only the petroleum oil was examined and the oil therein was cloudy and turbid and a clearly visible sludgy mass or precipitate had deposited out on the bottom of the beaker. The beakers containing the solution of petroleum oil and the benzyl, amyl or ethyl ethers of hydrogenated cardanol were examined and the oil containing Number the benzyl ether of hydrogenated cardanol as well as the 011 containing the amyl ether of hydrogenated cardanol showed greatly reduced sludging measuring about 25 of that of the control sample whereas the oil containing the ethyl ether of hydrogenated cardanol was found to be clear and showed no evidence whatever of sludging.
Besides improving said oils to decrease their tendency to sludge, the incorporation of an ether of hydrogenated cardanol in said oils improves the quality of greases made therewith. The various greases may be made by heat dissolving or dispersing a soap, such as sodium stearate, aluminum stearate or the like in said combination of mineral oil and an ether of hydrogenated cardanol and then cooling said mass.
Having thus described our invention, what we claim and desire to have protected by Letters Patent is:
l. A hydrocarbon ether of hydrogenated cardanol dissolved in a mineral hydrocarbon oil whose flash point is above 250 F. said other being present in small amounts, sufficient to inhibit sludging of said oil.
2. Methyl ether of hydrogenated cardanol dissolved in a mineral hydrocarbon oil whose flash point is above 250 F. said ether being present in small amounts, sufiicient to inhibit sludging of said oil.
3. Ethyl ether of hydrogenated cardanol dissolved in a mineral hydrocarbon oil whose flash point is above 250 F. said ether being present in small amounts, sufiicient to inhibit sludging of said 011.
4. Amyl ether of hydrogenated card-anol dissolved in a mineral hydrocarbon oil whose flash point is above 250 F. said other being present in small amounts, sufficient to inhibit sludging of said oil.
5. An ether dissolved in a mineral hydrocarbon oil whose flash point is above 250 F. said other being a hydrocarbon ether of a phenol having a 15 carbon atom alkyl substituent the ratio by weight of said other to said oil being in the range of 1-1000 to 10-100.
SOLOMON CAPLAN. PETER L. ROSAMILIA.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Name Date 2,181,119 Caplan Nov. 28, 1939 2,240,034 Caplan Apr. 29, 1941 2,384,323 McCleary Sept. 4, 1945
US633045A 1945-12-05 1945-12-05 Mineral oil composition Expired - Lifetime US2476696A (en)

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GB21506/47A GB643489A (en) 1945-12-05 1947-08-07 Improvements in or relating to petroleum oils and greases made therewith

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2774709A (en) * 1953-11-16 1956-12-18 Gen Aniline & Film Corp Polyoxyethylated alkyl phenol emulsification of insoluble hydrocarbon insecticides
US2786745A (en) * 1950-10-17 1957-03-26 California Research Corp Fuel oil
CN102408315A (en) * 2011-09-16 2012-04-11 中国林业科学研究院林产化学工业研究所 Synthesis method of anacardol and butyl ether composition
US20120103303A1 (en) * 2010-10-28 2012-05-03 Hartley Joseph P Marine engine lubrication

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2181119A (en) * 1939-11-28 Derivatives of a phenol obtained
US2240034A (en) * 1937-05-19 1941-04-29 Harvel Corp Ethers of cashew nut sheell liquid and process of making them
US2384323A (en) * 1943-03-26 1945-09-04 Texas Co Aliphatic-ether-alcohol derivatives of cashew nut shell oil

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2181119A (en) * 1939-11-28 Derivatives of a phenol obtained
US2240034A (en) * 1937-05-19 1941-04-29 Harvel Corp Ethers of cashew nut sheell liquid and process of making them
US2384323A (en) * 1943-03-26 1945-09-04 Texas Co Aliphatic-ether-alcohol derivatives of cashew nut shell oil

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2786745A (en) * 1950-10-17 1957-03-26 California Research Corp Fuel oil
US2774709A (en) * 1953-11-16 1956-12-18 Gen Aniline & Film Corp Polyoxyethylated alkyl phenol emulsification of insoluble hydrocarbon insecticides
US20120103303A1 (en) * 2010-10-28 2012-05-03 Hartley Joseph P Marine engine lubrication
CN102533398A (en) * 2010-10-28 2012-07-04 英菲诺姆国际有限公司 Marine engine lubrication
US8609599B2 (en) * 2010-10-28 2013-12-17 Infineum International Limited Marine engine lubrication
CN102408315A (en) * 2011-09-16 2012-04-11 中国林业科学研究院林产化学工业研究所 Synthesis method of anacardol and butyl ether composition

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