US2124628A - Process for manufacturing lubricants - Google Patents

Process for manufacturing lubricants Download PDF

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Publication number
US2124628A
US2124628A US12247A US1224735A US2124628A US 2124628 A US2124628 A US 2124628A US 12247 A US12247 A US 12247A US 1224735 A US1224735 A US 1224735A US 2124628 A US2124628 A US 2124628A
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US
United States
Prior art keywords
acids
acid
lubricants
mineral lubricating
manufacturing
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
Application number
US12247A
Inventor
Moser Frans Rudolf
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SHEIL DEV Co
SHEIL DEVELOPMENT Co
Original Assignee
SHEIL DEV Co
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Publication date
Application filed by SHEIL DEV Co filed Critical SHEIL DEV Co
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Publication of US2124628A publication Critical patent/US2124628A/en
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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26Carboxylic acids; Salts thereof
    • C10M129/28Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/42Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/22Acids obtained from polymerised unsaturated acids
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
    • C10M2207/288Partial esters containing free carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

  • the invention relates to a process for manufacturing lubricants, such as mineral lubricating carboxylic acids are much more suitable for the object in view and moreover frequently have still other properties which are of importance in ap- 18 plying the lubricants.
  • lubricants such as mineral lubricating carboxylic acids
  • Suitable poiycarboxylic acids are for instance those obtained by a condensation reaction of oleflnes with maleic acid, anhydride, which reso action is related to them described by Diehls and Alder, Ann. 460, page 98 (i928) Ber. 62,
  • Another suitable acid is agaric or l-cetyl citric acid (Chem. Abst. 25, page 1213, 1931). 5
  • polycarboxylic acids obtained by polymerization, e. g., by heating and/or boiling, voltolizing, etc), of fatty acids, or acids produced from polymerized fats by hydrolyzing, or saponifying same and liberating the acids m from the soap.
  • the added quantities of polycarboxylic acids are, as a rule, comparatively small, e. g. less than 5%, in many cases even below 1%.
  • Example I The addition of 0.5% voltolized oleic acid to a mineral lubricating oil, either compounded or not, is suflicient to obtain the above efiect when using the oil as lubricant for cylinders of aeroengines.
  • Example I A technical quick-drying oil, upon the soapsolution obtained being saponifled and acidified, yieldsa polycarboxylic acid-containing product 5 which when added in a quantity of 1% to a mineral lubricating oil has the property of preventing rust-formation in acre-engine cylinders.
  • a lubricant capable of reducing corrosion in internal combustion engines consisting essentially of a mineral lubricating 011 containing as an active anticorrosion ingredient a small quan-' tity of a polycarboxylic acid obtained by condensatio'n of maleic acid anhydride and oleflnes.
  • a lubricant capable of reducing corrosion in internal combustion engines consisting essentially of a mineral lubricating oil containing as an active anti-corrosion ingredient less than 5% of a polycarboxylic acid obtained by condensation of maleic acid anhydride and an oleflne.
  • a lubricant capable of reducing corrosion in internal combustion engines consisting essentially of a mineral lubricating oil containing as an active anti corrosion ingredient less than 1% -of a polycarboxylic acid obtained by condensation ofmaleic acid anhydrlde and an oleflne.

Landscapes

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

Description

Passed July as, was
UNITED STATES PATENT OFFICE i PROCESS FOR MANUFACTURING LUBRICANTS Fran: Rudolf Moser, Amsterdam, Netherlands, assignor to Shell Development. Company, San 'FranciscmCaliL, a'corporation of Delaware No Drawmg.
cation March 21,1935, Se-
Anv rial No. 12,247. In the Netherlands March 26,
1934 8 Claims.
The invention relates to a process for manufacturing lubricants, such as mineral lubricating carboxylic acids are much more suitable for the object in view and moreover frequently have still other properties which are of importance in ap- 18 plying the lubricants. Thus, for instance. it has been foundthat in the case of lubricating oils for cylinders of aero-engines the presence of polycarboxylic acids in these oils results .in an appreciably reduced attack of the piston and the 20 cylinder wall through rust-formation.
As higher molecular polycarbomiic acids there may be considered both substituted, e. g. containing groups of hydroxyls or esters, and nonsubstituted saturated or unsaturated acids. It is as essential, however, that more than one tree carboxyl group is present.
- Suitable poiycarboxylic acids are for instance those obtained by a condensation reaction of oleflnes with maleic acid, anhydride, which reso action is related to them described by Diehls and Alder, Ann. 460, page 98 (i928) Ber. 62,
.pagelifi (1929) and Ann. 470, page 62, (1929).
and of which the following is a typical example:
200 grams of a highly cracked hydrocarbon 35 distillate boiling from 150 to 200 0. obtained by cracking paraflln wax in the vapor phase and haying a bromine number or 116 is heated with 140 grams maleic acid anhydride during 14 hours at 150460 0. and then for '30 hours at zoo-230 40 6., whereafter it is fractionated under a vacuum of 13 'mm. mercury. .146 grams of a fraction 'boiling from 155 to "165 C. are subsequently hydrated by boiling-for 2 hours with 500 milliliters of water to produce the free acid. Upon extrac 4,5 tion with ether an extract amounting to 155 grams oflish'tyellow acid-reacting viscous oil is obtained. w
When adding .25 to this acidto aminferallubricatingoibtheresultingblendedoilis capable of eifectively preventing corrosion of internal combustion engines, whether such engines have been in use or not.
Another suitable acid is agaric or l-cetyl citric acid (Chem. Abst. 25, page 1213, 1931). 5
Further examples are polycarboxylic acids obtained by polymerization, e. g., by heating and/or boiling, voltolizing, etc), of fatty acids, or acids produced from polymerized fats by hydrolyzing, or saponifying same and liberating the acids m from the soap.
The added quantities of polycarboxylic acids are, as a rule, comparatively small, e. g. less than 5%, in many cases even below 1%.
Example I The addition of 0.5% voltolized oleic acid to a mineral lubricating oil, either compounded or not, is suflicient to obtain the above efiect when using the oil as lubricant for cylinders of aeroengines.
Example I! A technical quick-drying oil, upon the soapsolution obtained being saponifled and acidified, yieldsa polycarboxylic acid-containing product 5 which when added in a quantity of 1% to a mineral lubricating oil has the property of preventing rust-formation in acre-engine cylinders.
I claim: a
l. A lubricant capable of reducing corrosion in internal combustion engines, consisting essentially of a mineral lubricating 011 containing as an active anticorrosion ingredient a small quan-' tity of a polycarboxylic acid obtained by condensatio'n of maleic acid anhydride and oleflnes.
V 2. A lubricant capable of reducing corrosion in internal combustion engines consisting essentially of a mineral lubricating oil containing as an active anti-corrosion ingredient less than 5% of a polycarboxylic acid obtained by condensation of maleic acid anhydride and an oleflne.
3. A lubricant capable of reducing corrosion in internal combustion engines consisting essentially of a mineral lubricating oil containing as an active anti corrosion ingredient less than 1% -of a polycarboxylic acid obtained by condensation ofmaleic acid anhydrlde and an oleflne.
FRANZ RUDOLF MOBER.
US12247A 1934-03-26 1935-03-21 Process for manufacturing lubricants Expired - Lifetime US2124628A (en)

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2442672A (en) * 1941-02-18 1948-06-01 Shell Dev Rust-preventive hydrocarbon compositions
US2631979A (en) * 1950-08-30 1953-03-17 Standard Oil Dev Co Rust inhibiting composition
US2647872A (en) * 1950-01-27 1953-08-04 Shell Dev Grease composition
DE917027C (en) * 1941-02-18 1954-08-23 Bataatsche Petroleum Mij Nv De Rust-preventing hydrocarbon mixtures
US2806860A (en) * 1955-07-20 1957-09-17 Union Carbide Corp Epoxyalkyl succinic anhydrides
US2833713A (en) * 1955-04-18 1958-05-06 Standard Oil Co Corrosion inhibited motor oils
US2960469A (en) * 1956-04-19 1960-11-15 Sinclair Refining Co Load carrying lubricant
US3208945A (en) * 1963-05-31 1965-09-28 California Research Corp Rust resistant lubricant composition
US3923671A (en) * 1974-10-03 1975-12-02 Aluminum Co Of America Metal working lubricant
US4042515A (en) * 1974-08-16 1977-08-16 B. V. Beverolfabrieken Anhydrous deep-drawing lubricant
WO1994005746A1 (en) * 1992-09-07 1994-03-17 Henkel Kommanditgesellschaft Auf Aktien Amine-free cooling lubricants
US5866521A (en) * 1995-09-05 1999-02-02 Nalco Chemical Company ISO-steric acid-2-amino-2-methyl-1-propanol salt for improving petroleum oil rejection properties of synthetic and semi-synthetic metal-working fluids
WO2011033526A2 (en) 2009-09-17 2011-03-24 Bharat Petroleum Corporation Limited Gasohol fuel composition for internal combustion engines
US9034808B2 (en) 2005-01-18 2015-05-19 Bestline International Research, Inc. Universal synthetic lubricant additive with micro lubrication technology to be used with synthetic or miner host lubricants from automotive, trucking, marine, heavy industry to turbines including, gas, jet and steam
US9284507B2 (en) 2005-01-18 2016-03-15 Bestline International Research, Inc. Universal synthetic diesel fuel additive product-by-process to replace the lost sulfur lubrication when using low-sulfur diesel fuels
US9309482B2 (en) 2005-01-18 2016-04-12 Bestline International Research, Inc. Universal synthetic water displacement multi-purpose penetrating lubricant, method and product-by-process
US10400192B2 (en) 2017-05-17 2019-09-03 Bestline International Research, Inc. Synthetic lubricant, cleaner and preservative composition, method and product-by-process for weapons and weapon systems
US11377616B2 (en) 2015-01-29 2022-07-05 Bestline International Research Inc. Motor oil blend and method for reducing wear on steel and eliminating ZDDP in motor oils by modifying the plastic response of steel

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2442672A (en) * 1941-02-18 1948-06-01 Shell Dev Rust-preventive hydrocarbon compositions
DE917027C (en) * 1941-02-18 1954-08-23 Bataatsche Petroleum Mij Nv De Rust-preventing hydrocarbon mixtures
US2647872A (en) * 1950-01-27 1953-08-04 Shell Dev Grease composition
US2631979A (en) * 1950-08-30 1953-03-17 Standard Oil Dev Co Rust inhibiting composition
US2833713A (en) * 1955-04-18 1958-05-06 Standard Oil Co Corrosion inhibited motor oils
US2806860A (en) * 1955-07-20 1957-09-17 Union Carbide Corp Epoxyalkyl succinic anhydrides
US2960469A (en) * 1956-04-19 1960-11-15 Sinclair Refining Co Load carrying lubricant
US3208945A (en) * 1963-05-31 1965-09-28 California Research Corp Rust resistant lubricant composition
US4042515A (en) * 1974-08-16 1977-08-16 B. V. Beverolfabrieken Anhydrous deep-drawing lubricant
US3923671A (en) * 1974-10-03 1975-12-02 Aluminum Co Of America Metal working lubricant
WO1994005746A1 (en) * 1992-09-07 1994-03-17 Henkel Kommanditgesellschaft Auf Aktien Amine-free cooling lubricants
US5866521A (en) * 1995-09-05 1999-02-02 Nalco Chemical Company ISO-steric acid-2-amino-2-methyl-1-propanol salt for improving petroleum oil rejection properties of synthetic and semi-synthetic metal-working fluids
US9034808B2 (en) 2005-01-18 2015-05-19 Bestline International Research, Inc. Universal synthetic lubricant additive with micro lubrication technology to be used with synthetic or miner host lubricants from automotive, trucking, marine, heavy industry to turbines including, gas, jet and steam
US9284507B2 (en) 2005-01-18 2016-03-15 Bestline International Research, Inc. Universal synthetic diesel fuel additive product-by-process to replace the lost sulfur lubrication when using low-sulfur diesel fuels
US9309482B2 (en) 2005-01-18 2016-04-12 Bestline International Research, Inc. Universal synthetic water displacement multi-purpose penetrating lubricant, method and product-by-process
US9834735B2 (en) 2007-12-19 2017-12-05 Bestline International Research, Inc. Universal synthetic lubricant, method and product-by-process to replace the lost sulfur lubrication when using low-sulfur diesel fuels
WO2011033526A2 (en) 2009-09-17 2011-03-24 Bharat Petroleum Corporation Limited Gasohol fuel composition for internal combustion engines
US9447343B2 (en) 2009-09-17 2016-09-20 Bharat Petroleum Corporation Limited Gasohol fuel composition for internal combustion engines
US9932538B2 (en) 2010-09-22 2018-04-03 Bestline International Research, Inc. Universal synthetic water displacement multi-purpose penetrating lubricant, method and product-by-process
US11473031B2 (en) 2010-09-22 2022-10-18 Bestline International Research, Inc. Motor oil blend and method for reducing wear on steel and eliminating ZDDP in motor oils by modifying the plastic response of steel
US11377616B2 (en) 2015-01-29 2022-07-05 Bestline International Research Inc. Motor oil blend and method for reducing wear on steel and eliminating ZDDP in motor oils by modifying the plastic response of steel
US10400192B2 (en) 2017-05-17 2019-09-03 Bestline International Research, Inc. Synthetic lubricant, cleaner and preservative composition, method and product-by-process for weapons and weapon systems

Also Published As

Publication number Publication date
FR781570A (en) 1935-05-18

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