WO2002092733A2 - Biodegradable synthetic lubricants - Google Patents
Biodegradable synthetic lubricants Download PDFInfo
- Publication number
- WO2002092733A2 WO2002092733A2 PCT/US2002/011825 US0211825W WO02092733A2 WO 2002092733 A2 WO2002092733 A2 WO 2002092733A2 US 0211825 W US0211825 W US 0211825W WO 02092733 A2 WO02092733 A2 WO 02092733A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acids
- ester
- fatty acids
- derived
- linear fatty
- Prior art date
Links
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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/40—Esters containing free hydroxy or carboxyl groups
-
- 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
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
-
- 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
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/2875—Partial esters used as base material
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/081—Biodegradable compounds
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/64—Environmental friendly compositions
-
- 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
-
- 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
-
- 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
- C10N2040/30—Refrigerators lubricants or compressors lubricants
-
- 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
- C10N2040/32—Wires, ropes or cables lubricants
-
- 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
- C10N2040/34—Lubricating-sealants
-
- 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
- C10N2040/36—Release agents or mold release agents
-
- 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
- C10N2040/38—Conveyors or chain belts
-
- 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
- C10N2040/40—Generators or electric motors in oil or gas winning field
-
- 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
- C10N2040/42—Flashing oils or marking oils
-
- 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
- C10N2040/44—Super vacuum or supercritical use
-
- 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
- C10N2040/50—Medical uses
Definitions
- This invention is in the art of synthetic lubricants based on esters.
- biodegradable based fluids are used.
- biodegradability In addition to the environmentally friendly qualities such as biodegradability, recent regulatory initiatives are directed to using fluids derived from renewable resources (e.g., from agricultural products).
- TMP oleate (trimethylolpropane trioleate) is considered the industry standard in formulating biodegradable hydraulic fluids. It has the appropriate viscosity (circa 46 cst at 40° C) and biodegradability. However, TMP oleate has poor oxidative and thermal stability, and poor low temperature fluidity (e.g., pour point). An effective replacement for TMP oleate has heretofore been unavailable.
- U.S. Patent Nos. 5,658,863; 5,681,800; 5,728,658; 5,757,047; and 5,817,607 are directed to biodegradable lubricants comprising, inter alia, esters derived from branched acids. These acids are based on propylene oligomers, which are not considered renewable natural products.
- esters prepared by esterifying linear acids with alcohols wherein both the acids and alcohols are derived from natural products, provide lubricants having good biodegradability and eco-toxicity requirements, as well as technical requirements that are similar to or even superior to lubricants currently used by equipment manufacturers.
- an ester made by reacting sorbitol with 3-6 molar equivalents of a mixture of at least two different fatty acids provides a lubricant equal to or superior to TMP oleate.
- Sorbitol can be derived from natural products such as corn oil (hydrogenation of glucose) and certain linear fatty acids are derived from natural products such as coconut oil.
- a polyol derived from natural sources is partially or fully esterified with at least two different linear acids derived from natural sources (e.g., renewable), preferably two or more different fatty acids, each independently having from 6 to 12 carbon atoms, still more preferably two different linear fatty acids selected from C 6 , C 8 , C 10 , and C 12 fatty acids. It is preferred that sorbitol is esterified with 3-6 molar equivalents of the mixed fatty acids.
- the term "mixed" means at least two fatty acids having different carbon number. Three or more different fatty acids may also be used. Examples of suitable acids include, but are not limited to, caprylic acid, capric acid, and lauric acid.
- a sorbitol ester fluid was made by refluxing 1.25 moles of sorbitol with 5.5 moles of a commercially available 60:40 wt% mixture of caprylic acid/capric acid (C 8 and Cio, respectively) at 240 °C. The reaction proceeded until the hydroxyl number was less than 3. The hydroxyl number can be determined by one of skill in the art. Unreacted acids were removed by vacuum distillation. A further reduction in acidity was obtained by neutralizing the free acid with Ca(OH) 2 until the total acid number (TAN), as determined by ASTM D974, was less than 0.1. The properties of this ester fluid are compared with TMP oleate in Table 1, below.
- Viscosity was determined according to ASTM D445. Pour point is determined according to ASTM D97. Flash point is determined according to ASTM D92.
- the properties of the ester fluid according to the present invention are similar with respect to the technical aspects of the industry standard TMP oleate, but having an improved biodegradability and pour point.
- An ISO VG 46 hydraulic oil meaning that the oil has a viscosity of 46 centistokes, or "46 cSt" at 40° C
- a standard additive package Rosin Chemie RC 9308
- rust inhibitor rust inhibitor
- anti-oxidants anti-oxidants
- anti-wear additive anti-wear additive
- the stability of the oil based on the sorbitol ester fluid is superior to the oil based on the oleate ester.
- This is shown in the dry TOST test (Modified ASTM D943) and the oxidation and corrosion test.
- the TOST test is modified from the published method D943 in that no water is included in the test.
- the oxidation and corrosion test is according to FTM 5308, modified in that only copper, aluminum, and steel are used as metal specimens.
- the TOST life is reported in hours to achieve a TAN of greater than 2.
- the oil based on TMP oleate lasted 332 hours while the oil based on the sorbitol ester lasted more than 1000 hours.
- the present invention is directed to an hydraulic oil formulated using an ester lubricant based on polyols and fatty acids derived from natural products, preferably an ester derived by esterifying sorbitol with a mixture of at least two linear fatty acids, even more preferably wherein the at least two linear acids are independently selected from acids having from 6 to 12 carbon atoms, and most preferably wherein the acids mixture comprises caprylic acid [CH 3 (CH 2 ) 6 COOH] and capric acid [CH 3 (CH 2 ) 8 COOH].
- the polyol most preferably sorbitol, can be esterified using at least 3 molar equivalents of total acids in the linear fatty acid mixture, preferably at least 4 molar equivalents of total acids in the linear fatty acid mixture, and more preferably at least 5 molar equivalents of total acids in the linear fatty acid mixture (equivalents based on the number of hydroxyl groups in the polyol). It can be esterified using less than 4 molar equivalents of mixed linear fatty acids (i.e., less than four alcohol groups esterified) or more than 4 molar equivalents, up to fully esterified.
- the hydraulic oil according to the present invention is preferably used in environmentally sensitive applications such as forestry, mining, and agriculture.
- a lubricant formulation having an ester as the base material comprising making said ester by reacting sorbitol with 3 to 6 molar equivalents of mixed linear fatty acids; or more preferably wherein said mixed linear fatty acids are selected from C 6 to C 12 acids; or even more preferably wherein said mixed linear fatty acids are selected from C 6 , C 8 , C 10 , and C 1 acids; or still more preferably wherein said mixed linear fatty acids are caprylic and capric acids; yet still more preferably wherein said base material is made by reacting sorbitol with a 60:40 wt% mixture of caprylic and capric acids.
- the present invention is directed to:
- An hydraulic fluid for equipment used in forestry, mining, or agricultural operations comprising a base stock consisting essentially of an ester derived from natural products; more preferably wherein said ester is made esterifying at least one linear acid derived from corn with linear alcohols derived from coconut oil.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2002303357A AU2002303357A1 (en) | 2001-05-17 | 2002-04-16 | Biodegradable synthetic lubricants |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29181601P | 2001-05-17 | 2001-05-17 | |
US60/291,816 | 2001-05-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002092733A2 true WO2002092733A2 (en) | 2002-11-21 |
WO2002092733A3 WO2002092733A3 (en) | 2003-03-20 |
Family
ID=23121965
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/011825 WO2002092733A2 (en) | 2001-05-17 | 2002-04-16 | Biodegradable synthetic lubricants |
Country Status (3)
Country | Link |
---|---|
US (1) | US20030004071A1 (en) |
AU (1) | AU2002303357A1 (en) |
WO (1) | WO2002092733A2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009095824A1 (en) * | 2008-01-29 | 2009-08-06 | The Procter & Gamble Company | A highly esterified oligosaccharide polyester lubricant for machinery |
GB2553340A (en) * | 2016-09-02 | 2018-03-07 | Illinois Tool Works | Wire Rope lubricant |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8124572B2 (en) * | 2007-09-27 | 2012-02-28 | Chevron U.S.A. Inc. | Production of biofuels and biolubricants from a common feedstock |
JP6669343B2 (en) * | 2015-02-27 | 2020-03-18 | 出光興産株式会社 | Biodegradable lubricating oil composition |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4783274A (en) * | 1983-02-11 | 1988-11-08 | Oy Kasvioljy-Vaxtolje Ab | Hydraulic fluids |
US5346724A (en) * | 1991-04-12 | 1994-09-13 | Nippon Oil Company, Ltd. | Oil and fat composition for lubricating food processing machines and use thereof |
US5658863A (en) * | 1994-12-08 | 1997-08-19 | Exxon Chemical Patents Inc. | Biodegradable branched synthetic ester base stocks and lubricants formed therefrom |
US5710030A (en) * | 1995-09-13 | 1998-01-20 | Henkel Corporation | Process for preparing fuels, fuel substitutes, and fuel supplements from renewable resources |
US5733853A (en) * | 1993-09-30 | 1998-03-31 | The Lubrizol Corporation | Lubricants containing carboxylic esters from polyhydroxy compounds, suitable for ceramic containing engines |
US5744434A (en) * | 1995-03-14 | 1998-04-28 | Exxon Chemical Patents Inc. | Polyol ester compositions with unconverted hydroxyl groups |
EP0879872A1 (en) * | 1997-05-20 | 1998-11-25 | Igol Industrie | Lubricating oil composition containing a biodegradable and non-toxic sugar polyester |
WO2001028961A2 (en) * | 1999-10-15 | 2001-04-26 | Danisco Cultor America, Inc. | Method for the direct esterification of sorbitol with fatty acids |
-
2002
- 2002-04-16 AU AU2002303357A patent/AU2002303357A1/en not_active Abandoned
- 2002-04-16 WO PCT/US2002/011825 patent/WO2002092733A2/en not_active Application Discontinuation
- 2002-05-15 US US10/146,124 patent/US20030004071A1/en not_active Abandoned
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4783274A (en) * | 1983-02-11 | 1988-11-08 | Oy Kasvioljy-Vaxtolje Ab | Hydraulic fluids |
US5346724A (en) * | 1991-04-12 | 1994-09-13 | Nippon Oil Company, Ltd. | Oil and fat composition for lubricating food processing machines and use thereof |
US5733853A (en) * | 1993-09-30 | 1998-03-31 | The Lubrizol Corporation | Lubricants containing carboxylic esters from polyhydroxy compounds, suitable for ceramic containing engines |
US5658863A (en) * | 1994-12-08 | 1997-08-19 | Exxon Chemical Patents Inc. | Biodegradable branched synthetic ester base stocks and lubricants formed therefrom |
US5744434A (en) * | 1995-03-14 | 1998-04-28 | Exxon Chemical Patents Inc. | Polyol ester compositions with unconverted hydroxyl groups |
US5710030A (en) * | 1995-09-13 | 1998-01-20 | Henkel Corporation | Process for preparing fuels, fuel substitutes, and fuel supplements from renewable resources |
EP0879872A1 (en) * | 1997-05-20 | 1998-11-25 | Igol Industrie | Lubricating oil composition containing a biodegradable and non-toxic sugar polyester |
WO2001028961A2 (en) * | 1999-10-15 | 2001-04-26 | Danisco Cultor America, Inc. | Method for the direct esterification of sorbitol with fatty acids |
Non-Patent Citations (1)
Title |
---|
ARCOS JOSE A ET AL: "Quantitative enzymatic production of 1,6-diacyl sorbitol esters" BIOTECHNOL BIOENG;BIOTECHNOLOGY AND BIOENGINEERING OCT 5 1998 JOHN WILEY & SONS INC, NEW YORK, NY, USA, vol. 60, no. 1, 5 October 1998 (1998-10-05), pages 53-60, XP002205639 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009095824A1 (en) * | 2008-01-29 | 2009-08-06 | The Procter & Gamble Company | A highly esterified oligosaccharide polyester lubricant for machinery |
GB2553340A (en) * | 2016-09-02 | 2018-03-07 | Illinois Tool Works | Wire Rope lubricant |
WO2018045337A1 (en) * | 2016-09-02 | 2018-03-08 | Illinois Tool Works Inc. | Wire rope lubricant |
Also Published As
Publication number | Publication date |
---|---|
US20030004071A1 (en) | 2003-01-02 |
AU2002303357A1 (en) | 2002-11-25 |
WO2002092733A3 (en) | 2003-03-20 |
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