WO2001072691A2 - Low pour point primary amides - Google Patents
Low pour point primary amides Download PDFInfo
- Publication number
- WO2001072691A2 WO2001072691A2 PCT/US2001/040381 US0140381W WO0172691A2 WO 2001072691 A2 WO2001072691 A2 WO 2001072691A2 US 0140381 W US0140381 W US 0140381W WO 0172691 A2 WO0172691 A2 WO 0172691A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pour point
- fatty acid
- carbon atoms
- etheramine
- low pour
- 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
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
- C10M105/68—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
-
- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/40—Lubricating compositions characterised by the base-material being a macromolecular compound containing nitrogen
- C10M107/44—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
Definitions
- This invention relates to amides, and, more particularly, to low pour point primary amides that are particularly useful in metalworking applications.
- Amides of fatty acids are widely used in metalworking applications because of their lubricity and emulsification properties.
- these amides also have other properties that tend to make them difficult to use in metalworking applications.
- amides derived from secondary amines tend to form nitrosamines, which are suspected to be carcinogens.
- the use of these amides in metalworking applications is not favored because most metalworking applications involve humans.
- amides derived from primary amines typically have high pour points, meaning they are solids even at high temperatures. Such high pour points make the use of these amides impractical under standard metalworking conditions. Accordingly, numerous methods have been developed to reduce the pour point of amides derived from primary amines.
- Another conventional method involves mixing the amide with one or more high molecular weight fatty acids. While this method may reduce the pour point of the amide, the excess fatty acid tends to considerably dilute the amide, thereby reducing the lubricity and emulsification properties of the amide.
- the present invention includes a method of reducing the pour point of amides derived from primary amines.
- the method involves reacting an etheramine and a fatty acid, or a methyl ester thereof, in a molar ratio from about 0.1:1 to about 10:1.
- the resulting low pour point amides have the following general structure:
- is independently a straight or branched chain alkyl group with from about one to about eighteen carbon atoms;
- R 2 is an alkylene group with from about two to about four carbon atoms;
- R is a straight or branched chain alkyl group with from about six to about fifty-four carbon atoms;
- x is an integer from about one to about one hundred.
- the present invention also includes low pour point amides derived from the reaction between an etheramine and a fatty acid, or a methyl ester thereof. These amides have the following general structure:
- the present invention further includes a method of reducing the pour point of high pour point amides. This method involves blending the low pour point amides of the present invention with amides having pour points higher than the pour point of the primary amides of the present invention.
- R ⁇ is independently a straight or branched chain alkyl group with from about one to about eighteen carbon atoms;
- R 2 is an alkylene group with from about two to about four carbon atoms;
- R 3 is a straight or branched chain alkyl group with from about six to about fifty-four carbon atoms;
- x is an integer from about one to about one hundred.
- a first reactant either an etheramine or a fatty acid, or a methyl ester thereof, should be charged to a reactor.
- An inert gas sparge stream should then be run through the first reactant. Then, the reactant that was not charged to the reactor (i.e.
- either the fatty acid (or the methyl ester thereof) or the etheramine), should be added to the reactor, and preferably is added to the reactor periodically, and in incremental amounts.
- the second reactant may be added to the reactor simultaneously, along with the sparge stream, or the sparge stream may be temporarily removed to allow for the addition of the second reactant.
- the temperature of the reaction should be closely monitored to ensure that a proper reaction rate is maintained. Because the reaction between the fatty acid, or the methyl ester thereof, and the etheramine is an exothermic reaction, the temperature within the reactor increases as the reaction proceeds. This increased temperature tends to cause the reaction to proceed more rapidly, which in turn further elevates the temperature within the reactor.
- the reaction temperature In order to maintain a proper reaction rate, the reaction temperature must be controlled.
- the temperature is controlled by controlling the rate at which the second reactant is added to the reactor.
- the second reactant should be added to the reactor so that the temperature within the reactor remains less than about 250°C.
- the etheramine used in the present invention may include any number of commercially available etheramines suitable for forming a primary amide, including, but not limited to, etheramines and polyetheramines derived from alcohol alkoxylates and alkyl phenol alkoxylates, and etheramines and polyetheramines derived from cyanoethylated alcohols.
- the etheramine comprises an etheramine having the following general structure:
- the etheramine comprises an etheramine from the JEFFAMINE® M series, the JEFF AMINES® D series, or JEFFAMINE® C-300 (all commercially available from the Huntsman Corporation, Houston, Texas), and has branching in its structure.
- JEFFAMINE® C-300 comprises a mixture of amines having the following general structure:
- the fatty acid, or the methyl ester thereof, used in the present invention may comprise any number of commercially available fatty acids, or the methyl esters thereof, that react with an etheramine to form a primary amide.
- the fatty acid, or methyl ester thereof may include, but is not limited to, fatty acids with from about six to about twenty-four carbon atoms, fatty diacids with from about six to about twenty-four carbon atoms, and fatty dimer trimer acids with from about thirty-six to about fifty-four carbon atoms.
- the fatty acid comprises ACINTOL® FA-2 Tall Oil Fatty Acid ("TOFA”) (commercially available from Arizona Chemical, Panama City, Florida), which is a blend of fatty acids having the following general structure:
- R 3 is independently a straight or branched chain alkyl group with from about fifteen to about seventeen carbon atoms.
- the inert gas sparge stream used in the present invention may comprise any number of inert gases suitable for use as a sparge stream.
- the sparge stream is nitrogen gas.
- the sparge stream preferably is utilized throughout the entire course of the reaction, and is removed only if it becomes necessary to add reactants to the reactor.
- the preparation of the low pour point primary amides of the present invention may be represented by the following general equations: O O
- the presence of excess reactants i.e. etheramines, fatty acids, or the methyl esters thereof
- the etheramine and the fatty acid, or methyl ester thereof should be reacted in a molar ratio of about 1.1 : 1.
- the present invention also includes reduced pour point primary amides.
- the reduced pour point amides of the present invention are derived from the reaction between an etheramine and a fatty acid, or a methyl ester thereof. These reduced pour point amides have the following general structure:
- R.-(0-R 2 ) ⁇ -N- C- R 3 H where R] is independently a straight or branched chain alkyl group with from about one to about eighteen carbon atoms; R 2 is an alkylene group with from about two to about four carbon atoms; R 3 is a straight or branched chain alkyl group with from about six to about fifty-four carbon atoms; and x is an integer from about one to about one hundred.
- the low pour point primary amides of the present invention have a low vapor pressure, making these amides safer to use in poorly ventilated metalworking environments.
- the amides of the present invention also exhibit excellent emulsifying and lubricating properties.
- the low pour point primary amides of the present invention may be used for a variety of purposes, including, but not limited to, use as a lubricant or as an additive in metalworking formulations.
- the low pour point primary amides of the present invention may be used alone, or in combination with other amides and/or formulation aids.
- formulation aids may include, but are not limited to, polyalkylene glycols, amine fatty acids, and mineral oil.
- Such amides may include, but are not limited to, tall oil fatty acid amides, decanoic acid amides, and soya fatty acid amides.
- the pour point and free amine content of the JEFFAMINE®/TOFA amide produced in Example I was determined, and then compared with the pour point and free amine content of other amides commonly used in metalworking applications. Table 1 details the results of the comparison.
- Table 1 shows that the JEFFAMINE®/TOFA amide prepared in Example 1 is the only amide having both a low pour point and a low free amine content.
- Example 3 The JEFFAMINE®/TOFA amide produced in Example 1 was then blended in the following proportions:
- Emulsifier 1 13.5%
- the emulsifier comprises 54% SURFONIC®L24-4, 17%SURFONIC®L24-9, 17% TOFA, and 12% water.
- a comparative formulation was also blended as follows:
- the emulsifier comprises 54% SURFONIC®L24-4, 17% SURFONIC®L24-9, 17% TOFA, and 12% water.
- Table 2 demonstrates that the JEFFAMINE®/TOFA amide prepared in Example 1 exhibits excellent lubricating properties. Table 2 also shows that the JEFFAMINE®/TOFA amide prepared in Example 1 is also an effective additive for improving the lubricating properties of other formulations.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0109899-3A BR0109899A (en) | 2000-03-29 | 2001-03-28 | low moisture primary amides |
CA002404150A CA2404150A1 (en) | 2000-03-29 | 2001-03-28 | Low pour point primary amides |
MXPA02009493A MXPA02009493A (en) | 2000-03-29 | 2001-03-28 | Low pour point primary amides. |
AU2001255814A AU2001255814A1 (en) | 2000-03-29 | 2001-03-28 | Low pour point primary amides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US53712100A | 2000-03-29 | 2000-03-29 | |
US09/537,121 | 2000-03-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001072691A2 true WO2001072691A2 (en) | 2001-10-04 |
WO2001072691A3 WO2001072691A3 (en) | 2002-01-31 |
Family
ID=24141297
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/040381 WO2001072691A2 (en) | 2000-03-29 | 2001-03-28 | Low pour point primary amides |
Country Status (5)
Country | Link |
---|---|
AU (1) | AU2001255814A1 (en) |
BR (1) | BR0109899A (en) |
CA (1) | CA2404150A1 (en) |
MX (1) | MXPA02009493A (en) |
WO (1) | WO2001072691A2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017044366A1 (en) * | 2015-09-11 | 2017-03-16 | Dow Global Technologies Llc | Polyalkoxy fatty compound |
JP2018528956A (en) * | 2015-09-11 | 2018-10-04 | ダウ グローバル テクノロジーズ エルエルシー | Composition comprising protein and polyalkoxy aliphatic compound |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3801609A (en) * | 1971-08-31 | 1974-04-02 | Us Agriculture | N-substituted fatty acid amide lubricants |
US3894958A (en) * | 1973-11-05 | 1975-07-15 | Texaco Inc | Mixed secondary alkyl amide synthetic lubricant compositions |
GB2101998A (en) * | 1981-07-21 | 1983-01-26 | Cincinnati Milacron Inc | Polyoxyalkylene polyamide lubricants |
DE4336247A1 (en) * | 1993-10-22 | 1995-04-27 | Basf Ag | Use of end-capped fatty acid amide alkoxylates |
DE19650537A1 (en) * | 1996-12-05 | 1998-06-10 | Basf Ag | Detergents for e.g. textiles, metal processing or paper making |
WO1999046356A1 (en) * | 1998-03-11 | 1999-09-16 | Mona Industries, Inc. | Improved alkanolamides |
WO2000066543A1 (en) * | 1999-04-30 | 2000-11-09 | Huntsman Petrochemical Corporation | Primary alkanolamides |
-
2001
- 2001-03-28 WO PCT/US2001/040381 patent/WO2001072691A2/en active Application Filing
- 2001-03-28 AU AU2001255814A patent/AU2001255814A1/en not_active Abandoned
- 2001-03-28 MX MXPA02009493A patent/MXPA02009493A/en not_active Application Discontinuation
- 2001-03-28 BR BRPI0109899-3A patent/BR0109899A/en not_active IP Right Cessation
- 2001-03-28 CA CA002404150A patent/CA2404150A1/en not_active Abandoned
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3801609A (en) * | 1971-08-31 | 1974-04-02 | Us Agriculture | N-substituted fatty acid amide lubricants |
US3894958A (en) * | 1973-11-05 | 1975-07-15 | Texaco Inc | Mixed secondary alkyl amide synthetic lubricant compositions |
GB2101998A (en) * | 1981-07-21 | 1983-01-26 | Cincinnati Milacron Inc | Polyoxyalkylene polyamide lubricants |
DE4336247A1 (en) * | 1993-10-22 | 1995-04-27 | Basf Ag | Use of end-capped fatty acid amide alkoxylates |
DE19650537A1 (en) * | 1996-12-05 | 1998-06-10 | Basf Ag | Detergents for e.g. textiles, metal processing or paper making |
WO1999046356A1 (en) * | 1998-03-11 | 1999-09-16 | Mona Industries, Inc. | Improved alkanolamides |
WO2000066543A1 (en) * | 1999-04-30 | 2000-11-09 | Huntsman Petrochemical Corporation | Primary alkanolamides |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017044366A1 (en) * | 2015-09-11 | 2017-03-16 | Dow Global Technologies Llc | Polyalkoxy fatty compound |
CN108026264A (en) * | 2015-09-11 | 2018-05-11 | 陶氏环球技术有限责任公司 | Poly-alkoxyl aliphatic compound |
JP2018528956A (en) * | 2015-09-11 | 2018-10-04 | ダウ グローバル テクノロジーズ エルエルシー | Composition comprising protein and polyalkoxy aliphatic compound |
JP2018531294A (en) * | 2015-09-11 | 2018-10-25 | ダウ グローバル テクノロジーズ エルエルシー | Polyalkoxy aliphatic compounds |
US10301428B2 (en) | 2015-09-11 | 2019-05-28 | Dow Global Technologies Llc | Polyalkoxy fatty compound |
US10647782B2 (en) | 2015-09-11 | 2020-05-12 | DDP Specialty Electronic Materials US, Inc. | Polyalkoxy fatty compound |
Also Published As
Publication number | Publication date |
---|---|
WO2001072691A3 (en) | 2002-01-31 |
CA2404150A1 (en) | 2001-10-04 |
MXPA02009493A (en) | 2003-09-22 |
AU2001255814A1 (en) | 2001-10-08 |
BR0109899A (en) | 2006-08-29 |
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