EP2402957A1 - Fettsäure und Fettsäure-Alkylester-Öladditive - Google Patents
Fettsäure und Fettsäure-Alkylester-Öladditive Download PDFInfo
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- EP2402957A1 EP2402957A1 EP10168019A EP10168019A EP2402957A1 EP 2402957 A1 EP2402957 A1 EP 2402957A1 EP 10168019 A EP10168019 A EP 10168019A EP 10168019 A EP10168019 A EP 10168019A EP 2402957 A1 EP2402957 A1 EP 2402957A1
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- Prior art keywords
- fatty acid
- acid
- alkyl
- dielectric oil
- dielectric
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
- H01B3/24—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils containing halogen in the molecules, e.g. halogenated oils
Definitions
- the present invention pertains to fatty acid- and/or fatty acid alkyl ester-based dielectric oil additives, methods for preparing said additives, as well as uses thereof.
- Insulating, dielectric fluids are used in electrical apparatuses like transformers, capacitors, switchgear, bushings, etc., and have a multitude of functions.
- Dielectric fluids act as electrically insulating medium separating the high voltage and the grounded parts within the apparatus and function as a cooling medium to transfer the heat generated in the current-carrying conductors. Additionally, the fluids provide a medium to monitor the health of a transformer during operation.
- the insulating liquid should also comply with other necessary and desired requirements.
- the fluid should have a high efficiency, long life, and minimal environmental impact. Further, the fluid has to be compatible with the materials used in the electrical equipment and it should not constitute a hazard for the health and safety of personnel.
- insulating fluids should fulfill various physical, electrical, and chemical properties and all these properties are regulated through standards and specifications that stipulate the minimum requirements for each one of the important properties.
- the dielectric breakdown withstand voltage can be defined as the voltage required to obtain a flashover in the oil between two electrodes of specified shape and placed at a certain distance from each other.
- the standards specify the type of electrodes and the gap distances required for the tests.
- the breakdown withstand is essentially an indicator of the oil purity from water, conducting particles, organic acids, and other electrolytes.
- an insulating fluid for applications in power and/or electrical apparatuses is pour point, impregnation capability, blendability and water solubility/max water content.
- the fluid has to be inert with many different materials, should not contain sulphur and halogens, should possess high flash/fire points and should not release or absorb gasses.
- a negative gassing tendency is a desirable property for the prevention of partial discharge.
- ester based fluids are good alternatives to mineral oil, primarily due to their high biodegradability (lower environmental risk) and high values of flash points and fire points (high fire safety factor). Further, natural esters based on vegetable oils, with the main constituent being triglycerides, are preferred due to their renewability.
- the present invention aims at providing novel uses of fatty acids and/or fatty acid alkyl esters, obtainable from naturally occurring triglycerides, in improving the performance of fluids for power and/or electrical applications.
- dielectric oil additives obtainable from triglycerides may provide a novel way of modifying the properties of the rather disadvantageous insulation fluids currently utilized within the industry, as well as other vegetable oil-based insulation fluids under development.
- Biodegradable natural ester based liquids have high pour point temperatures as compared to mineral oil, which can be considered as a major drawback if the electrical apparatuses comprising the fluid have to be operated in extremely cold environments, a problem that is especially pronounced at higher voltage ratings. Further, a low pour point can cause changes in the dielectric and/or other properties of the fluid and the solid insulation impregnated with this fluid. This in turn can force design changes in the transformer which can lead to an increase in the manufacturing costs. A very low value of pour point is therefore desired for the vegetable fluid, which can be achieved using the dielectric oil additives of the present invention.
- Oxidation behavior of the materials is an important parameter when it comes to insulation degradation in a transformer.
- the aging of pressboard insulation over time releases small amounts of oxygen into the oil, and therefore the oil has to withstand the oxidation-induced degradation.
- the inherent stability to oxidation is highly dependent on the compositions of fatty acids in the base oil. Ester oils which are composed only of saturates (only C-C bonds in its structure) are stable against oxidation, but the addition of dielectric oil additives with desirable oxidation stability may be an alternative way of addressing issues pertaining to oxidation stability.
- Specific heat in combination with thermal conductivity is also an important property of dielectric fluids.
- a higher specific heat will cause a lower rise in the temperature of the oil and a higher thermal conductivity will ensure that even if the speed of circulation of the oil is marginally slower than what it is in the case of mineral oil, the amount of heat conducted from the hot-spot regions in the transformer will be higher.
- a higher thermal conductivity can also result in an enhanced heat transfer at slightly higher temperatures because the viscosity of the ester fluid would be reduced at those temperatures.
- addition of dielectric oil additives based on modified fatty acids and/or fatty acid alkyl esters may endow insulation fluids with improved properties relating to specific heat and thermal conductivity.
- dielectric fluid additives preferably derived from renewable resources, having the capability of modulating numerous desirable properties in terms of inter alia reduced viscosity, improved heat transfer, reduced pour point, improved oxidation stability, and biodegradability, allowing for improved thermal management and better impregnation of pressboard/paper insulation, increased personnel health and safety, facilitated clean-up and prolonged service life of power and/or electrical apparatuses.
- the present invention fulfils the above-identified needs, as it provides, inter alia, dielectric, dielectric oil additives based on modified fatty acids and/or fatty acid alkyl esters bestowing insulation oils with improved properties in terms of inter alia reduced viscosity, improved heat transfer properties, reduced pour point, improved oxidation stability, and biodegradability, allowing for improved thermal management and better impregnation of pressboard/paper insulation, increased personnel health and safety, facilitated clean-up and prolonged service life of power and/or electrical apparatuses. Further, the present invention relates to processes and methods for preparing said dielectric oil additives, as well as their uses in electrical and/or power apparatuses, in addition to the electrical and/or power apparatuses per se comprising said dielectric oil additives.
- the present invention pertains to a dielectric oil additive comprising a fatty acid and/or a fatty acid alkyl ester comprising at least one carbon-carbon double bond.
- the dielectric oil additive is obtained by reacting said at least one carbon-carbon double bond with at least one alkyl halide and/or at least one acyl halide.
- the present invention relates to a method for preparing dielectric oil additives.
- the method comprises the steps of providing a suitable fatty acid and/or a fatty acid alkyl ester, preferably naturally derived, comprising at least one carbon-carbon double bond. Subsequently, the at least one carbon-carbon double bond is reacted with at least one alkyl halide and/or at least one acyl halide, normally in the presence of a catalyst, generating the dielectric oil additives in accordance with the present invention.
- the present invention concerns a method for preparing a dielectric oil, wherein the method comprises the steps of providing a suitable fatty acid and/or a fatty acid alkyl ester comprising at least one carbon-carbon double bond, subsequently reacting the at least one carbon-carbon double bond with at least one alkyl halide and/or at least one acyl halide, and finally adding to alkylated and/or acylated fatty acid and/or fatty acid alkyl ester to a suitable oil.
- the reaction may take place in the presence of a catalyst.
- the present invention relates to an electrical apparatus comprising the dielectric oil additive and/or the dielectric oil of the present invention.
- the present invention pertains to various uses of the dielectric oil additive and/or the dielectric oil in electrical apparatuses, and/or in apparatuses for power applications, or in components utilized in said apparatuses.
- Apparatuses of interest as per the present invention may for instance be transformers, capacitors, switchgear, bushings, etc., as well components and/or parts utilized in power or electrical applications.
- the present invention relates to the use of a chemically modified fatty acid and/or fatty acid alkyl ester in a dielectric fluid, wherein said chemically modified fatty acid and/or fatty acid alkyl ester is obtainable by reacting at least one carbon-carbon double bond of the fatty acid and/or of the fatty acid alkyl ester with at least one alkyl halide and/or at least one acyl halide.
- the present invention pertains to dielectric oil additives and/or dielectric oils suitable for various power and/or electrical applications and/or uses, methods for preparing said oil additives and/or oils, as well as electrical and/or power apparatuses and components comprising said oil additives and/or oils.
- fatty acids shall be understood to relate to carboxylic acids with aliphatic tails, for instance, but not limited to, oleic acid, linoleic acid, ⁇ -linolenic acid, myristoleic acid, arachidonic acid, icosapentaenoic acid, palmitoleic acid, erucic acid, and docosahexaenoic acid, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, vaccenic acid, gamma-linolenic acid, behenic acid, erucic acid, and lignoceric acid.
- the fatty acids may be saturated or un-saturated, branched or linear, conjugated or un-conjugated, and optionally having additional moieties attached to any part of the molecule.
- naturally derived shall be understood to pertain to natural fluids and/or oils derived from renewable resources, for instance natural and/or genetically modified (GMO) plant vegetable seeds and/or fat from various animal sources.
- Said fluids and/or oils are generally comprised of triglycerides, i.e. three fatty acids linked to a glycerol moiety.
- the fatty acids may be saturated or un-saturated, with the unsaturations being either conjugated and/or unconjugated. Conjugation may be introduced synthetically, enzymatically, or by using any other types of physical and/or chemical means, or it may be naturally occurring.
- Vegetable fluids and/or oils may for instance be selected from the group comprising, but that is not limited to, peanut, rapeseed, castor, olive, corn, cotton, canola, soybean, sesame, linseed, safflower, grapeseed, palm, avocado, pumpkin kernel, macadamia nut, sunflower, and any combinations and/or mixtures thereof. Additionally, fluids and/or oils may be obtained from essentially any organisms being a suitable fluid and/or oil source. Fluids and/or oils derived from animal sources may be selected from the group comprising beef tallow, fish oils, lard, and any combinations and/or mixtures thereof. Naturally, various combinations of the above fluids and/or oils may be utilized, irrespective of the source.
- the fatty acids may be of essentially any length, having essentially any number of unsaturations, either conjugated and/or unconjugated.
- Fatty acids may be for instance be selected from the group comprising, but that is not limited to, oleic acid, linoleic acid, ⁇ -linolenic acid, myristoleic acid, arachidonic acid, icosapentaenoic acid, palmitoleic acid, erucic acid, and docosahexaenoic acid, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, vaccenic acid, gamma-linolenic acid, behenic acid, erucic acid, lignoceric acid, or any other fatty acids.
- alkyl or "alkylene”, as used herein, is a (C 1 -C 50 )alkyl or (C 1 -C 50 )alkylene moiety, e.g. a (C 2 -C 30 )alkyl or (C 10 -C 40 )alkylene moiety and is intended to encompass also the alkyl or alkylene portion of any functional group, e.g. an alkoxy, alkylamino, or carboxypolyoxyalkylene group.
- any alkyl or alkylene group in accordance with the present invention may be branched or unbranched, and/or cyclic.
- alkyl includes the monoradical derived from a branched or unbranched and/or cyclic alkane.
- the present invention relates to a dielectric oil additive comprising a fatty acid and/or a fatty acid alkyl ester comprising at least one carbon-carbon double bond.
- the dielectric oil additive is obtained by reacting said at least one carbon-carbon double bond with at least one alkyl halide and/or at least one acyl halide.
- the reaction between the fatty acids and/or the fatty acid alkyl ester comprising at least one carbon-carbon double bond and the at least one alkyl halide and/or at least one acyl halide may take place through a Friedel-Crafts reaction mechanism, or a radical mechanism, or through any other reaction mechanism, known and/or unknown.
- Said reaction between a fatty acid and/or a fatty acid alkyl ester comprising at least one carbon-carbon double bond and the at least one alkyl halide and/or at least one acyl halide leads to inter alia reduced viscosity of oils comprising the dielectric oil additive, as well as increased permittivity, increased oxidation stability, and reduced pour point, etc.
- the fatty acids and/or the fatty acid alkyl ester comprising at least one carbon-carbon double bond are obtained from naturally derived oils and/or fluids, inter alia vegetable oil and/or oil from animal sources.
- the fatty acids and/or the fatty acid alkyl esters may be obtained through numerous different procedures, for instance acid-catalyzed hydrolysis of naturally derived triglycerides, and/or base-catalyzed hydrolysis of naturally derived triglycerides, and/or enzymatic treatments, and/or by any other chemical and/or physical means.
- the number of unsaturations in the fatty acids and/or the fatty acid alkyl esters may be reduced or increased, depending on the desired characteristics of the resultant dielectric oil additive, and the fatty acids may additionally also be esterified into for instance methyl, ethyl, propyl, isopropyl, butyl, and essentially any type of alkyl esters.
- the at least one alkyl halide and/or the at least one acyl halide optionally further comprise at least one moiety that further increases fatty acid and/or a fatty acid alkyl ester fluidity.
- said moiety increasing the fatty acid and/or a fatty acid alkyl ester fluidity may be saturated or unsaturated, branched, linear and/or cyclic hydrocarbon, optionally substituted with at least one heteroatom.
- Said moiety that further increases the fatty acid and/or a fatty acid alkyl ester fluidity may be attached to any part of alkyl the moiety of the alkyl halide and/or any part of the acyl moiety of the acyl halide, and, in yet another embodiment, said moiety may for instance be selected from the group comprising inter alia branched or linear, and/or cyclic, (C 1 -C 50 )alkyl, (C 1 -C 50 )alkenyl, and (C 1 -C 50 )alkynyl, any hydrocarbyl, aromatic hydrocarbons comprising at least one aromatic ring structure, any combination of the above and all of the above optionally substituted with at least one heteroatom, selected from the group comprising inter alia nitrogen, oxygen, phosphorous, boron, silicone, etc, and optionally further comprising various functional groups and/or moieties such as carboxylic acids, carboxylates, amines, primary amines, secondary amines,
- the at least one alkyl halide may for instance be selected from the group comprising any alkyl halide, isopropyl chloroformate, isobutyl chloroformate, butyl chloroformate, octyl chloroformate, alkyl chloroformate, alkyl haloformate, cyclohexyl chloroformate, cyclohexyl haloformate, and di-tert-butylpyrocarbonate.
- the at least one acyl halide may for instance be selected from the group comprising any acyl halide, propanoyl chloride, butanoyl chloride, alkanoyl chloride, alkenoyl chloride, alkynoyl chloride, alkanoyl halogen, alkenoyl halogen, alkynoyl halogen.
- the dielectric oil additive may comprise inter alia a fatty acid exemplified in a non-limiting manner by the following structural formula (I), drawn merely in a schematic manner, as will be immediately recognized by a person skilled in the art: wherein x may be selected from integers of 0-50, R 1 may be selected from the group comprising saturated or unsaturated, branched, linear, and/or cyclic (C 0 -C 50 )alkyl, each R 2 and R 3 may be independently selected from hydroxy, hydroxyalkyl, hydroxyalkoxy, hydroxyalkoxyalkyl, hydroxypolyoxyalkylene, alkoxy, alkoxyalkyl, polyoxyalkylene, carboxy, carboxyalkyl, carboxyalkoxy, carboxyalkoxyalkyl, carboxypolyoxyalkylene, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, alkoxycarbonylalkoxyalkyl, alkoxycarbony
- the above structural formula may be varied, for instance in terms of inter alia the number and location of the alkyl and/or acyl moieties introduced by the reaction between fatty acids having at least one carbon-carbon double bond and at least one alkyl halide and/or at least one acyl halide (e.g.the position along the fatty acid chain(s)), the number and locations of unsaturations of the fatty acid chains (e.g. the presence of conjugated or unconjugated unsaturation(s), whether the unsaturations are located on the acid side or on the alkyl side of the introduced alkyl(s) and/or acyl(s)), and the length and the branching of the fatty acid chains (e.g.
- the introduction of the at least one the alkyl(s) and/or acyl(s) increases the fluidity of the fatty acids, rendering the fluid inter alia less viscous as well as more oxidation stable, as well as endowing the fluid with properties such as improved permittivity, reduced pour point, and improved insulation properties.
- the at least one second moiety that further increases the fatty acid fluidity may correspond to any one of R 2 and/or R 3 , in accordance with structural formula (I) above.
- the dielectric oil additive may comprise inter alia a fatty acid alkyl ester exemplified in a non-limiting manner by the following structural formula (II), drawn merely in a schematic manner, as will be immediately recognized by a person skilled in the art: wherein x may be selected from integers of 0-50, R 1 and R 5 may each be independently selected from the group comprising saturated or unsaturated, branched, linear, and/or cyclic (C 0 -C 50 )alkyl, each R 2 , R 3 , and R 4 may be independently selected from hydroxy, hydroxyalkyl, hydroxyalkoxy, hydroxyalkoxyalkyl, hydroxypolyoxyalkylene, alkoxy, alkoxyalkyl, polyoxyalkylene, carboxy, carboxyalkyl, carboxyalkoxy, carboxyalkoxyalkyl, carboxypolyoxyalkylene, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkyl, al
- the above structural formula may be varied, for instance in terms of inter alia the number and location of the alkyl and/or acyl moieties introduced by the reaction between fatty acid alkyl esters having at least one carbon-carbon double bond and at least one alkyl halide and/or at least one acyl halide (e.g. the position along the fatty acid chain), the number and locations of unsaturations of the fatty acid alkyl ester chains (e.g.
- the person skilled in the art moreover recognizes that additional groups and moieties not specifically mentioned above are within the scope of the present invention.
- the introduction of the at least one the alkyl(s) and/or acyl(s) increases the fluidity of the fatty acid alkyl esters, rendering the fluid inter alia less viscous as well as more oxidation stable, as well as endowing the fluid with properties such as improved permittivity, reduced pour point, and improved insulation properties.
- the at least one second moiety that further increases the fatty acid alkyl ester fluidity may correspond to any one of R 2 , R 3 , and/or R 4 , in accordance with structural formula (II) above.
- the dielectric oil additive may comprise inter alia a fatty acid alkyl ester exemplified in a non-limiting manner by the following structural formula (III), drawn merely in a schematic manner, as will be immediately recognized by a person skilled in the art: wherein x may be selected from integers of 0-50, R 1 and R 3 may each be independently selected from the group comprising saturated or unsaturated, branched, linear, and/or cyclic (C 0 -C 50 )alkyl, R 2 may be independently selected from hydroxy, hydroxyalkyl, hydroxyalkoxy, hydroxyalkoxyalkyl, hydroxypolyoxyalkylene, alkoxy, alkoxyalkyl, polyoxyalkylene, carboxy, carboxyalkyl, carboxyalkoxy, carboxyalkoxyalkyl, carboxypolyoxyalkylene, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, alkoxycarbonylalkoxy, alk
- the above structural formula may be varied, for instance in terms of inter alia the number and location of the alkyl and/or acyl moieties introduced by the reaction between fatty acid alkyl esters having at least one carbon-carbon double bond and at least one alkyl halide and/or at least one acyl halide (e.g. the position along the fatty acid chain), the number and locations of unsaturations of the fatty acid alkyl ester chain (e.g.
- the person skilled in the art moreover recognizes that additional groups and moieties not specifically mentioned above are within the scope of the present invention.
- the introduction of the at least one the alkyl(s) and/or acyl(s) increases the fluidity of the fatty acid alkyl esters, rendering the fluid inter alia less viscous as well as more oxidation stable, as well as endowing the fluid with properties such as improved permittivity, reduced pour point, and improved insulation properties.
- the at least one second moiety that further increases the fatty acid alkyl ester fluidity may correspond to R 2 , in accordance with structural formula (III) above.
- the dielectric oil comprises at least one triglyceride, or a triglyceride composition having properties that needs to be enhanced in various ways, using the oil additive of the present invention.
- the dielectric oil may preferably be naturally derived, for instance oil and/or fluid from vegetable and/or animal sources.
- the dielectric oil may have a permittivity value in the range between approximately 2.2 and approximately 4.5, in order to provide a dielectric oil with optimized properties.
- Yet another aspect as per the present invention relates to a method for preparing dielectric oil additives.
- the method comprises the steps of providing a suitable fatty acid and/or a fatty acid alkyl ester, preferably naturally derived, comprising at least one carbon-carbon double bond. Subsequently, the at least one carbon-carbon double bond is reacted with at least one alkyl halide and/or at least one acyl halide, normally in the presence of a catalyst, generating the dielectric oil additives in accordance with the present invention.
- the catalyst is a Lewis acid
- the Lewis acid may be selected from the group comprising aluminium chloride, ethylaluminium dichloride, and/or ethylaluminium sesquichloride.
- reaction step may be carried out at ambient temperature.
- the present invention relates to a naturally derived fatty acid and/or fatty acid alkyl ester having one, two, or three carbon-carbon double bonds.
- the fatty acid and/or fatty acid alkyl ester may for instance be oleic acid or an oleic acid methyl or ethyl ester.
- Said carbon-carbon double bond of the naturally derived oleic acid and/or oleic acid alkyl ester may preferably be reacted with isopropyl chloroformate, cyclohexyl chloroformate, propanoyl chloride, or butanoyl chloride, di-tert-butylpyrocarbonate, in order to generate a modified fatty acid and/or fatty acid alkyl ester having increased fluidity, implying improved properties in terms of reduced viscosity, improved insulation, reduced pour point, improved oxidation stability, permittivity, and/or biodegradability.
- a further aspect of the present invention pertains to a method for preparing an dielectric oil, wherein the method comprises the steps of providing a suitable fatty acid and/or a fatty acid alkyl ester comprising at least one carbon-carbon double bond, subsequently reacting the at least one carbon-carbon double bond with at least one alkyl halide and/or at least one acyl halide, and finally adding to alkylated and/or acylated fatty acid and/or fatty acid alkyl ester to a suitable oil.
- the reaction may take place in the presence of a catalyst, and the catalyst may, in accordance with one embodiment of the present invention, be a Lewis acid.
- the Lewis acid may be selected from the group comprising aluminium chloride, ethylaluminium dichloride, and/or ethylaluminium sesquichloride.
- the reaction step may be carried out at ambient temperature.
- the oil comprises at least one triglyceride, and said oil may optionally be naturally derived.
- One aspect of the present invention relates to an electrical apparatus comprising the dielectric oil additive of the present invention.
- a further aspect pertains to an electrical apparatus comprising the dielectric oil as per the present invention.
- Another aspect of the present invention pertains to various uses of the dielectric oil additive and/or the dielectric oil in electrical apparatuses, and/or in apparatuses for power applications, or in components utilized in said apparatuses.
- Apparatuses of interest as per the present invention may for instance be transformers, capacitors, switchgear, bushings, etc., as well components and/or parts utilized in power or electrical applications.
- the dielectric oil additive and/or the dielectric oil may be utilized in for instance paints and coatings, printing inks, lubricants, surfactants, or within the food and/or cosmetics industry.
- Yet another aspect of the present invention relates to the use of a chemically modified fatty acid and/or fatty acid alkyl ester in a dielectric fluid, wherein said chemically modified fatty acid and/or fatty acid alkyl ester is obtainable by reacting at least one carbon-carbon double bond of the fatty acid and/or of the fatty acid alkyl ester with at least one alkyl halide and/or at least one acyl halide.
- the at least one alkyl halide and/or the at least one acyl halide may optionally further comprise at least one moiety that further increases fatty acid and/or a fatty acid alkyl ester fluidity.
- the at least one moiety that further increases fatty acid and/or a fatty acid alkyl ester fluidity may comprise a saturated or unsaturated, branched, linear and/or cyclic hydrocarbon, optionally substituted with at least one heteroatom.
- the at least one alkyl halide may be selected from the group comprising isopropyl chloroformate, isobutyl chloroformate, butyl chloroformate, octyl chloroformate, alkyl chloroformate, alkyl haloformate, cyclohexyl chloroformate, cyclohexyl haloformate, and di-tert-butylpyrocarbonate.
- the at least one acyl halide is selected from the group comprising propanoyl chloride, butanoyl chloride, alkanoyl chloride, alkenoyl chloride, alkynoyl chloride, alkanoyl halogen, alkenoyl halogen, and alkynoyl halogen.
- At least one carbon-carbon double bond of a suitable fatty acid or a suitable fatty acid alkyl ester is reacted with isopropyl chloroformate at ambient temperature in the presence of ethylaluminium sesquichloride (Et 3 Al 2 Cl 3 ), with CH 2 Cl 2 as the solvent. After a reaction time of 2 h, fatty acids or fatty acid alkyl esters having a isopropyl-alkylated fatty acid chain are formed.
- the isopropylated fatty acids and fatty acid alkyl esters generated through the alkylation reaction has increased fluidity, rendering a composition comprising the isopropyl-alkylated compounds less viscous, with higher oxidation stability, increased permittivity, and reduced pour point.
- At least one carbon-carbon double bond of a suitable fatty acid or a suitable fatty acid alkyl ester is reacted with cyclohexyl chloroformate at ambient temperature in the presence of Et 3 Al 2 Cl 3 , with CH 2 Cl 2 as the solvent.
- fatty acids or fatty acid alkyl esters comprising at least one cyclohexyl moiety are generated.
- the cyclohexylated fatty acids or fatty acid alkyl esters have increased fluidity, rendering a composition comprising cyclohexylated fatty acids or fatty acid alkyl esters-based dielectric oil additive less viscous, with higher oxidation stability, increased permittivity, and reduced pour point.
- At least one carbon-carbon double bond of a suitable fatty acid or a suitable fatty acid alkyl ester is reacted with di-tert-butylpyrocarbonate at ambient temperature in the presence of Et 3 Al 2 Cl 3 , with CH 2 Cl 2 as the solvent.
- a fatty acids or fatty acid alkyl esters having at least one tert-butyl-alkylated moiety are formed.
- the fatty acids or fatty acid alkyl esters generated through the alkylation reaction has increased fluidity, rendering a composition comprising the tert-butyl-alkylated fatty acids or fatty acid alkyl esters less viscous, with higher oxidation stability, increased permittivity, and reduced pour point.
- Suitable fatty acids or fatty acid alkyl esters comprising at least one carbon-carbon are reacted with propanoyl chloride at ambient temperature in the presence of ethylaluminium dichloride. After a reaction time of 3 h, fatty acids or fatty acid alkyl esters having at least one propanoylated fatty acid chain are formed.
- the fatty acids or fatty acid alkyl esters generated through the alkylation reaction have increased fluidity, rendering a composition comprising the propanoylated fatty acids or fatty acid alkyl esters less viscous, with higher oxidation stability, increased permittivity, and reduced pour point.
- Suitable fatty acids or fatty acid alkyl esters comprising at least one carbon-carbon are reacted with butanoyl chloride at ambient temperature in the presence of ethylaluminium dichloride. After a reaction time of 3 h, fatty acids or fatty acid alkyl esters having at least one butanoylated fatty acid chain are formed.
- the fatty acids or fatty acid alkyl esters generated through the alkylation reaction have increased fluidity, rendering a composition comprising the butanoylated fatty acids or fatty acid alkyl esters less viscous, with higher oxidation stability, increased permittivity, and reduced pour point.
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Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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EP10168019A EP2402957A1 (de) | 2010-06-30 | 2010-06-30 | Fettsäure und Fettsäure-Alkylester-Öladditive |
PCT/EP2011/060909 WO2012001043A1 (en) | 2010-06-30 | 2011-06-29 | Fatty acid and fatty acid alkyl ester oil additives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10168019A EP2402957A1 (de) | 2010-06-30 | 2010-06-30 | Fettsäure und Fettsäure-Alkylester-Öladditive |
Publications (1)
Publication Number | Publication Date |
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EP2402957A1 true EP2402957A1 (de) | 2012-01-04 |
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Application Number | Title | Priority Date | Filing Date |
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EP10168019A Withdrawn EP2402957A1 (de) | 2010-06-30 | 2010-06-30 | Fettsäure und Fettsäure-Alkylester-Öladditive |
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EP (1) | EP2402957A1 (de) |
WO (1) | WO2012001043A1 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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FR3053521B1 (fr) | 2016-06-29 | 2020-11-06 | Arkema France | Fluide dielectrique comprenant des esters d'acides gras |
CN114106903B (zh) * | 2021-10-29 | 2023-04-07 | 广东电网有限责任公司广州供电局 | 绝缘油及其制备方法 |
WO2024035945A1 (en) * | 2022-08-12 | 2024-02-15 | University Of Utah Research Foundation | Efficient synthesis of very-long-chain polyunsaturated fatty acids |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4187188A (en) * | 1978-11-13 | 1980-02-05 | The Dow Chemical Company | Electrical device containing a halogenated alkanoate dielectric fluid |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5949017A (en) * | 1996-06-18 | 1999-09-07 | Abb Power T&D Company Inc. | Electrical transformers containing electrical insulation fluids comprising high oleic acid oil compositions |
FR2855527B1 (fr) * | 2003-05-30 | 2006-07-28 | Electricite De France | Compositions liquides dielectriques, a base d'huile de colza oleique modifiee, et dispositifs electriques les contenant, a titre de liquides isolants et caloporteurs |
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2010
- 2010-06-30 EP EP10168019A patent/EP2402957A1/de not_active Withdrawn
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2011
- 2011-06-29 WO PCT/EP2011/060909 patent/WO2012001043A1/en active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4187188A (en) * | 1978-11-13 | 1980-02-05 | The Dow Chemical Company | Electrical device containing a halogenated alkanoate dielectric fluid |
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