EP3328978A1 - Composition for solubilization of organic residues - Google Patents

Composition for solubilization of organic residues

Info

Publication number
EP3328978A1
EP3328978A1 EP16750704.5A EP16750704A EP3328978A1 EP 3328978 A1 EP3328978 A1 EP 3328978A1 EP 16750704 A EP16750704 A EP 16750704A EP 3328978 A1 EP3328978 A1 EP 3328978A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
esters
acid esters
composition
weight
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.)
Withdrawn
Application number
EP16750704.5A
Other languages
German (de)
French (fr)
Inventor
Sébastien BARREAU
Marine FOUQUET
Christophe BRIGE
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.)
Oleon NV
Original Assignee
Oleon NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Oleon NV filed Critical Oleon NV
Publication of EP3328978A1 publication Critical patent/EP3328978A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/266—Esters or carbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/04—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction
    • C10G1/042—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction by the use of hydrogen-donor solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/032—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/107—Atmospheric residues having a boiling point of at least about 538 °C
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1077—Vacuum residues
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1081—Alkanes
    • C10G2300/1085—Solid paraffins
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/80—Additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/16—Residues
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/20—Industrial or commercial equipment, e.g. reactors, tubes or engines

Definitions

  • the present invention relates to a composition that can be used to dissolve or disperse organic residues from crude oil including paraffin waxes and asphaltenes. It also relates to the uses of such a composition, as well as formulations containing such a composition in combination with other excipients.
  • paraffin deposits or similar products can accumulate in the production and storage devices, thus limiting performance.
  • bitumen when using petroleum fractionation products, particularly in the field of road coatings, it may be desirable to thin the bitumen to facilitate mixing with the mixes and / or spreading.
  • EP 1012211 discloses detergents based on fatty acid lower alkyl esters having from 6 to 22 carbon atoms, mixed with solvents such as hydrocarbons or DMSO. It remains desirable to have compositions having good solvent properties or dispersing raw materials from the fractionation of heavy oils, but derived from renewable raw material and do not have such harmful effects.
  • compositions which are not easily flammable to be able to transport them without special precautions and to use them under temperature conditions compatible with petroleum installations for example.
  • compositions also have a satisfactory fluidity.
  • the subject of the present invention is a composition for solubilizing organic residues of fossil material comprising a mixture of fatty acid esters of formula:
  • R1 represents a C5 to C23, in particular C5 to C21, and especially C5 to C19 carbon chain, linear or branched, optionally containing one or more unsaturations,
  • R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations
  • composition comprising:
  • the content of C8 to C14 saturated fatty acid esters is greater than or equal to 38% by weight, the percentages by weight being given relative to the total mass of fatty acid esters in the composition.
  • R 1 represents a linear carbon chain.
  • R2 represents a saturated carbon chain, in particular C1 to C8. It is understood that for at least a portion of the fatty acid esters present in the composition, in the formula (I) at least one of the R 1 or R 2 chains comprises at least one unsaturation, in particular at least R 1 comprises at least one unsaturation.
  • the mixture comprises esters of fatty acids for which R 1 represents a C 5 to C 23 carbon chain as defined above comprising one or more unsaturations, and fatty acid esters for which R 1 represents a carbon chain in 05 to 023 as defined above, not containing any unsaturation.
  • at least one unsaturation is meant in particular at least one double bond or at least one triple bond.
  • the fatty acid esters mentioned in a are, in particular, fatty acid esters in the range from 0 to 10.
  • fatty acid esters in the range from 0 to 10.
  • methyl or ethyl esters in particular methyl esters, are used.
  • the fatty acid esters mentioned in b are in particular 018 fatty acid esters containing at least one unsaturation, such as 0-18: 1 fatty acids, 018: 2 fatty acids and mixtures thereof in all proportions.
  • fatty acid esters in 018 to 024 comprising at least one unsaturation, and in particular comprising at least one double bond, at least 10% by weight, and in particular at least 12% by weight, are fatty acid esters in 018: 1, the percentages by mass being given with respect to the total mass of esters of fatty acids in the composition.
  • the fatty acid esters come either from an esterification of fatty acids or from a transesterification of triglycerides.
  • the fatty acids and triglycerides are advantageously derived from renewable resources, such as vegetable oils and vegetable and animal fats.
  • the C6 to C10 fatty acids are preferably saturated. These fatty acids may especially be chosen from hexanoic acid, caprylic acid, capric acid, pelargonic acid and mixtures thereof in all proportions.
  • C8-C10 fatty acids are preferably saturated fatty acids; they may in particular be selected from caprylic acid, capric acid, pelargonic acid and mixtures thereof in all proportions.
  • a mixture of caprylic acid and capric acid esters is used, in particular a mixture of methyl esters comprising 45 to 70% of caprylate and 30 to 55% of caprate.
  • Such fatty acid ester fractions can in particular be obtained from coconut oil and / or palm kernel oil, advantageously from coconut oil.
  • the C 8 to C 14 fatty acid esters may in particular be selected from caprylic acid, capric acid, pelargonic acid, lauric acid, myristic acid and mixtures thereof in all proportions. They can be introduced into the composition according to the invention via a particular fraction obtained from coconut oil, palm kernel oil, tallow and / or fish oil, and / or via one of these oils. vegetable / animal fats transesterified.
  • the C 8 -C 14 fatty acid esters are introduced into the composition according to the invention via a coconut oil or a transesterified palm oil. It is thus possible to prepare compositions containing methyl, ethyl, isopropyl, butyl, isoamyl or 2-ethylhexyl esters of coconut oil and palm kernel oil.
  • C8-C14 fatty acid esters are coconut oil esters.
  • the invention thus relates to compositions comprising fatty acid esters of coconut oil and C1 to C8 alcohols at a concentration of 0 to 60% by weight.
  • the total concentration of esters is greater than or equal to 35% of the total composition of esters of coconut oil.
  • fatty acids and less than or equal to 85%, preferably less than or equal to 80%.
  • the subject of the present invention is thus a solubilization composition for organic residues of fossil material comprising a mixture of fatty acid esters characterized in that the mixture of fatty acid esters comprises a mixture of formula : in which
  • R1 represents a C5 to C23, in particular C5 to C21, and especially C5 to C19 carbon chain, linear or branched, optionally containing one or more unsaturations,
  • R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations
  • composition comprising:
  • the total concentration of C8 to C10 fatty acid esters and coconut oil fatty acid esters being greater than or equal to 35% of the total fatty acid ester composition, and less than or equal to 85%, preferably less than or equal to 80%.
  • concentrations are expressed throughout the present text by mass, based on the total mass of the composition.
  • the concentration of C8 to C10 fatty acid esters is less than or equal to 25%, or even less than or equal to 21%
  • the concentration of coconut oil fatty acid esters is greater than or equal to 25%. %, in particular greater than or equal to 30%.
  • the C18: 2 fatty acid esters are in particular linoleic acid esters.
  • the C18: 1 fatty acids may be selected from the group consisting of oleic acid, vaccenic acid and ricinoleic acid; preferably, the ester (s) of C18: 1 fatty acids present in the compositions according to the invention are chosen from oleic acid esters.
  • esters may in particular be obtained by esterification or transesterification of rapeseed oil fatty acids, this oil may comprise up to 65% of oleic acid.
  • the C 18: 1 fatty acid esters may also, in a manner known per se, be obtained from olive oil or avocado.
  • esters may also be obtained from other oils of vegetable or animal origin which may contain at least 20% oleic acid such as: palm, peanut, corn, soya, sunflower, grape, flax, rosin, tallow or fat animal.
  • the oleic acid ester is provided in the composition in the form of rapeseed oil ester.
  • the subject of the invention is therefore also a solubilization composition for the organic residues of raw material of fossil origin as defined above, comprising a mixture of fatty acid esters of formula: in which
  • R1 represents a linear or branched C5 to C23, in particular C17 to C21, carbon chain optionally comprising one or more unsaturations,
  • R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations
  • composition comprising:
  • the total concentration of C 8 to C 10 fatty acid methyl esters and coconut oil fatty acid esters being greater than or equal to 35%, in particular 40% of the total composition, and less than or equal to 85%.
  • the coconut oil (or cocoate) esters will comprise a mixture of lauric, myristic, caprylic, capric, oleic, linoleic, stearic and palmitic acid esters. It has been unexpectedly found that compositions having the above characteristics, which can be prepared from renewable raw materials, namely vegetable or animal raw materials, preferably plant materials, have very good properties of dissolution and dispersion of paraffin waxes and by-products of petroleum fractionation and distillation in wide temperature ranges. Generally, from 35 ° C, 70% of the organic residues are dissolved. In addition, these compositions are not flammable or combustible, as is apparent from the measurement of their flash point. Finally, the compositions according to the invention remain liquid at low temperatures, this property being objectified by the measurement of their pour point. The pour point of a product is the temperature at which the product no longer flows.
  • compositions according to the invention have a pour point of less than -20 ° C.
  • the flash point is the minimum temperature at which the concentration of vapors emitted is sufficient to produce a deflagration on contact with a flame or hot spot under standard conditions, but insufficient to produce the propagation of combustion in the absence of the "pilot" flame.
  • a minimum temperature is demonstrated at which the emission of vapors is sufficient to form with the air the flammable gas mixture under the external action of a flame.
  • This minimum temperature level is called a flash point.
  • fire point There is a second temperature level, beyond the flash point, called fire point, necessary and sufficient for the combustion of the gaseous mixture to be maintained and maintained.
  • compositions according to the invention have a flash point greater than 80 ° C., and especially greater than or equal to 90 ° C., advantageously greater than or equal to 93 ° C., in particular greater than or equal to 95 ° C., or even greater than or equal to 100 ° C.
  • the composition contains at least 12% by weight of C 18: 1 fatty acid esters, in particular at least 15%, in particular at least 18%.
  • the sum of the concentrations of C 8 to C 10 fatty acid methyl esters and of the C 18: 1 fatty acid ester (s) is greater than or equal to 40%, especially greater than or equal to 45%. %, in particular greater than or equal to 50%.
  • compositions particularly meeting the objectives of the invention are those for which the C 18: 1 fatty acid esters are alcohol esters for which R 2 represents a C 1 -C 8, in particular C 1 -C 5, carbon chain, more especially C1-C4.
  • It may be in particular methyl, ethyl, propyl, isopropyl, butyl, pentyl or isoamyl ester, or mixtures thereof, in particular esters formed with oleic acid.
  • compositions containing methyl, butyl or isoamyl esters of rapeseed oil, in particular rapeseed oil methyl esters are chosen from n-butyl oleate, methyl oleate and mixtures thereof; the methyl oleate can be added to the composition in the form of rapeseed oil methyl esters.
  • the fatty acid esters mentioned in c) are advantageously chosen from methylcocoate, 2-ethylhexylcocoate and mixtures thereof in all proportions, preferably the fatty acid esters mentioned in c) are esters of coconut and 2-ethylhexanol, also called 2-ethylhexylcocoate.
  • the solubilization composition contains at least 36% of methyl esters of C8 to C10 fatty acids.
  • composition particularly suitable for the implementation of the invention contains a mixture of fatty acids consisting of:
  • C18: 1 fatty acid esters selected from methyl esters, ethyl esters, butyl esters, isoamyl esters, 2-ethylhexyl esters and mixtures thereof, in particular from among the esters methyl, butyl esters and mixtures thereof.
  • compositions will advantageously comprise a concentration of rapeseed oil methyl esters greater than or equal to 30%.
  • composition may comprise:
  • the solubilization composition contains:
  • compositions according to any one of the embodiments according to the invention may be used in pure form, or mixed with a solvent.
  • the solvent may especially be selected from xylene or mineral oils.
  • compositions according to any one of the embodiments of the invention may be used to solubilize or disperse solid bitumens, especially heavy oils, such as paraffins and paraffin waxes or asphaltenes.
  • paraffin means saturated hydrocarbons of formula C n H 2 n + 2 with n ranging from 8 to 40.
  • the paraffin waxes generally have n greater than or equal to 20.
  • the compositions according to any one of the embodiments of the invention may be used to strip and maintain the extraction, refining, transport and storage facilities for oil and its derivatives. They will also be useful for cleaning and stripping any type of device in contact with petroleum derivatives of paraffin or asphaltene type, especially for the degreasing of metal parts in industry or printing presses.
  • the compositions according to any one of the embodiments of the invention may also be used in the field of painting, for example as a thinner or binder in paints, or for cleaning surfaces or tools after use.
  • compositions according to any one of the embodiments of the invention will also be useful in the construction, as concrete release agent.
  • a composition according to the invention can also be used in the field of road coatings, within bituminous binders, for fluidifying the bituminous composition.
  • the composition acts as a fluxing agent and facilitates the spreading of the bitumen and the coating of the minerals contained in the bituminous composition.
  • compositions and formulations are also included in the invention.
  • the subject of the invention is also a process for the preparation of a solubilization composition of the organic residues of raw material of fossil origin, comprising the following mixture of fatty acid esters:
  • the rapeseed oil methyl ester composition of the following composition is used:
  • n-butyl oleate composition corresponds to a mixture comprising from 68 to 92% of n-butyl oleate, at least 8% of butyl ester of linoleic acid, and from 0 to 2% of butyl ester. of linolenic acid, the remainder being optionally constituted of saturated fatty acid ester in 016 and 018.
  • the various constituents of the formulations are mixed in a container at ambient temperature until the formulation is homogenized.
  • the flash point and pour point of the formulations are determined by the methods according to ASTM D92 and ASTM D97 respectively.
  • Comparative Example 1 for which the total concentration of Methyl C8 / C10 and coconut oil fatty acid esters is 30%, has a pour point greater than -20 ° C, and therefore not suitable for the implementation of the invention, the content of C8 to C14 fatty acid esters of this composition is less than 38% by mass required for the compositions according to the invention.
  • the 4X, 5bisX and 8X formulations all have a pour point less than or equal to -20 ° C and a flash point greater than or equal to 100 ° C,
  • Example 2 Tests to Determine the Dissolution Temperature The tests are performed with solid organic residues from oil sands oilfields
  • the dissolution temperatures of the waxes in the formulations tested are:
  • Example 4 Thinner of a composition
  • Paraffin was purchased from Panreac: Paraffin CAS [8002-74-2] EC number (EINECS): 232-315-6.
  • the fatty acid ester composition is mixed with paraffin in various proportions and heated to 50 ° C.-55 ° C. with 200 rpm magnetic stirring.
  • the viscosity of the resulting composition is measured with a Anton Paar Stabinger SVM 300 / G2 Viscometer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Fats And Perfumes (AREA)

Abstract

Composition for solubilization of organic residues of raw materials of fossil origin comprising a mixture of fatty acid esters of formula R1COOR2 in which R1 represents a linear or branched C5 to C23 carbon-based chain, optionally compromising one or more unsaturations, R2 represents a linear or branched C1 to C10 carbon-based chain, optionally comprising one or more unsaturations; said composition comprising: a) at least 18% by weight of C6 to C10 fatty acid esters, b) at least 18% by weight of C18 to C24, in particular C18 to C22 fatty acid esters, comprising at least one double bond, and the invention also relates to the use of the compositions.

Description

Composition de solubilisation des résidus organiques  Solubilization composition of organic residues
La présente invention concerne une composition pouvant être utilisée pour dissoudre ou disperser des résidus organiques provenant d'huile brute et notamment des cires paraffinées et des asphaltènes. Elle concerne également les utilisations d'une telle composition, ainsi que des formulations contenant une telle composition en association avec d'autres excipients. The present invention relates to a composition that can be used to dissolve or disperse organic residues from crude oil including paraffin waxes and asphaltenes. It also relates to the uses of such a composition, as well as formulations containing such a composition in combination with other excipients.
La solubilisation de résidus de matières premières d'origine fossile présente un intérêt prédominant dans le domaine de l'extraction pétrolière. En effet, cette extraction nécessite des forages pour atteindre le gisement, et le pétrole brut est ensuite récupéré à travers des tubes, soit qu'il remonte naturellement grâce à la pression du pétrole au début de la vie du puits, soit à l'aide de pompe. Il est ensuite acheminé par des oléoducs jusqu'au lieu de raffinage. The solubilization of residues of fossil raw materials is of primary interest in the field of petroleum extraction. Indeed, this extraction requires drilling to reach the deposit, and the crude oil is then recovered through tubes, either it goes back naturally thanks to the pressure of the oil at the beginning of the life of the well, or by means of pump. It is then transported by pipelines to the refining site.
Tout au long des processus d'extraction et de raffinage, des dépôts de paraffines ou de produits analogues peuvent s'accumuler dans les dispositifs de production et de stockage, limitant ainsi le rendement.  Throughout the extraction and refining processes, paraffin deposits or similar products can accumulate in the production and storage devices, thus limiting performance.
Par ailleurs, lors de l'utilisation des produits de fractionnement du pétrole, en particulier dans le domaine des revêtements routiers, il peut être souhaitable de fluidifier le bitume pour faciliter le mélange avec les enrobés et/ou son étalement. Furthermore, when using petroleum fractionation products, particularly in the field of road coatings, it may be desirable to thin the bitumen to facilitate mixing with the mixes and / or spreading.
De manière générale, les divers produits du fractionnement du pétrole brut doivent pouvoir être éliminés lors de leur utilisation, lors d'une étape de nettoyage ou de décapage. In general, the various products of the fractionation of crude oil must be able to be eliminated during their use, during a cleaning or stripping step.
On utilise classiquement des produits chimiques eux-mêmes d'origine pétrolière, comme des composés organiques volatils et des solvants toxiques, à cette fin. Conventional chemicals of petroleum origin, such as volatile organic compounds and toxic solvents, are conventionally used for this purpose.
Cependant ces produits peuvent avoir des effets nocifs pour la santé humaine ou animale, et pour l'environnement.  However, these products may have harmful effects on human or animal health, and on the environment.
US 2014/0328625 propose d'utiliser des agents fluidifiants de bitumes comprenant des esters méthyliques en C6-C14, provenant en particulier d'huile de palme. US 2014/0328625 proposes the use of bitumen blowing agents comprising C6-C14 methyl esters, especially from palm oil.
EP 1012211 décrit des décapants à base d'esters d'alkyle inférieur d'acide gras ayant de 6 à 22 atomes de carbone, mélangés à des solvants comme les hydrocarbures ou le DMSO. Il demeure souhaitable de pouvoir disposer de compositions possédant de bonnes propriétés de solvant ou dispersant des matières premières issues du fractionnement des huiles lourdes, mais issues de matière première renouvelable et ne présentant pas de tels effets nocifs. EP 1012211 discloses detergents based on fatty acid lower alkyl esters having from 6 to 22 carbon atoms, mixed with solvents such as hydrocarbons or DMSO. It remains desirable to have compositions having good solvent properties or dispersing raw materials from the fractionation of heavy oils, but derived from renewable raw material and do not have such harmful effects.
II est en outre souhaitable de disposer de compositions qui ne soient pas facilement inflammables, pour pouvoir les transporter sans précaution particulière et les utiliser dans des conditions de températures compatibles avec les installations pétrolières par exemple.  It is further desirable to have compositions which are not easily flammable, to be able to transport them without special precautions and to use them under temperature conditions compatible with petroleum installations for example.
Il est en outre souhaitable que les compositions présentent aussi une fluidité satisfaisante.  It is further desirable that the compositions also have a satisfactory fluidity.
Ces buts et d'autres sont atteints par la présente invention. These and other objects are achieved by the present invention.
La présente invention a pour objet une composition de solubilisation des résidus organiques de matière première d'origine fossile comprenant un mélange d'esters d'acides gras de formule : The subject of the present invention is a composition for solubilizing organic residues of fossil material comprising a mixture of fatty acid esters of formula:
dans laquelle in which
R1 représente une chaîne carbonée en C5 à C23, en particulier en C5 à C21 , et notamment en C5 à C19, linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations,  R1 represents a C5 to C23, in particular C5 to C21, and especially C5 to C19 carbon chain, linear or branched, optionally containing one or more unsaturations,
R2 représente une chaîne carbonée en C1 à C10, linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations;  R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations;
ladite composition comprenant :  said composition comprising:
a) au moins 18% en masse d'esters d'acides gras en C6 à C10,  a) at least 18% by weight of C6 to C10 fatty acid esters,
b) au moins 18% en masse d'esters d'acides gras en C18 à C24, en particulier en C18 à C22, comportant au moins une insaturation, en particulier au moins une double liaison et  b) at least 18% by weight of C 18 to C 24, in particular C 18 to C 22, fatty acid esters comprising at least one unsaturation, in particular at least one double bond, and
à la condition que la teneur en esters d'acides gras saturés en C8 à C14 soit supérieure ou égale à 38% en masse, les pourcentages en masse étant donnés par rapport à la masse totale d'esters d'acides gras dans la composition.  provided that the content of C8 to C14 saturated fatty acid esters is greater than or equal to 38% by weight, the percentages by weight being given relative to the total mass of fatty acid esters in the composition.
De préférence, R1 représente une chaîne carbonée linéaire. Preferably, R 1 represents a linear carbon chain.
De préférence, R2 représente une chaîne carbonée saturée, en particulier en C1 à C8. On comprend que pour au moins une partie des esters d'acides gras présents dans la composition, dans la formule (I) au moins une des chaînes R1 ou R2 comporte au moins une insaturation, en particulier au moins R1 comporte au moins une insaturation.Preferably, R2 represents a saturated carbon chain, in particular C1 to C8. It is understood that for at least a portion of the fatty acid esters present in the composition, in the formula (I) at least one of the R 1 or R 2 chains comprises at least one unsaturation, in particular at least R 1 comprises at least one unsaturation.
Selon un mode de réalisation avantageux, le mélange comprend des esters d'acides gras pour lesquels R1 représente une chaîne carbonée en 05 à C23 telle que définie plus haut comportant une ou plusieurs insaturations, et des esters d'acides gras pour lesquels R1 représente une chaîne carbonée en 05 à 023 telle que définie plus haut ne comportant pas d'insaturation. Par au moins une insaturation on entend en particulier au moins une double liaison ou au moins une triple liaison. According to an advantageous embodiment, the mixture comprises esters of fatty acids for which R 1 represents a C 5 to C 23 carbon chain as defined above comprising one or more unsaturations, and fatty acid esters for which R 1 represents a carbon chain in 05 to 023 as defined above, not containing any unsaturation. By at least one unsaturation is meant in particular at least one double bond or at least one triple bond.
Les esters d'acides gras mentionnés en a sont en particulier des esters d'acides gras en 08 à 010. On utilise par exemple des esters méthyliques ou éthyliques, notamment des esters méthyliques. The fatty acid esters mentioned in a are, in particular, fatty acid esters in the range from 0 to 10. For example, methyl or ethyl esters, in particular methyl esters, are used.
Les esters d'acides gras mentionnés en b sont notamment des esters d'acides gras en 018 comportant au moins une insaturation, tels que les acides gras en 018:1 , les acides gras en 018:2 et leurs mélanges en toutes proportions. The fatty acid esters mentioned in b are in particular 018 fatty acid esters containing at least one unsaturation, such as 0-18: 1 fatty acids, 018: 2 fatty acids and mixtures thereof in all proportions.
Avantageusement, dans la composition de solubilisation des résidus organiques de matière première d'origine fossile selon l'invention, parmi les au moins 18% en masse d'esters d'acides gras en 018 à 024 comportant au moins une insaturation, et en particulier comportant au moins une double liaison, au moins 10% en masse, et notamment au moins 12% en masse, sont des esters d'acide gras en 018 :1 , les pourcentages en masse étant donnés par rapport à la masse totale d'esters d'acides gras dans la composition. Advantageously, in the solubilizing composition of the organic residues of raw material of fossil origin according to the invention, among at least 18% by weight of fatty acid esters in 018 to 024 comprising at least one unsaturation, and in particular comprising at least one double bond, at least 10% by weight, and in particular at least 12% by weight, are fatty acid esters in 018: 1, the percentages by mass being given with respect to the total mass of esters of fatty acids in the composition.
Les esters d'acides gras proviennent soit d'une estérification d'acides gras, soit d'une transestérification de triglycérides. The fatty acid esters come either from an esterification of fatty acids or from a transesterification of triglycerides.
Les acides gras et les triglycérides sont issus avantageusement de ressources renouvelables, telles que les huiles végétales et les graisses végétales et animales.  The fatty acids and triglycerides are advantageously derived from renewable resources, such as vegetable oils and vegetable and animal fats.
Une fraction particulière d'acides gras ou d'esters gras, telles qu'en C6-C10 et 08- 010, est obtenue par toute méthode connue de l'homme du métier, en particulier par distillation d'un mélange d'acides gras ou d'esters gras. Les acides gras en C6 à C10 sont de préférence saturés. Ces acides gras pourront notamment être choisis parmi l'acide hexanoïque, l'acide caprylique, l'acide caprique, l'acide pélargonique et leurs mélanges en toutes proportions. Les acides gras en C8-C10 sont de préférence des acides gras saturés; ils pourront notamment être choisis parmi l'acide caprylique, l'acide caprique, l'acide pélargonique et leurs mélanges en toutes proportions. En particulier, on utilise un mélange d'esters d'acide caprylique et d'acide caprique, notamment un mélange d'esters méthyliques comprenant 45 à 70% de caprylate et de 30 à 55% de caprate, A particular fraction of fatty acids or of fatty esters, such as C 6 -C 10 and O 8-10, is obtained by any method known to those skilled in the art, in particular by distillation of a mixture of fatty acids. or fatty esters. The C6 to C10 fatty acids are preferably saturated. These fatty acids may especially be chosen from hexanoic acid, caprylic acid, capric acid, pelargonic acid and mixtures thereof in all proportions. C8-C10 fatty acids are preferably saturated fatty acids; they may in particular be selected from caprylic acid, capric acid, pelargonic acid and mixtures thereof in all proportions. In particular, a mixture of caprylic acid and capric acid esters is used, in particular a mixture of methyl esters comprising 45 to 70% of caprylate and 30 to 55% of caprate.
De telles fractions d'esters d'acides gras peuvent notamment être obtenues à partir d'huile de coco et/ou d'huile de palmiste, avantageusement à partir d'huile de coco. Such fatty acid ester fractions can in particular be obtained from coconut oil and / or palm kernel oil, advantageously from coconut oil.
Les esters d'acides gras en C8 à C14 pourront notamment être choisis parmi l'acide caprylique, l'acide caprique, l'acide pélargonique, l'acide laurique, l'acide myristique et leurs mélanges en toutes proportions. Ils peuvent être introduits dans la composition selon l'invention via une fraction particulière obtenue à partir d'huile de coco, d'huile de palmiste, de suif et/ou d'huile de poisson, et/ou via une de ces huiles/graisses végétales/animales transéstérifiée. The C 8 to C 14 fatty acid esters may in particular be selected from caprylic acid, capric acid, pelargonic acid, lauric acid, myristic acid and mixtures thereof in all proportions. They can be introduced into the composition according to the invention via a particular fraction obtained from coconut oil, palm kernel oil, tallow and / or fish oil, and / or via one of these oils. vegetable / animal fats transesterified.
Avantageusement, les esters d'acides gras en C8 à C14 sont introduits dans la composition selon l'invention via une huile de coco ou une huile de palmiste transéstérifiée. On peut ainsi préparer des compositions contenant des esters méthyliques, éthyliques, isopropyliques, butyliques, isoamyliques ou 2-éthylhexyliques d'huile de coco et d'huile de palmiste. Advantageously, the C 8 -C 14 fatty acid esters are introduced into the composition according to the invention via a coconut oil or a transesterified palm oil. It is thus possible to prepare compositions containing methyl, ethyl, isopropyl, butyl, isoamyl or 2-ethylhexyl esters of coconut oil and palm kernel oil.
En particulier, les esters d'acides gras en C8 à C14 sont des esters d'huile de coco. L'invention concerne ainsi des compositions comprenant des esters d'acides gras d'huile de coco et d'alcools en C1 à C8, à une concentration de 0 à 60% en masse. In particular, C8-C14 fatty acid esters are coconut oil esters. The invention thus relates to compositions comprising fatty acid esters of coconut oil and C1 to C8 alcohols at a concentration of 0 to 60% by weight.
Avantageusement, la concentration totale d'esters, en particulier d'esters méthyliques d'acides gras en C8 à C10 et des esters d'acides gras d'huile de coco est supérieure ou égale à 35% de la composition totale d'esters d'acides gras, et inférieure ou égale à 85%, de préférence inférieure ou égale à 80%. La présente invention a ainsi pour objet une composition de solubilisation des résidus organiques de matière première d'origine fossile comprenant un mélange d'esters d'acides gras caractérisée en ce que le mélange d'esters d'acides gras comprend un mélange de composés de formule : dans laquelle Advantageously, the total concentration of esters, in particular of C 8 to C 10 fatty acid methyl esters and coconut oil fatty acid esters, is greater than or equal to 35% of the total composition of esters of coconut oil. fatty acids, and less than or equal to 85%, preferably less than or equal to 80%. The subject of the present invention is thus a solubilization composition for organic residues of fossil material comprising a mixture of fatty acid esters characterized in that the mixture of fatty acid esters comprises a mixture of formula : in which
R1 représente une chaîne carbonée en C5 à C23, en particulier en C5 à C21 , et notamment en C5 à C19, linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations,  R1 represents a C5 to C23, in particular C5 to C21, and especially C5 to C19 carbon chain, linear or branched, optionally containing one or more unsaturations,
R2 représente une chaîne carbonée en C1 à C10, linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations;  R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations;
ladite composition comprenant :  said composition comprising:
a) au moins 18% en masse d'esters d'acides gras en C8 à C10, notamment d'esters méthyliques ou d'esters éthyliques d'acides gras en C8 à C10,  a) at least 18% by weight of C8 to C10 fatty acid esters, especially of methyl esters or of C8 to C10 fatty acid ethyl esters,
b) au moins 18% en masse d'esters d'acides gras en C18 à C24, en particulier en C18 à C22, comportant au moins une double liaison, et  b) at least 18% by weight of C 18 to C 24, in particular C 18 to C 22, fatty acid esters comprising at least one double bond, and
c) optionnellement des esters d'acides gras d'huile de coco et d'alcools en C1 à C8, à une concentration de 0 à 60% en masse,  c) optionally fatty acid esters of coconut oil and C1 to C8 alcohols, at a concentration of 0 to 60% by weight,
la concentration totale d'esters d'acides gras en C8 à C10 et des esters d'acides gras d'huile de coco étant supérieure ou égale à 35% de la composition totale d'esters d'acides gras, et inférieure ou égale à 85%, de préférence inférieure ou égale à 80%.  the total concentration of C8 to C10 fatty acid esters and coconut oil fatty acid esters being greater than or equal to 35% of the total fatty acid ester composition, and less than or equal to 85%, preferably less than or equal to 80%.
A moins qu'il ne soit spécifié différemment, les concentrations sont exprimées tout au long du présent texte en masse, par rapport à la masse totale de la composition. Unless otherwise specified, concentrations are expressed throughout the present text by mass, based on the total mass of the composition.
Avantageusement, lorsque la concentration en esters d'acides gras en C8 à C10 est inférieure ou égale à 25%, voire inférieure ou égale à 21 %, la concentration en esters d'acides gras d'huile de coco est supérieure ou égale à 25%, en particulier supérieure ou égale à 30%. Advantageously, when the concentration of C8 to C10 fatty acid esters is less than or equal to 25%, or even less than or equal to 21%, the concentration of coconut oil fatty acid esters is greater than or equal to 25%. %, in particular greater than or equal to 30%.
Les esters d'acides gras en C18:2 sont en particulier des esters d'acide linoléique. The C18: 2 fatty acid esters are in particular linoleic acid esters.
Les acides gras en C18:1 pourront être choisis dans le groupe comprenant l'acide oléique, l'acide vaccénique et l'acide ricinoléique; de préférence, le ou les ester(s) d'acide gras en C18:1 présents dans les compositions selon l'invention sont choisis parmi les esters d'acide oléique. The C18: 1 fatty acids may be selected from the group consisting of oleic acid, vaccenic acid and ricinoleic acid; preferably, the ester (s) of C18: 1 fatty acids present in the compositions according to the invention are chosen from oleic acid esters.
De tels esters peuvent notamment être obtenus par estérification ou transestérification des acides gras d'huile de colza, cette huile pouvant comporter jusqu'à 65% d'acide oléique. Les esters d'acides gras en C18:1 peuvent aussi, de manière connue en soi, être obtenus à partir d'huile d'olive ou d'avocat. Such esters may in particular be obtained by esterification or transesterification of rapeseed oil fatty acids, this oil may comprise up to 65% of oleic acid. The C 18: 1 fatty acid esters may also, in a manner known per se, be obtained from olive oil or avocado.
Ces esters peuvent également être obtenus à partir d'autres huiles d'origine végétale ou animale pouvant contenir au moins 20% d'acide oléique telles que : palme, arachide, maïs, soja, tournesol, raisin, lin, collophane, suif ou graisse animale.  These esters may also be obtained from other oils of vegetable or animal origin which may contain at least 20% oleic acid such as: palm, peanut, corn, soya, sunflower, grape, flax, rosin, tallow or fat animal.
Selon l'un des modes de réalisation de l'invention, l'ester d'acide oléique est apporté dans la composition sous forme d'ester d'huile de colza. L'invention a donc également pour objet une composition de solubilisation des résidus organiques de matière première d'origine fossile telle que définie ci-dessus, comprenant un mélange d'esters d'acides gras de formule : dans laquelle According to one embodiment of the invention, the oleic acid ester is provided in the composition in the form of rapeseed oil ester. The subject of the invention is therefore also a solubilization composition for the organic residues of raw material of fossil origin as defined above, comprising a mixture of fatty acid esters of formula: in which
R1 représente une chaîne carbonée en C5 à C23, en particulier en C17 à C21 , linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations,  R1 represents a linear or branched C5 to C23, in particular C17 to C21, carbon chain optionally comprising one or more unsaturations,
R2 représente une chaîne carbonée en C1 à C10, linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations;  R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations;
ladite composition comprenant :  said composition comprising:
a) au moins 18% en masse d'esters méthyliques d'acides gras en C8 à C10, b) au moins 20% en masse d'esters d'acides gras d'huile de colza, et  a) at least 18% by weight of C 8 to C 10 fatty acid methyl esters, b) at least 20% by weight of rapeseed oil fatty acid esters, and
c) optionnellement des esters d'acides gras d'huile de coco et d'alcools en C1 à C8, à une concentration de 0 à 60% en masse,  c) optionally fatty acid esters of coconut oil and C1 to C8 alcohols, at a concentration of 0 to 60% by weight,
la concentration totale d'esters méthyliques d'acides gras en C8 à C10 et des esters d'acides gras d'huile de coco étant supérieure ou égale à 35%, en particulier à 40% de la composition totale, et inférieure ou égale à 85%.  the total concentration of C 8 to C 10 fatty acid methyl esters and coconut oil fatty acid esters being greater than or equal to 35%, in particular 40% of the total composition, and less than or equal to 85%.
Les esters d'huile de coco (ou cocoate) comprendront un mélange d'esters d'acide laurique, myristique, caprylique, caprique, oléique, linoléique, stéarique et palmitique. Il a été trouvé de manière inattendue que des compositions répondant aux caractéristiques ci-dessus, pouvant être préparées à partir de matières premières renouvelables à savoir les matières premières végétales ou animales, de préférence végétales, présentent de très bonnes propriétés de dissolution et de dispersion des cires paraffinées et des sous-produits du fractionnement et de la distillation du pétrole, et ce dans de larges gammes de températures. Généralement, à partir de 35°C, 70% des résidus organiques sont dissouts. En outre, ces compositions ne sont pas inflammables ni combustibles, comme cela ressort de la mesure de leur point éclair. Enfin, les compositions selon l'invention restent liquides à de basses températures, cette propriété étant objectivée par la mesure de leur point d'écoulement. Le point d'écoulement d'un produit est la température à laquelle le produit ne s'écoule plus. The coconut oil (or cocoate) esters will comprise a mixture of lauric, myristic, caprylic, capric, oleic, linoleic, stearic and palmitic acid esters. It has been unexpectedly found that compositions having the above characteristics, which can be prepared from renewable raw materials, namely vegetable or animal raw materials, preferably plant materials, have very good properties of dissolution and dispersion of paraffin waxes and by-products of petroleum fractionation and distillation in wide temperature ranges. Generally, from 35 ° C, 70% of the organic residues are dissolved. In addition, these compositions are not flammable or combustible, as is apparent from the measurement of their flash point. Finally, the compositions according to the invention remain liquid at low temperatures, this property being objectified by the measurement of their pour point. The pour point of a product is the temperature at which the product no longer flows.
De manière générale, les compositions conformes à l'invention ont un point d'écoulement inférieur à -20°C. In general, the compositions according to the invention have a pour point of less than -20 ° C.
Le point éclair est la température minimale pour laquelle la concentration des vapeurs émises est suffisante pour produire une déflagration au contact d'une flamme ou d'un point chaud dans les conditions normalisées, mais insuffisante pour produire la propagation de la combustion en l'absence de la flamme "pilote". The flash point is the minimum temperature at which the concentration of vapors emitted is sufficient to produce a deflagration on contact with a flame or hot spot under standard conditions, but insufficient to produce the propagation of combustion in the absence of the "pilot" flame.
On met en évidence une température minimale à laquelle l'émission de vapeurs est suffisante pour former avec l'air le mélange gazeux inflammable sous l'action extérieure d'une flamme. A minimum temperature is demonstrated at which the emission of vapors is sufficient to form with the air the flammable gas mixture under the external action of a flame.
Ce niveau de température minimale est appelé point éclair (ou flash point).  This minimum temperature level is called a flash point.
Plus le point éclair est bas, plus la substance est inflammable, donc dangereuse.  The lower the flash point, the more flammable and therefore dangerous the substance.
On note un second niveau de température, au-delà du point éclair, nommé point d'inflammation (fire point), nécessaire et suffisant pour que la combustion du mélange gazeux soit entretenue et perdure. There is a second temperature level, beyond the flash point, called fire point, necessary and sufficient for the combustion of the gaseous mixture to be maintained and maintained.
A noter que cette inflammation peut avoir lieu sous l'action d'une source extérieure (flamme) ou être spontanée, on parlera alors de point d'auto-inflammation. Des normes définissent les divers protocoles de mesures; il peut s'agir de tests à coupelle ouverte (ex : Pensky-Martens, Abel, Miniflash, Tag,) ou à coupelle fermée (Cleveland). Dans le cadre de l'invention les mesures sont effectuées selon la norme ASTM D92, qui correspond à un test à coupelle ouverte (Cleveland). It should be noted that this inflammation can take place under the action of an external source (flame) or be spontaneous, one will speak then of point of auto-ignition. Standards define the various measurement protocols; they may be open cup tests (eg Pensky-Martens, Abel, Miniflash, Tag,) or closed cup (Cleveland). In the context of the invention measurements are made according to ASTM D92, which corresponds to an open cup test (Cleveland).
Les compositions selon l'invention présentent un point éclair supérieur à 80°C, et notamment supérieur ou égal à 90°C, avantageusement supérieur ou égal à 93°C, en particulier supérieur ou égal à 95°C, voire supérieur ou égal à 100°C. Selon une variante de l'invention, la composition contient au moins 12% en masse d'esters d'acides gras en C18:1 , en particulier au moins 15%, notamment au moins 18%. The compositions according to the invention have a flash point greater than 80 ° C., and especially greater than or equal to 90 ° C., advantageously greater than or equal to 93 ° C., in particular greater than or equal to 95 ° C., or even greater than or equal to 100 ° C. According to a variant of the invention, the composition contains at least 12% by weight of C 18: 1 fatty acid esters, in particular at least 15%, in particular at least 18%.
Selon un mode de réalisation avantageux, la somme des concentrations d'esters méthylique d'acides gras en C8 à C10 et du ou des esters d'acides gras en C18:1 est supérieure ou égale à 40%, notamment supérieure ou égale à 45%, en particulier supérieure ou égale à 50%. According to an advantageous embodiment, the sum of the concentrations of C 8 to C 10 fatty acid methyl esters and of the C 18: 1 fatty acid ester (s) is greater than or equal to 40%, especially greater than or equal to 45%. %, in particular greater than or equal to 50%.
Des compositions répondant particulièrement aux objectifs de l'invention sont celles pour lesquelles les esters d'acides gras en C18:1 sont des esters d'alcool pour lesquels R2 représente une chaîne carbonée en C1 -C8, en particulier en C1 -C5, plus particulièrement en C1 -C4. Compositions particularly meeting the objectives of the invention are those for which the C 18: 1 fatty acid esters are alcohol esters for which R 2 represents a C 1 -C 8, in particular C 1 -C 5, carbon chain, more especially C1-C4.
Il peut s'agir notamment d'ester méthylique, éthylique, propylique, isopropylique, butylique, pentylique ou isoamylique, ou de leurs mélanges, en particulier des esters formés avec l'acide oléique.  It may be in particular methyl, ethyl, propyl, isopropyl, butyl, pentyl or isoamyl ester, or mixtures thereof, in particular esters formed with oleic acid.
On peut ainsi préparer des compositions contenant des esters méthyliques, butylique ou isoamylique d'huile de colza, en particulier, des esters méthyliques d'huile de colza. Selon l'un des modes de réalisation de l'invention, les esters d'acides gras en C18:1 présents dans la composition sont choisis parmi l'oléate de n-butyle, l'oléate de méthyle et leurs mélanges; l'oléate de méthyle peut être apporté dans la composition sous forme d'esters méthyliques d'huile de colza. It is thus possible to prepare compositions containing methyl, butyl or isoamyl esters of rapeseed oil, in particular rapeseed oil methyl esters. According to one embodiment of the invention, the C18: 1 fatty acid esters present in the composition are chosen from n-butyl oleate, methyl oleate and mixtures thereof; the methyl oleate can be added to the composition in the form of rapeseed oil methyl esters.
Par ailleurs, les esters d'acides gras mentionnés en c) sont avantageusement choisis parmi le méthylcocoate, le 2-éthylhexylcocoate et leurs mélanges en toutes proportions, de préférence les esters d'acides gras mentionnés en c) sont des esters d'huile de coco et de 2-éthylhexanol, également appelés le 2-éthylhexylcocoate. Selon encore une variante de l'invention, la composition de solubilisation contient au moins 36% d'esters méthyliques d'acides gras en C8 à C10. Moreover, the fatty acid esters mentioned in c) are advantageously chosen from methylcocoate, 2-ethylhexylcocoate and mixtures thereof in all proportions, preferably the fatty acid esters mentioned in c) are esters of coconut and 2-ethylhexanol, also called 2-ethylhexylcocoate. According to another variant of the invention, the solubilization composition contains at least 36% of methyl esters of C8 to C10 fatty acids.
Ainsi, une composition particulièrement adaptée à la mise en œuvre de l'invention contient un mélange d'acides gras consistant en :  Thus, a composition particularly suitable for the implementation of the invention contains a mixture of fatty acids consisting of:
a) 36 à 43% d'esters méthyliques d'acides gras en C8 à C10,  a) 36 to 43% of methyl esters of C8 to C10 fatty acids,
b) au moins 18% d'esters d'acides gras en C18:1 choisis parmi les esters méthyliques, les esters éthyliques, les esters butyliques, les esters isoamyliques, les esters 2-éthylhexyliques et leurs mélanges, en particulier, parmi les esters méthyliques, les esters butyliques et leurs mélanges. b) at least 18% of C18: 1 fatty acid esters selected from methyl esters, ethyl esters, butyl esters, isoamyl esters, 2-ethylhexyl esters and mixtures thereof, in particular from among the esters methyl, butyl esters and mixtures thereof.
De telles compositions comprendront avantageusement une concentration d'esters méthyliques d'huile de colza supérieure ou égale à 30%. Such compositions will advantageously comprise a concentration of rapeseed oil methyl esters greater than or equal to 30%.
En particulier, la composition pourra comprendre: In particular, the composition may comprise:
a) 40% d'esters méthyliques d'un mélange d'acides gras comprenant de 78 à a) 40% of methyl esters of a fatty acid mixture comprising from 78 to
100% d'acide gras saturés en C8 et en C10, 100% saturated C8 and C10 fatty acids,
b) 30% d'esters méthyliques ou éthyliques d'huile de colza et 30% d'une composition contenant au moins 68% d'oléate de n-butyle. Selon un autre mode de réalisation de l'invention, la composition de solubilisation contient:  b) 30% of methyl or ethyl esters of rapeseed oil and 30% of a composition containing at least 68% of n-butyl oleate. According to another embodiment of the invention, the solubilization composition contains:
a) 40% d'esters méthyliques d'un mélange d'acides gras comprenant de 78 à 100% d'acide gras saturés en C8 et en C10,  a) 40% of methyl esters of a fatty acid mixture comprising from 78 to 100% of saturated C8 and C10 fatty acids,
b) 30% d'esters méthyliques ou éthyliques d'huile de colza  b) 30% of methyl or ethyl esters of rapeseed oil
c) 30% de 2-éthylhexyl-cocoate.  c) 30% of 2-ethylhexyl-cocoate.
Les compositions selon l'un quelconque des modes de réalisation selon l'invention pourront être utilisées pures, ou en mélange avec un solvant. Le solvant pourra notamment être choisi parmi le xylène ou les huiles minérales. The compositions according to any one of the embodiments according to the invention may be used in pure form, or mixed with a solvent. The solvent may especially be selected from xylene or mineral oils.
Les compositions selon l'un quelconque des modes de réalisation de l'invention peuvent être utilisées pour solubiliser ou disperser des bitumes solides, en particulier des huiles lourdes, telles que des paraffines et cires paraffinées ou des asphaltènes. Par paraffine on entend des hydrocarbures saturés de formule CnH2n+2 avec n variant de 8 à 40. Les cires paraffiniques ont en général n supérieur ou égal à 20. Les compositions selon l'un quelconque des modes de réalisation de l'invention pourront être utilisées pour décaper et entretenir les installations d'extraction, de raffinage, de transport et de stockage du pétrole et de ses dérivés. Elles seront également utiles pour le nettoyage et le décapage de tout type de dispositif en contact avec des dérivés pétroliers de type paraffine ou asphaltène, notamment pour le dégraissage de pièces métalliques dans l'industrie ou des presses d'imprimerie. Les compositions selon l'un quelconque des modes de réalisation selon l'invention peuvent aussi être utilisées dans le domaine de la peinture, par exemple comme diluant ou liant dans des peintures, ou pour nettoyer les surfaces ou les outils après usage. The compositions according to any one of the embodiments of the invention may be used to solubilize or disperse solid bitumens, especially heavy oils, such as paraffins and paraffin waxes or asphaltenes. By paraffin means saturated hydrocarbons of formula C n H 2 n + 2 with n ranging from 8 to 40. The paraffin waxes generally have n greater than or equal to 20. The compositions according to any one of the embodiments of the invention may be used to strip and maintain the extraction, refining, transport and storage facilities for oil and its derivatives. They will also be useful for cleaning and stripping any type of device in contact with petroleum derivatives of paraffin or asphaltene type, especially for the degreasing of metal parts in industry or printing presses. The compositions according to any one of the embodiments of the invention may also be used in the field of painting, for example as a thinner or binder in paints, or for cleaning surfaces or tools after use.
Les compositions selon l'un quelconque des modes de réalisation selon l'invention seront également utiles dans la construction, comme agent de démoulage du béton. The compositions according to any one of the embodiments of the invention will also be useful in the construction, as concrete release agent.
Une composition selon l'invention peut également être utilisée dans le domaine des revêtements routiers, au sein de liants bitumineux, pour fluidifier la composition bitumineuse. La composition intervient comme fluxant et facilite l'épandage du bitume et l'enrobage des minéraux contenus dans la composition bitumineuse. A composition according to the invention can also be used in the field of road coatings, within bituminous binders, for fluidifying the bituminous composition. The composition acts as a fluxing agent and facilitates the spreading of the bitumen and the coating of the minerals contained in the bituminous composition.
Toutes ces utilisations des compositions et formulations sont également comprises dans l'invention. L'invention a encore pour objet un procédé de préparation de composition de solubilisation des résidus organiques de matière première d'origine fossile, comprenant le mélange d'esters d'acides gras suivant : All these uses of the compositions and formulations are also included in the invention. The subject of the invention is also a process for the preparation of a solubilization composition of the organic residues of raw material of fossil origin, comprising the following mixture of fatty acid esters:
a) au moins 20% en masse d'un mélange comprenant au moins 90% d'esters d'acides gras saturés en C6 à C10, en particulier d'esters méthyliques d'acides gras en C8 à C10,  a) at least 20% by weight of a mixture comprising at least 90% of saturated C 6 -C 10 fatty acid esters, in particular of C 8 -C 10 fatty acid methyl esters,
b) au moins 15% en masse d'esters d'acides gras en C18 à C24, notamment en C18 à C22 comportant au moins une double liaison, et  b) at least 15% by weight of C18 to C24 fatty acid esters, especially C18 to C22 fatty esters containing at least one double bond, and
c) optionnellement des esters d'acides gras d'huile de coco et d'alcools en C1 à C8, à une concentration de 0 à 60% en masse.  c) optionally fatty acid esters of coconut oil and C1 to C8 alcohols, at a concentration of 0 to 60% by weight.
En particulier, on mélange au moins 20% d'un mélange d'esters méthyliques d'acides gras comportant de 48 à 70% d'ester méthylique en C8 (caprylate), de 30 à 50% d'ester méthylique en C10 (caprate), une quantité inférieure ou égale à 4,5% d'ester méthylique en C6, une quantité inférieure ou égale à 2% d'esters méthyliques en C12, avec les constituants b) et c), tels que définis dans ce qui précède. D'autres caractéristiques et avantages de l'invention apparaîtront à la lecture des exemples qui suivent. In particular, at least 20% of a mixture of fatty acid methyl esters containing from 48 to 70% of C 8 (caprylate) methyl ester, from 30 to 50% of C10 methyl ester (caprate), less than or equal to 4.5% of C6 methyl ester, less than or equal to 2% of C12 methyl esters, with components b) and c), as defined in the foregoing. Other features and advantages of the invention will appear on reading the examples which follow.
Exemple 1 : préparation de compositions selon l'invention Example 1 Preparation of Compositions According to the Invention
On utilise la composition d'ester méthylique d'huile de colza , de composition suivante: The rapeseed oil methyl ester composition of the following composition is used:
- C16 :0 4,3%  - C16: 0 4.3%
- 018 :1 62-63,5%  - 018: 1 62-63.5%
- 018 :2 19,1 -19,3%  - 018: 2 19.1 -19.3%
- 018 :3 9,1 -9,7%  - 018: 3 9.1 -9.7%
Le mélange d'esters méthyliques en C8/C10 (Methyl C8/C10), de composition suivante: The mixture of C8 / C10 methyl esters (Methyl C8 / C10), of following composition:
-06 : inférieur ou égal 4,5  -06: less than or equal to 4.5
-08 48-70%  -08 48-70%
-010 30-50%  -010 30-50%
-012 inférieur ou égal 2  -012 less than or equal 2
La composition d'oléate de n-butyle correspond à un mélange comprenant de 68 à 92% d'oléate de n-butyle, au moins 8% d'ester butylique d'acide linoléique, et de 0 à 2% d'ester butylique d'acide linolénique, le reste étant le cas échéant constitué d'ester d'acides gras saturés en 016 et 018. The n-butyl oleate composition corresponds to a mixture comprising from 68 to 92% of n-butyl oleate, at least 8% of butyl ester of linoleic acid, and from 0 to 2% of butyl ester. of linolenic acid, the remainder being optionally constituted of saturated fatty acid ester in 016 and 018.
Les différents constituants des formulations sont mélangés dans un contenant à température ambiante jusqu'à homogénéisation de la formulation. The various constituents of the formulations are mixed in a container at ambient temperature until the formulation is homogenized.
Esters esters
Composition 2-Ethyl 2-Ethyl Composition
Methyl Methyl éthyliques Methyl methyl ethyl
Formulation d'oléate de Hexyl  Hexyl oleate formulation
C8/C10 cocoate d'huile de  C8 / C10 coconut oil from
n-butyle cocoate colza  n-butyl cocoate rapeseed
Form. 4X 40% 30% 30%  Form. 4X 40% 30% 30%
Form. 5  Form. 5
30% 10% 30% 30% bisX Form. 8X 20% 30% 20% 30% 30% 10% 30% 30% bisX Form. 8X 20% 30% 20% 30%
Le point éclair et le point d'écoulement des formulations sont déterminés par les méthodes selon les normes ASTM D92 et ASTM D97 respectivement Caractéristiques des formulations The flash point and pour point of the formulations are determined by the methods according to ASTM D92 and ASTM D97 respectively.
D'autres formulations sont préparées de la même façon, avec les compositions suivantes : Other formulations are prepared in the same way, with the following compositions:
Les points d'écoulement sont mesurés Pour points are measured
La formulation de l'exemple comparatif 1 , pour laquelle la concentration totale en Methyl C8/C10 et en esters d'acides gras d'huile de coco est égale à 30%, présente un point d'écoulement supérieur à -20°C, et ne convient donc pas à la mise en œuvre de l'invention, La teneur en esters d'acides gras en C8 à C14 de cette composition est inférieure à 38% en masse requise pour les compositions selon l'invention.  The formulation of Comparative Example 1, for which the total concentration of Methyl C8 / C10 and coconut oil fatty acid esters is 30%, has a pour point greater than -20 ° C, and therefore not suitable for the implementation of the invention, the content of C8 to C14 fatty acid esters of this composition is less than 38% by mass required for the compositions according to the invention.
Les formulations 4X, 5bisX et 8X présentent toutes un point d'écoulement inférieur ou égal à -20°C et un point éclair supérieur ou égal à 100°C,  The 4X, 5bisX and 8X formulations all have a pour point less than or equal to -20 ° C and a flash point greater than or equal to 100 ° C,
Exemple 2: Tests pour déterminer la température de dissolution Les tests sont réalisés avec des résidus organiques solides provenant de champs pétroliers des sables bitumineux Example 2 Tests to Determine the Dissolution Temperature The tests are performed with solid organic residues from oil sands oilfields
Méthode / procédure: Method / procedure:
Dans un contenant en verre, on met environ 1 g de cire paraffinique dans 100ml de solvant sous agitation magnétique (140rpm). Le contenant est chauffé progressivement dans un bain marie de la température ambiante jusqu'à la température avec une complète dissolution des résidus introduits. La température du test est maintenue environ 15min avant d'être augmentée de 5°C, jusqu'à la température de dissolution.  In a glass container, about 1 g of paraffinic wax is placed in 100 ml of solvent with magnetic stirring (140 rpm). The container is progressively heated in a water bath from room temperature to temperature with complete dissolution of the introduced residues. The temperature of the test is maintained for about 15 minutes before being increased by 5 ° C. to the dissolution temperature.
Résultats: Results:
Les températures de dissolution des cires dans les formulations testées se situent:  The dissolution temperatures of the waxes in the formulations tested are:
- pour avoir une dissolution > 70%: entre 30 et 40°C selon le type de cire - to have a dissolution> 70%: between 30 and 40 ° C according to the type of wax
- pour avoir une dissolution totale: entre 40°C et 45°C selon le type de cire Dans les conditions testées, les températures de dissolution totale du xylène et du cyclohexane sont entre 30 et 35°C. - To have a total dissolution: between 40 ° C and 45 ° C depending on the type of wax Under the conditions tested, the total dissolution temperatures of xylene and cyclohexane are between 30 and 35 ° C.
Exemple 3: Tests de la dissolution limite de résidus organiques: Example 3 Tests of the limit dissolution of organic residues
Les tests sont réalisés avec des résidus organiques solides provenant de champs pétroliers des sables bitumineux).  The tests are conducted with solid organic residues from oil sands fields.
Le test est basé sur la méthode de Baker Petrolite: (Expérimental solubility data of various n-alkane waxes: effects of alkane chain length, alkane odd versus even carbon number structures and solvent chemistry on solubility) D. W. Jennings, K. Weispfennig / Fluid Phase Equilibria 227 (2005) 27-35 a- Méthode The test is based on the method of Baker Petrolite: (Experimental solubility data of various n-alkane waxes: effects of alkane chain length, alkane odd versus even carbon number structures and solvent chemistry on solubility) DW Jennings, K. Weispfennig / Fluid Phase Equilibria 227 (2005) 27-35 a- Method
Dans un contenant en verre (200ml), 100ml de formulation (à évaluer) sont chargés sous agitation magnétique (140rpm). Le contenant est chauffé à 45°C dans un bain- marie. A cette température, 1 g de résidus organiques est ajouté toutes les 15 min. La dissolution de la cire est déterminée visuellement.  In a glass container (200ml), 100ml of formulation (to be evaluated) are loaded with magnetic stirring (140rpm). The container is heated to 45 ° C in a water bath. At this temperature, 1 g of organic residues is added every 15 min. The dissolution of the wax is determined visually.
Résultats: Results:
Dans ces conditions, il a été impossible de dissoudre environ 45g de cire sans observer la saturation de la solution. Des résultats identiques ont été observés en utilisant du xylène. Il a été observé que les solutions à 45°C étaient visqueuses mais homogènes sans dépôt apparent. En diminuant à la température ambiante, les solutions deviennent pâteuses avec 6g à 12g de cire dans la formulation. b- Méthode : Under these conditions, it was impossible to dissolve about 45g of wax without observing the saturation of the solution. Identical results were observed using xylene. It was observed that the solutions at 45 ° C were viscous but homogeneous without apparent deposit. By decreasing at room temperature, the solutions become pasty with 6g to 12g of wax in the formulation. b- Method:
Dans un contenant en verre (200ml), 100ml de formulation (ou xylène) sont chargés sous agitation magnétique (140rpm). Le contenant est chauffé à 40°C dans un bain- marie, contenant une quantité connue de cire (addition de 1 g de cire à la température). Après dissolution, une spatule métallique est plongée dans la solution:  In a glass container (200ml), 100ml of formulation (or xylene) are charged with magnetic stirring (140rpm). The container is heated to 40 ° C in a water bath, containing a known amount of wax (addition of 1 g of wax at the temperature). After dissolution, a metal spatula is immersed in the solution:
- si il n'y a pas de résidu observé sur la spatule alors le test est continué (une masse supplémentaire).  - if there is no residue observed on the spatula then the test is continued (an additional mass).
- si du résidu est observé sur la spatule alors le test est arrêté  - if residue is observed on the spatula then the test is stopped
Test 2 - solubilité de cire dans le xylène Test 2 - solubility of wax in xylene
Test 2 - solubilité de cire dans les formulations Test 2 - solubility of wax in the formulations
Les résultats montrent qu'il est possible de solubiliser une quantité de cire dans les formulations d'esters d'acide gras. The results show that it is possible to solubilize a quantity of wax in the fatty acid ester formulations.
En revanche, Il n'est pas possible de solubiliser de la cire dans l'Exemple comparatif 2, qui ne comporte pas assez d'esters d'acides gras en C6 à C10. En effet, ceux-ci ne peuvent provenir que des esters d'huile de coco qui représentent 50% en masse de la formulation. Il ne peut donc y avoir que maximum 10% en masse d'esters d'acides gras en C6 à C10, en particulier maximum 9% en masse d'esters d'acides gras en C8 à C10. c- Méthode : On the other hand, it is not possible to solubilize wax in Comparative Example 2, which does not have enough C 6 -C 10 fatty acid esters. Indeed, these can only come from coconut oil esters which represent 50% by weight of the formulation. There can therefore be only a maximum of 10% by weight of C 6 to C 10 fatty acid esters, in particular a maximum of 9% by weight of C 8 to C 8 fatty acid esters. C10. c- Method:
Afin d'avoir une meilleure idée de la limite de solubilité des cires, des tests sont réalisés en utilisant une paraffine (avec un point de fusion de 44°C). En effet, la paraffine est incolore à chaud et blanche à froid. Ainsi, il devrait être plus facile d'observer les phénomènes de dissolution des cires.  In order to have a better idea of the solubility limit of the waxes, tests are carried out using a paraffin (with a melting point of 44 ° C). Indeed, paraffin is colorless to hot and cold white. Thus, it should be easier to observe the dissolution phenomena of waxes.
Dans un contenant en verre (200ml), 100ml de formulation sont chargés sous agitation magnétique (140rpm). Le contenant est chauffé à 40°C dans un bain-marie, contenant une quantité connue de paraffine, jusqu'à dissolution des cires. Après refroidissement à température ambiante, les solutions sont gardées pour 2 jours avant de faire les observations. In a glass container (200ml), 100ml of formulation are loaded with magnetic stirring (140rpm). The container is heated to 40 ° C in a water bath containing a known amount of paraffin until the waxes are dissolved. After cooling to room temperature, the solutions are kept for 2 days before making the observations.
Solubilité de la paraffine dans les formulations d'acide gras Solubility of Paraffin in Fatty Acid Formulations
Exemple 4: fluidifiant d'une composition Example 4: Thinner of a composition
Composition d'esters d'acides gras : Fatty acid ester composition:
40% esters méthyliques C8/C10  40% C8 / C10 methyl esters
30% esters éthyliques de colza  30% rapeseed ethyl esters
30% oléate de butyle  30% butyl oleate
La paraffine a été achetée chez Panreac: Paraffin CAS [8002-74-2] EC number (EINECS): 232-315-6. Paraffin was purchased from Panreac: Paraffin CAS [8002-74-2] EC number (EINECS): 232-315-6.
On mélange la composition d'esters d'acides gras avec la paraffine en différentes proportions et on chauffe vers 50°C-55°C sous agitation magnétique 200rpm. On mesure la viscosité de la composition résultante avec un Viscosimètre Stabinger SVM 300/G2 de Anton Paar. The fatty acid ester composition is mixed with paraffin in various proportions and heated to 50 ° C.-55 ° C. with 200 rpm magnetic stirring. The viscosity of the resulting composition is measured with a Anton Paar Stabinger SVM 300 / G2 Viscometer.
Viscosité cinématique à 60°C : Kinematic viscosity at 60 ° C:
Paraffine seule : 4.8918mm2/sParaffin only: 4.8918mm 2 / s
Mélange d'esters d'acides gras seul: 2.2072mm2/s.Mixture of fatty acid esters alone: 2.2072mm 2 / s.
Mélange d'esters d'acides gras /Paraffine (90/10, w/w) : 2.2628mm2/sMixture of Fatty Acid Esters / Paraffin (90/10, w / w): 2.2628mm 2 / s
Mélange d'esters d'acides gras /Paraffine (85/15, w/w) : 2.4182mm2/s Mixture of Fatty Acid Esters / Paraffin (85/15, w / w): 2.4182mm 2 / s
Conclusion: le mélange d'esters d'acides gras fluidifie la paraffine. Conclusion: the mixture of fatty acid esters fluidizes the paraffin.

Claims

REVENDICATIONS
1 . Composition de solubilisation des résidus organiques de matière première d'origine fossile comprenant un mélange d'esters d'acides gras caractérisée en ce que le mélange d'esters d'acides gras comprend un mélange de composés de formule dans laquelle 1. A solubilization composition of organic raw material residues of fossil origin comprising a mixture of fatty acid esters characterized in that the mixture of fatty acid esters comprises a mixture of compounds of formula in which
R1 représente une chaîne carbonée en C5 à C23, linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations,  R1 represents a linear or branched C5 to C23 carbon chain optionally comprising one or more unsaturations,
R2 représente une chaîne carbonée en C1 à C10, linéaire ou ramifiée, comportant éventuellement une ou plusieurs insaturations;  R2 represents a linear or branched C1 to C10 carbon chain optionally comprising one or more unsaturations;
ladite composition comprenant :  said composition comprising:
a) au moins 18% en masse d'esters d'acides gras en C6 à C10,  a) at least 18% by weight of C6 to C10 fatty acid esters,
b) au moins 18% en masse d'esters d'acides gras en C18 à C24, en particulier en C18 à C22, comportant au moins une double liaison, et  b) at least 18% by weight of C 18 to C 24, in particular C 18 to C 22, fatty acid esters comprising at least one double bond, and
à la condition que la teneur en esters d'acides gras saturés en C8 à C14 soit supérieure ou égale à 38% en masse, les pourcentages en masse étant donnés par rapport à la masse totale d'esters d'acides gras dans la composition.  provided that the content of C8 to C14 saturated fatty acid esters is greater than or equal to 38% by weight, the percentages by weight being given relative to the total mass of fatty acid esters in the composition.
Composition de solubilisation des résidus organiques de matière première d'origine fossile selon la revendication 1 caractérisée en ce qu'elle comprend des esters d'acides gras d'huile de coco et d'alcools en C1 à C8, à une concentration de 0 à 60% en masse, Composition for solubilizing the organic residues of raw material of fossil origin according to Claim 1, characterized in that it comprises fatty acid esters of coconut oil and of C 1 to C 8 alcohols at a concentration of from 0 to 60% in mass,
la concentration totale d'esters d'acides gras en C8 à C10 et des esters d'acides gras d'huile de coco étant supérieure ou égale à 35% de la composition totale, et inférieure ou égale à 85%. 3. Composition de solubilisation des résidus organiques de matière première d'origine fossile selon l'une quelconque des revendications 1 ou 2, dans laquelle parmi les au moins 18% en masse d'esters d'acides gras en C18 à C24 comportant au moins une insaturation , au moins 10% en masse sont des esters d'acide gras en C18 :1 , les pourcentages en masse étant donnés par rapport à la masse totale d'esters d'acides gras dans la composition. the total concentration of C8 to C10 fatty acid esters and coconut oil fatty acid esters being greater than or equal to 35% of the total composition, and less than or equal to 85%. 3. The solubilization composition of the organic raw material residues of fossil origin according to any one of claims 1 or 2, wherein from at least 18% by weight of C18 to C24 fatty acid esters comprising at least unsaturation, at least 10% by weight are C18: 1 fatty acid esters, the percentages by weight being given relative to the total mass of fatty acid esters in the composition.
4. Composition selon l'une au moins des revendications 1 à 3, caractérisée en ce que les esters d'acides gras en particulier d'acides gras en C18:1 mentionnés en b) sont des esters d'alcool pour lesquels R2 représente une chaîne carbonée en C1 - C8, en particulier en C1 -C5. 4. Composition according to at least one of claims 1 to 3, characterized in that the esters of fatty acids in particular of C18: 1 fatty acids mentioned in b) are alcohol esters for which R2 represents a C1 - C8 carbon chain, in particular C1 - C5.
5. Composition selon l'une quelconque des revendications 1 à 4, caractérisée en ce que les esters d'acides gras en particulier d'acides gras en C18:1 mentionnés en b) sont choisis parmi les esters méthyliques, les esters éthyliques, les esters propyliques, les esters isopropyliques, les esters butyliques, les esters isoamyliques et leurs mélanges. 5. Composition according to any one of claims 1 to 4, characterized in that the esters of fatty acids, in particular of C18: 1 fatty acids mentioned in b) are chosen from methyl esters, ethyl esters, propyl esters, isopropyl esters, butyl esters, isoamyl esters and mixtures thereof.
6. Composition selon l'une quelconque des revendications 1 à 5, caractérisée en ce que les esters d'acides gras mentionnés en c) sont choisis parmi le méthylcocoate, le 2-éthylhexylcocoate et leurs mélanges. 6. Composition according to any one of claims 1 to 5, characterized in that the fatty acid esters mentioned in c) are selected from methylcocoate, 2-ethylhexylcocoate and mixtures thereof.
7. Composition selon l'une quelconque des revendications 1 à 6, caractérisée en ce qu'elle présente un point éclair supérieur à 90°C et un point d'écoulement inférieur à -20°C.  7. Composition according to any one of claims 1 to 6, characterized in that it has a flash point greater than 90 ° C and a pour point of less than -20 ° C.
8. Composition selon l'une au moins des revendications 1 à 7, caractérisée en ce que les esters d'acide gras en C18:1 sont des esters d'acide oléique.  8. Composition according to at least one of claims 1 to 7, characterized in that the C18: 1 fatty acid esters are oleic acid esters.
9. Utilisation d'une composition selon l'une quelconque des revendications 1 à 8 comme agent pour le nettoyage et le décapage de dispositif en contact avec des dérivés pétroliers de type paraffine ou asphaltène.  9. Use of a composition according to any one of claims 1 to 8 as an agent for cleaning and stripping device in contact with petroleum derivatives of paraffin or asphaltene type.
10. Utilisation selon la revendication 9, caractérisée en ce que la composition est utilisée comme fluxant dans une composition bitumineuse.  10. Use according to claim 9, characterized in that the composition is used as a fluxing agent in a bituminous composition.
1 1 . Utilisation d'une composition selon l'une au moins des revendications 1 à 8, caractérisé en ce que ladite composition est utilisée en mélange avec au moins un solvant choisi parmi le xylène ou les huiles minérales.  1 1. Use of a composition according to at least one of claims 1 to 8, characterized in that said composition is used in admixture with at least one solvent selected from xylene or mineral oils.
EP16750704.5A 2015-07-31 2016-08-01 Composition for solubilization of organic residues Withdrawn EP3328978A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1557410 2015-07-31
PCT/EP2016/068323 WO2017021365A1 (en) 2015-07-31 2016-08-01 Composition for solubilization of organic residues

Publications (1)

Publication Number Publication Date
EP3328978A1 true EP3328978A1 (en) 2018-06-06

Family

ID=54291479

Family Applications (1)

Application Number Title Priority Date Filing Date
EP16750704.5A Withdrawn EP3328978A1 (en) 2015-07-31 2016-08-01 Composition for solubilization of organic residues

Country Status (4)

Country Link
US (1) US20180223227A1 (en)
EP (1) EP3328978A1 (en)
CA (1) CA3006499A1 (en)
WO (1) WO2017021365A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220042348A (en) * 2019-07-30 2022-04-05 쉘 인터내셔날 리써취 마트샤피지 비.브이. Fuel composition with improved stability and method for preparing same
WO2022191718A1 (en) 2021-03-08 2022-09-15 Technix EnviroCutter IP Limited Bitumen cutback compositions and methods of use thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9101850D0 (en) * 1991-01-29 1991-03-13 Du Pont Howson Ltd Improvements in or relating to printing
DE19737071C2 (en) 1997-08-26 1999-09-09 Henkel Kgaa Paint remover
US6824623B1 (en) * 1999-09-22 2004-11-30 Cognis Corporation Graffiti remover, paint stripper, degreaser
EP1595940A1 (en) * 2004-05-12 2005-11-16 Malaysian Palm Oil Board High performance cleaning agent
EP2175010A1 (en) * 2008-10-10 2010-04-14 Eco Air S.r.l. Use of fatty acid esters as descaling and lubricating agents
EP2368971B1 (en) * 2010-03-18 2014-06-18 DENOLLE, Yann Use of a combination of a mixture of fatty acid methyl esters in C16-C20 castor oil with at least one ethoxylated glyceride as a cleaning agent
WO2013073973A1 (en) 2011-11-16 2013-05-23 Technix Industries Limited Bitumen cutback agents
US20150197683A1 (en) * 2014-01-16 2015-07-16 Elevance Renewable Sciences, Inc. Olefinic Ester Compositions and Their Use in Oil- and Gas-Related Applications

Also Published As

Publication number Publication date
WO2017021365A1 (en) 2017-02-09
US20180223227A1 (en) 2018-08-09
CA3006499A1 (en) 2017-02-09

Similar Documents

Publication Publication Date Title
EP0900822B1 (en) Bituminous binder, its composition and its use
EP1910503B1 (en) Use of a lubricant composition for hydrocarbon mixtures and products thus obtained
EP2791298B1 (en) Grease composition
EP2231728B1 (en) Use of graft-modified copolymers of ethylene and/or propylene and vinyl esters as bifunctional lubricity and cold-resistance additives for liquid hydrocarbons
Bora et al. Hybrid biofuels from non-edible oils: A comparative standpoint with corresponding biodiesel
RU2009141773A (en) OBTAINING AND APPLICATION OF COMPOSITIONS FOR INHIBITING PARAFFIN
FR2987052A1 (en) ADDITIVES ENHANCING WEAR AND LACQUERING RESISTANCE OF GASOLINE OR BIOGAZOLE FUEL
EP3328978A1 (en) Composition for solubilization of organic residues
CN104024355A (en) Bitumen cutback agents
AU2016315409B2 (en) Lubricating mixture having glycerides
CA2997494A1 (en) Lubricity additive for fuel with a low sulfur content
KR20160047771A (en) Lube base oil and method for preparing the same
FI128508B (en) Penetrating oil and method for producing the same
EP1124917A1 (en) Fuel composition in the form of an emulsion derived from heterogeneous greasy waste and method for making same
FR3045660A1 (en) COMPOSITION OF FATTY ACID METHYL ESTERS OF LOW FLOW POINT
FR3000101A1 (en) GELIFIED COMPOSITION OF FUEL OR HYDROCARBON FUEL AND PROCESS FOR PREPARING SUCH A COMPOSITION
US11279887B2 (en) Treatment composition and method for reducing viscosity of hydrocarbons
HU231294B1 (en) Polymer-tenside compositions for tertiary oil extraction process
FR3080384A1 (en) USE OF HYPOPHOSPHOROUS ACID FOR THE ESTERIFICATION OF FREE FATTY ACIDS
FR3038614A1 (en) CLEANING COMPOSITION.
EP3149120A1 (en) Gelled composition of liquid hydrocarbon fuel and method for preparing such a composition

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20180131

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

RIN1 Information on inventor provided before grant (corrected)

Inventor name: BRIGE, CHRISTOPHE

Inventor name: BARREAU, SEBASTIEN

Inventor name: FOUQUET, MARINE

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20180918