EP4448480A1 - Verfahren zur herstellung von diestern und diester, die nach diesem verfahren hergestellt werden - Google Patents

Verfahren zur herstellung von diestern und diester, die nach diesem verfahren hergestellt werden

Info

Publication number
EP4448480A1
EP4448480A1 EP22839264.3A EP22839264A EP4448480A1 EP 4448480 A1 EP4448480 A1 EP 4448480A1 EP 22839264 A EP22839264 A EP 22839264A EP 4448480 A1 EP4448480 A1 EP 4448480A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
composition
linear
diester
branched
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.)
Pending
Application number
EP22839264.3A
Other languages
English (en)
French (fr)
Inventor
Delphine CROZET
Alice LIMOGES
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.)
TotalEnergies Onetech SAS
Original Assignee
TotalEnergies Onetech SAS
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 TotalEnergies Onetech SAS filed Critical TotalEnergies Onetech SAS
Publication of EP4448480A1 publication Critical patent/EP4448480A1/de
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/36—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/085—Non-volatile compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • TITLE METHOD FOR MANUFACTURING DIESTERS AND DIESTERS THUS OBTAINED
  • the invention relates to a process for the preparation of diesters by a simple process to implement from widely accessible raw materials.
  • the invention also relates to diesters that can be obtained by the process of the invention and its use as base oil in a lubricating composition.
  • the composition of diesters according to the invention can also be used in cosmetic or pharmaceutical compositions.
  • the invention also relates to a cosmetic or pharmaceutical composition.
  • Lubricating compositions also called lubricants, are widely used to reduce friction between the surfaces of moving parts and thus reduce wear and prevent damage to the surface of these parts.
  • Lubricants typically include a base oil and one or more functional additives.
  • the lubricating composition When the lubricating composition is subjected to high stresses (i.e. high pressures) during its use, the lubricating compositions whose base oil consists of hydrocarbons tend to degrade and the parts are then damaged.
  • high stresses i.e. high pressures
  • Lubricant manufacturers must constantly improve their formulations to meet increased demands for fuel economy while maintaining engine cleanliness and reducing emissions. These requirements require manufacturers to look into their formulation capabilities and/or seek out new base oils that can meet performance requirements.
  • lubricants such as engine oils, transmission fluids, gear oils, industrial lubricating oils, metalworking oils, etc.
  • a petroleum-based oil of lubricating grade from a refinery, or from a suitable polymerized petrochemical fluid.
  • additives are blended into it to improve properties and performance, such as increased lubricity, anti-wear and anti-corrosion properties, and the lubricant's resistance to heat and/or oil. 'oxidation.
  • various additives such as antioxidants, corrosion inhibitors, dispersing agents, antifoaming agents, metal deactivators and other additives that can be used in lubricant formulations can be added in conventional effective amounts.
  • Environmental concerns and restrictions lead manufacturers to find alternatives to sources of petroleum origin (fossil). Oils of vegetable or animal origin have therefore proven to be interesting sources of base oils. In particular, these oils of plant or animal origin can be converted into an acid or an ester by conventional methods.
  • esters are referred to as Group V base oils. Synthetic esters can be used both as a base oil and as an additive in lubricants. In comparison to cheaper but less environmentally safe mineral oils, synthetic esters were mainly used as base oils in cases where the viscosity/temperature behavior had to meet strict requirements. Growing issues of environmental acceptance and biodegradability are driving the desire to find alternatives to mineral oil as a raw material in lubrication applications.
  • the emollients currently used in cosmetics are either isoparaffins derived from petrochemicals (mainly isododecane and isohexadecane), white oils, silicone oils or ester-based oils (synthetic or natural). Isoparaffins, white oils and silicone oils are widely distributed because they are very stable and odorless but are not made from renewable resources. Although volatile silicones such as cyclomethicone have long been considered harmless skin emollients and solvents (International Journal of Toxicology, Vol. 10, No. 1, pp. 9-19, 1991), concerns have been expressed in recent years concerning their potential deleterious effects on the environment, and even on human health (in particular as regards octa methyl cyclotetras i oxane).
  • oils of vegetable or animal origin have therefore proven to be interesting sources of base oils or emollients.
  • these oils of vegetable or animal origin can be transformed into acid or ester by conventional processes. These acids can then be transformed into unsaturated alcohols, for example from oil triglycerides, by one or more stages of hydrogenation of fatty acids or methyl esters.
  • WO2008100822 discloses lubricating compositions based on diesters obtained via an epoxy intermediate.
  • the diesters described in this document have a low viscosity index.
  • WO2011005604 discloses lubricating compositions comprising a mixture of isomers of at least two esters, obtained by epoxidation of a carbon-carbon double bond followed by the opening of the epoxy on each of the two positions.
  • the composition of diesters described in this document comprises a mixture of diesters which are distinguished by their central structure (structure between the two ester functions).
  • the invention thus aims to provide a composition of diesters with high selectivity towards a specifically targeted diester, and this with a high conversion.
  • This composition of diesters can also be obtained from raw materials of vegetable or animal origin.
  • the invention relates to a process for the preparation of at least one diester, said process comprising: a) a conversion reaction of the acid function of at least one hydroxycarboxylic acid, or of the ester function of at least one ester of hydroxycarboxylic acid and alcohol, as an alcohol function in order to obtain at least one diol, said hydroxycarboxylic acid comprising from 11 to 25 carbon atoms, b) an esterification reaction of the diol using at least one acid saturated or unsaturated containing from 2 to 24 carbon atoms in order to form at least one diester.
  • the method according to the invention further comprises, after step a) and before step b), a step a-bis) of purification of the diol composition resulting from step a) in order to to increase the diol content of the diol composition resulting from step a), said purification step a-bis) preferably comprising at least one diol crystallization step.
  • the method according to the invention further comprises, before step a), a preliminary step of purifying the composition of hydroxycarboxylic acid or of hydroxycarboxylic acid ester in order to increase the acid content hydroxycarboxylic acid or hydroxycarboxylic acid ester of the hydroxycarboxylic acid or hydroxycarboxylic acid ester composition implemented in the subsequent step a), said preliminary purification step preferably comprising at least one hydroxycarboxylic acid or hydroxycarboxylic acid ester crystallization step.
  • the hydroxycarboxylic acid corresponds to formula (1) and/or the saturated or unsaturated acid corresponds to formula (2):
  • R 1 represents an alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 3 to 18 carbon atoms, more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 23, preferably from 9 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms,
  • R 3 represents a linear or branched monovalent alkyl radical containing 1 to 19 carbon atoms, preferably a linear or branched alkyl containing 2 to 17 carbon atoms, advantageously a linear alkyl containing 4 to 12 carbon atoms.
  • the diol corresponds to formula (3) and the diester corresponds to formula (4):
  • R 1 represents a linear or branched alkyl radical containing from 1 to 22 carbon atoms or a linear or branched alkenyl radical containing from 2 to 22 carbon atoms, preferably an alkyl or alkenyl radical containing from 3 to 18 carbon atoms, of more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent linear or branched alkyl radical comprising from 1 to 22 carbon atoms or a linear or branched alkenyl radical comprising from 2 to 22 carbon atoms, preferably an alkyl or alkenyl radical comprising from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 23, preferably from 9 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms,
  • R 3 and R 4 represent, independently of each other, a monovalent alkyl radical, linear or branched, containing from 1 to 19 carbon atoms, or a monovalent alkenyl radical, linear or branched containing from 1 to 18 carbon atoms. carbon, preferably a linear or branched alkyl or alkenyl containing from 2 to 17 carbon atoms, advantageously a linear alkyl or alkenyl containing from 2 to 12 carbon atoms.
  • the invention also relates to a composition of diester(s) comprising at least one diester of formula (4):
  • R 1 represents a linear or branched alkyl radical containing from 1 to 22 carbon atoms or a linear or branched alkenyl radical containing from 2 to 22 carbon atoms, preferably an alkyl or alkenyl radical containing from 3 to 18 carbon atoms, of more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent linear or branched alkyl radical comprising from 1 to 22 carbon atoms or a linear or branched alkenyl radical comprising from 2 to 22 carbon atoms, preferably an alkyl or alkenyl radical comprising from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 23, preferably from 9 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms, R 3 and R 4 represent, independently of each other, a monovalent alkyl radical, linear or branched, containing from 1 to 19 carbon atoms, or a monovalent alkenyl radical, linear or branched containing from 1 to 18 carbon atoms.
  • composition of diester(s) comprising, relative to the total weight of the composition of diester(s), at least 70% by weight of diesters of formula (4) which are distinguished from each other only by the R3 and R4 groups.
  • composition of diester(s) according to the invention can be obtained by the process according to the invention.
  • R 3 and R 4 represent, independently of each other, a linear or branched monovalent alkyl radical comprising from 1 to 19 carbon atoms, or a linear or branched monovalent alkenyl radical, containing 12 to 17 carbon atoms.
  • the composition of diester(s) according to the invention comprises, relative to the total weight of the composition, at least 70% by weight of a single diester corresponding to formula (4), preferably at least 80% by weight of a single diester of formula (4), preferably at least 90% by weight of a single diester of formula (4).
  • the invention also relates to the use of the composition of diester(s) according to the invention, as a base oil in a lubricating composition or as an emollient in a cosmetic or pharmaceutical composition.
  • the invention relates to a lubricating composition
  • a lubricating composition comprising the composition of diester(s) according to the invention and:
  • R 3 and R 4 represent, independently of each other, a monovalent alkyl radical, linear or branched, containing from 1 to 19 carbon atoms, preferably a linear or branched alkyl containing from 2 to 17 carbon atoms. carbon, advantageously a linear alkyl comprising from 2 to 12 carbon atoms.
  • the invention also relates to a cosmetic or pharmaceutical composition
  • a cosmetic or pharmaceutical composition comprising (i) the composition of diesters according to the invention and (ii) at least one fatty substance and/or
  • the composition of diester(s) comprises at least one diester of formula (4) in which R 3 and R 4 independently represent one of the other, a linear or branched monovalent alkenyl radical comprising from 1 to 18 carbon atoms, preferably from 2 to 17 carbon atoms, more preferably from 12 to 17 carbon atoms.
  • the process of the invention makes it possible to obtain good selectivity towards the formation of a specific diester, without the formation of position isomer(s).
  • the process is simple to implement, using available raw materials.
  • the process of the invention makes it possible to obtain a composition of diesters having an improved viscosity index, in particular compared to diesters obtained by opening an epoxy function.
  • the invention relates to a method for preparing a composition of diesters, said method comprising: a) a conversion reaction of the acid function of at least one hydroxycarboxylic acid, or of the ester function of at least one ester of hydroxycarboxylic acid and alcohol, as an alcohol function in order to obtain at least one diol, said hydroxycarboxylic acid comprising from 11 to 25 carbon atoms, b) an esterification reaction of the diol using at least one acid comprising from 2 to 24 carbon atoms in order to form at least one diester.
  • the method according to the invention comprises, before step a), a preliminary step of purifying a composition of hydroxycarboxylic acid or hydroxycarboxylic acid ester in order to increase the acid content hydroxycarboxylic acid or hydroxycarboxylic acid ester of the hydroxycarboxylic acid or hydroxycarboxylic acid ester composition.
  • a purified composition of hydroxycarboxylic acid or hydroxycarboxylic acid ester is then obtained.
  • step a) of the process according to the invention (reduction reaction) will be implemented from the hydroxycarboxylic acid or hydroxycarboxylic acid ester composition purified in the preliminary step.
  • this preliminary purification step is carried out by crystallization.
  • a hydroxycarboxylic acid or hydroxycarboxylic acid ester composition may comprise impurities, such as saturated or unsaturated acids (without hydroxyl function) or saturated or unsaturated esters (without hydroxyl function).
  • impurities such as saturated or unsaturated acids (without hydroxyl function) or saturated or unsaturated esters (without hydroxyl function).
  • the preliminary purification will make it possible to eliminate these impurities in order to increase the content of hydroxycarboxylic acid or hydroxycarboxylic acid ester.
  • the purified hydroxycarboxylic acid or hydroxycarboxylic acid ester composition comprises at least 90% by weight of hydroxycarboxylic acid or hydroxycarboxylic acid ester, preferably at least 95% by weight of hydroxycarboxylic acid or hydroxycarboxylic acid ester, more preferably at least 98% by weight of hydroxycarboxylic acid or hydroxycarboxylic acid ester, based on the total weight of the hydroxycarboxylic acid or acid ester composition purified hydroxycarboxylic acid.
  • the purified hydroxycarboxylic acid or hydroxycarboxylic acid ester composition comprises at most 10% by weight of impurities, preferably at most 5% by weight of impurities, relative to the total weight of the composition of hydroxycarboxylic acid or hydroxycarboxylic acid ester, said impurities comprising for example saturated or unsaturated acids (without hydroxyl function) and/or saturated or unsaturated esters (without hydroxyl function).
  • the method according to the invention comprises, after step a) and before step b), a step a-bis) of purification of the diol composition resulting from step a) in order to increasing the diol content of the diol composition resulting from step a). If it must be implemented, this step a-bis) will preferably be implemented when the process does not include a preliminary purification step.
  • a hydroxycarboxylic acid or hydroxycarboxylic acid ester composition may include impurities, such as saturated or unsaturated acids (without hydroxyl function) or saturated or unsaturated esters (without hydroxyl function).
  • impurities such as saturated or unsaturated acids (without hydroxyl function) or saturated or unsaturated esters (without hydroxyl function).
  • the reduction step a) of the process according to the invention can form monoalcohols from these impurities. This intermediate purification will eliminate the initial impurities as well as the reaction by-products of these impurities (for example monoalcohols).
  • this purification step a-bis) is implemented by crystallization.
  • the purified composition of diols comprises at least 90% by weight of diols, preferably at least 95% by weight of diols, more preferably at least 98% by weight of diols, relative to the total weight of the composition of purified diols.
  • the method of the invention comprises one or more treatment steps, in particular to remove the crystallization solvent if the purification step is a crystallization step.
  • the treatment step can for example be a filtration step and a drying step.
  • the method of the invention may optionally comprise additional washing and/or purification steps.
  • the process of the invention can comprise one or more operations making it possible to separate the acid and/or the hydroxycarboxylic acid, starting reagents of the process of the invention. These operations can be, for example, stripping evaporation steps or distillation operations.
  • the process according to the invention can also comprise one or more washing operations to separate the homogeneous catalyst from the product resulting from the process of the invention or one or more filtration stages to separate the heterogeneous catalyst from the product resulting from the process of the invention. .
  • the method of the invention uses, as reactant, at least one hydroxycarboxylic acid or at least one ester of hydroxycarboxylic acid and alcohol.
  • the hydroxycarboxylic acid comprises at least one carboxylic acid function (-COOH) and at least one hydroxyl function (-OH).
  • the hydroxycarboxylic acid comprises a single carboxylic acid function and a single hydroxyl function.
  • the hydroxycarboxylic acid can be saturated or unsaturated.
  • the hydroxycarboxylic acid is a saturated acid which typically does not comprise any function other than the carboxylic acid function and the hydroxyl function.
  • the hydroxycarboxylic acid is preferably monounsaturated.
  • the hydroxycarboxylic acid comprises a linear or branched, preferably linear, alkyl chain.
  • the hydroxycarboxylic acid that can be implemented in the invention comprises from 11 to 25 carbon atoms, preferably from 12 to 24 carbon atoms, more preferably from 14 to 20 carbon atoms.
  • the hydroxycarboxylic acid used in the invention comprises at least one hydroxyl function carried by a secondary carbon atom (compound called secondary alcohol type).
  • the hydroxycarboxylic acid used in the invention comprises at least one carboxylic acid function carried by a primary carbon atom.
  • the hydroxycarboxylic acid corresponds to formula (1): [Chem 1] in which :
  • R 1 represents an alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 3 to 18 carbon atoms, more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 23, preferably from 9 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms.
  • R 1 represents an alkyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 3 to 18 carbon atoms, more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent alkyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 range from 9 to 20 carbon atoms, preferably from 10 to 18 carbon atoms.
  • R 1 represents a linear alkyl radical comprising from 3 to 18 carbon atoms, preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent linear alkylene radical comprising from 4 to 22 carbon atoms, preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 20 atoms carbon, preferably 10 to 18 carbon atoms.
  • the transformation reaction to obtain at least one diol is carried out with, as reagent, a hydroxycarboxylic acid ester (such as defined in the invention) and alcohol.
  • a hydroxycarboxylic acid ester such as defined in the invention
  • esters derived from the hydroxycarboxylic acid or the expression “ester of hydroxycarboxylic acid” or the expression “ester of hydroxycarboxylic acid and alcohol” denotes an ester obtained by reaction of a hydroxycarboxylic acid and an alcohol.
  • the hydroxycarboxylic acid at the base of the hydroxycarboxylic acid alcohol ester preferably exhibits one or more of the characteristics or preferences described above.
  • the alcohol at the base of the hydroxycarboxylic acid ester is preferably a saturated monoalcohol having preferably from 1 to 18 carbon atoms, preferably from 1 to 16 carbon atoms, preferably from 1 to 12 carbon atoms .
  • the hydroxycarboxylic acid used in the invention is 12-hydroxystearic acid.
  • the ester form is used in the process of the invention, the ester could be, according to a particular embodiment, the methyl or ethyl ester of 12-hydroxystearic acid.
  • the hydroxycarboxylic acid is unsaturated and is ricinoleic acid.
  • the method before the reduction step a), further comprises a step of preliminary purification of the composition C1 of hydroxycarboxylic acid(s) or ester(s) thereof .
  • Said preliminary purification step preferably comprises crystallization of the diol.
  • the crystallization step can be implemented using a solvent or a mixture of solvents in one or more crystallization steps.
  • the solvent(s) can be chosen from heptane, toluene, acetone, methanol, ethanol, ethyl acetate, or a mixture thereof.
  • the ratio between the volume of crystallization solvent (in mL) and the mass of diol (in g) preferably ranges from 1 to 50, preferably from 2 to 30.
  • the process according to the invention may comprise, before step a) and before the optional preliminary purification step, a step of supplying a composition C1 of hydroxycarboxylic acid(s) or ester(s) ) of these.
  • the reduction reaction according to the invention transformation of acid or ester function into alcohol function
  • a composition C1 comprising at least 50% by weight of hydroxycarboxylic acid(s) or ester(s) of these, of preferably at least 70% by weight, more preferably at least 75% by weight, or even at least 80% by weight of hydroxycarboxylic acid(s) or ester(s) thereof, relative to the total weight of composition CT
  • the composition C1 implemented in the invention comprises at least 50% by weight of 12-hydroxystearic acid or of methyl or ethyl ester of 12-hydroxystearic acid, preferably at least 70% by weight, more preferably at least 80% by weight of 12-hydroxystearic acid or of methyl or ethyl ester of 12-hydroxystearic acid, relative to the total weight of the composition CT
  • composition C1 used in the invention comprises at least 50% by weight of 12-hydroxystearic acid, preferably at least 70% by weight, more preferably at least 80% by weight of 12- hydroxystearic, relative to the total weight of the composition CT
  • stage a) of reduction of the process will preferably be implemented in the presence of a CT composition comprising at least 90% by weight of hydroxycarboxylic acid or of hydroxycarboxylic acid ester, preferably at least 95% by weight of hydroxycarboxylic acid or hydroxycarboxylic acid ester, more preferably at least 98% by weight of hydroxycarboxylic acid or hydroxycarboxylic acid ester , based on the total weight of the purified hydroxycarboxylic acid or hydroxycarboxylic acid ester CT composition.
  • the CT composition that can be implemented in the invention comprises at least 90% by weight of 12-hydroxystearic acid, preferably at least 95% by weight, more preferably at least 98% by weight of acid 12-hydroxystearic, relative to the total weight of the composition CT.
  • Composition C1 or CT may be commercially available.
  • Composition C2 of saturated or unsaturated acids may be commercially available.
  • step b) of esterification at least one acid comprising from 2 to 20 carbon atoms, preferably an acid comprising from 2 to 18 carbon atoms, as reagent in order to react on the alcohol functions of the diol.
  • said at least one acid is a monoacid.
  • the acid can be a linear or branched, saturated or unsaturated acid.
  • said at least one saturated acid corresponds to formula (2): [Chem 2] in which R 3 represents a linear or branched monovalent alkyl radical containing from 1 to 19 carbon atoms, or a linear or branched monovalent alkenyl radical containing from 1 to 18 carbon atoms, preferably a linear or branched alkyl or alkenyl comprising from 2 to 17 carbon atoms, advantageously a linear alkyl or alkenyl comprising from 2 to 12 carbon atoms.
  • R 3 is an alkenyl
  • said alkenyl is monounsaturated.
  • the acid is a saturated fatty acid and contains from 2 to 12 carbon atoms. This chain length makes it possible to further optimize the cold properties of the diester composition resulting from the process, which is particularly preferred in lubricating applications.
  • the acid is an unsaturated acid and has 8 to 18 carbon atoms.
  • Unsaturated acids may be particularly preferred in diesters intended for cosmetic applications.
  • the acid used in the invention is chosen from one or more acids from: acetic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid and their mixture, these acids can be linear or branched.
  • the process according to the invention can implement a single acid or a mixture of several acids.
  • the method according to the invention uses a single acid.
  • the process according to the invention will implement for the esterification step either only saturated acids (i.e. from a composition of saturated acids with at least 90% by weight of saturated acids), or only unsaturated acids (i.e. from a composition of unsaturated acids with at least 85% by weight of unsaturated acids).
  • the two esterification reactions (on the two alcohol functions of the diol) can be implemented simultaneously or sequentially.
  • the saturated or unsaturated acids can be introduced simultaneously or sequentially, depending on the desired diester.
  • the process according to the invention is selective since it makes it possible to obtain precisely chosen diesters with a specific structure.
  • the esterification reaction is implemented using a composition C2 of saturated acid(s) typically comprising at least 90% by weight of saturated acid(s). s), preferably at least 95% by weight, or even at least 98% by weight of saturated acid(s), relative to the total weight of composition C2.
  • the esterification reaction is implemented using a composition C2 of unsaturated acid(s) typically comprising at least 85% by weight of unsaturated acid(s). (s), preferably at least 90% by weight, or even at least 95% by weight of unsaturated acid(s), relative to the total weight of composition C2.
  • Composition C2 may be commercially available and may be of natural or synthetic origin, preferably of natural origin.
  • the process of the invention implements two chemical reactions: reduction reaction of the acid or ester function to alcohol function, and esterification reaction.
  • step b) of esterification of the diols are typically implemented in the presence of one or more catalysts. Nevertheless, it is possible to implement step b) of esterification of the diols in the absence of a catalyst.
  • the acid function of the hydroxycarboxylic acid or the ester function of the hydroxycarboxylic acid ester is transformed into the alcohol function by a reduction reaction.
  • the reduction reaction can be implemented by a hydrogenation step or by bringing the hydroxycarboxylic acid or its ester into contact with a reducing agent.
  • a person skilled in the art knows the methods for reducing an acid or ester function to an alcohol function.
  • the reducing agent can be chosen from metal hydrides, preferably from lithium hydrides and sodium hydrides.
  • the reducing agent is chosen from lithium aluminum hydride and sodium borohydride.
  • the temperature of the mixture ranges from -10°C to +15°C, preferably from -5°C to +10°C .
  • the step of reducing the acid function of the hydroxycarboxylic acid or the ester function of the ester derived from the hydroxycarboxylic acid can be implemented under conditions known to those skilled in the art.
  • the hydrogenation step can be implemented under the following conditions: a temperature ranging from 100 to 450° C., preferably from 200 to 400° C., more preferably from 250 to 380° C., and/or a pressure ranging from 30 to 300 bars, preferably from 50 to 250 bars, more preferably from 150 to 230 bars.
  • a non-limiting example of a hydrogenation catalyst allowing the reduction of acid or ester functions to alcohol is copper chromite.
  • the hydrogenation is carried out at a temperature of 350° C. and a pressure of 200 bars in the presence of hydrogen and copper chromite.
  • the diol formed at the end of the reduction step corresponds to formula (3):
  • R 1 represents a linear or branched alkyl radical containing from 1 to 22 carbon atoms or a linear or branched alkenyl radical containing from 2 to 22 carbon atoms, preferably an alkyl or alkenyl radical containing from 3 to 18 carbon atoms, of more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent linear or branched alkyl radical comprising from 1 to 22 carbon atoms or a linear or branched alkenyl radical comprising from 2 to 22 carbon atoms, preferably an alkyl or alkenyl radical comprising from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 23, preferably from 9 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms.
  • the reduction reaction uses a hydroxycarboxylic acid of formula (1) in order to obtain a diol of formula (3), according to the following scheme: [Chem 5] wherein R 1 and R 2 are as defined in formulas (1) and (3) respectively.
  • the hydroxycarboxylic acid reduction step by-products may form.
  • by-products mention may be made of the monoalcohols obtained by reduction of the acid function of the acid impurities possibly present in the hydroxycarboxylic acid composition C1.
  • the 12-hydroxystearic acid composition may comprise, in addition to 12-hydroxystearic acid, palmitic acid and/or stearic acid.
  • the method further comprises a step a-bis) of purification of the composition of diol(s) obtained at the end of step a).
  • Said step a-bis) of purification preferably comprises crystallization of the diol.
  • the crystallization step can be implemented using a solvent or a mixture of solvents in one or more crystallization steps.
  • the solvent(s) can be chosen from heptane, toluene, acetone, methanol, ethanol, ethyl acetate, or a mixture thereof.
  • the ratio between the volume of crystallization solvent (in mL) and the mass of diol (in g) preferably ranges from 1 to 50, preferably from 2 to 30.
  • the method may further comprise a step a-ter) of washing the diol, for example using a solvent, for example heptane.
  • the washing step reduces the residual content of monoalcohols.
  • the esterification reaction can be carried out using homogeneous catalysis, heterogeneous catalysis and/or enzymatic catalysis. It is also possible to carry out the esterification reaction in the absence of a catalyst.
  • the catalyst can for example be a supported enzymatic catalyst.
  • the esterification reaction can be implemented according to any method well known to those skilled in the art for the esterification of alcohols.
  • the catalyst for the esterification can be chosen from catalysts based on Lewis acid, for example based on tin, titanate or boron trifluoride type.
  • the catalyst can be paratoluene sulfonic acid (p-TSA), methanesulfonic acid (AMS), sulfuric acid, boron trifluoride etherate (BF3.EtO), tetrachloride of tin (FASCAT 4400), tin dichloride (FASCAT 2004), dibutyl tin dichloride (FASCAT 4210), monobutyl tin oxide (FASCAT 4100, TIB KAT 256), dibutyl tin oxide (FASCAT 4201 , Tl B KAT 248), dioctyl tin oxide (FASCAT 8201 , TIB KAT 232), monobutyl tin tris(2-ethylhexanoate) (FASCAT 4102) tin oxalate (FASCAT 2001 , Tl B KAT 160), dibutyl tin diacetate (FASCAT 4200, Tl B KAT 233), di
  • step b) of esterification of the process of the invention is implemented at a temperature ranging from 50 to 200°C.
  • the esterification reaction uses a diol of formula (3) and one or more saturated acid(s) of formula (2), according to the following scheme: [Chem 6] in which R 1 , R 2 and R 3 have the same definition as in formulas (1) and (2) respectively, it being understood that the R 3 groups may be identical or different in the diester formed.
  • the R 3 groups may be identical or different in the diester formed.
  • the reaction of the diol with the saturated acid in the presence of the catalyst is carried out according to one or more of the following conditions: the molar ratio diol to saturated acid ranges from 1/2 to 1/10, preferably 1/2 to 1/8, more preferably 1/2 to 1/6; the catalyst for the esterification reaction with the fatty acid or acids is used in a proportion ranging from 0.01 to 3.0% by weight, preferably from 0.02 to 2.5% by weight, with respect to to the total weight of the reaction medium.
  • the process according to the invention will not lead to a mixture of position isomers depending on the position of the addition of the saturated fatty acid to the carbon-carbon double bond of the unsaturated compound.
  • the saturated fatty acid can react on one or other of the carbon atoms of the carbon-carbon double bond of the unsaturated compound, which then leads to two position isomers .
  • part of unsaturated compounds can be isomerized under the acid addition reaction condition, so the carbon-carbon double bond can change position for part of unsaturated compounds.
  • this double bond can migrate along the alkyl chain, leading to a large number of isomers differing by the position of the functionalization and to the possible formation of lactones.
  • the process according to the invention leads to a composition of diesters free of position isomers, insofar as the addition reaction of the saturated fatty acid is carried out selectively only in position fixed by the hydroxyl function of the hydroxycarboxylic acid.
  • the diesters that can be obtained at the end of the process can be represented by the formula (4):
  • R 1 represents an alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 3 to 18 carbon atoms, more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 23, preferably from 9 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms,
  • R 3 and R 4 represent, independently of each other, a monovalent alkyl radical, linear or branched, containing from 1 to 19 carbon atoms, or a monovalent alkenyl radical, linear or branched containing from 1 to 18 carbon atoms, preferably a linear or branched alkyl or alkenyl containing from 2 to 17 carbon atoms, advantageously a linear alkyl or alkenyl containing from 2 to 12 carbon atoms.
  • the process according to the invention makes it possible to prepare a diester of formula (4) in which R 3 and R 4 represent, independently of each other, a linear or branched monovalent alkyl radical, comprising from 1 to 19 carbon atoms, or a monovalent alkenyl radical, linear or branched, containing from 12 to 17 carbon atoms.
  • composition resulting from the process it is appropriate to consider the reactants, the products, as well as the by-products of the reaction.
  • the catalyst is not taken into consideration when designating the composition resulting from the process. Thus, it will generally be appropriate to separate the catalyst from the reaction medium to obtain the composition of diesters resulting from the process.
  • the method can be implemented continuously or semi-continuously or in batch.
  • the progress of the reaction can be monitored by gas chromatography coupled with a flame ionization detector (GC-FID), by high performance liquid chromatography (HPLC) or by infrared, according to methods known to those skilled in the art.
  • GC-FID flame ionization detector
  • HPLC high performance liquid chromatography
  • infrared infrared
  • composition of diesters obtained at the end of the process advantageously has a kinematic viscosity at 100° C. ranging from 1 to 50 mm 2 /s, preferably from 2 to 25 mm 2 /s, advantageously from 3 to 10 mm 2 /s , measured according to ASTM D445.
  • composition of diesters may optionally comprise from 0.1 to 30% by weight of unreacted reactants or intermediates (monoesters of the diol or monoalcohols) possibly formed in situ, relative to the total weight of the composition. of diesters, preferably from 0.2 to 10% by weight, more preferably from 0.5 to 5% by weight.
  • the process according to the invention may optionally further comprise, after the diester formation reaction, a separation step in which the unreacted reactants of the saturated fatty acid, hydroxycarboxylic acid and/or hydroxycarboxylic acid ester type, are eliminated from the composition of diesters.
  • the diesters are not reactants.
  • the method for preparing at least one diester consists of the steps: a) a transformation reaction of the acid function of at least one hydroxycarboxylic acid, or of the ester function of at least one ester of hydroxycarboxylic acid and alcohol, as an alcohol function in order to obtain at least one diol, said hydroxycarboxylic acid comprising from 11 to 25 carbon atoms, b) an esterification reaction of the diol using at least a saturated or unsaturated acid comprising from 2 to 24 carbon atoms in order to form at least one diester.
  • the method for preparing at least one diester consists of the steps: a) a transformation reaction of the acid function of at least one hydroxycarboxylic acid, or of the ester function of at least one ester of hydroxycarboxylic acid and alcohol, as an alcohol function in order to obtain at least one diol, said hydroxycarboxylic acid comprising from 11 to 25 carbon atoms, a-bis) a step of purifying the composition of diols resulting from the step a) in order to increase the diol content of the diol composition resulting from step a), said purification step a-bis) preferably comprising at least one step of crystallization of the diol and preferably being followed by one or more washing steps, b) an esterification reaction of the diol using at least one saturated or unsaturated acid containing from 2 to 24 carbon atoms in order to form at least one diester.
  • the process for preparing at least one diester consists of the steps:
  • a preliminary step of purifying a hydroxycarboxylic acid or hydroxycarboxylic acid ester composition in order to increase the hydroxycarboxylic acid or hydroxycarboxylic acid ester content of the hydroxycarboxylic acid or ester composition of hydroxycarboxylic acid said preliminary purification step preferably comprising at least one step of crystallization of the hydroxycarboxylic acid or its ester and preferably being followed by one or more washing steps a) a transformation reaction of the function acid of at least one hydroxycarboxylic acid, or of the ester function of at least one ester of hydroxycarboxylic acid and alcohol of the composition purified in step 0), as an alcohol function in order to obtain at least one diol , said hydroxycarboxylic acid containing from 11 to 25 carbon atoms, b) an esterification reaction of the diol using at least one saturated or unsaturated acid containing from 2 to 24 carbon atoms in order to form at least one diester . Diesters
  • a subject of the present invention is also a composition of diester(s) of formula (4) as such and a composition of diester(s) capable of being obtained by the process of the invention.
  • composition of diester(s) according to the invention comprises at least one diester corresponding to formula (4):
  • R 1 represents an alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 3 to 18 carbon atoms, more preferably from 5 to 12 carbon atoms,
  • R 2 represents a divalent alkyl or alkenyl radical, linear or branched, comprising from 1 to 22 carbon atoms, preferably from 4 to 22 carbon atoms, more preferably from 8 to 18 carbon atoms, it being understood that the total number of carbon atoms of R 1 and R 2 ranges from 9 to 23, preferably from 9 to 20 carbon atoms, more preferably from 10 to 18 carbon atoms,
  • R 3 and R 4 represent, independently of each other, a monovalent alkyl radical, linear or branched, containing from 1 to 19 carbon atoms, or a monovalent alkenyl radical, linear or branched containing from 1 to 18 carbon atoms. carbon, preferably a linear or branched alkyl or alkenyl containing from 2 to 17 carbon atoms, advantageously a linear alkyl or alkenyl containing from 2 to 12 carbon atoms.
  • composition of diester(s) comprising, relative to the total weight of the composition of diester(s), at least 70% by weight of diesters of formula (4) which are distinguished from each other only by the R 3 and R 4 groups
  • composition of diester(s) comprising, relative to the total weight of the composition of diester(s), at least 70% by weight of diesters of formula (4 ) in which the R 1 groups are identical and in which the R 2 groups are identical, it being understood that R 1 may be different from R 2 ”.
  • composition of diester(s) according to the invention does not comprise, or does not substantially comprise, position isomers where the branch R 3 COO- (or R 4 COO-) at the level of the R 1 chain CHR 2 - could be at different locations of said chain (as is the case with acid addition reactions on a carbon-carbon double bond).
  • the diesters can be monounsaturated or polyunsaturated, the unsaturation(s) possibly being in one or more of the groups R1, R2, R3 and R4 .
  • radicals R 3 and R 4 are monounsaturated.
  • the composition of diester(s) according to the invention comprises at least 75% by weight, preferably at least 80% by weight, more preferably at least 85% by weight, of diesters of formula ( 4) in which the R 1 groups are identical and in which the R 2 groups are identical, it being understood that R 1 may be different from R 2 .
  • R 1 is a linear alkyl having 5 to 8 carbon atoms, preferably is a linear alkyl having 6 carbon atoms, and/or
  • R 2 is a linear alkyl having 8 to 12 carbon atoms, preferably is a linear alkyl having 10 carbon atoms.
  • composition of diesters according to the invention advantageously has a kinematic viscosity at 100° C. ranging from 1 to 50 mm 2 /s, preferably from 2 to 25 mm 2 /s, advantageously from 3 to 10 mm 2 /s, measured according to the ASTM D445 standard.
  • the composition of diester(s) comprises from 70 to 99.8% by weight, preferably from 75 to 99% by weight, more preferably from 80 to 98% by weight, of diester(s) of formula (4), relative to the total weight of the composition of diester(s).
  • the composition of diester(s) according to the invention comprises from 70 to 99.8% by weight, preferably from 75 to 99% by weight, more preferably from 80 to 98% by weight, of diester(s) of formula (7), relative to the total weight of the composition of diester(s), the diesters corresponding to formula (7) are:
  • R 3 and R 4 represent, independently of each other, a monovalent alkyl radical, linear or branched, containing from 1 to 19 carbon atoms, or a monovalent alkenyl radical, linear or branched containing from 1 to 18 carbon atoms. carbon, preferably a linear or branched alkyl comprising from 2 to 17 carbon atoms, advantageously a linear or branched alkyl comprising from 2 to 12 carbon atoms.
  • the composition of diester(s) according to the invention comprises at least one diester of formula (4), for example at least one diester of formula (7), in which R 3 and R 4 represent, independently one from the other, a monovalent alkyl radical, linear or branched, containing from 1 to 19 carbon atoms, or a monovalent alkenyl radical, linear or branched, containing from 12 to 17 carbon atoms.
  • composition of diester(s) according to the invention is preferably obtained according to the process of the invention.
  • the composition of diester(s) according to the invention will typically not comprise position isomers, since it does not involve unsaturated compounds, such as unsaturated alcohols undergoing an addition reaction of an acid saturated on the carbon-carbon double bond.
  • the process according to the invention makes it possible to obtain a composition of diesters having a high selectivity in favor of a single diester.
  • the composition of diester(s) according to the invention can thus be used as base oil in a lubricating composition.
  • the diester composition can be used in a lubricating composition as the sole base oil, but advantageously in combination with another base oil.
  • “Other base oil” should be understood to mean a base oil different from the diesters.
  • the lubricating composition comprising the composition of diesters according to the invention can be used to lubricate the various parts of a vehicle, in particular the various parts of a vehicle engine or transmission or the various parts of a marine engine or an industrial machine engine, for example public works.
  • composition of diesters which can be obtained can also be used as an emollient of a cosmetic or pharmaceutical composition, alone or in combination with another fatty substance.
  • other fatty substance it is appropriate to understand a fatty substance different from the diesters according to the invention.
  • the cosmetic or pharmaceutical composition comprising the composition of diesters according to the invention can be used for topical application, typically on the skin, the nails, the lips, the hair and the scalp.
  • a subject of the invention is also the (non-therapeutic) cosmetic or pharmaceutical use of the composition of diesters according to the invention as a skin care product (serums, creams, balms, etc.) as a hygiene product, as sunscreen/after-sun product, as a make-up product, as a make-up remover, as a perfumed product, as an antiperspirant product.
  • a skin care product salivas, creams, balms, etc.
  • sunscreen/after-sun product as a make-up product
  • a make-up remover as a perfumed product, as an antiperspirant product.
  • the invention also relates to a (non-therapeutic) cosmetic or pharmaceutical process for treating the skin, the nails, the lips, the hair or the scalp, comprising at least one step of application to the skin, the nails , the lips, the hair or the scalp, of a composition of diesters according to the invention.
  • the invention also covers a cosmetic treatment process comprising at least one step of applying, preferably by spreading, on the skin, the nails, the lips, the hair or the scalp of the composition of diesters according to invention.
  • a subject of the invention is also a lubricating composition comprising the composition of diester esters according to the invention and at least one additive and/or at least one other base oil.
  • the composition of diesters used in the lubricating composition has one or more of the characteristics defined above in the context of the composition of diesters.
  • the composition of diesters according to the invention used in the lubricating composition comprises at least one saturated diester.
  • the composition of diesters used in the lubricating composition according to the invention corresponds to formula (4) in which R 3 and R 4 represent, independently of each other, a monovalent radical alkyl, straight or branched, with 1 to 19 carbon atoms, preferably straight or branched alkyl comprising from 2 to 17 carbon atoms, advantageously a linear alkyl comprising from 2 to 12 carbon atoms.
  • base oils can be chosen from the base oils conventionally used in the field of lubricating oils, such as mineral, synthetic or natural, animal or vegetable oils or mixtures thereof.
  • the other base oils of the lubricating compositions according to the invention may in particular be oils of mineral or synthetic origin belonging to groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) and presented in Table 1 below or mixtures thereof.
  • mineral base oils include all types of base oils obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, desalpha, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofinishing.
  • Blends of synthetic and mineral oils, which may be biosourced, can also be used.
  • the other base oils of the lubricating compositions according to the invention can also be chosen from synthetic oils, such as certain esters of carboxylic acids and alcohols, polyalphaolefins (PAO), and polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms.
  • synthetic oils such as certain esters of carboxylic acids and alcohols, polyalphaolefins (PAO), and polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms.
  • the PAOs used as other base oils are for example obtained from monomers comprising from 4 to 32 carbon atoms, for example from octene or decene.
  • the weight average molecular weight of PAO can vary quite widely. Preferably, the weight-average molecular mass of the PAO is less than 600 Da.
  • the weight-average molecular mass of the PAO can also range from 100 to 600 Da, from 150 to 600 Da, or even from 200 to 600 Da.
  • PAO 2 and/or PAO 4 will typically be chosen.
  • the other base oil(s) of the lubricating composition according to the invention are chosen from polyalphaolefins (PAO), polyalkylene glycol (PAG) and esters of carboxylic acids and alcohols.
  • PAO polyalphaolefins
  • PAG polyalkylene glycol
  • esters of carboxylic acids and alcohols are chosen from polyalphaolefins (PAO), polyalkylene glycol (PAG) and esters of carboxylic acids and alcohols.
  • the other base oil(s) of the lubricating composition according to the invention can be chosen from group II or III base oils.
  • the lubricating composition according to the invention comprises: from 5 to 95% by weight, preferably from 10 to 70% by weight, advantageously from 15 to 50% by weight, of the composition of diesters according to invention, and from 5 to 95% by weight, preferably from 30 to 90% by weight, advantageously from 50 to 85% by weight, of one or more other base oils, relative to the total weight of the lubricating composition according to the invention.
  • the additive or additives of the lubricating composition are chosen from friction modifiers, detergents, anti-wear additives, extreme pressure additives, dispersants, antioxidants, pour point depressants, antifoaming agents, metal passivators, and mixtures thereof. These additives are well known to those skilled in the art in the field of the lubrication of mechanical parts.
  • additives can be introduced separately and/or in the form of a mixture like those already available for sale for the formulations of commercial lubricants for vehicle engines, with a performance level as defined by the ACEA ( Association of European Automobile Manufacturers) and/or API (American Petroleum Institute), well known to those skilled in the art.
  • ACEA Association of European Automobile Manufacturers
  • API American Petroleum Institute
  • a lubricating composition according to the invention may comprise at least one friction modifier additive.
  • the friction modifier additive can be selected from a compound providing metallic elements and an ash-free compound.
  • the compounds providing metallic elements mention may be made of complexes of transition metals such as Mo, Sb, Sn, Fe, Cu, Zn, the ligands of which may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus.
  • the ash-free friction modifier additives are generally of organic origin and can be chosen from monoesters of fatty acids and polyols, amines alkoxylated, alkoxylated fatty amines, fatty epoxides, borate fatty epoxides; fatty amines or fatty acid glycerol esters.
  • the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
  • a lubricating composition according to the invention may comprise from 0.01 to 2% by weight or from 0.01 to 5% by weight, preferably from 0.1 to 1.5% by weight or from 0.1 to 2% by weight of friction modifier additive, relative to the total weight of the lubricating composition.
  • a lubricating composition implemented according to the invention may comprise at least one antioxidant additive.
  • the antioxidant additive generally makes it possible to delay the degradation of the composition in service. This degradation can in particular result in the formation of deposits, in the presence of sludge or in an increase in the viscosity of the composition.
  • Antioxidant additives act in particular as free radical inhibitors or destroyers of hydroperoxides.
  • antioxidant additives commonly employed, mention may be made of antioxidant additives of the phenolic type, antioxidant additives of the amine type, phosphosulfur antioxidant additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can be ash generators.
  • the phenolic antioxidant additives may be ash-free or may be in the form of neutral or basic metal salts.
  • the antioxidant additives may in particular be chosen from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted with at least one C1-C12 alkyl group, N,N '-dialkyl-aryl-diamines and mixtures thereof.
  • the sterically hindered phenols are chosen from compounds comprising a phenol group of which at least one carbon vicinal to the carbon carrying the alcohol function is substituted by at least one alkyl group in CICI 0, preferably an alkyl group in C1-C6, preferably a C4 alkyl group, preferably by the tert-butyl group.
  • Amino compounds are another class of antioxidant additives that can be used, possibly in combination with phenolic antioxidant additives.
  • Examples of amino compounds are aromatic amines, for example aromatic amines of formula NQ1Q2Q3 in which Q1 represents an aliphatic group or an optionally substituted aromatic group, Q2 represents an optionally substituted aromatic group, Q3 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula Q4S(O)ZQ5 in which Q4 represents an alkylene group or an alkenylene group, Q5 represents a alkyl group, an alkenyl group or an aryl group and z represents 0, 1 or
  • Sulfurized alkyl phenols or their alkali and alkaline earth metal salts can also be used as antioxidant additives.
  • antioxidant additives are that of copper compounds, for example copper thio- or dithio-phosphates, salts of copper and carboxylic acids, dithiocarbamates, sulphonates, phenates, copper acetylacetonates. Copper I and II salts, succinic acid or anhydride salts can also be used.
  • copper compounds for example copper thio- or dithio-phosphates, salts of copper and carboxylic acids, dithiocarbamates, sulphonates, phenates, copper acetylacetonates.
  • Copper I and II salts, succinic acid or anhydride salts can also be used.
  • a lubricating composition according to the invention may contain all types of antioxidant additives known to those skilled in the art.
  • a lubricating composition according to the invention comprises at least one ash-free antioxidant additive.
  • a lubricating composition according to the invention may comprise from 0.5 to 2% by weight of at least one antioxidant additive, relative to the total weight of the composition.
  • a lubricating composition according to the invention can also comprise at least one detergent additive.
  • Detergent additives generally reduce the formation of deposits on the surface of metal parts by dissolving secondary products of oxidation and combustion.
  • detergent additives which can be used in a lubricating composition according to the invention are generally known to those skilled in the art.
  • Detergent additives can be anionic compounds comprising a long lipophilic hydrocarbon chain and a hydrophilic head.
  • the associated cation can be a metal cation of an alkali or alkaline earth metal.
  • the detergent additives are preferably chosen from alkali metal or alkaline-earth metal salts of carboxylic acids, sulfonates, salicylates, naphthenates, as well as phenate salts.
  • the alkali and alkaline-earth metals are preferably calcium, magnesium, sodium or barium.
  • These metallic salts generally comprise the metal in a stoichiometric quantity or else in excess, therefore in a quantity greater than the stoichiometric quantity.
  • These are then overbased detergent additives; the excess metal providing the overbased character to the detergent additive is then generally in the form of an oil-insoluble metal salt, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferentially a carbonate .
  • a lubricating composition according to the invention may for example comprise from 2 to 4% by weight of detergent additive, relative to the total weight of the composition. Also, a lubricating composition according to the invention may comprise at least one dispersing agent, distinct from the compounds of succinimide type defined according to the invention.
  • the dispersing agent can be chosen from Mannich bases, succinimides, for example of the polyisobutylene succinimide type.
  • a lubricating composition implemented according to the invention may for example comprise from 0.2 to 10% by weight of dispersing agent(s) distinct from the succinimide-type compounds defined according to the invention, relative to the total weight of the composition.
  • a lubricating composition according to the invention may also comprise at least one anti-wear and/or extreme pressure agent.
  • the anti-wear additives are chosen from organophosphates. They have the advantage of not forming ash and being thermally stable. Mention may be made, for example, of phospho-sulphur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
  • phospho-sulphur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
  • the preferred compounds are of formula Zn((SP(S)(OQ6)(OQ7))2, in which Q6 and Q7, which are identical or different, independently represent an alkyl group, preferably an alkyl group comprising from 1 to 18 carbon atoms .
  • Amine phosphates are also anti-wear and extreme pressure additives which can be used in a composition according to the invention.
  • the phosphorus provided by these additives can act as a poison for the catalytic systems of automobiles because these additives generate ash.
  • These effects can be minimized by partially replacing the amine phosphates with additives that do not provide phosphorus, such as, for example, polysulphides, in particular sulphur-containing olefins.
  • a lubricating composition according to the invention may comprise from 0.01 to 15% by weight, preferably from 0.1 to 10% by weight, preferably from 1 to 5% by weight of anti-wear agent(s), relative to the total weight of the composition.
  • a lubricating composition according to the invention may also comprise at least one antifoaming agent.
  • the antifoaming agent can be chosen from polyacrylates, polysiloxanes or their hybrids.
  • a lubricating composition according to the invention may comprise from 0.01 to 2% by mass or from 0.01 to 5% by mass, preferably from 0.1 to 1.5% by mass or from 0.1 to 2% by mass of agent antifoam, relative to the total weight of the composition.
  • a lubricating composition suitable for the invention may also comprise at least one pour point depressant additive (also called “PPD” agents for “Pour Point Depressant” in English).
  • pour point depressants By slowing down the formation of paraffin crystals, pour point depressants generally improve the cold behavior of the composition.
  • pour point depressant additives mention may be made of polyalkyl methacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkylated polystyrenes.
  • the lubricating composition according to the invention may comprise: from 5 to 94.9% by weight, preferably from 10 to 70% by weight, advantageously from 15 to 50% by weight, of the composition of diesters according to the invention, and from 5 to 94.9% by weight, preferably from 30 to 90% by weight, advantageously from 50 to 85% by weight, of one or more other base oils, from 0.1 to 15% by weight, of preferably from 0.5 to 10% by weight, advantageously from 1 to 5% by weight of one or more additives chosen from friction modifiers, viscosity index modifiers, detergents, dispersants, anti- wear and/or extreme pressure, antioxidants, pour point depressants, anti-foaming agents and mixtures thereof, relative to the total weight of the lubricating composition according to the invention.
  • the lubricating composition according to the invention may comprise: from 5 to 94.9% by weight, preferably from 10 to 70% by weight, advantageously from 15 to 50% by weight, of the composition of diesters according to the invention comprising at least one diester of formula (4) in which R 3 and R 4 represent, independently of each other, a linear or branched monovalent alkyl radical containing from 1 to 19 carbon atoms, preferably a linear alkyl or branched chain comprising from 2 to 17 carbon atoms, advantageously a linear alkyl comprising from 2 to 12 carbon atoms, and from 5 to 94.9% by weight, preferably from 30 to 90% by weight, advantageously from 50 to 85% by weight, of one or more other base oils, from 0.1 to 15% by weight, preferably from 0.5 to 10% by weight, advantageously from 1 to 5% by weight of one or more selected additives among friction modifiers, viscosity index modifiers, detergents, dispersants, anti-wear and/or extreme-pressure additives, antioxidants, pour point de
  • the lubricating composition according to the invention can be obtained by mixing the constituents of the lubricating composition.
  • the present invention also relates to a method for preparing a lubricating composition comprising the steps: preparing a composition of diesters according to the method described above, and mixing at least one other base oil and/or at least one additive with the composition of diesters.
  • the method for preparing a lubricating composition according to the invention does not comprise an intermediate step of separating the products formed during the step of preparing the composition of diesters, before the mixing step.
  • the process for preparing a lubricating composition according to the invention does not comprise a hydrogenation step, in particular the hydrogenation of the composition of diesters obtained at the end of the step for preparing the composition of diesters.
  • the other base oil(s) and the additive(s) used in the process for preparing the lubricating composition may have one or more of the characteristics described above in the context of the lubricating composition of the invention.
  • the lubricating composition obtained by this preparation process may exhibit one or more of the characteristics described above in the context of the lubricating composition according to the invention.
  • a subject of the invention is also a cosmetic or pharmaceutical composition
  • a cosmetic or pharmaceutical composition comprising (i) the composition of diesters according to the invention and (ii) at least one fatty substance and/or (iii) at least one cosmetic additive.
  • the composition of diesters used in the cosmetic or pharmaceutical composition has one or more of the characteristics defined above in the context of the composition of diesters.
  • the composition of diesters according to the invention used in the cosmetic or pharmaceutical composition comprises at least one unsaturated diester.
  • the composition of diesters used in the cosmetic or pharmaceutical composition comprises at least one diester of formula (4) in which R 3 and R 4 represent, independently of each other, a radical monovalent alkenyl, linear or branched comprising from 1 to 18 carbon atoms, preferably from 2 to 17 carbon atoms, more preferably from 12 to 17 carbon atoms.
  • the fatty substance can be chosen from hydrocarbon oils of biological or petrochemical origin, vegetable oils, vegetable butters, fatty ethers and alcohols, oily esters (different from the diesters of the invention), alkanes and silicone oils. .
  • Hydrocarbon oils are fatty substances resulting from petrochemical processes.
  • mineral oils isoparaffins, waxes, paraffins, polyisobutenes or else polydecenes.
  • vegetable oils examples include wheat germ, sunflower, grapeseed, sesame, corn, apricot, castor, shea, avocado, olive, soy, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose oil , millet, barley, quinoa, rye, safflower, bankoulier, passionflower, muscat rose or camellia.
  • Vegetable butters are fatty substances that have the same properties as vegetable oils. The difference between the two is that butters are in solid form at room temperature.
  • the raw material from which a butter is extracted (pulp, seeds or almonds) is heated after being crushed to extract the fat.
  • butters can be refined to ensure better preservation, neutralize odours, improve color and consistency. Rich in antioxidants and nourishing, the cosmetic properties of vegetable butters improve the elasticity of the skin, protect against external aggressions by leaving a protective film on the epidermis and thus reduce dehydration, repair and soothe by regenerating the natural hydrolipidic film of the skin .
  • Examples of vegetable butters are in particular shea butter, cocoa butter, mango butter, shorea butter or even olive butter.
  • Ethers and fatty alcohols are long-chain fatty waxy substances with remarkable properties including film-forming, emollient, moisturizing, softening and protective properties. They act as moisturizing oils and as emulsifiers.
  • fatty alcohol or ethers are: cetyl alcohol, stearyl alcohol, myristyl alcohol, auryl alcohol, behenyl alcohol, cetearyl alcohol, dicaprylyl ethers, stearyl ethers or octyldodecanol (identified by their I NCI denomination).
  • oily esters or esterified oils are the product of a reaction between fatty acids (acids with longer chains, such as for example stearic acid, oleic acid, palmitic acid ) and alcohols (fatty alcohols or polyols such as glycerol). These oils may contain substances derived from petrochemicals, as is the case for Isopropyl Palmitate.
  • oils may contain substances derived from petrochemicals, as is the case for Isopropyl Palmitate.
  • oily esters are caprylic capric triglyceride, coco caprylate caprate, oleyl erucate, oleyl linoleate, decyl oleate or else PPG-3 benzyl ether myristate (identified by their I NCI name).
  • silicone oils means an oil comprising at least one silicon atom, and in particular at least one Si—O group.
  • silicone oil mention may in particular be made of phenylpropyldimethylsiloxysilicate, dimethicones or else cyclopentasiloxane (identified by their I NCI name).
  • the additive distinct from the fatty substance and from the composition of diesters, can be chosen from any adjuvant or additive usually used in the fields considered and in particular in the cosmetic, dermatological or pharmaceutical fields.
  • any adjuvant or additive usually used in the fields considered and in particular in the cosmetic, dermatological or pharmaceutical fields.
  • those skilled in the art will take care to choose the possible additive(s) of the composition according to the invention in such a way that the advantageous properties intrinsically attached to the emollient composition in accordance with the invention are not, or substantially not, altered by the proposed addition.
  • anionic foaming surfactants such as sodium lauryl ether sulphate, sodium alkyl phosphate, sodium trideceth sulphate), amphoteric (such as alkyl betaine, disodium cocoamphodiacetate) or nonionics with an HLB greater than 10 (such as POE/PPG/POE, Alkylpolyglucoside, polyglyceryl-3hydroxylauryl ether); conservatives ; sequestrants (EDTA); antioxidants; the perfumes ; dyestuffs such as soluble dyes, pigments and nacres; mattifying, tensor, whitening or exfoliating fillers; cosmetic active agents having the effect of improving the cosmetic properties of the skin, hydrophilic or lipophilic; electrolytes; hydrophilic or lipophilic, anionic, nonionic, cationic or amphoteric,
  • anionic foaming surfactants such as sodium lauryl ether sulphate, sodium alkyl phosphate, sodium trideceth sulphate
  • the cosmetic, dermatological or pharmaceutical composition of the invention is a dermatological or pharmaceutical composition
  • said composition may comprise one or more therapeutic active principles.
  • active agents which can be used in the dermatological or pharmaceutical composition of the invention, mention may be made, for example, of sunscreens; water-soluble or fat-soluble vitamins such as vitamin A (retinol), vitamin E (tocopherol), vitamin C (ascorbic acid), vitamin B5 (panthenol), vitamin B3 (niacinamide), derivatives of these vitamins (in particular esters ) and mixtures thereof; antiseptics; antibacterial active ingredients such as 2,4,4'-trichloro-2'-hydroxy diphenyl ether (or triclosan), 3,4,4'-trichlorocarbanilide (or triclocarban); antimicrobials such as benzoyl peroxide, niacin (vit. PP); and their mixtures.
  • This cosmetic or pharmaceutical composition comprises a physiologically acceptable medium, that is to say which does not have deleterious side effects and in particular which does not produce redness, heating, tightness or tingling that is unacceptable for a user. .
  • the cosmetic, dermatological or pharmaceutical composition has a content of diester composition according to the invention ranging from 0.5 to 80%, preferably from 1 to 50% and advantageously from 5 to 30% by weight relative to the total weight of the cosmetic or pharmaceutical composition.
  • the cosmetic or pharmaceutical composition comprises, relative to the total weight of the cosmetic or pharmaceutical: from 0.5 to 80% by weight, preferably from 1 to 50% by weight and advantageously from 5 to 30% by weight, of the diester composition according to the invention, from 0 to 90% by weight, preferably from 5 to 80% by weight and advantageously from 10 to 70% by weight, preferably from 20 to 60 % by weight, and advantageously from 30 to 50% by weight, of fatty substances, from 0 to 20% by weight of additives, from 0 to 20% by weight of therapeutic active ingredients, it being understood that the composition comprises at least one additive or at least one fatty substance.
  • the cosmetic or pharmaceutical composition comprises, relative to the total weight of the cosmetic or pharmaceutical: from 0.5 to 80% by weight, preferably from 1 to 50% by weight and advantageously from 5 to 30% by weight, of the diester composition according to the invention, from 0 to 90% by weight, preferably from 5 to 80% by weight and advantageously from 10 to 70% by weight, preferably from 20 to 60 % by weight, and advantageously from 30 to 50% by weight, of fatty substances chosen from hydrocarbon oils of biological or petrochemical origin, vegetable oils, vegetable butters, fatty ethers and alcohols, oily esters (different from diesters ), alkanes and silicone oils, from 0 to 20% by weight of additives chosen from anionic, amphoteric or nonionic foaming surfactants with an HLB greater than 10; conservatives ; sequestrants; antioxidants; the perfumes ; dyestuffs; mattifying, tensor, whitening or exfoliating fillers; cosmetic active agents having the effect of improving the cosmetic properties of the
  • the cosmetic or pharmaceutical composition according to the invention can thus be an anhydrous composition, an emulsion such as a water-in-oil (W/O) emulsion, an oil-in-water (O/W) emulsion or a multiple emulsion (in particular W/O/W or O/W/O), a nanoemulsion, or even a dispersion.
  • an emulsion such as a water-in-oil (W/O) emulsion, an oil-in-water (O/W) emulsion or a multiple emulsion (in particular W/O/W or O/W/O), a nanoemulsion, or even a dispersion.
  • the cosmetic or pharmaceutical composition according to the invention is in the form of a more or less flexible cream or a vaporizable emulsion, it can constitute for example a composition for removing make-up or for cleaning the skin, the lips, an after-sun composition , a composition for massaging the skin, a shower care balm composition, an antiperspirant composition, a mask composition, a repairing balm composition, an exfoliating and/or exfoliating composition for both the face and the hands (when it contains exfoliating particles), a make-up composition, a shaving composition, an after-shave balm composition, a perfumed composition, a composition for wipes or even a vaporizable composition.
  • a composition for removing make-up or for cleaning the skin, the lips an after-sun composition
  • a composition for massaging the skin a shower care balm composition, an antiperspirant composition, a mask composition, a repairing balm composition, an exfoliating and/or exfoliating composition for both the face and the hands
  • the cosmetic or pharmaceutical composition according to the invention can also constitute a sunscreen composition when it includes at least one sunscreen.
  • the cosmetic or pharmaceutical composition according to the invention is a cosmetic composition when it provides only a cosmetic effect.
  • the cosmetic composition according to the invention is free of therapeutic active agents.
  • the cosmetic or pharmaceutical composition according to the invention is a dermatological or pharmaceutical composition when it provides a therapeutic effect.
  • the dermatological or pharmaceutical composition according to the invention comprises at least one therapeutic active ingredient, for example chosen from sunscreens; antiseptics; antibacterial active agents such as 2,4,4'-trichloro-2'-hydroxy diphenyl ether (or triclosan), 3,4,4'-trichlorocarbanilide (or triclocarban); antimicrobials such as benzoyl peroxide, niacin (vit. PP); and their mixtures.
  • Example 1 process for the preparation of a diester
  • 12-HSA 12-hydroxystearic acid
  • LAH lithium aluminum hydride
  • the mixture is cooled to -5°C.
  • the 12-HSA solution is added over 30 min using the dropping funnel without exceeding +10°C. There is caking of the reaction medium. 200 mL of THF are added. Agitation overnight at room temperature until complete conversion of the starting material.
  • Control by COM indicates the end of the reaction.
  • the medium is cooled to +10°C.
  • Hydrolysis is carried out by adding 250 mL (3.3 vol.) of potable water dropwise.
  • the aqueous phase is extracted with 3 ⁇ 150 mL of MTBE.
  • the combined organic phases are washed with 250 mL of drinking water, 250 mL of saturated NaHCO3 solution and 250 mL of brine.
  • the organic phase is concentrated to dryness on a rotary evaporator at 45°C.
  • 1,12-octadecanediol is obtained in the form of a white solid.
  • Crude 1,12-octadecanediol was recrystallized by refluxing 5 to 20 g of diol suspended in 30 to 200 mL of heptane. The mixture remains cloudy and heptane is gradually added in 10 mL portions, leaving 10 min at reflux between each addition. The mixture is left under slow stirring at room temperature for 2 hours. The diol begins to crystallize around 50-55°C.
  • the precipitate is isolated by filtration on a No. 4 sintered plate.
  • a white solid is obtained, dried for 2 hours by nitrogen percolation.
  • Crystallization makes it possible to obtain a 1,12-octadecanediol purity of at least 80% or even at least 90%.
  • step a-bis mainly composed of 1,12-octadecanediol
  • step a-bis mainly composed of 1,12-octadecanediol
  • the 1,12-octadecanediol diol is esterified using butyric acid in the presence of a catalyst (APTS) in toluene with a diol/acid mass ratio 1/4 full.
  • APTS a catalyst
  • the diester obtained is tested for its physico-chemical properties.
  • the results are shown in Table 2 and show that the diesters obtained by the process of the invention have properties making them suitable for lubricating applications.
  • the results in Table 3 show that the diesters of the invention have good physico-chemical properties, in particular a good viscosity index, allowing use as a lubricating base oil or as an emollient in cosmetics.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Lubricants (AREA)
EP22839264.3A 2021-12-16 2022-12-15 Verfahren zur herstellung von diestern und diester, die nach diesem verfahren hergestellt werden Pending EP4448480A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2113737A FR3130798B1 (fr) 2021-12-16 2021-12-16 Procede de fabrication de diesters et diesters ainsi obtenus
PCT/EP2022/086078 WO2023111143A1 (fr) 2021-12-16 2022-12-15 Procede de fabrication de diesters et diesters ainsi obtenus

Publications (1)

Publication Number Publication Date
EP4448480A1 true EP4448480A1 (de) 2024-10-23

Family

ID=81580789

Family Applications (1)

Application Number Title Priority Date Filing Date
EP22839264.3A Pending EP4448480A1 (de) 2021-12-16 2022-12-15 Verfahren zur herstellung von diestern und diester, die nach diesem verfahren hergestellt werden

Country Status (8)

Country Link
US (1) US20250109089A1 (de)
EP (1) EP4448480A1 (de)
JP (1) JP2024546794A (de)
KR (1) KR20240124937A (de)
CN (1) CN118786114A (de)
AU (1) AU2022409608A1 (de)
FR (1) FR3130798B1 (de)
WO (1) WO2023111143A1 (de)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL92698C (de) * 1954-08-13
US5008126A (en) 1989-06-27 1991-04-16 Nabisco Brands, Inc. Long chain diol diesters as low calorie fat mimetics
US7871967B2 (en) * 2007-02-12 2011-01-18 Chevron U.S.A. Inc. Diester-based lubricants and methods of making same
US9109238B2 (en) 2008-11-13 2015-08-18 Chevron U.S.A. Inc. Synthesis of diester-based lubricants from enzymatically-directed epoxides
US20110009300A1 (en) * 2009-07-07 2011-01-13 Chevron U.S.A. Inc. Synthesis of biolubricant esters from unsaturated fatty acid derivatives
EP3052600B1 (de) 2013-10-02 2018-02-21 Biosynthetic Technologies, LLC Estolide-zusammensetzungen mit hervorragenden eigenschaften in schmierstoffzusammensetzungen
FR3105221B1 (fr) * 2019-12-20 2022-08-05 Total Marketing Services Procede de preparation de diesters a partir d’alcool gras insatures et diesters ainsi obtenus

Also Published As

Publication number Publication date
KR20240124937A (ko) 2024-08-19
WO2023111143A1 (fr) 2023-06-22
FR3130798A1 (fr) 2023-06-23
AU2022409608A1 (en) 2024-07-25
JP2024546794A (ja) 2024-12-26
US20250109089A1 (en) 2025-04-03
CN118786114A (zh) 2024-10-15
FR3130798B1 (fr) 2026-03-13

Similar Documents

Publication Publication Date Title
EP3600227B1 (de) Biobasierte gelierte zusammensetzung
FR2968951A1 (fr) Composition cosmetique comprenant un compose d'acide cucurbique et une inuline hydrophobe
EP3908248B1 (de) Biobasierte verdickungszusammensetzung mit einem (poly)farnesen
EP4077264A1 (de) Verfahren zur herstellung von diestern aus ungesättigten fettalkoholen und so erhaltene diester
WO2003004590A1 (fr) Substitut de lanoline son procede d obtention et ses applications
EP3187166B1 (de) Verdickendes und/oder dilatantes polyester
WO2023111143A1 (fr) Procede de fabrication de diesters et diesters ainsi obtenus
EP3600229A1 (de) Nichttherapeutische verwendung eines biologisch abbaubaren kohlenwasserstofföls
EP4143152A1 (de) Ester-estolid-zusammensetzung und verfahren zur herstellung von ester-estoliden
CA2003595A1 (fr) Utilisation de diorganopolysiloxanes comme anti-oxydants en cosmetique ou en dermatologie
EP4120994A1 (de) Estolidzusammensetzung für topische anwendungen
WO2018172227A1 (fr) Huile hydrocarbonee pour une utilisation therapeutique
FR2838049A1 (fr) Composition comprenant un milieu physiologiquement acceptable qui contient une phase grasse comprenant un ester particulier
EP4370634A1 (de) 2-octanolmonoester als schmiermittel
FR3142758A1 (fr) Utilisation d’esters de polyol en tant qu’agent conservateur
FR2984119A1 (fr) Composition cosmetique comprenant un acide imido-carboxylique
EP4073212A1 (de) Schmiermittelzusammensetzung zur reibungsbegrenzung
FR3127398A1 (fr) Composition cosmétique comprenant au moins une huile polaire, un polyol et de l’acide ascorbique
FR3015236A1 (fr) Composition huileuse comprenant un compose d'acide cucurbique et un sel divalent
FR2972354A1 (fr) Composition cosmetique comprenant un alun, un compose d'acide salicylique et de la gomme arabique

Legal Events

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

Free format text: STATUS: UNKNOWN

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: 20240620

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 ME MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)