Classifications

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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C9/00—Aliphatic saturated hydrocarbons
  • C07C9/22—Aliphatic saturated hydrocarbons with more than fifteen carbon atoms
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
  • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
  • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C11/00—Aliphatic unsaturated hydrocarbons
  • C07C11/02—Alkenes
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
  • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
  • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
  • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
  • C07C2/08—Catalytic processes
  • C07C2/10—Catalytic processes with metal oxides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
  • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
  • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
  • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
  • C07C2/08—Catalytic processes
  • C07C2/26—Catalytic processes with hydrides or organic compounds
  • C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
  • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
  • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
  • C07C2521/16—Clays or other mineral silicates
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2525/00—Catalysts of the Raney type
  • C07C2525/02—Raney nickel
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2529/00—Catalysts comprising molecular sieves
  • C07C2529/03—Catalysts comprising molecular sieves not having base-exchange properties

Definitions

• the present invention relates to branched alkanes or mixture of branched alkane isomers comprising n carbon atoms, n representing an integer between 9 and 50.
• the present application also relates to branched alkanes or mixture of branched alkane isomers comprising n carbon atoms, n representing 16, 24 or 32, said alkane or mixture of alkanes being free from branched alkanes comprising n-4 or n + 4 carbon atoms.
• the present application finally relates to branched olefins making it possible, by hydrogenation, to obtain the alkanes of the invention.
• Branched alkanes comprising a large number of carbon atoms, especially 9 or more carbon atoms, preferably 16 or more carbon atoms, have various applications. They can in particular be used as ingredients in cosmetic formulations, in agrochemical formulations, as plasticizers additives, lubricants, etc. in formulations belonging to various other fields of application
• alkanes with impurities such as aromatic compounds.
• alkanes (after hydrogenation of olefins) comprising n carbon atoms which have impurities at n-4 and n + 4 carbon atoms.
• impurities are not desired since they are too volatile for the n-4s and for the n + 4s too viscous in relation to the desired properties.
• An objective of the present invention is therefore to provide higher branched alkanes, in particular comprising n carbon atoms, n representing a integer between 9 and 50, preferably comprising 16, 24, 32, 40 or 48 carbon atoms.
• Another objective of the present invention is to provide such alkanes, in particular comprising 16, 24, 32, 40 or 48 carbon atoms, exhibiting a lower level of impurities.
• Another objective of the present invention is also to provide a process for the preparation of such alkanes.
• the present application relates to a branched alkane comprising n carbon atoms, n being an integer between 9 and 50, preferably n is equal to 16, 24, 32, 40 or 48, preferably the alkanes for which n represents 16, 24 , 32, 40 or 48 are free from branched alkanes comprising n-4 or n + 4 carbon atoms.
• n is equal to 12.
• the branched alkane is free from alkanes comprising n-4 or n + 4 carbon atoms which the alkane does not contain, as impurities, alkanes comprising n- 4 or n + 4 carbon atoms.
• alkanes according to the invention are of formula (I) below:
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being between 7 and 48; provided that :
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• one of the groups R 1 , R 2 , R 3 or R 4 is a methyl group.
• the total number of carbon atoms of the groups R 1 , R 2 , R 3 and R 4 is equal to 10.
• the alkanes according to the invention are of formula (I) below:
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being equal to 14, 22, 30, 38 or 46; provided that :
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• alkanes according to the invention are of formula (I) below:
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being equal to 14, 22, 30, 38 or 46; provided that :
• alkanes according to the invention are of formula (I) below:
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being equal to 14, 22, 30, 38 or 46; provided that :
• the groups R 1 and R 2 are (Ci-C46) alkyl groups.
• alkanes according to the invention are of formula (I) below:
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being equal to 14, 22, 30, 38 or 46; provided that :
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• an alkyl group denotes a saturated, linear or branched aliphatic hydrocarbon group comprising, unless otherwise specified, from 1 to 46 carbon atoms. Mention may be made, by way of examples, of methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, tertbutyl, pentyl, undecenyl, lauryl, palmyl, oleyl, linoleyl, erucyl or ricinoleyl groups.
• one of the groups R 1 , R 2 , R 3 or R 4 contains a tert-butyl group. According to one embodiment, in formula (I), one of the groups R 1 , R 2 , R 3 or R 4 is a tert-butyl group.
• one of the groups R 1 , R 2 , R 3 or R 4 contains a tert-butyl group and corresponds to the formula -AC (CH 3 ) 3, A representing a radical alkylene comprising from 1 to 6 carbon atoms.
• alkylene designates according to the invention a radical comprising from 1 to 6 carbon atoms, and preferably from 1 to 4 carbon atoms.
• An alkylene radical corresponds to an alkyl radical as defined here from which one atom has been removed. of hydrogen.
• the alkanes according to the invention are free from aromatic compounds.
• the present application also relates to mixtures of branched alkane isomers according to the invention comprising n carbon atoms, n being an integer between 9 and 50.
• the mixture of isomers can be composed different alkane isomers comprising n carbon atoms, n having a single value between 9 and 50 or a mixture of alkane isomers for which the values of n are different.
• the present application also relates to mixtures of branched alkane isomers comprising n carbon atoms, n being equal to 16, 24, 32, 40 or 48, said mixture being free from branched alkanes comprising n-4 or n + 4 carbon atoms.
• the mixture of isomers can be composed of different isomers of alkanes comprising n carbon atoms, n having a single value chosen from 16, 24, 32, 40 or 48.
• the mixture of isomers according to the invention can also be composed of different alkane isomers comprising 16 carbon atoms and / or 24 carbon atoms and / or 32 carbon atoms and / or 40 carbon atoms and / or 48 carbon atoms.
• the mixtures of branched alkane isomers according to the invention are free from aromatic compounds.
• the mixture of branched alkane isomers according to the invention comprises at least two branched alkane isomers of the following formula (I):
• R 1 , R 2 , R 3 and R 4 identical or different, are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being between 7 and 48; provided that :
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• one of the groups R 1 , R 2 , R 3 or R 4 is a methyl group.
• the mixture of branched alkane isomers according to the invention comprises at least two branched alkane isomers of the following formula (I):
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being between 7 and 48; provided that :
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• one of the groups R 1 , R 2 , R 3 or R 4 is a methyl group.
• the mixture of branched alkane isomers according to the invention comprises at least two branched alkane isomers of the following formula (I):
• R 1 , R 2 , R 3 and R 4 identical or different, are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms and the total number of carbon atoms of the R 1 groups, R 2 , R 3 and R 4 being equal to 14, 22, 30, 38 or 46; provided that :
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• the mixture of branched alkane isomers according to the invention comprises at least two branched alkane isomers of the following formula (I):
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms; the total number of carbon atoms of the groups R 1 , R 2 , R 3 and R 4 being equal to 14, 22, 30, 38 or 46, provided that:
• the groups R 1 and R 2 are (Ci-C46) alkyl groups.
• the mixture of branched alkane isomers according to the invention comprises at least two branched alkane isomers of the following formula (I):
• R 1 , R 2 , R 3 and R 4 are chosen from H, alkyls, linear or branched, comprising from 1 to 46 carbon atoms; the total number of carbon atoms of the groups R 1 , R 2 , R 3 and R 4 being equal to 14, 22, 30, 38 or 46, provided that: - at most two of the groups R 1 , R 2 , R 3 and R 4 are H;
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• the mixtures of the invention are such that all the compounds of formula (I) as defined above comprise n carbon atoms, n being as defined above and being identical for all the compounds. of said mixture.
• said mixtures are free from aromatic compounds.
• the present application also relates to a process for preparing branched alkanes or a mixture of branched alkanes according to the invention.
• This preparation process comprises a step of hydrogenating branched olefins or a mixture of branched olefins comprising n carbon atoms, n being defined above, preferably n being equal to 16, 24, 32, 40 or 48. De preferably, when n is equal to 16, 24, 32, 40 or 48, the branched olefins or mixture of branched olefins are free from olefins comprising n-4 or n + 4 carbon atoms, and preferably free from aromatic compounds .
• the hydrogenation step corresponds to bringing the branched olefin or mixtures of branched olefins into contact with dihydrogen (H 2 ).
• the hydrogenation step can be carried out in the presence of a hydrogenation catalyst chosen from metal derivatives such as Pd, Pt, Ni, in solution when they are put in the form of organometallic complexes or in supported form. on solids such as silica, alumina or carbon, and preferably Raney nickel.
• a hydrogenation catalyst chosen from metal derivatives such as Pd, Pt, Ni, in solution when they are put in the form of organometallic complexes or in supported form. on solids such as silica, alumina or carbon, and preferably Raney nickel.
• the hydrogenation step can be carried out without a solvent or in the presence of a solvent
• the solvent can in particular be chosen from alkanes which can separate from the branched alkanes obtained as a result of the hydrogenation by techniques known from a person skilled in the art, in particular isooctane, ethers, by example diisopropylether, dibutylether, or heavy alcohols, for example alcohols comprising more than 4 carbon atoms, for example octanol, decanol, dodecanol, isododecanol.
• the solvents are bio-based solvents (derived from biological resources), in particular isododecanol derived from bio-based isododecene.
• the hydrogenation step is preferably carried out at a temperature between 50 and 150 ° C, for example at 80 ° C.
• the hydrogen is introduced by adjusting the pressure to a constant value between 1.013.10 e and 5.066.10 e Pa, for example 2.027.10 e Pa.
• the hydrogenation step has a duration of between 2 and 6 hours, for example 3 hours.
• the excess hydrogen can be removed by expansion and the reactor is purged three times with an inert gas, preferably nitrogen.
• the catalyst if it is heterogeneous, can be recovered by filtration and can be recycled.
• the reaction solvent can be separated by distillation and can be recycled.
• continuous reactors can be used advantageously.
• the branched alkane isomers according to the invention can be separated and purified by distillation.
• the present invention also relates to a branched olefin comprising n carbon atoms, n being an integer between 9 and 50, preferably, n being equal to 16, 24, 32, 40 or 48.
• n being an integer between 9 and 50, preferably, n being equal to 16, 24, 32, 40 or 48.
• the branched olefin is free of aromatic compounds.
• the branched olefin, when n is equal to 16, 24, 32, 40 or 48 is free of olefin comprising n-4 or n + 4 carbon atoms, and preferably free of aromatic compounds.
• the branched olefin according to the invention is preferably of formula (II) in which R 1 , R 2 , R 3 and R 4 have the definition given for formula (I).
• the groups R 1 and R 2 are (Ci-C46) alkyl groups.
• the compounds of formula (II) are branched compounds comprising a total of 8 + 4x carbon atoms with x representing 2, 4, 6, 8 or 10.
• the compounds of formula (II) are therefore branched compounds whose main chain contains 16, 24, 32, 40 or 48 carbon atoms.
• the olefins of formula (II) therefore correspond to one of the following formulas: in which R'1, R'2, R ' 3 and R'4 are preferably (C1-C3o) alkyl groups
• the olefins of formula (II) may comprise two hydrogen atoms, one corresponding to the group R'i or R ' 2 and the other to the group R' 3 or R'4.
• the mixture of branched olefin isomers according to the invention is a mixture comprising at least two olefins of formula (II).
• the mixtures of the invention are such that all the compounds of formula (II) as defined above comprise n carbon atoms, n being as defined above and being identical for all the compounds of said mixture.
• the present invention also relates to a mixture of branched olefin isomers comprising n carbon atoms, n being equal to 16, 24, 32, 40 or 48, the mixture of branched olefin isomers being free of olefin comprising n -4 or n + 4 carbon atoms, and preferably free of aromatic compounds.
• the branched olefins are of formula (II).
• the present invention also relates to branched olefins comprising n carbon atoms, n representing an odd number between 9 and 49 or n represents 10, 14, 18, 22, 26, 30, 32, 34, 36, 40, 42, 44 , 46, 50.
• the olefins then correspond to the following formula (III): in which R 1 , R 2 , R 3 and R 4 , identical or different, are chosen from H, alkyls, linear or branched, at least one of these alkyls being branched, comprising from 1 to 48 carbon atoms and the total number of carbon atoms of formula (I) is equal to n; with the proviso that: at least two of R 1 , R 2 , R 3 and R 4 is different from H; and - R 1 and R 2 cannot simultaneously be H; and R 3 and R 4 cannot be H.
• R 1 is H or linear or branched alkyl comprising from 1 to 15 carbon atoms
• R 2 , R 3 and R 4 which are identical or different, are chosen from alkyls, linear or branched, comprising from 1 to 15 carbon atoms.
• R 1 is H
• R 2 is an alkyl, linear comprising from 1 to 15 carbon atoms
• R 3 and R 4 are chosen from alkyls, linear or branched, comprising from 1 to 15 carbon atoms.
• the olefins then correspond to the following formula (III): in which R 1 , R 2 , R 3 and R 4 , identical or different, are chosen from H, alkyls, linear or branched, at least one of these alkyls being branched, comprising from 1 to 48 carbon atoms and the total number of carbon atoms of formula (I) is equal to n; with the proviso that: at least two of R 1 , R 2 , R 3 and R 4 is different from H.
• R 1 , R 2 , R 3 and R 4 identical or different, are chosen from H, alkyls, linear or branched, at least one of these alkyls being branched, comprising from 1 to 48 carbon atoms and the total number of carbon atoms of formula (I) is equal to n; with the proviso that: at least two of R 1 , R 2 , R 3 and R 4 is different from H.
• the olefins then correspond to the following formula (III): in which R 1 , R 2 , R 3 and R 4 , identical or different, are chosen from H, alkyls, linear or branched, at least one of these alkyls being branched, comprising from 1 to 48 carbon atoms and the total number of carbon atoms of formula (I) is equal to n; provided that : at least two of R 1 , R 2 , R 3 and R 4 is different from H,
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• the olefins then correspond to the following formula (III): in which R 1 , R 2 , R 3 and R 4 , identical or different, are chosen from H, alkyls, linear or branched, at least one of these alkyls being branched, comprising from 1 to 48 carbon atoms and the total number of carbon atoms of formula (I) is equal to n; with the proviso that: at least two of R 1 , R 2 , R 3 and R 4 is different from H; and R 1 and R 2 cannot simultaneously be H; and
• one of the groups R 1 , R 2 , R 3 or R 4 comprises or is a tert-butyl group.
• branched olefins or mixture of branched olefin isomers according to the invention comprising n carbon atoms, n being equal to 16, 24, 32, 40 or 48 carbon atoms can be obtained by dimerization of a mixture of isomers branched olefin comprising n / 2 carbon atoms.
• branched olefins comprising 16 carbon atoms can be obtained by dimerization of branched olefins comprising 8 carbon atoms.
• Branched olefins comprising 24 carbon atoms can be obtained by dimerization of branched olefins comprising 12 carbon atoms.
• Branched olefins comprising 32 carbon atoms can be obtained by dimerization of branched olefins comprising 16 carbon atoms.
• Branched olefins comprising 40 carbon atoms can be obtained by dimerization of branched olefins comprising 20 carbon atoms.
• Branched olefins comprising 48 carbon atoms can be obtained by dimerization of branched olefins comprising 24 carbon atoms.
• the branched olefin isomers comprising n / 2 carbon atoms may have undergone purification, in particular by distillation, before the dimerization step.
• the dimerization step can be carried out in the presence of a catalyst chosen from Bronsted acids in solution, for example H2SO4, H3PO4, HF, methanesulfonic acid, triflic acid (CF3SO3H); solid Bronsted acids, for example organic resins, clays, zeolites, FI3PO4 on silica; Lewis acids, for example ZnCl2, AICI3; organometallic compounds, for example Ni complexes, mixtures of Ni and Al complexes; ionic liquids, for example [BMIm] [N (CF3S02) 2] / HN (CF3S02) 2; clays with lamellar structures such as Montmorillonite; organic resins such as amberlysts, sulphonic resins; organometallic compounds such as, for example [LNi
• the dimerization step is preferably carried out at a temperature between 30 and 250 ° C, preferably between 100 and 200 ° C.
• the branched olefins comprising 8, 12 and 16 carbon atoms are obtained from isobutene.
• said isobutene is obtained from bioresources, in particular as described in applications WO2012052427, WO2017085167 and WO 2018206262, for example from polysaccharides (sugars, starches, celluloses, etc.).
• the olefins (II) of the invention can also be obtained by co-dimerization of lower olefins or by metathesis of lower olefins.
• lower olefins is understood to mean olefins comprising less than n carbon atoms.
• the lower olefins used in the co-dimerization process can for example be of formulas (IV) and (V):
• R 5 R 6 C CR 7 R 8 (IV)
• R 7 and R 8 represent H and R 5 and R 6 , identical or different, represent an alkyl group, linear or branched, comprising in total, with the carbon atoms carrying the double bond, m carbon atoms; or
• R 5 , R 6 , R 7 and R 8 identical or different, represent a linear or branched alkyl group comprising in total, with the carbon atoms carrying the double bond, m carbon atoms; or
• R 5 represents H and R 6 , R 7 and R 8 , which may be identical or different, represent a linear or branched alkyl group comprising in total, with the carbon atoms carrying the double bond, m carbon atoms;
• R 9 , R 10 , R 11 and R 12 which may be identical or different, represent an alkyl group, linear or branched, comprising in total, with the carbon atoms carrying the double bond, p carbon atoms; or
• R 9 , R 11 and R 12 represent H and R 10 represents an alkyl group, linear or branched, comprising in total, with the carbon atoms carrying the double bond, p carbon atoms.
• the metathesis process is carried out between an olefin comprising q carbon atoms and an olefin comprising r carbon atoms, q and r being integers chosen so that q + r is greater than n with n representing an integer between 9 and 50.
• the metathesis reaction is at the origin of the loss of carbon atoms in the final compound (loss of at least two carbon atoms), the number of carbon atoms lost being a function of the olefins involved and in particular of the nature of the substituents of the two carbon atoms of the double bond.
• the lower olefins used in the metathesis process can, for example, be of formulas (VI) and (VII):
• R 13 R 14 C CR 15 R 16 (VI)
• R 17 R 18 C CR 19 R 20 (VII) the olefin (VI) being an exo (terminal double bond) or endo (non-terminal double bond) olefin comprising q carbon atoms; the olefin (VII) comprising r carbon atoms, q is between 4 and 32 and r is between 3 and 40; thus, in formulas (VI) and (VII) R 15 and R 16 represent H and R 13 and R 14 , identical or different, represent an alkyl group, linear or branched, comprising in total, with the carbon atoms carrying the double bond, q carbon atoms; or
• R 13 , R 14 , R 15 and R 16 identical or different, represent a linear or branched alkyl group comprising in total, with the carbon atoms carrying the double bond, q carbon atoms; or
• R 13 represents H and R 14 , R 15 and R 16 , identical or different, represent a linear or branched alkyl group comprising in total, with the carbon atoms carrying the double bond, q carbon atoms;
• R 17 , R 18 , R 19 and R 20 which may be identical or different, represent an alkyl group, linear or branched, comprising in total, with the carbon atoms carrying the double bond, r carbon atoms; or
• R 17 , R 19 and R 20 represent H and R 18 represents an alkyl group, linear or branched, comprising in total, with the carbon atoms bearing the double bond, r carbon atoms.
• n represents an odd number between 9 and 49 or a number n represents 10, 14, 18, 22, 26, 30, 32 , 34, 36, 40, 42, 44, 46, 50:
• the lower olefins used in the co-dimerization process can for example be of formulas (IV) and (V):
• R 5 R 6 C CR 7 R 8 (IV)
• R 9 R 10 C CR 11 R 12 (V) the olefin (IV) being an exo (terminal double bond) or endo (non-terminal double bond) olefin comprising 4t carbon atoms, t being an integer between 1 and 6 thus, in formulas (IV) and (V)
• R 7 and R 8 represent H and R 5 and R 6 , identical or different, represent an alkyl group, linear or branched, comprising from 1 to 12 carbon atoms; or
• R 5 , R 6 , R 7 and R 8 identical or different, represent a linear or branched alkyl group comprising from 1 to 12 carbon atoms; or
• R 5 represents H and R 6 , R 7 and R 8 , identical or different, represent a linear or branched alkyl group comprising from 1 to 12 carbon atoms;
• R 9 , R 10 , R 11 and R 12 which are identical or different, represent an alkyl group, linear or branched, comprising from 1 to 12 carbon atoms; or
• R 9 , R 11 and R 12 represent H and R 10 represents an alkyl group, linear or branched, comprising from 1 to 12 carbon atoms; the number of total carbon atoms of formula (IV) being m and the number of total carbon atoms of formula (V) being p.
• n represents an odd number between 9 and 49 or a number n represents 10, 14, 18, 22, 26, 30, 32 , 34, 36, 40, 42, 44, 46, 50:
• the metathesis process is carried out between an olefin comprising q carbon atoms and an olefin comprising r carbon atoms, q and r being integers chosen so that q + r is greater than n.
• the metathesis reaction is at the origin of the loss of carbon atoms in the final compound (loss of at least two carbon atoms), the number of carbon atoms lost being a function of the olefins used. game and in particular the nature of the substituents of the two carbon atoms of the double bond.
• the lower olefins used in the metathesis process can, for example, be of formulas (VI) and (VII):
• R 15 and R 16 represent H and R 13 and R 14 , identical or different, represent an alkyl group, linear or branched, comprising from 1 to 12 carbon atoms; or
• R 13 , R 14 , R 15 and R 16 identical or different, represent a linear or branched alkyl group comprising from 1 to 12 carbon atoms; or
• R 13 represents H and R 14 , R 15 and R 16 , identical or different, represent a linear or branched alkyl group comprising from 1 to 12 carbon atoms;
• R 17 , R 18 , R 19 and R 20 identical or different, represent an alkyl group, linear or branched, comprising from 1 to 12 carbon atoms; or
• R 17 , R 19 and R 20 represent H and R 18 represents an alkyl group, linear or branched, comprising from 1 to 12 carbon atoms; the number of total carbon atoms of formula (VI) being q and the number of total carbon atoms of formula (VII) being r.
• the amount of catalyst used in the codimerization is between 1000 ppm and 10% by weight, preferably between 1000 ppm and 5% by weight, relative to the weight of the olefin.
• the co-dimerization step is preferably carried out at a temperature between 30 and 250 ° C, preferably between 100 and 200 ° C.
• the olefins can be obtained from isobutene.
• said isobutene is obtained from bioresources, in particular as described in applications WO2012052427, WO2017085167 and WO 2018206262, for example from polysaccharides (sugars, starches, celluloses, etc.).
• the metathesis step is carried out by reacting the two olefins in the presence of a metathesis catalyst, in particular a catalyst chosen from catalysts known to those skilled in the art for metathesis, in particular ruthenium catalysts, in particular Grubbs catalysts.
• a metathesis catalyst in particular a catalyst chosen from catalysts known to those skilled in the art for metathesis, in particular ruthenium catalysts, in particular Grubbs catalysts.
• 2nd generation for example Benzylidene 1, 3-bis (2,4,6-trimethylphenyl) -2-imidazolidinylidene dichloro (tricyclohexyl- phosphine) ruthenium or (1, 3-dimesitylimidazolidine- 2-ylidene) (tricyclohexylphosphine) benzylidene ruthenium dichloride.
• the amount of catalyst is preferably between 50 ppm and 5% by weight of element Ru, preferably between 200 ppm and 1%, relative to the weight of olefin.
• the reaction is preferably carried out at a temperature between 0 and 150 ° C, for example between 20 and 100 ° C.
• the medium then undergoes a purification step, for example the reaction medium is dissolved in a solvent, for example toluene, then the mixture obtained is filtered, for example on neutral alumina.
• the olefins according to the invention can be used for the formulation of cosmetic compositions, plasticizer compositions or alternatively lubricant compositions.
• the olefins of the invention can also be hydrogenated to the corresponding alkanes or undergo reactions transforming them into functionalized alkanes, said alkanes being able to be used in the formulation of cosmetic compositions, of plasticizer compositions or of lubricant compositions.
• the present application also relates to the use of branched alkanes according to the invention or a mixture of branched alkanes according to the invention for the formulation of cosmetic compositions, plasticizer compositions or alternatively lubricant compositions.
• the mixture is kept under stirring and at this temperature level for 3 hours.
• the Montmorillonite catalyst is separated from the liquid phase by filtration.
• the liquid phase is diluted in a cyclohexane solvent for the purposes of analysis.
• the catalyst used in this example is marketed by AXEN and corresponds to a solution of dichloroalkylaluminum at 50% by weight in a C6-C8 paraffinic gasoline cut, and liquid nickel-based catalyst.
• the reaction mixture is maintained between 45 and 50 ° C for 2 hours
• the mixture is cooled to room temperature.
• the mixture is treated with a basic aqueous solution of sodium carbonate or sodium hydroxide and the organic and aqueous phases are then separated by decantation.
• the organic phase is analyzed.
• the conversion of isooctene is between 70 and 100%.
• the yields of isooctene dimerization products are between 60 and 90%.
• Example 3 Hydroqénation of the compounds resulting from Examples 1 and 2
• the stirred mixture is brought to a temperature of 80 ° C.
• the hydrogen is introduced by adjusting the pressure to a constant value of 20 atmospheres.
• the stirred reaction mixture is maintained at 50 ° C under constant pressure of hydrogen for a period of 3 hours.
• the reaction medium is diluted in cyclohexane for analytical needs
• the reaction medium is analyzed:
• the yield of hydrogenated dimer (branched alkane according to the invention) is 100%.
• the mixture is kept under stirring and at this temperature level for 3 hours.
• the reaction mixture is cooled to room temperature.
• the Montmorillonite catalyst is separated from the liquid phase by filtration.
• the liquid phase is diluted in a cyclohexane solvent for the purposes of analysis.
• the conversion is between 70 and 95%.
• the yields of hexadodecene, products of co-dimerization of isooctene with n octene, are between 50 and 90%.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Cosmetics (AREA)
• Lubricants (AREA)

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• 2020
  • 2020-08-17 US US17/635,427 patent/US20220340503A1/en not_active Abandoned
  • 2020-08-17 EP EP20753965.1A patent/EP4013736A1/fr not_active Withdrawn
  • 2020-08-17 CN CN202080069009.1A patent/CN114502523A/zh active Pending
  • 2020-08-17 JP JP2022510210A patent/JP2022545206A/ja active Pending
  • 2020-08-17 WO PCT/EP2020/072987 patent/WO2021032672A1/fr unknown

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