WO2021032675A2

WO2021032675A2 - Esterified or etherified compounds, processes for producing same and uses thereof

Info

Publication number: WO2021032675A2
Application number: PCT/EP2020/072993
Authority: WO
Inventors: Serge Ratton; Marc Lemaire; Luc MATHIS; Estelle METAY
Original assignee: Global Bioenergies
Priority date: 2019-08-16
Filing date: 2020-08-17
Publication date: 2021-02-25
Also published as: WO2021032675A3; FR3099929B1; FR3099929A1

Abstract

The present invention relates to a compound of the following formula (I): in which: - R₁, R₂, R₃ and R₄ are, independently of one another, H or a (C₁-C₃₀)alkyl group, the total sum of the number of carbon atoms of R₁, R₂, R₃ and R₄ being equal to 6+4x, x being an integer from 0 to 6, with the proviso that: - at most two among the R₁, R₂, R₃ and R₄ groups are H, - when one of the R₁ or R₂ groups is H or when the R₁ and R₂ groups are H, then the R₃ and R₄ groups are (C₁-C₃₀)alkyl groups, and - when one of the R₃ or R₄ groups is H or when the R₃ and R₄ groups are H, then the R₁ and R₂ groups are (C₁-C₃₀)alkyl groups; and - R is chosen from the group consisting of (C₁-C₃₀)alkyl groups, (C_2-C₃₀)alkenyl groups, (hetero)arylalkyl groups, (C₁-C₃₀)alkyl groups substituted with at least one hydroxyl group, and -C(=O)-R₅ groups, R₅ being H or an alkyl group comprising from 1 to 29 carbon atoms, it being possible for said alkyl group to be substituted with at least one hydroxyl group.

Description

ESTERIFIED OR ETHERIFIED COMPOUNDS, THEIR PREPARATION PROCESSES AND THEIR USES

The present invention relates to novel isomers of esterified or etherified branched alkanes, alone or in mixtures, as well as their preparation processes. It also relates to the use of said compounds alone or in mixtures.

Functionalized branched alkanes comprising a large number of carbon atoms, in particular 8 or more carbon atoms, have various applications. They can in particular be used as surfactants, emollients, solvents or monomers for the preparation of various polymers.

However, these compounds are generally derived from fossil resources, in particular petroleum. In addition to having a negative impact on the environment, the use of fossil resources, and in particular oil, results in alkanes with impurities such as aromatic compounds. In addition, to obtain higher alkanes, in particular with a number of carbon atoms at least equal to 16, it is necessary in particular to go through oligomerization reactions, these reactions leading to mixtures of olefins and then to mixtures. alkanes (after hydrogenation of the olefins) comprising n carbon atoms which exhibit impurities at n-4 and n + 4 carbon atoms when the olefins are accessed by oligomerization. Such impurities are not desired.

The object of the present invention is to provide new etherified or esterified compounds which can in particular be used as plasticizers, lubricants, surfactants or for cosmetic applications, said compounds being biobased.

Thus, the present invention relates to a compound of formula (I) below:

in which :

- Ri, R ₂ , R3 and R4 represent, independently of each other, H or a (Ci-C3o) alkyl group, the total sum of the number of carbon atoms of Ri, R ₂ , R ₃ and R ₄ being equal to 6 + 4x, x being an integer from 0 to 6, provided that:

- two at most among the groups Ri, R ₂ , R ₃ and R ₄ are H,

- when one of the groups R 1 or R ₂ is H or when the groups R 1 and R ₂ are H, then the groups R ₃ and R ₄ are (Ci-C ₃ o) alkyl groups, and

- when one of the groups R ₃ or R ₄ is H or when the groups R ₃ and R ₄ are H, then the groups R 1 and R ₂ are (Ci-C ₃ o) alkyl groups;

- R is chosen from the group consisting of (Ci-C ₃ o) alkyl groups, (C ₂ -C ₃ o) alkenyl groups, (hetero) arylalkyl groups, _{substituted (C 1} - C ₃ o) alkyl groups with at least one hydroxyl group, and groups -C (= 0) -R ₅ , R ₅ representing H or an alkyl group comprising from 1 to 29 carbon atoms, said alkyl group possibly being substituted by at least one hydroxyl group.

The present invention relates to a compound of formula (I) below:

in which :

- Ri, R ₂ , R ₃ and R ₄ represent, independently of each other, H or a (Ci-C ₃ o) alkyl group, the total sum of the number of carbon atoms of Ri, R ₂ , R ₃ and R ₄ being equal to 6 + 4x, x being an integer from 1 to 6, provided that:

- two at most among the groups Ri, R ₂ , R ₃ and R ₄ are H,

- one of the groups R ₃ or R ₄ comprises or is a tert-butyl group;

- R is chosen from the group consisting of groups -C (= 0) -R ₅ , R ₅ representing H or an alkyl group comprising from 1 to 29 carbon atoms, said alkyl group possibly being substituted by at least one hydroxyl group, (Ci-C ₃ o) alkyl groups, (C ₂ -C ₃ o) alkenyl groups, (hetero) arylalkyl groups and (Ci-C ₃ o) alkyl groups substituted by at least one hydroxyl group. The present invention relates to a compound of formula (I) below:

in which :

- two at most among the groups Ri, R ₂ , R ₃ and R ₄ are H,

- one of the groups R ₃ or R ₄ comprises or is a tert-butyl group;

- R is chosen from the group consisting of groups -C (= 0) -R ₅ , R ₅ representing H or an alkyl group comprising from 1 to 29 carbon atoms, said alkyl group possibly being substituted by at least one hydroxyl group, (Ci-C ₃ o) alkyl groups, (C ₂ -C ₃ o) alkenyl groups, (hetero) arylalkyl groups and (Ci-C ₃ o) alkyl groups substituted by at least one hydroxyl group.

The compounds of formula (I) correspond to isomers of branched alkanes etherified or esterified, depending on the nature of the above-mentioned R group.

These compounds comprise in total (without counting the group R) 8 + 4x carbon atoms, which corresponds to the total number of carbon atoms of the groups Ri, R ₂ , R ₃ and R ₄ and of the two carbon atoms carrying these groups. The compounds of formula (I) according to the invention are therefore branched compounds whose main chain comprises 12, 16, 20, 24, 28 or 32 carbon atoms and carrying an OR side chain as defined above.

In the above-mentioned formula (I), according to one embodiment, one of the groups R ₃ or R ₄ contains a tert-butyl group. According to one embodiment, in formula (I), one of the groups R ₃ or R ₄ is a tert-butyl group. According to one embodiment, in formula (I), one of the groups R3 or FU contains a tert-butyl group and corresponds to the formula -AC (CH ₃ ) 3, A representing an alkylene radical comprising from 1 to 6 atoms of carbon.

The term “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.

In the context of the present invention, by C _t -C _z is meant a carbon chain which may have from t to z carbon atoms, for example C1-C3, a carbon chain which may have from 1 to 3 carbon atoms.

According to the invention, an alkyl group denotes a saturated, linear or branched aliphatic hydrocarbon group comprising, unless otherwise specified, from 1 to 30 carbon atoms. By way of examples, mention may be made of methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, tertbutyl or pentyl groups, or also undecenyl, lauryl, palmyl, oleyl, linoleyl, erucyl and ricinoleyl groups.

According to the invention, an alkenyl group denotes an aliphatic hydrocarbon group corresponding to the radical derived from an alkene. Such a group therefore comprises an unsaturation and can be represented by the formula C _n H _2n -i, n representing the number of carbon atoms.

According to the invention, an aryl group denotes a cyclic aromatic group comprising between 6 and 10 carbon atoms. As examples of aryl groups, mention may be made of phenyl or naphthyl groups.

According to the invention, a heteroaryl group denotes a monocyclic or bicyclic aromatic group of 5 to 10 members containing from 1 to 4 heteroatoms chosen from O, S or N. By way of examples, mention may be made of the imidazolyl, thiazolyl and oxazolyl groups. , furanyl, thiophenyl, pyrazolyl, oxadiazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzimidazolyl, indazolyl, benzothiazolyl, isobenzotriazolyl, isobenzotriazoleol.

By way of heteroaryl comprising 5 to 6 atoms, including 1 to 4 nitrogen atoms, there may be mentioned in particular the following representative groups: pyrrolyl, pyrazolyl, 1, 2,3-triazolyl, 1, 2, 4-triazolyl, tetrazolyl , 1, 2,3-triazinyl.

Mention may also be made, by way of heteroaryl, of thiophenyl, oxazolyl, furazanyl, 1, 2,4-thiadiazolyle, naphthyridinyle, quinoxalinyl, phthalazinyl, rimidazo [1, 2-a] pyridine, l 'imidazo [2,1 -b] thiazolyl, cinnolinyl, benzofurazanyl, azaindolyl, benzimidazolyl, benzothiophenyl, thienopyridyl, thienopyrimidinyl, pyrrolopyridyl, imidazopyridyl, benzoazaindole, 1, 2,4-triazinyl, indolizinyl, isoxazolyl, risisoquiniazolyl, purinyl, quinazolinyl, quinolinyl, isoquinolyl, 1, 3,4-thiadiazolyl, thiazolyl, isothiazolyl, carbazolyl, as well as the corresponding groups resulting from their fusion or fusion with the phenyl ring.

According to the invention, the term "(hetero) arylalkyls" denotes both heteroarylalkyl and arylalkyl groups.

When an alkyl radical is substituted by an aryl group, it is referred to as an "arylalkyl" or "aralkyl" radical. The “arylalkyl” or “aralkyl” radicals are aryl-alkyl- radicals, the aryl and alkyl groups being as defined above. Among the arylalkyl radicals, mention may in particular be made of the benzyl or phenethyl radical.

When an alkyl radical is substituted by a heteroaryl group, it is called a "heteroarylalkyl" radical. The “heteroarylalkyl” radicals are heteroaryl-alkyl- radicals, the heteroaryl and alkyl groups being as defined above. Among the heteroarylalkyl radicals, mention may in particular be made of the furfuryl radical.

The etherified branched alkane isomers of the invention are compounds of formula (I) as defined above in which R is chosen from the group consisting of (Ci-C3o) alkyl groups, (C2-C3o) groups alkenyl, (hetero) arylalkyl groups, in particular benzyl or furfuryl and (Ci-C3o) alkyl groups substituted with at least one hydroxyl group, in particular groups or radicals derived from nonanol or dodecanol, or from polyols such as sorbitan, glycol, glycerol, erythritol, sorbitol or polyglycerols.

According to one embodiment, the esterified branched alkane isomers of the invention are compounds of formula (II) below:

in which : - Ri, R ₂ , R ₃ and R ₄ represent, independently of each other, H or a (Ci-C ₃ o) alkyl group, the total sum of the number of carbon atoms of Ri, R ₂ , R ₃ and R ₄ being equal to 6 + 4x, x being an integer from 0 to 6, with the proviso that:

- two at most among the groups Ri, R ₂ , R ₃ and R ₄ are H,

- R ₅ represents H or an alkyl group comprising from 1 to 29 carbon atoms, preferably from 1 to 21 carbon atoms, said alkyl group possibly being substituted by at least one hydroxyl group.

in which :

- Ri, R ₂ , R ₃ and R ₄ represent, independently of each other, H or a (Ci-C ₃ o) alkyl group, the total sum of the number of carbon atoms of Ri, R ₂ , R ₃ and R ₄ being equal to 6 + 4x, x being an integer from 0 to 6, with the proviso that:

- two at most among the groups Ri, R ₂ , R ₃ and R ₄ are H,

According to one embodiment, the esterified branched alkane isomers of the invention are compounds of above-mentioned formula (II) in which x is comprised from 1 to 6, and in which one of the groups R3 or FU comprises or is a tert-butyl group as defined above.

Preferably x is equal to 1.

The present invention also relates to a mixture of esterified or etherified branched alkane isomers, each esterified or etherified branched alkane comprising a main hydrocarbon chain and a side chain of formula OR, R being chosen from the group consisting of (Ci-C3o ) alkyls, (C2-C3o) alkenyl groups, (hetero) arylalkyl groups, (Ci-C3o) alkyl groups substituted by at least one hydroxyl group, and -C (= 0) -R _{5 groups} , R5 representing H or an alkyl group comprising from 1 to 29, preferably from 1 to 21, carbon atoms, said alkyl group possibly being substituted by at least one hydroxyl group, said main hydrocarbon chain of each esterified branched alkane comprising 8 + 4x atoms of carbon, x being an integer ranging from 0 to 6, preferably ranging from 1 to 6.

According to one embodiment, the mixture of esterified or etherified branched alkane isomers according to the invention comprises at least two compounds of formula (I) as defined above.

According to one embodiment, the mixture of etherified branched alkane isomers according to the invention comprises at least two compounds of formula (I) as defined above, in which R is chosen from the group consisting of groups (Ci -C3o) alkyls, (C2-C3o) alkenyl groups, (hetero) arylalkyl groups and (Ci-C3o) alkyl groups substituted by at least one hydroxyl group.

According to one embodiment, the mixture of esterified branched alkane isomers according to the invention comprises at least two compounds of formula (II) as defined above.

According to one embodiment, the mixtures of the invention are such that all the compounds of formula (I) as defined above comprise 8 + 4x carbon atoms, x being as defined above and being identical for all the compounds of said mixture. The present invention also relates to a process for preparing a compound as defined above, corresponding in particular to one of formulas (I) or (II), or to the mixture as defined above, comprising a step d 'addition of a ROH compound, R being as defined above in formula (I), to at least one branched olefin isomer, each branched olefin being formed of a hydrocarbon chain comprising 8 + 4x carbon atoms , x being as defined above.

Thus, the process of the invention consists of an addition of a primary, secondary or tertiary alcohol (such as methanol, ethanol, n-butanol, furfurol or terpineol) or of a polyol (such as glycol , glycerol, sorbitol, erythritol or polyglycerols), on a branched olefin corresponding to an alkylating agent, to obtain an etherified compound, or by adding a carboxylic acid, on a branched olefin corresponding to an alkylating agent , to obtain an esterified compound.

According to one embodiment, the aforementioned addition step is carried out by acid catalysis.

Preferably, said addition step is carried out in the presence of an acid catalyst selected from Bronsted acids or Lewis acids.

The catalysts below can in particular be used:

- Bronsted acids such as: H ₂ SO ₄ , HF, Ar-SOsH, CH ₃ SO ₃ H or CF ₃ SO ₃ H;

- solid Bronsted acids such as sulfonic resins, zeolites or clays; and

- Lewis acids such as FeC, AICI3, ZnCh, salts of lanthanides or metal triflates, in particular iron triflate.

According to one embodiment, the addition step is carried out at a temperature between 20 ° C and 200 ° C, preferably between 50 ° C and 120 ° C.

According to one embodiment, the addition step is carried out for a period of between 1 h and 15 h, preferably between 4 h and 10 h.

Preferably, the ratio between the number of moles of ROFI compound and the number of moles of olefin of formula (I) or (II) is between 1 and 10, preferably between 1, 2 and 5.

Preferably, the ratio between the number of moles of catalyst and of olefin of formula (I) or (II) depends on the nature of the catalyst. Preferably, this ratio is between 0.0001 and 0.1, and preferably between 0.001 and 0.05. According to one embodiment of the process of the invention, the mixture of branched olefin isomers comprises at least two branched olefin isomers of the following formula (III):

in which R 1, R ₂ , R ₃ and R ₄ are as defined above in formula (I).

As mentioned above, in formula (III):

- two at most among the groups Ri, R ₂ , R ₃ and R ₄ are H,

- When one of the groups R ₃ and R ₄ or H or when the groups R ₃ and R ₄ are H, then the groups R 1 and R ₂ are (Ci-C ₃ o) alkyl groups.

According to one embodiment of the process of the invention, the mixture of branched olefin isomers comprises at least two branched olefin isomers of the following formula (III):

in which R 1, R ₂ , R ₃ and R ₄ are as defined above in formula (I).

As mentioned above, in formula (III):

- at most two of the groups Ri, R ₂ , R ₃ and R ₄ are H.

According to a preferred embodiment, in formula (III), one of the groups R ₃ or R ₄ contains a tert-butyl group. According to a preferred embodiment, in formula (III), one of the groups R ₃ or R ₄ is a tert-butyl group.

The process of the invention can use a branched olefin of formula (III) or a mixture of branched olefins of formula (III) comprising the same number of carbon atoms or a different number of carbon atoms, from preferably the same number of carbon atoms. According to one embodiment of the process of the invention, the mixture of branched olefin isomers comprises at least two branched olefin isomers of formula (III).

The olefins of formula (III) therefore correspond to one of the following formulas:

in which R'i, R'2, R ' ₃ and R'4 are (C1-C3o) alkyl groups. preferably

According to one embodiment, the olefins of formula (III) can comprise two hydrogen atoms, one corresponding to the group R 1 or R ₂ , and the other to the group R ₃ or R 4.

As mentioned above, the compounds of formula (II) are branched compounds comprising in total 8 + 4x carbon atoms with x ranging between 0 and 6, preferably between 1 and 6. The compounds of formula (II) are therefore branched compounds whose main chain comprises 8, 12, 16, 20, 24, 28 or 32 carbon atoms, and preferably 12, 16, 20, 24, 28 or 32 carbon atoms.

The mixture of branched olefin isomers according to the invention is a mixture comprising at least two olefins of formula (III). Preferably, the mixtures of the invention are such that all the compounds of formula (III) as defined above comprise 8 + 4x carbon atoms, x being as defined above and being identical for all the compounds of said mixture.

The branched olefins or mixture of branched olefin isomers according to the invention, in particular the main chain of which comprises n carbon atoms (where n = 8 + 4x = 16, 24 or 32), can be obtained by dimerization of a mixture of branched olefin isomers comprising n / 2 (ie 4 + 2x, x being an even number) carbon atoms.

According to one embodiment, the mixture of branched olefin isomers as defined above is obtained by dimerization of a mixture of branched olefin isomers comprising 4 + 2x carbon atoms, when x represents an even number , preferably obtained from bioresources.

Thus, 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.

The dimerization step can be carried out in the presence of a catalyst chosen from Bronsted acids in solution, for example H2SO4, H3PO4, HF; solid Bronsted acids, for example organic resins, clays, zeolites, H3PO4 on silica; Lewis acids, for example ZnCh, AICI3; organometallic compounds, for example Ni complexes, mixtures of Ni and Al complexes; ionic liquids, for example [BMIm] [N (CF ₃ S02) 2] / HN (CF ₃ SC> 2) 2; clays with lamellar structures such as Montmorillonite; organic resins such as Amberlysts, sulfonic resin; organometallic compounds such as for example [LNiCH ₂ FÎ ⁹ ] [AICl4] in which L = PR ¹⁰ , R ⁹ represents an alkyl, linear or branched, comprising 9 carbon atoms and R ¹⁰ represents a group - CH2-R ⁹ .

The dimerization step is preferably carried out at a temperature between 30 ° C and 250 ° C. In a particularly advantageous manner, the branched olefins comprising 8 and 12 carbon atoms are obtained from isobutene. Preferably, said isobutene is obtained from bioresources, in particular as described in application WO 2012/052427, for example from polysaccharides (sugars, starches, celluloses, etc.).

Particularly advantageously, the production of branched olefins by dimerization makes it possible to obtain branched olefins or a mixture of branched olefins free of n-4 and n + 4 olefins.

According to one embodiment, the mixture of branched olefin isomers is obtained by co-dimerization of at least two mixtures of branched olefin isomers comprising respectively m and p carbon atoms, m and p being whole numbers different equal to 4, 8, 12 or 16, and being such that m + p = 8 + 4x.

The co-dimerization step can also be followed by one or more purification steps, for example by distillation, for example to remove the olefins in n-4 and n + 4.

The olefins of the invention can also be obtained by metathesis of at least two mixtures of branched olefin isomers comprising respectively m and p carbon atoms, m + p being greater than n. The metathesis step can also be followed by one or more purification steps, for example by distillation, for example to remove the olefins in n-4 and n + 4.

Preferably, the branched olefins comprising m + p carbon atoms are obtained from bioresources and in particular from isobutene obtained according to the process described in application WO 2012/052427, WO2017085167 and WO 2018206262, for example from polysaccharides (sugars, starches, celluloses, etc.).

The present invention also relates to the use of a compound as defined above, corresponding to formula (I) or (II) above, or of the mixture as defined above, as a plasticizer, lubricant, surfactant or in a cosmetic composition. EXAMPLES

Example 1: Esterification of isooctene with acetic acid

In a reactor equipped with stirring and able to withstand the pressure, we introduce:

- 100 g of isooctene

- 150 g of acetic acid

- 1.5 g of triflic acid CF ₃ SO ₃ H

The mixture is heated at 80 ° C for 12 hours.

The triflic acid is cooled and then neutralized with a stoichiometric amount of bicarbonate to avoid hydrolysis.

The excess acetic acid is removed by distillation.

The residue is analyzed:

- Conversion of iosoctene: 100%

- Acetic ester yield: 90%

Example 2: Esterification of isododecene with gluconic acid

In a reactor equipped with stirring and able to withstand the pressure, we introduce

- 100 g of isododecene

- 120 g of gluconic acid

- 1.5 g of iron triflate

The mixture is heated at 80 ° C for 12 hours.

The unconverted gluconic acid is cooled and then neutralized with stirring with an aqueous sodium hydroxide solution so that the pH is between 6 and 9. Unconverted gluconic acid, in the form of sodium salt, and the iron triflate which are in the aqueous phase are removed by decantation.

The organic phase contains the formed isododecane gluconate and a small amount of unconverted isododecene.

This organic phase is analyzed:

- Conversion of isododecene: 95%

- Isododecane gluconate yield: 85%

Example 3: Addition of glycerol to isododecene

0.12 mol of glycerol, 0.24 mol of a mixture of isododecene and 1 g of H-Beta zeolite are introduced into a stainless steel PARR instrument type reactor of 100 mL. After purging the autoclave with argon. The system is placed under a pressure of 10 bar of argon, then heated to 130 ° C with stirring at 800 rpm. After 6 hours of heating, the reactor is cooled to 25 ° C then the reaction medium is diluted in 50 ml of ethanol and then filtered. The filtrate analyzed reveals a complete conversion of the glycerol towards the formation of mono and di- and trialkyl ether of glycerol, the dialkyl ether being predominant with a mono-di-tri- ratio (18-67-15).

The mono, di and tri alkyl glycerol ether distribution depends on the stoichiometry between olefin (or mixture of isomers) and the glycerol involved. The proportion of glycerol monoalkyl ether can be promoted with a higher glycerol / isododecene ratio.

Claims

1. Compound of formula (I) below:

in which :

- two at most among the groups Ri, R ₂ , R ₃ and R ₄ are H,

- one of the groups R ₃ or R ₄ comprises or is a tert-butyl group; - R is chosen from the group consisting of groups -C (= 0) -R ₅ , R ₅ representing H or an alkyl group comprising from 1 to 29 carbon atoms, said alkyl group possibly being substituted by at least one hydroxyl group, (Ci-C ₃ o) alkyl groups, (C ₂ -C ₃ o) alkenyl groups, (hetero) arylalkyl groups and (Ci-C ₃ o) alkyl groups substituted by at least one hydroxyl group.

2. Compound according to claim 1, corresponding to the following formula (II):

in which :

- Ri, R ₂ , R3 and R4 represent, independently of each other, H or a (Ci-C3o) alkyl group, the total sum of the number of carbon atoms of Ri, R ₂ , R3 and R4 being equal to 6 + 4x, x being an integer from 1 to 6, provided that:

- two at most among the groups Ri, R ₂ , R3 and R4 are H, and

- one of the groups R3 or R4 contains or is a tert-butyl group;

- R ₅ represents an alkyl group comprising from 1 to 21 carbon atoms, said alkyl group possibly being substituted by at least one hydroxyl group.

3. A compound according to claim 1 or 2, for which

- when one of the groups Ri or R ₂ is H or when the groups Ri and R ₂ are H, then the groups R3 and R4 are (Ci-C3o) alkyl groups, and

- When one of the groups R3 or R4 is H or when the groups R3 and R4 are H, then the groups Ri and R ₂ are (Ci-C3o) alkyl groups.

4. A mixture of esterified or etherified branched alkane isomers comprising at least two compounds of formula (I) according to any one of claims 1 to 3.

5. Mixture according to claim 4, in which all the compounds of formula (I) comprise 8 + 4x carbon atoms, x being as defined in claim 1 and being identical for all the compounds of said mixture.

6. A process for preparing a compound according to any one of claims 1 to 3 or the mixture according to claim 4 or 5, comprising a step of adding an ROH compound, R being as defined in claim 1. , on at least one branched olefin isomer, each branched olefin being formed of a hydrocarbon chain comprising 8 + 4x carbon atoms, x being as defined in claim 1.

7. Preparation process according to claim 6, wherein the addition step is carried out by acid catalysis.

8. Preparation process according to claim 6 or 7, in which the mixture of branched olefin isomers comprises at least two branched olefin isomers of the following formula (III):

wherein Ri, R ₂ , R ₃ and R ₄ are as defined in claim 1.

9. A method according to any one of claims 6 to 8, wherein the mixture of branched olefin isomers is obtained by dimerization of a mixture of branched olefin isomers comprising 4 + 2x carbon atoms, when x represents an even number, preferably obtained from bioresources.

10. A method according to any one of claims 6 to 8, wherein the mixture of branched olefin isomers is obtained by oligomerization of at least two mixtures of branched olefin isomers comprising respectively m and p carbon atoms. , m and p being different integers equal to 4, 8, 12 or 16, and being such that m + p = 8 + 4x.

11. Use of a compound according to any one of claims 1 to 3 or of the mixture according to claim 4 or 5, as a plasticizer, lubricant, surfactant or in a cosmetic composition.