Carbonyl Compounds, Methods for Preparing Same and Uses Thereof

Abstract

The present application relates to a compound of the following formula (I)

##STR00001## in which —R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represent independently of each other H or a (C.sub.1-C.sub.30) alkyl group, the total sum of the number of carbon atoms of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 being equal to 6+4x, x being a whole number of between 1 and 6, provided that: at most two of the groups R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H, R.sup.5 represents H, OR, or NR′R″ R, R′ and R″, identical or different, represent H, a (C1-C10) alkyl group, at least one of groups R.sup.1, R.sup.2, R.sup.3 or R.sup.4 comprises or is a tertiobutyl group. (I) the method for preparing same and the uses thereof as a plasticising lubricant, surfactant or in a cosmetic composition.

Claims

1-13. (canceled)

14. A compound of following formula (I): ##STR00012## wherein: R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently H or a (C.sub.1-C.sub.30) alkyl group, provided: the total sum of the number of carbon atoms of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is equal to 6+4x, wherein x is an integer of 1 to 6; at most two among R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are H; and at least one of groups R.sup.1, R.sup.2, R.sup.3, or R.sup.4 comprises or is a tert-butyl group; and R.sup.5 is H, OR, or NR′R″, wherein R, R′ and R″, the same or different, are H or a (C.sub.1-C.sub.10) alkyl group.

15. The compound according to claim 14, wherein R.sup.5 is H or OH.

16. The compound according to claim 14, wherein: x is 1, 4, or 6, or x is 2, 3, 4, 5, or 6; and R.sup.5 is OR or NR′R″.

17. A mixture of isomers of branched alkanes functionalised by a C=OR.sup.5 function, the mixture comprising a least two compounds of formula (I) according to claim 14.

18. The mixture according to claim 17, wherein all the compounds of formula (I), in addition to the C(O)R.sup.5 group, comprise 8+4x carbon atoms, wherein x the same for all the compounds of said mixture.

19. A method of preparing a compound according to claim 14, the method comprising a carbonylation step of at least one isomer of branched olefins, each branched olefin being formed of a hydrocarbon chain having 8+4x carbon atoms.

20. The method according to claim 19, wherein the carbonylation step is performed via organometallic catalysis.

21. The preparation method according to claim 19, wherein the mixture of isomers of branched olefins comprises at least two isomers of branched olefins of following formula (II): ##STR00013##

22. A method for preparing a mixture of claim 17, the method comprising a dimerizing a mixture of isomers of branched olefins having 4+2x carbon atoms, with x being an even number.

23. The method according to claim 22, wherein the mixture of isomers of branched olefins is obtained by oligomerization of at least two mixtures of isomers of branched olefins respectively having m and p carbon atoms, wherein m and p, differing, are integers of 4, 8, 12 or 16, and m+p=8+4x.

24. Isomers of branched olefins of the following formula (II): ##STR00014## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently H or a (C.sub.1-C.sub.30) alkyl group, provided: the total sum of the number of carbon atoms of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is equal to 6+4x, wherein x is an integer of 1 to 6; and at most two among R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are H; at least one of groups R.sup.1, R.sup.2, R.sup.3, or R.sup.4 comprises or is a tert-butyl group.

Description

EXAMPLES

Example 1: Preparation of Formula (I) Compounds of the Invention

[0088] ##STR00008##

[0089] After solubilizing 40 mg (0.156 mmol) of Rh(CO).sub.2(acac) and 466 mg (0.82 mmol) of TPP (triphenyl phosphine) in toluene (150 mL), the addition is made of isododecene (22 mmol). After transferring the solution to a stainless-steel reactor, the system was purged 3 times with argon. The reaction medium was then heated to 80° C. and placed under a pressure of 50 bar Syngas (CO/H2=1:1). The reaction medium was stirred at a speed of 800 rpm. After a heating time of 6 hours, the reactor was cooled to ambient temperature, degassed, and the reaction medium was hydrolysed with 75 mL of water. After extraction with ethyl acetate (3×50 mL), the organic phase was dried over Na.sub.2SO.sub.4 and concentrated under reduced pressure. The aldehydes were obtained in a mixture in a ratio of 43:56 (Branched/Linear) with a yield of 75%.

Example 2: Oxidation of the Compounds Derived from Example 1

[0090] ##STR00009##

[0091] A 300 mL PARR instrument reactor was charged with 15 g of 43:56 aldehyde mixture (B/L=5.5-dimethyl-3-neopentylhexanal) 6 mol % Ru/Al.sub.2O.sub.3 (5 wt. %), 40 mL of dodecane and 200 mL of water. After purging the system under argon, the reactor was placed under 4 bar oxygen pressure and left under agitation. After heating for 2 hours at 150° C., the reactor was cooled to 25° C. and the reaction medium was filtered. 50 mL of water were added after which the two phases were separated. The aqueous phase was extracted with ethyl acetate 2×40 mL. The combined organic phases were concentrated under reduced pressure to afford the corresponding acids with a good yield of 81%.

Example 3: Reduction of the Compounds Derived from Example 1

[0092] ##STR00010##

[0093] A 300 mL autoclave of PARR instrument type was charged with 10 g of 43:56 aldehyde mixture (B/L=5,5-dimethyl-3-neopentylhexanal) in 120 mL of cyclohexane and 200 mg of Raney Nickel. After purging the system with argon, a pressure of 10 bar hydrogen was set and the autoclave heated to 80° C., mechanical stirring was adjusted to 800 rpm. After a reaction time of 4 hours, the system was cooled to 25° C., the reaction medium was filtered to remove the catalyst and concentrated under reduced pressure to afford a mixture of alcohols with a yield of 92%.

Example 4: Dismutation of the Compounds Derived from Example 1

[0094] ##STR00011##

[0095] To 100 g of 43:56 aldehyde mixture (B/L=5,5-dimethyl-3-neopentylhexanal) placed in a reactor under perfect agitation, 5 g of calcium oxide were added and the whole heated to 80° C. for 8 hours. After return of the reactor to 25° C., 200 mL of diisopropyl ester or isooctane were added after which the reaction medium was filtered to separate the catalyst. The filtrate was concentrated under reduced pressure leading to the statistical mixture of expected esters with a yield of 76%.