PROCESS FOR PRODUCING PARA-EUGENOL AND/OR ORTHO-EUGENOL
The present invention relates to a process for manufacturing para-eugenol and/or ortho-eugenol, comprising a step (i) of deallylation of at least one compound of formula (I): in which R 1 and R 2 are different, and are chosen from the group consisting of hydrogen and an allyl group (—CH 2 —CH═CH 2 )
1 . A process for manufacturing para-eugenol and/or ortho-eugenol, comprising a step (i) of deallylation of at least one compound of formula (I):
in which R 1 and R 2 are different, and are chosen from the group consisting of hydrogen and an allyl group (—CH 2 —CH═CH 2 ), characterized in that step (i) is performed in the presence of a solvent or a solvent/water mixture.
2 . The process for manufacturing para-eugenol and/or ortho-eugenol as claimed in claim 1 , comprising a step of deallylation of a mixture comprising at least one compound of formula (Ia) and one compound of formula (Ib)
3 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , in which step (i) also comprises the formation of guaiacol by deallylation of a compound of formula (III):
4 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that step (i) is performed in the presence of a catalyst.
5 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that step (i) is performed in the presence of Pd/C or Pt/C.
6 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that the content of catalyst during step (i) is between 0.1% and 30% by weight relative to the total amount of compound of formula (I) and optionally of compound of formula (II).
7 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that step (i) is performed in the presence of a water/solvent mixture.
8 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that step (i) is performed in the presence of a base which has a pKa in water of greater than or equal to 8.
9 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that the base is selected from the group consisting of KOH, NaOH, K 2 CO 3 , Na 2 CO 3 , Ba(OH) 2 , Ca(OH) 2 , CsOH, LiOH, a compound of formula NR 3 OH, and combinations thereof, in which R is a linear or branched alkyl chain comprising from 1 to 6 carbon atoms.
10 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that step (i) is performed at a temperature of greater than or equal to 20° C.
11 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , characterized in that the compound of formula (I) is derived from a process for the allylation of guaiacol in the presence of an allyl halide or an allyl alcohol.
12 . The process for manufacturing para-eugenol and/or ortho-eugenol of claim 1 , comprising at least one step, after step (i), of separating the guaiacol, para-eugenol and/or ortho-eugenol.
13 . A process for manufacturing para-eugenol and/or ortho-eugenol, comprising:
a step of allylation of guaiacol in the presence of an allyl halide,
a step (i) of deallylation of at least one compound of formula (I) as defined in claim 1 ,
a step of separating the guaiacol, para-eugenol and/or ortho-eugenol.