Process for preparation of cinnamate sunscreen agents

C - Chemistry – Metallurgy – 07 – C

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Details

C07C 69/734 (2006.01) C07C 67/343 (2006.01)

Patent

CA 2202756

This invention relates to an improved process for the manufacture of cinnamate compounds, particularly sunscreen agents, useful in cosmetic skin and hair care formulations. The process comprises: (a) dissolving a water insoluble C1 to C4 alkoxy benzaldehyde and a C1 to C4 alkyl acetate in a common hydrocarbon solvent; (b) reacting the resulting solution in the presence of a strong alkali metal-containing base under mild conditions to form a mixture containing the corresponding C1 to C4 alkyl C1 to C4 alkoxy cinnamate, the alkali metal salt of the enol corresponding to the C1 to C4 alkyl C1 to C4 alkoxy cinnamate, the alkali metal salt of a C1 to C4 alkoxycinnamic acid, and a C1 to C4 alkanol; (c) acidifying the resulting mixture with from about 0.5 to about 1 mole of a strong polybasic acid per mole of base to release acetic acid, to convert the alkali metal salt of the C1 to C4 alkoxycinnamic acid to the corresponding C1 to C4 alkoxycinnamic acid and to form an alcohol suspension of an alkali metal salt of said strong polybasic acid; (d) esterifying said acetic acid with a C1 to C4 alkanol and stripping the resulting acetic acid ester from the mixture; (e) reacting the remaining C1 to C4 alkyl C1 to C4 alkoxycinnamate and C1 to C4 alkoxycinnamic acid with a C5 to C14 alkanol in the presence of said strong polybasic acid alkali metal salt suspension at a temperature of from about 60~ to about 130 ~C; and (f) recovering the C5 to C14 alkyl C1 to C4 alkoxy cinnamate as a product of the process.

La présente invention concerne un procédé amélioré pour fabriquer des composés à base de cinnamates, en particulier des écrans anti-solaires, utiles dans des formulations cosmétiques de soin de la peau et des cheveux. Le procédé consiste à: (a) dissoudre un alcoxy benzaldéhyde en C¿1?-C¿4? insoluble dans l'eau et un alkyl acétate en C¿1?-C¿4? dans un solvant hydrocarburé commun; (b) faire réagir la solution obtenue en présence d'une base forte contenant un métal alcalin, dans des conditions modérées, pour former un mélange contenant l'alkyl C¿1?-C¿4? alcoxy C¿1?-C¿4? cinnamate correspondant, le sel de métal alcalin de l'énol correspondant à l'alkyl C¿1?-C¿4? alcoxy C¿1?-C¿4? cinnamate, le sel de métal alcalin d'un acide alkoxycinnamique en C¿1?-C¿4?, et un alcanol en C¿1?-C¿4?; (c) acidifier le mélange obtenu avec environ 0,5 à environ 1 mole d'un acide polybasique fort par mole de base pour libérer l'acide acétique, transformer le sel de métal alcalin de l'acide alkoxycinnamique en C¿1?-C¿4? en l'acide alkoxycinnamique en C¿1?-C¿4? correspondant et former une suspension alcoolique d'un sel de métal alcalin dudit acide polybasique fort; (d) estérifier ledit acide acétique avec un alcanol C¿1?-C¿4? et séparer du mélange l'ester de l'acide acétique formé; (e) faire réagir l'alkyl C¿1?-C¿4? alcoxycinnamate C¿1?-C¿4? restant et l'acide alcoxycinnamique C¿1?-C¿4? avec un alcanol C¿5?-C¿14? en présence de la suspension de sel de métal alcalin dudit acide polybasique fort, à une température comprise entre environ 60~ et environ 130~; et (f) récupérer l'alkyl C¿5?-C¿14? alcoxy C¿1?-C¿4? cinnamate, en tant que produit obtenu par ce procédé.

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