Process for the synthesis of compounds which absorb ultraviolet radiation in flow conditions and formulations comprising same
OwnerElie Abou KHALIL, Renan CARIOU +3inventors
InventorsElie Abou KHALIL, Renan CARIOU, Shawn PARISIEN-COLLETTE, Julie CHANTEAU, Sophie LANGIS-BARSETTI
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Abstract
The present invention generally relates to a chemical process under flow conditions for manufacturing compounds which absorb ultraviolet (UV) radiation and protect biological materials as well as non-biological materials from damaging exposure to UV radiation. The present invention further includes formulations and compositions comprising such compounds for use in absorbing UV radiation, as well as methods for protecting biological materials as well as non-biological materials from damaging exposure to UV radiation.
Claims37
A method of producing an ultraviolet radiation absorbing compound in flow conditions, the method comprising the steps of:
- a. providing a source of dimedone;
- b. providing a source of IPA;
- c. forming a reaction mixture by adding portion wise NBS to form a white slurry;
- d. stirring the white slurry;
- e. forming a reaction mixture by adding pyridine and adding portion wise cysteine ethyl ester HCl while maintaining an internal temperature below 30° C.;
- f. heating the mixture at 40° C. until the reaction mixture is red;
- and
- g. crystalizing the reaction mixture to form the ultraviolet radiation absorbing compound.
A method of producing an ultraviolet radiation absorbing compound in flow conditions, the method comprising the steps of:
- a. providing a source of dimedone, NBS, MeCN and distilled water into a first mixture;
- b. forming a homogeneous solution of the first mixture;
- c. providing a source of L-cysteine ethyl ester hydrochloride, pyridine, MeCN and distilled water into a second mixture;
- d. eluting the first and second mixtures into a final mixture;
- e. removing the solvent under reduced pressure;
- and
- f. forming crystals by concentrating the final mixture.
A method of producing an ultraviolet radiation absorbing compound in flow conditions, the method comprising the steps of:
- a. providing a source of dimedone, N-Bromosuccinimidel and MeCN into a first mixture under inert atmosphere;
- b. adding 2,6-lutidine and L-cysteine ethyl ester hydrochloride;
- c. stirring the first mixture;
- d. adding dropwise phosphoryl chloride;
- e. adding dropwise a solution comprising EK-0c-HCl, N,N-diisopropylethylamine and MeCN;
- f. stirring the first mixture;
- g. obtaining saponification using a 20% solution of NaOH in water;
- h. acidifying the first mixture with acetic acid to a pH between 4 and 5;
- and
- i. filtering the first mixture.
A method of producing an ultraviolet radiation absorbing compound in flow conditions, the method comprising the steps of:
- a. combining dimedone, glycine ethyl ester hydrochloride and pyridine in acetonitrile to form a suspension;
- b. heating the suspension;
- c. stirring the suspension;
- d. removing the acetonitrile under vacuum to form a viscous liquid;
- e. diluting the viscous liquid in CH2Cl2;
- f. extracting with water and brine;
- g. drying with MgSO4;
- h. evaporating the remaining acetonitrile;
- i. crystalizing the ultraviolet radiation absorbing compound in acetonitrile.
Dependencies are inferred from the claim text.