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 Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organcleptic utilities therefor

Details
Inventors: Wiener, Charles; Pittet, Alan O.;
Assignee: International Flavors & Fragrances Inc. (New York, NY)
Primary Examiner: Millin; V.
Assistant Examiner:
Attorney, Agent or Firm: Liberman; Arthur L.

Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities therefor, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in the absence of any other reagents except inert solvent.

DETAILED DESCRIPTION Our invention is directed to the production of "natural" benzaldehyde and/or "natural" acetaldehyde taken alone or in admixture with "natural" cinnamaldehyde according to a reaction where "natural" cinnamaldehyde is subject to a "retro-aldol" reaction, thusly: ##STR9## The cinnamaldehyde reactant may occur in either the "cis" form having the structure: ##STR10## and/or the "trans" form having the structure: ##STR11## The cinnamaldehyde may be in recovered form from natural sources as by distillation or extraction or the cinnamaldehyde may exist in its natural state immediately prior to the reaction, thusly: (i) Oil of Cinnamon Ceylon; (ii) Ceylon Cinnamon Bark (Cinnamomum zeylanicum Nees ex Blume (fam.
Lauraceae)); (iii) The Bark of Saigon Cinnamon (Cinnamomum loureirii Nees (fam.
Lauraceae); (iv) The Bark of Cassia cinnamon (ex Cinnamomum cassia (Nees)) Nees ex Blume (fam.
Lauraceae); (v) The Bark of Saigon cinnamon; (vi) Oil of Cinnamon Bark Ceylon; (vii) "Quills" from Ceylon cinnamon (including "fines", "Barcelona" and "Hamburg"); (viii) Ceylon cinnamon quillings and featherings; (ix) Ceylon cinnamon chips; (x) Ceylon cinnamon bark oil; (xi) Oil of cinnamon Seychelles; (xii) Oil of cinnamon Madagascar; (xiii) Leaves of Cassia; (xiv) Cassia Bark (Cassia lignes) in ground or powdered form; (xv) Oil of Cassia.
Thus, the cinnamaldehyde source may be treated with a base such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium carbonate, lithium bicarbonate, magnesium hydroxide, calcium hydroxide, calcium carbonate, proline having the structure: ##STR12## choline having the structure: ##STR13## or a natural choline source such as natural lecithin having the structure: ##STR14## in the presence of base (wherein the residues: ##STR15## represent palmitoyl, stearoyl, oleyl, linoleyl, linolenyl and C.
sub.
20 -C.
sub.
22 acid residues) [examples of naturally occurring lecithin are soybean lecithin (reference: "Soybeans, Volume II, (Interscience Publishing Company, New York, 1951), pages 593-647 and natural phosphatide lecithin] whereby a "retro-aldol" reaction takes place, thusly: ##STR16## A requirement of our invention is that no other reagents be present which would cause the reaction to give rise to a composition containing benzaldehyde or acetaldehyde which cannot be described as "natural"



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