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Fragrance Chemicals

Fragrance Chemicals

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Fragrance Chemicals

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  1. Fragrance Chemicals

  2. Chemical Types • Alcohols • Aldehydes & Ketones • Aliphatic & Aromatic Esters • Terpenes • Phenols • Nitriles • Lactones • Heterocyclics • Acids • Sulphur compounds

  3. Hydrocarbons Mild, Sweet, Warm Woody Spicy Caryphyllene Beta Farnesene

  4. Esters O II R-OH + R’COOH R-C-O-R’ Hydrolyze at high and low pH, acid product may precipitate

  5. OH Alcohols R-OH Aliphatic Aromatic

  6. Aldehydes & Ketones H C=O R Aldehyde Ketone R’ C=O R

  7. “Aldehydes” The so-called aldehydes C14, C16, and C18 are not really aldehydes. the confusion came from the original manufacturers to conceal their identity.

  8. Aldehyde C14, So-called O O Peach

  9. Aldehyde C16, So-called O O O Strawberry

  10. Aldehyde C18, So-called O O Coconut

  11. Terpenes Isoprene Units Joined Head To Tail (C5H8)n C I C=C-C=C

  12. CHO CHO OH OH Five Key Terpenes Isomerization Hydrogenation Oxidation Geraniol & Nerol OH Citronellol Linalool Citral Citronellal

  13. Nomenclature n Name Formula 2 Monoterpene C10H16 3 Sesquiterpene C15H24 4 Diterpene C20H32 6 Triterpene C30H48 8 Tetraterpene C40H64

  14. Acyclic Terpenes -Myrcene

  15. Monocyclic Terpenes Limonene

  16. Bicyclic Terpenes Pinene

  17. Sesquiterpene -Bisabolene

  18. Nitriles R-C=N Aliphatic C=N Aromatic

  19. Geranyl Nitrile N C Banned 2007!

  20. Substitution When a material is banned, must find alternative. For geranyl nitrile, citronellal nitrile (agrunitril) is good in formulas with low level, <2% Perfumery skill is needed for perfecting on a formula-by-formula basis

  21. Lactone A Cyclic Ester • or  Hydroxy Acid forms 5 or 6 member ring by intramolecular • esterfication RCHCH2CH2COO-Na+ I OH

  22. O Lactones Coumarin O

  23. Ionones O   iso- n-  N- or iso- refer to position of alkyl group ,, refer to position of double bond

  24. -Isomethylionone O

  25. Acids Acetic CH3COOH Propionic C2H5COOH Butyric C3H7COOH Alkali (NaOH) form salts which can be solid and water-soluble

  26. C((CH)3)3 C((CH)3)3 NO2 NO2 NO2 NO2 CH3 NO2 CH3 CH3 CH3 NO2 C=O I CH3 Nitromusks Musk Xylene Musk Ketone

  27. Polycyclic Musks O Galaxolide

  28. Leopold Ruzicka1887-1976 The Scientist

  29. "For his work on polymethylenes and higher terpenes" Ruzicka received the 1939 Nobel Prize in Chemistry Ruzicka was interested in the large ring ketones civetone and muscone, and showed that they had 17- and 15-membered carbon rings. This was highly novel work at the time, because Adolph von Bayer, a giant of 19th century chemistry had predicted that such rings would be strained and too unstable to exist.

  30. In his work on terpenes, Ruzicka made extensive use of the isoprene rule, first formulated by Otto Wallach in 1887 but largely ignored until Ruzicka recognized its general significance.

  31. Muskone

  32. Civetone O

  33. OH OMe Derivatives Phenol OMe OMe Anethole Anisole Estragole

  34. Reactions Phenols + NaOH Na salts NaSalt + O2 turns dark. All aromatics with phenolic group react with air, high pH, elevated temperature. Iron and copper will form highly colored complexes.

  35. Vanillin CHO OCH3 OH Phenol

  36. Sulphur Compounds SH S OH O 4-methyl-3-mercapto- 2-pentanone 3-mercapto-1-hexanol Oxford Chemicals

  37. SH Example 1-p-Menthene-8-Thiol

  38. Polar Diluents CH3CHCH2-O-CH2CHCH3 I I OH OH Dipropylene Glycol (DPG) CH3CHCH2OH I OH Propylene Glycol (PG)

  39. Nonpolar Diluents O II C-OCH2CH3 C-OCH2CH3 II O DEP Also Benzyl Benzoate, Dioctyl Adipate

  40. R – C C O n Solubilizers Usually nonionics-ethoxylates, propoxylates

  41. Chemical Reactions Helpful Reactions Part of the natural maturing process Harmful Reactions Occur in isolated perfume oils or in reaction with base environment

  42. Schiff Base Aldehyde + Amine COOCH3 H2N + CHO OH Methyl Anthranilate Hydroxy- Citronellal

  43. Example COOCH3 CH=N + H2O OH Aurantiol

  44. Storage Effects • Elevated Temperatures • UV Radiation • Moisture • Oxidation Accelerate change or deterioration

  45. Autooxidation CHO COOH Benzoic Acid Benzaldehyde

  46. Polymerization Aldehydes can Solidify OH I CH2CH-CHCHO CH2CHO 2 Phenylacetaldehyde

  47. Hemiacetals Aldehyde/Ketone + Alcohol O OH II I I C +- C- OH C O C Loose, reversible Aging of hydroalcoholics

  48. Acetals O 2CH2H5OH O O HO HO Hydroxy Citronellal Hydroxy Citronellal Demethy Acetal

  49. Ester Hydrolysis O O OH -OH Benzyl Alcohol Benzyl Acetate