Novel decenal mixtures and their use in perfume compositions
a technology of decenal mixture and perfume composition, which is applied in the direction of perfume formulations, detergent compounding agents, biocide, etc., can solve the problems of complex and expensive procedures, unpredictable commercial scale production of fragrance molecules, and synthesis of dec-8-enal, etc., to enhance, improve or modify the fragrance of perfumes, colognes, etc.
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example i
[0037]
Preparation of 6,7,8-Decene-1-ol (Mixture of 6-Decene-1-ol, 7-Decene-1-ol, and 8-Decene-1-ol)
[0038]A reaction flask was charged with toluene (500 g), 9-decenol (Rosalva) (500 g), and rhodium trichloride (RhCl3) (1.25 g). Water (2 g) was added. The reaction mixture was heated with stirring to about 65-80° C. The reaction mixture was heated for about 20 hours till a steady state of 6,7,8-decene-1-ol isomers was reached. The reaction mixture was then cooled. The organic layer was transferred to a rush-over distillation flask and Primol oil (15 g) was added. Toluene was then removed at atmospheric pressure. The crude product was distilled to afford 6,7,8-decene-1-ol (463 g) having a boiling point of 98° C. at a pressure of 3.2 mmHg The broken line in the above formula of 6,7,8-decene-1-ol represents one double bond and two single bonds.
[0039]6,7,8-Decene-1ol was described as having aldehydic, green, floral, rosy, and waxy notes.
example ii
[0040]
[0041]Preparation of Dec-6-enal (Formulas II), Dec-7-enal (Formulas III), And Dec-8-enal (Formulas IV)
[0042]A reaction flask was charged with Primol oil (100 g) and Pricat catalyst (25 g, commercially available at Johnson Matthey Catalysts). The reaction mixture was heated with stirring to about 250-290° C. The mixture of 6,7,8-decene-1ol (238 g, synthesized as above in EXAMPLE I) was then added slowly while the temperature was maintained at about 290-295° C. The reaction was vented properly during the reaction. After the reaction was completed, the reaction mixture was transferred into a distillation flask and further fractional distillation afforded the mixture of Formulas II, III, and IV (141 g) having a boiling point of 80° C. at a pressure of 6.8-7.8mmHg It was surprisingly found that the double bond position along the carbon chain could be specified and only careful control of the reaction conditions in both steps (EXAMPLEs I and II) would lead to the desired decenal iso...
example iii
Preparation And Evaluation of Dec-6-enal, Dec-7-enal, And Dec-8-enal Mixture of Different Ratios
[0049]The decenal mixture (synthesized as above in EXAMPLE II) was further carefully distilled through a GOODLOE column with high theoretical plates to afford a series of decenal mixture of different mixing ratios.
[0050]The following specific mixture samples were evaluated for odor properties:
Decenal Mixture (% by weight)SampleDec-6-enal Dec-7-enalDec-8-enalOdor Profile134651Off notes, too lactonic223365Off notes, too fruity and toococonut3274330Dirty off notes, solventy, and phenolic4202555Strong, clean, aldehydic, and crispy5222058Strong, clean, aldehydic,crispy, and slightly green693853Strong, clean, aldehydic, crispy slightly green, bright,and melon7224335Strong, clean, aldehydic, crispy, green, ambrette seed-like, and slightly sweet8123147Powerful, very clean, aldehydic, crispy, green, ambrette seed-like, sweet, bright, and melon9193340Strong, clean, aldehydic,crispy, slightly green...
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