Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0007—Aliphatic compounds
  • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
  • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/50—Perfumes

Definitions

• the present invention relates to the field of perfumery. It relates more particularly to the use of an aliphatic keto-ester of formula or ethyl 2-acetyl-4-methyl-4-pentenoate.
• Ethyl 2-acetyl-4-methyl-4-pentenoate is used to develop a fruity-floral, aromatic and natural, slightly herbaceous odor; odor that evokes an aspect of the chamomile decoction as well as the fruity character of the pineapple.
• the keto-ester of the invention can lend itself to the scent of various articles such as soaps, cosmetics, shampoos, air fresheners, fabric softeners or cationic liquid or solid detergents , anionic, nonionic or zwitterionic. It has been found that ethyl 2-acetyl-4-methyl-4-pentenoate has good stability even in relatively aggressive media as well as good substantivity on different fabrics, both natural and artificial.
• the proportions in which it can be used to produce the desired fragrance effects vary within a fairly wide range of values. Concentrations of the order of 1 or 2-5% by weight, relative to the weight of the composition in which it is incorporated, can be used when the compound of the invention is used as a shade. Such concentrations, or even lower, are perfectly suitable for perfuming articles such as cosmetics, creams or shampoos, soaps or detergents. These values, of course, should not be interpreted restrictively; from experience, those skilled in the art can indeed determine the appropriate proportion according to the desired effect or the nature of the co-ingredients in a given composition.
• the compound of the invention can be used as a single ingredient, but preferably it is used in admixture with perfuming co-ingredients and solvents customary in the art (by way of example, mention may be made for this purpose natural or synthetic compounds mentioned in the European patent application published under the number 0096243).
• the keto-ester of the invention is a chemical compound of known structure. It has in fact been described, as a synthesis intermediary, by TF Wood and aL [J. Org. Chem. 28, 2248 (1963)] in a study relating to the preparation of certain aromatic musks. Its odorous properties, however, have remained unknown to this day.
• ethyl 2-acetyl-4-methyl-4-pentenoate is obtained by an addition reaction, in basic medium, between ethyl acetoacetate and methallyl chloride according to the reaction scheme that here:
• the reaction is preferably carried out in a medium consisting of an aqueous, aqueous-alcoholic or alcoholic solvent, preferably in ethyl alcohol.
• aqueous, aqueous-alcoholic or alcoholic solvent preferably in ethyl alcohol.
• Other inert organic solvents such as acetone or an aromatic hydrocarbon, such as benzene, toluene or xylene, can also be used.
• an alkali metal alcoholate can be used, for example sodium ethylate, sodium carbonate, lithium or potassium carbonate or a hydroxide, such as potassium hydroxide.
• potassium carbonate is preferably used and the reaction is carried out in ethanol. Under these conditions, the operation is carried out at the boiling temperature of the reaction mixture, ie at approximately 75 ° C.
• the reaction temperature can be between about 50 and 110 ° C. It is at such temperatures that the reaction times are relatively short, while the formation of side products is reduced.
• the process for the preparation of ethyl 2-acetyl-4-methyl-4-pentenoate will be illustrated in detail in the examples which follow; also illustrated will be his use. In the said examples, the temperatures are indicated in degrees centigrade and the abbreviations have the usual meaning in the art.
• the crude product (740 g) is distilled under nitrogen on a filled column packed with stainless steel propellers using a distillation head with total reflux. 555.8 g of the desired keto ester having Eb are thus obtained. 115 ° / 2.66x10 3 Pa (yield by weight 107%, theor. 7596).
• a perfuming composition for shampoos was prepared by mixing the following ingredients (parts by weight):
• Two powdered detergent bases were prepared by mixing the following ingredients (parts by weight):.
• Ethyl 2-acetyl-4-methyl-4-pentenoate has been used to flavor various products, the nature of which is given in the table below. In the said table also appear the respective concentration values of the ester used in the finished product as well as the indication as to the stability of the odor obtained.

Landscapes

• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Detergent Compositions (AREA)
• Cosmetics (AREA)
• Fats And Perfumes (AREA)

Applications Claiming Priority (2)

Publications (3)

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ID=4285949

Family Applications (1)

Country Status (4)

Cited By (2)

Families Citing this family (3)

Family Cites Families (5)

• 1985
  • 1985-10-02 EP EP85112461A patent/EP0178532B1/de not_active Expired - Lifetime
  • 1985-10-02 DE DE8585112461T patent/DE3578082D1/de not_active Expired - Lifetime
  • 1985-10-04 US US06/784,125 patent/US4647407A/en not_active Expired - Lifetime
  • 1985-10-18 JP JP60231450A patent/JPS6197214A/ja active Granted

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