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
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/0084—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing more than six atoms
• • 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
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
  • C11D3/2093—Esters; Carbonates
• • 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 invention relates to the use of macrocyclic lactones as Fragrances.
• 15-pentadecanolide of the formula is a component of angelica root oil and has a delicate musky smell and the ability to act as a fixative. It has therefore been intensively concerned with the production of such macrocyclic lactones.
• Another method involves adding hydrogen peroxide or alkyl peroxide 13-Oxabicyclo [10.4.0] hexadec-1 (12) en in the presence of sulfuric acid. Thermal or UV-initiated cleavage of the resulting 12-hydroperoxy-13-oxabicyclo [10.4.0] hexadecane (III) leads to 15-pentadecanolide (I) and to 15-pentadecenolides, which too I can be hydrogenated (DE-AS 2 026 056).
• the 12-oxo-15-pentadecanolide reduced in the presence of Raney nickel to 12-hydroxy-15-pentadecanolide, this then for example in the presence of phosphoric acid to the corresponding 15-Pentadec-11- and -12-enolids dehydrated and these products in the presence hydrogenated a nickel catalyst to I.
• Lactones II and thus III can be produced in different ways. This is how they are produced by a metathesis reaction on nickel catalysts (p. Inoue et al; Nippon Kagaku Kaishi (1985), 425), by Claisen rearrangement (D.W. Knight et al., J. Chem. Soc., Perkin Trans. I (1986), 161; R. L. Funk et al. Tetrahedron 42 (1986), 2831) and thermal or photochemical fragmentation of peroxides (DE-OS 20 26 056) or other derivatives (DE-OS 41 15 182).
• lactones II and III are particularly advantageous if this is done easily prepared 12-hydroperoxy-13-oxabicyclo [10.3.0] pentadecane or 12-hydroperoxy-14-methyl-oxabicyclo [10.30] pentadecane with the addition of copper (II) - and Iron (II) salts based on one of S.L. Schreiber et al. (J. Amer. Chem. Soc. 102 (1980), 6163) fragmented for the synthesis of recifeiolide.
• fragrances listed can be used individually or in a mixture because of their excellent olfactory properties in a wide range of Fragrance compositions are used. It has been shown that through skillful mixing of these compounds with other ingredients can be reinforced. Another important characteristic of these connections is their suitability for "rounding" when mixed with other ingredients and to cause "intensity of the initial smell" of fragrance compositions.
• “Rounding” refers to a property of a fragrance composition that is expresses that when combining the individual components a harmonious Odor impression arises and none of the individual fragrance components from the Bouquet of composition stands out.
• the term "intensity of the initial smell” refers to the first impression that a fragrance composition gives, ie on the characterization of the initial smell.
• Lactones II and III allow the formulation of new and interesting compositions. Amounts of 8-15% by weight Lactone, based on composition, are preferred.
• compositions can be used to perfume Cosmetics such as creams, lotions, aerosols, toilet soaps, technical articles, Detergents, fabric softeners, disinfectants and textile treatment agents to serve.
• perfume Cosmetics such as creams, lotions, aerosols, toilet soaps, technical articles, Detergents, fabric softeners, disinfectants and textile treatment agents to serve.
• a solution of 114 g of copper (II) acetate in 2,250 g of water is placed in a 6 liter three-necked flask and a suspension of 150 g of IV in 500 g (MTBE) is added with stirring.
• a solution of 172 g of iron (II) sulfate in 760 g of water is then metered in at RT within 15 min, the mixture is stirred for a further 30 min after the addition and the pH is adjusted to 1 with 550 g of 2N hydrochloric acid x 1,500 g MTBE extracted, the org.
• Phase washed neutral with bicarbonate and distilled, after which 107 g of cyclotetradecenolide IIa are present as a mixture of isomers.
• this sweet oriental composition receives an enhanced base note through a musky impression, which can best be characterized with nitro musk.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Pyrane Compounds (AREA)
• Fats And Perfumes (AREA)
• Cosmetics (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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Publications (2)

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Cited By (8)

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• 1997
  • 1997-03-05 DE DE19708924A patent/DE19708924A1/de not_active Withdrawn
• 1998
  • 1998-02-20 EP EP98102945A patent/EP0862911A3/fr not_active Withdrawn
  • 1998-02-27 JP JP10062018A patent/JPH10251684A/ja active Pending
  • 1998-03-02 US US09/033,336 patent/US6008185A/en not_active Expired - Fee Related

Non-Patent Citations (1)

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