Classifications

• • 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
• • 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

Definitions

• Subject of the invention is 4-methyl-2-pentanol crotonate, a process for its production whereby 4-methyl-2- pentanol is esterified with crotonic acid and the use of the crotonate for perfume compositions and as an odorant.
• This invention relates to the crotonic acid ester of 4-methyl-2-pentanol, to its preparation and to its application.
• the compound according to this invention can be obtained by esterification methods known per se, preferably by the direct esterification of crotonic acid with 4-methyl- 2-pentanol, the water of reaction formed preferably being removed azeotropically, in the presence of an acid catalyst, for example concentrated sulphuric acid or p-toluene sulphonic acid, and a hydrocarbon boiling at 80 to 150 C., preferably toluene or xylene, as entraining agents.
• an acid catalyst for example concentrated sulphuric acid or p-toluene sulphonic acid
• a hydrocarbon boiling at 80 to 150 C. preferably toluene or xylene
• the ester according to the invention is distinguished by desirable odoriferous properties and adds a valuable odorant to the perfume materials hitherto available for synthesizing fruit-like notes.
• odorants preferably used for the synthesis of fruitlike notes, such as iso-amyl acetate, hexyl acetate, ethyl acetate and other esters of lower fatty acids, readily bring to mind undesirable notions of bonbons or solvents or commercial products. For this reason they are not easy to handle in the composition of perfumes and have to be harmonically rounded off in terms of odor by skillfully combining several of these substances in order to restrict the occurrence of aesthetically unpleasant notes.
• 4-methyl-2-pentanol crotonate does not have any of these disadvantages. It has a very pleasant, pure fruit-like note reminiscent in particular of plum and apple preserves. It differs from conventional fruit-like odorants not only in its type of odor but also in the fact that it can be used more easily and more widely. Although distinct effects in the perfume composition can be obtained even with small quantities of the odorant, it can also be used in a high concentration in the composition or even without any other odorants for perfuming preparations by virtue of its aesthetically pleasing odor, without the aforementioned negative side etfects encountered in conventional fruity odorants.
• the compound according to the invention can be used for a very wide variety of applications. It is suitable for use in perfume compositions for numerous end products of the cosmetics, fine-perfumery, detergent and chemical specialities industries.
• compositions are further enriched by using 4-methyl-2-pentanol crotonate insofar as novel extremely harmonic odor accords can be obtained with this odorant, especially by combining it with flower and green odorants.
• EXAMPLE 1 The following formulation is given as an example of the preparation of a perfume with a plum-like odor which is a suitable fragrance for dishwashing detergents:
• a dishwashing detergent scented with this formulation can have the following composition for example:
• a skin cream perfumed with this composition can be prepared as follows for example:
• Phase A 50 g. of oleic acid decyl ester, 125 g. of glycerine monostearate (self-emulsifying), 50 g. of paraffinum per liquidum, 20 g. of cetaceum DAB 7, 1 g. of p-hydroxybenzoic acid propyl ester.
• Phase B 720 g. of distilled water, 1 g. of p-hydroxybenzoic acid methyl ester, 30 g. of sorbitol, 3 g. of perfume oil.
• Phase A and phase B are heated to 75 C., after which phase B is stirred into phase A, cooled with stirring to 40 C. and perfumed.
• EXAMPLE 3 The following formulation is given as an example of the preparation of a perfume with a lemon odor which is suitable for perfuming an insect spray:
• the fruit component is enhanced by the 4-methyl-2-pentanol crotonate, the odor is fuller and more pleasant.
• An insect spray. perfumed with this composition can be prepared as follows, for example:
• EXAMPLE 4 The following formulation is given as an example of the preparation of a lavender composition which is suitable for perfuming tissues:
• Difluorodichloromethane 12 The herb-like, lavandin oil note is sweetened by the 4-methyl-2-pentanol crotonate and displaced more towards the lavender type.
• Tissues perfumed with this composition can be produced by impregnating paper webbing with a solution which can have the following composition for example:
• reaction mixture is washed first with 2 litres of 10% soda solution to remove the acids and then with water until the reaction mixture reacts neutrally.

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)
• Fats And Perfumes (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=5767702

Family Applications (1)

Country Status (6)

Cited By (5)

Families Citing this family (2)

• 1970
  • 1970-04-10 DE DE19702017208 patent/DE2017208A1/de active Pending
  • 1970-09-21 US US00074228A patent/US3709929A/en not_active Expired - Lifetime
  • 1970-09-28 NL NL7014250A patent/NL7014250A/xx unknown
• 1971
  • 1971-03-26 CH CH446971A patent/CH550133A/de not_active IP Right Cessation
  • 1971-04-09 FR FR7112797A patent/FR2089509A5/fr not_active Expired
  • 1971-04-19 GB GB26162/71A patent/GB1279080A/en not_active Expired

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