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4-ethyl-octene-2/3-nitrile as a fragrance

A fragrance and fragrance technology, applied in the field of changing and/or strengthening specific fragrance notes, and can solve the problems of strong changes in sensory properties, affecting human tissue tolerance, etc.

Active Publication Date: 2019-12-06
SYMRISE GMBH & CO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] - In general, even small changes in the structural configuration of known fragrances can cause strong changes in the organoleptic properties and affect the tolerance of human tissues

Method used

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  • 4-ethyl-octene-2/3-nitrile as a fragrance
  • 4-ethyl-octene-2/3-nitrile as a fragrance
  • 4-ethyl-octene-2/3-nitrile as a fragrance

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0126] Example 1: Preparation of 4-ethyl-octene-2-carbonitrile / 4-ethyl-octene-3-carbonitrile

[0127] 254 g of 2-ethylhexanal, 38 g of ammonium acetate and 46 g of acetic acid were supplied to 520 g of toluene in a 1000 ml stirrer with a water separator. Subsequently, 189 g of cyanoacetic acid were added in parts at room temperature while stirring. Thereafter, it was refluxed in a water separator for 14 hours and washed with 10% sulfuric acid, 5% sodium hydroxide or water, respectively, after cooling. The organic phase was confined and the crude product (280 g) was fractionated under vacuum on a 40 cm Vigreux column.

[0128] Yield: 190g (63.9% of theoretical value), boiling point: 80°C to 85°C / 0.8mbar GC evaluation (20m DB-WAX, inner diameter 0.18μm / 60-9-220°C temperature programmed evaporator) product from 4 One isomer composition: 4.5% (E / Z) 4-ethyl-octene-2-carbonitrile and 95.5% (E / Z) 4-ethyl-octene-3-carbonitrile.

[0129] (E / Z)4-Ethyl-octene-2-carbonitrile

[0130]...

Embodiment 1a

[0135] Example 1a: Preparation of 4-ethyl-octene-2-carbonitrile / 4-ethyl-octene-3-carbonitrile

[0136]254 g of 2-ethylhexanal and 189 g of cyanoacetic acid were introduced into 500 ml of cyclohexane in a 1000 ml stirrer with water separator and dropping funnel. Thereafter, 65 g of 3-picoline were added under stirring and boiling conditions. Subsequently, it was refluxed in a water trap for 26 hours and washed with 10% sulfuric acid, 5% sodium hydroxide or water, respectively, after cooling. The organic phase was bound and the crude product (250 g) was obtained. The crude product consisted of 4 isomers: 16.5% (E / Z) 4-ethyl-octene-2-carbonitrile and 63.9% (E / Z) 4-ethyl-octene-3-carbonitrile.

[0137] The crude product was fractionated on a canned-column in vacuo.

[0138] Product yield: 37.5 g (E / Z) 4-ethyl-octene-2-carbonitrile (95.4%)

[0139] Boiling point: 75°C-80°C / 0.8 mbar

[0140] GC analysis (20m DB-WAX, inner diameter 0.18μm / 60-9-220℃ programmed temperature evapo...

example 2

[0141] Example 2: Perfume Composition (Fragrance Composition)

[0142]

[0143]

[0144] According to the perfumer's opinion, the perfume composition becomes drier, powdery, smooth transition by adding 0.5% by weight of a compound of formula (Ia) or (Ib) or a mixture consisting of (Ia) or (Ib) Harmonious, where pronounced iris violet and rose notes are added and intensified woody and floral aspects. Compositions or uses according to the invention give the compositions individuality and combine different odor elements. Example 3: Perfume Composition (Fragrance Composition)

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Abstract

The invention primarily relates to the use of 4-ethyl-octene-2-nitrile and / or 4-ethyl-octene-3-nitrile as a fragrance. The invention also relates to novel fragrance compositions comprising 4-ethyl-octene-2 / 3-nitrile, to perfumed articles comprising 4-ethyl-octene-2 / 3-nitrile and to various methods for conveying, modifying and / or intensifying specific fragrance notes.

Description

technical field [0001] The present invention mainly relates to the use of 4-ethyl-octene-2-carbonitrile and / or 4-ethyl-octene-3-carbonitrile, ie compounds of formula (I) as described herein, as fragrances. The present invention furthermore relates to novel fragrance compositions comprising 4-ethyl-octene-2 / 3-carbonitrile, to perfumed articles comprising 4-ethyl-octene-2 / 3-carbonitrile, and to imparting, changing and / or various ways of intensifying specific notes. [0002] Further aspects and preferred embodiments of the invention emerge from the ensuing embodiments, the appended examples and especially the appended claims. Background technique [0003] While a large number of fragrances already exist, there continues to be a general need for new fragrances in the perfume industry. Thus, for example, there is a need for fragrances which are able to generate (in fragrance compositions) other interesting notes besides the main fragrance type and which, through their new or un...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C11B9/00C11D3/50C07C255/07
CPCC07C255/07C11B9/0023C11D3/50
Inventor 贝恩德·霍尔舍托比亚斯·瓦格纳
Owner SYMRISE GMBH & CO KG
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