Method for producing cyclic esters

A technology of macrocyclic compounds and general formulas, which is applied in the field of preparation of cyclic esters, and can solve problems affecting catalyst activity, etc.

Inactive Publication Date: 2018-02-13
BASF AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] The choice of solvent used as the bottoms diluent is also critical, as this in some cases co-distills during the distillation of the monomeric cyclization product and can thus entrain catalyst at the bottom and / or in other ways. way to adversely affect the activity of the catalyst

Method used

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  • Method for producing cyclic esters
  • Method for producing cyclic esters
  • Method for producing cyclic esters

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0343] Example II.1: Cyclization of butyl 15-hydroxypentadecanoate to 15-cyclopentadecanolide

[0344] At room temperature, 2.48 grams of titanium (IV) isopropoxide (0.01 mol, 0.10 equivalents) were added to 80 g 2000 (PEG 2000). The mixture was heated to 140 to 150°C and the resulting isopropanol was stripped from the solution with nitrogen over about 3 hours. The mixture was then cooled to 120 °C and 36.0 g (0.11 mol) of 15-hydroxypentadecanoic acid butyl ester melting at 70 °C were added, and the mixture was evacuated to 5 mbar and heated to 250 °C over about 20 minutes. ℃. At 250° C., metering of ethylene glycol (approximately 25 ml / h) was started, whereby a mixture of cyclopentadecanolactone and ethylene glycol was distilled off. After about 6 hours, the distillate was monophasic and after phase separation, 25.5 g of cyclopentadecanolide were obtained with a content of 96.8% by weight, which corresponds to a yield of 89.7%. A further 4.3% of product was obtained in t...

Embodiment II

[0345] Example II.2: Cyclization of methyl 15-hydroxypentadecanoate to 15-cyclopentadecanolide

[0346] At room temperature, 2.84 grams of titanium (IV) isopropoxide (0.01 mol, 0.1 equivalents) was added to 80 g E600S. The mixture was heated to 140 to 145°C and the resulting isopropanol was stripped from the solution with nitrogen over about 3 hours. The mixture was then cooled to 120 °C and 28.7 g (0.1 mol) of 15-hydroxypentadecanoic acid methyl ester melting at 70 °C were added and the mixture was evacuated to 5 mbar and heated to 250 °C over about 20 minutes. ℃. It is also optionally cooled to room temperature and the hydroxyester is added at room temperature, and the catalyst can also be stored. At 250° C., metering of ethylene glycol (approximately 28 ml / h) was started, whereby a mixture of cyclopentadecanolactone and ethylene glycol was distilled off. After about 5 hours, the distillate was monophasic and after phase separation, 22.7 g of cyclopentadecanolide were o...

Embodiment III

[0358] Example III.1a: Isolation and preparation of (ω-1)- and ω-hydroxymethyl oleate from fermented sophorolipids

[0359] 160.8 g of sophorolipid aqueous solution was extracted three times with 400 ml of acetate at room temperature. The combined acetate phases were concentrated to yield 68.6 g of residue. The residue was dissolved in 250 g of methanol and 6.9 g of concentrated sulfuric acid were added at room temperature. The batch was then heated at reflux for 10 hours. The reaction solution was cooled and 13.8 g of potassium carbonate was added, and the mixture was after-stirred at room temperature for 30 minutes. The suspension was filtered and the filtrate was concentrated by evaporation. The final weight was 81.6 grams. The product was placed in 400 ml of ethyl acetate and 400 ml of water and extracted. After phase separation, the aqueous phase is extracted with a further 400 ml of acetate. The ethyl acetate phases were combined and concentrated by evaporation to ...

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Abstract

The invention relates to a method for producing cyclic esters of general formula (I.a) or (I.b) in the presence of at least one high-boiling metal alkoxide catalyst. The invention further relates to the stereoisomers of 18-methyl-1-oxacyclooctadec-10-en-2-one and to the use thereof as an odorous substance and / or flavoring substance, to compositions that contain at least one of the stereoisomers of18-methyl-1-oxacyclooctadec-10-en-2-one and additionally a carrier material, to fragrance compositions and / or to fragrant-substance materials that contain at least one of these compounds, and to a method for giving an odor or flavor to or changing an odor or flavor of compositions by adding at least one of the mentioned compounds to said compositions.

Description

[0001] The present invention relates to a process for the preparation of cyclic esters in the presence of at least one high boiling metal alkoxide catalyst. The present invention also relates to stereoisomers of 18-methyl-1-oxacyclooctadec-10-en-2-one and their use as essences and / or fragrances, comprising 18-methyl-1-oxa Compositions of at least one stereoisomer of cyclooctadec-10-en-2-one and additionally comprising carrier materials, fragrance compositions and / or fragrance materials comprising at least one of these compounds, and by incorporating at least one The method by which specified compounds are added to these compositions to impart or alter the composition's odor or taste. Background of the invention [0002] Macrocyclic compounds with musky-type odors have long been valuable aroma chemicals in the fragrance industry. These compounds include macrocyclic ketones (such as cyclopentadecanone or (Z)-9-cyclohexadecen-1-one (zibetone)) and macrocyclic esters or diester...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/00
CPCC07D313/00
Inventor W·塞格尔K·沙因-阿尔布雷奇特R·派尔泽
Owner BASF AG
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