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Synthesis method of delta-dodecalactone

A synthesis method and technology of laurolactone, applied in the field of synthesis of delta-dodecolactone, can solve the problems of difficult industrialization, low yield, long steps, etc., and achieve reduction of cardiovascular disease, energy consumption, operation easy effect

Active Publication Date: 2013-04-17
HUAIAN WAN BANG SPICE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are currently three main synthetic routes for δ-laurolactone: one is to react cyclohexanedione with n-hexane bromide, then oxidize ring-opening, reduction and cyclization to obtain δ-laurolactone. The synthesis process of this method More loaded down with trivial details, productive rate is lower; The 2nd is to carry out Dieckman condensation with diethyl adipate, then react with bromo-n-heptane in acetone with anhydrous potassium carbonate, get δ-dodecanolactone through decarboxylation and oxidation, The steps of this method are relatively long, the yield is not high, and it is difficult to industrialize; the third is to use cyclopentanone and n-heptanal as raw materials, through aldol condensation, catalytic hydrogenation stepwise reaction to obtain 2-heptylcyclopentanone, and then use Baeyer- Villiger rearrangement reaction to obtain δ-laurolactone, this method has more steps

Method used

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  • Synthesis method of delta-dodecalactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Synthesis of 2-heptylcyclopentanone

[0021] Add 1780g of 1.20% sodium hydroxide solution and 50.0g of Pd / C (50% water) catalyst into a 5L reactor, N 2 Replace three times, raise the temperature to 90 ℃, pass hydrogen and keep the pressure at 3.5MPa, add dropwise a mixture of 861.4g (10.24mol) cyclopentanone and 1216.9g (10.66mol) n-heptanal, dropwise add in 4 hours, continue to keep warm after dropwise addition Pressure holding reaction 0.5h, release pressure, N 2 Replaced three times, filtered after cooling down to 60°C, recovered the catalyst and used mechanically, separated, and distilled the oil layer to recover the crude product after cyclopentanone was rectified to obtain 1570 g of 2-heptylcyclopentanone, with a content of 95% by GC analysis.

[0022] (2) Synthesis of δ-Lauryl Lactone

[0023] Add 1500g of toluene to the three-necked flask as a solvent, then add 1570g of crude 2-heptylcyclopentanone, and slowly add 3734g of 20% peracetic acid dropwise under...

Embodiment 2

[0025] (1) Synthesis of 2-heptylcyclopentanone

[0026] Add 2897g of 5.0% potassium hydroxide solution and 70.0g of Pd / C (50% water) catalyst into a 5L reactor, N 2 Substitute three times, raise the temperature to 50°C, pass hydrogen and keep the pressure at 2.0MPa, add dropwise a mixture of 861.4g (10.24mol) cyclopentanone and 586.9g (5.14mol) n-heptanal, dropwise add in 2 hours, and continue to keep warm after the dropwise addition Hold the pressure for 15 minutes, release the pressure, N 2 Replaced three times, filtered after cooling down to 60°C, recovered the catalyst and used it mechanically, separated, and distilled the oil layer to recover the crude product after cyclopentanone was rectified to obtain 675 g of 2-heptylcyclopentanone with a content of 95% by GC analysis.

[0027] (2) Synthesis of δ-Lauryl Lactone

[0028] Add 1350.0g of toluene to the three-necked flask as a solvent, then add 675g of crude 2-heptylcyclopentanone, and slowly add 272.6g of 50.8% hydroge...

Embodiment 3

[0030] (1) Synthesis of 2-heptylcyclopentanone

[0031] Add 1600g of 0.5% lithium hydroxide solution and 3.2g of Pd / C (50% water) catalyst into a 5L reactor, N 2 Substitute three times, raise the temperature to 100°C, pass hydrogen and keep the pressure at 5.0MPa, add dropwise a mixture of 861.4g (10.24mol) cyclopentanone and 2338.4g (20.48mol) n-heptanal, dropwise add in 5 hours, and continue to keep warm after the dropwise addition Reaction under pressure for 3h, release pressure, N 2 Replaced three times, filtered after cooling down to 60°C, recovered the catalyst and used mechanically, separated, and distilled the oil layer to recover the crude product after cyclopentanone was rectified to obtain 1413g of 2-heptylcyclopentanone, the content of GC analysis was 95.5%.

[0032] (2) Synthesis of δ-Lauryl Lactone

[0033] Add 70.7g of xylene to the three-necked flask as a solvent, then add 1413g of crude 2-heptylcyclopentanone, and slowly add 4420g of 20% peracetic acid dropw...

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Abstract

The invention discloses a synthesis method of delta-dodecalactone. The synthesis method of the delta-dodecalactone comprises the following steps of: firstly, under a pressure and temperature preserving condition, uniformly mixing cyclopentanone and n-heptaldehyde, and adding a mixture dropwise into an alkaline solution containing hydrogenation catalyst; secondly, performing aldol condensation and catalytic hydrogenation simultaneously, and synthesizing a 2-heptyl cyclopentanone intermediate by a one-pot method; and finally, synthesizing the delta-dodecalactone through oxidation and ring expansion. The synthesis method is easy, simple and convenient in operation and few in steps; by the synthesis method, the product yield is 3-4% higher than that of aldol condensation, catalytic hydrogenation and oxidation in different steps; and only two-step distillation is required, so that energy consumption is lowered and the synthesis method is applicable to industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for synthesizing δ-laurolactone. Background technique [0002] The product of the present invention, δ-dodecalactone, has another name called 5-hydroxydodecalactone, with a CAS number of 713-95-1, a molecular formula of C12H22O2, and an English name of δ-Dodecalactone. It has a strong fat aroma of fresh fruit. As a new lactone fragrance, it is widely used in the preparation of strong floral fragrances such as aldehyde fragrance fragrances, gardenia, and tuberose. In addition, since lactone is the main component of natural butter flavor, and natural animal butter contains a lot of fat, excessive introduction can easily cause cardiovascular disease. Therefore, add butter flavor to vegetable oil as margarine instead of natural cream, and δ-laurolactone is the main component of cream flavor. Therefore, the synthesis of δ-laurolactone is of great sign...

Claims

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Application Information

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IPC IPC(8): C07D309/30
Inventor 华建军刘晓涛张健安利民万猛续文文
Owner HUAIAN WAN BANG SPICE IND CO LTD
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