Method for synthesizing 2-pentylidene cyclopentanone using morpholine as catalyst

A technology of pentylidene cyclopentanone and cyclopentanone, which is applied in the field of synthesizing 2-pentylidene cyclopentanone with morpholine as a catalyst, can solve the problems of increased safety risks, complex process, increased energy consumption, etc., and achieve comprehensive cost Low, simple process flow, conducive to the effect of rectification and fractionation

Inactive Publication Date: 2017-01-04
浙江裕昌慎香料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Complex process and many equipment
Using toluene as a solvent increases safety risks in the production process, toluene recovery increases energy consumption, and invalid catalysts involve hazardous solid waste disposal

Method used

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  • Method for synthesizing 2-pentylidene cyclopentanone using morpholine as catalyst
  • Method for synthesizing 2-pentylidene cyclopentanone using morpholine as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Put 420g (5.00mol) of cyclopentanone and 84g (0.97mol) of morpholine into a 1-liter three-necked flask, raise the temperature to 80°C, add 215g of n-valeraldehyde (2.50mol) dropwise, add dropwise in 8 times, and add dropwise 1 / After 8 n-valeraldehyde, 1 / 8 glacial acetic acid was added dropwise, and 115 (1.92 mol) g of acetic acid was added dropwise 8 times for a total of 8 hours. The addition of n-valeraldehyde and acetic acid was completed, and the reaction was carried out at a constant temperature for 45 minutes. After standing still for 30 minutes, the crude product of acetylmorpholine in the lower layer was separated, washed with 127 g of water, and the aqueous phase in the lower layer was separated to obtain the crude product of 2-pentylidene cyclopentanone.

[0019] The crude acetylmorpholine was distilled under reduced pressure and deacidified, and the fraction at 94-97°C / 550Pa was collected to obtain 115.1g of acetylmorpholine finished product, with a GC conten...

Embodiment 2

[0022] Put 300g (3.57mol) of cyclopentanone and 90g (1.03mol) of morpholine into a 1-liter three-necked flask, raise the temperature to 60°C, add 307g (3.57mol) of n-valeraldehyde dropwise, add dropwise in 6 times, and add dropwise 1 / After 6 doses of n-valeraldehyde, 1 / 6 glacial acetic acid was added dropwise, the amount of acetic acid added was 62.1 g (1.03 mol) g in total, and the adding time was 6 hours. The addition of n-valeraldehyde and acetic acid was completed, and the reaction was carried out at a constant temperature for 60 minutes. After standing still for 30 minutes, the crude product of acetylmorpholine in the lower layer was separated. Add 121 g of water for washing, and remove the lower aqueous phase to obtain the crude product of 2-pentylidene cyclopentanone.

[0023] The crude acetylmorpholine was distilled under reduced pressure and deacidified, and the fraction at 94-97°C / 550Pa was collected to obtain 112.5g of acetylmorpholine finished product, with a GC ...

Embodiment 3

[0026] Put 704g (8.38mol) of cyclopentanone and 66g (0.76mol) of morpholine into a 2-liter three-necked flask, raise the temperature to 100°C, add 616g of n-valeraldehyde (7.16mol) dropwise, add dropwise in 10 times, and add dropwise 1 / After 10 n-valeraldehyde, add 1 / 10 glacial acetic acid dropwise, and add 68.3 (1.14 mol) g of acetic acid dropwise for 10 times, for a total of 10 hours. The addition of n-valeraldehyde and acetic acid was completed, and the reaction was carried out at a constant temperature for 30 minutes. After standing still for 30 minutes, the crude product of acetylmorpholine in the lower layer was separated, washed with 264 g of water, and the aqueous phase in the lower layer was separated to obtain the crude product of 2-pentylidene cyclopentanone.

[0027] The crude acetylmorpholine was distilled under reduced pressure and deacidified, and the fraction at 94-97°C / 550Pa was collected to obtain 88.7g of acetylmorpholine finished product, with a GC content...

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Abstract

The invention discloses a method for synthesizing 2-pentylidene cyclopentanone using morpholine as a catalyst. The method comprises the steps that cyclopentanone and morpholine are mixed at a weight ratio of 1:0.1-0.3, then n-valeraldehyde is added dropwise at a reaction temperature of 60 DEG C-100 DEG C, wherein the molar ratio of n-valeraldehyde and cyclopentanone is 1:0.5-1.0, and n-valeraldehyde is added dropwise by 6-10 times, the total dropping time is 6-10 hours, when dropping addition of n-valeraldehyde is paused, acetic acid is added dropwise into the reactants by 6-10 times, wherein the molar ratio of acetic acid and morpholine is 1:0.5-1; after the dropping addition of all the materials are completed, the reaction is continued for 0.5-1 hour at a constant temperature, and still standing is carried out to separate N-ethylmorpholine crude product; the N- ethylmorpholine crude product is washed with water to separate aqueous phase, thus 2-pentylidene cyclopentanone crude product is obtained; the N-ethylmorpholine crude product is subjected to decompression dehydration to obtain N-ethylmorpholine finished product, and the 2-pentylidene cyclopentanone crude product is subjected to decompression to recycle cyclopentanone, then 2-pentylidene cyclopentanone finished product is obtained. According to the method, the distillation time is short, energy consumption is low, and 2-pentylidene cyclopentanone finished product completely meets the quality indicators.

Description

technical field [0001] The invention relates to the technical field of fine chemical products, in particular to a method for synthesizing 2-pentylidene cyclopentanone by using morpholine as a catalyst. Background technique [0002] 2-Pentylidene cyclopentanone is an intermediate for the synthesis of butyl-decalactone, which is an important food flavoring, with strong milky, coconut and fruity aromas, and is the main body of creamy flavors Spices are widely used in fructose, soft drinks, margarine, baked food, condiments and other food industries, and the market demand is large. [0003] Acetylmorpholine is a very important pesticide and pharmaceutical intermediate, which is used to synthesize various pesticides and pharmaceutical products such as fungicides dimethomorph and flumorph. [0004] In the industrial reaction of preparing 2-pentylidene cyclopentanone by condensation of cyclopentanone and n-valeraldehyde at the present stage, the commonly used catalyst is sodium hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/647C07C45/74
CPCC07C45/74C07C49/647
Inventor 朱晓晖何志斌
Owner 浙江裕昌慎香料有限公司
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