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Method for synthesizing allyl phenoxyacetate

A synthesis method and technology of pineapple ether, applied in the field of organic synthesis, can solve the problems of equipment corrosion, large amount of waste water, and difficult treatment, and achieve the effects of no serious corrosion, improved selectivity, and improved conversion rate.

Inactive Publication Date: 2019-01-11
HUAIAN WAN BANG SPICE IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this method mainly include: 1. the amount of waste water is large, and allyl alcohol used is a highly toxic drug, which can be miscible with water, so the treatment is difficult and the pollution is serious; 2. the equipment is severely corroded; 3. the product yield is not too high, generally About 90%

Method used

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  • Method for synthesizing allyl phenoxyacetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Drop into phenol 94g (1mol), caustic soda 48g (1.2mol), water 195g in the flask, heat up, control 80 ℃~90 ℃ and stir reaction 2 hours, normal pressure sloughs off 100g water, cools down to 50 ℃, drops into toluene 500g, Raise the temperature, and use toluene to carry out the water to obtain a suspension of sodium phenate in toluene.

[0027] 116.5 g (1 mol) of sodium chloroacetate was dropped into the toluene suspension of the above-mentioned sodium phenate, and the temperature was raised to reflux for 4 hours to obtain a toluene suspension of sodium phenoxyacetate.

[0028] Add 114.75 g (1.5 mol) of allyl chloride and 4.7 g of benzyltriethylammonium chloride into the toluene suspension of sodium phenoxyacetate, and heat up and reflux for 6-10 hours until the content of allyl chloride does not change when analyzed by GC After finishing the reaction, the temperature was lowered, and the catalyst and the sodium chloride produced by the reaction were filtered off to obtain...

Embodiment 2

[0031] Put 94g (1mol) of phenol, 40g (1mol) of caustic soda, and 120g of water into the flask, heat up, control 80°C to 90°C to stir and react for 1 hour, remove 60g of water under normal pressure, cool to 50°C, add 470g of toluene, and heat up , Use toluene to bring the water to the end to obtain a suspension of sodium phenate in toluene.

[0032] 139.8 g (1.2 mol) of sodium chloroacetate was dropped into the toluene suspension of the above-mentioned sodium phenate, and the temperature was raised to reflux for 3 hours to obtain a toluene suspension of sodium phenoxyacetate.

[0033] Add 133.88 g (1.75 mol) of allyl chloride and 2.82 g of benzyltriethylammonium bromide into the toluene suspension of sodium phenoxyacetate, and heat up and reflux for 6-10 hours until the content of allyl chloride does not change when analyzed by GC After finishing the reaction, the temperature was lowered, and the catalyst and the sodium chloride produced by the reaction were filtered off to obt...

Embodiment 3

[0036] Drop into phenol 94g (1mol), caustic soda 60g (1.5mol), water 300g in the flask, heat up, control 80 ℃~90 ℃ stirring reaction 3 hours, normal pressure sloughs off 180g water, cools down to 50 ℃, drops into toluene 517g, Raise the temperature, and use toluene to carry out the water to obtain a suspension of sodium phenate in toluene.

[0037] 174.8 g (1.5 mol) of sodium chloroacetate was dropped into the toluene suspension of the above-mentioned sodium phenate, and the temperature was raised to reflux for 5 hours to obtain a toluene suspension of sodium phenoxyacetate.

[0038] Add 153 g (2 mol) of allyl chloride and 7.52 g of benzyltriethylammonium chloride into the toluene suspension of sodium phenoxyacetate, heat up and reflux for 6-10 hours, and end the reaction when the content of allyl chloride does not change after GC analysis , lower the temperature, filter off the catalyst and the sodium chloride produced by the reaction, and obtain the crude product containing ...

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Abstract

The invention discloses a method for synthesizing allyl phenoxyacetate. The method comprises: putting phenol, caustic soda flakes and water into a flask in a proportion, carrying out stirring at 80-90DEG C for a reaction for 1-3h, removing a part of water under normal pressure, thoroughly removing water through toluene to obtain a toluene suspension of sodium phenolate, adding sodium chloroacetate into the toluene suspension of sodium phenolate, carrying out heating reflux for a reaction for 3-5h to obtain a toluene suspension of sodium phenoxyacetate, adding chloropropene and a phase transfer catalyst into the toluene suspension of sodium phenoxyacetate, carrying out heating reflux for a reaction for 6-10h, carrying out cooling, filtering to remove the catalyst and the product sodium chloride so that a crude product containing chloropropene and a toluene solvent is obtained, recovering excess chloropropene and toluene solvent from the crude product under normal pressure and carryingout rectification under vacuum to obtain an allyl phenoxyacetate finished product. Compared with the conventional method, the method provided by the invention has a high product yield, is not seriously corroded, produces the minimal amount of waste water and has environmentally friendly processes.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for preparing perfume products, in particular to a method for synthesizing pineapple ether. Background technique [0002] Pineapple ether, the chemical name is allyl phenoxyacetate. Appearance is oily liquid with sweet, fruity and medicinal aroma. Molecular formula is C 11 h 12 o 2 , the molecular weight is 192.22, the normal pressure boiling point is 265 ℃, insoluble in water, soluble in organic solvents such as alcohol. Pineapple ether is a fruity fragrance with pure aroma. It is widely used in daily chemical flavors and food flavors. It can produce good effects in food flavors with a small amount. It is mainly used in pineapple and honey flavors. [0003] The traditional production process of pineapple ether is generally formed by esterification of phenoxyacetic acid and allyl alcohol under strong acid catalysis. The disadvantages of this method mainly include: 1....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/712C07C67/11C07C59/125C07C51/367C07C39/235C07C37/66
CPCC07C37/66C07C51/367C07C67/11C07C39/235C07C59/125C07C69/712
Inventor 陈文抗谢雨杨丽
Owner HUAIAN WAN BANG SPICE IND CO LTD
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