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Method for preparing bio-based 2-phenylethanol

A phenylethanol, bio-based technology, applied in the field of preparation of bio-based 2-phenylethanol, can solve the problems of large environmental pollution, difficulty in concentration and enrichment, unsuitable for industrial production, etc., and achieve the effect of simplifying the operation process

Active Publication Date: 2019-09-06
WANHUA CHEM GRP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The biosynthetic 2-phenylethanol has an isotopic composition similar to that of natural extraction products, and the aroma quality also meets the requirements of high-end applications. However, the common disadvantages of the fermentation method are: the concentration of the product in the fermentation liquid is very low, and it is difficult to concentrate and enrich, and The cost of wastewater treatment is high, which affects the overall cost
The disadvantage of this scheme is that sodium borohydride, sodium periodate or chromium reagents, etc. are used in the multi-step conversion process, or the raw materials are expensive or pollute the environment, so they are not suitable for industrial production.

Method used

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  • Method for preparing bio-based 2-phenylethanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Decarboxylation operation:

[0049] In a 500mL three-neck flask, dissolve 49.56g of L-phenylalanine (0.3mol) into 200mL of cyclohexanol, add 2.88g (0.03mol) of cyclohexenone, stir evenly, then raise the temperature to 140°C, and continue heating for 12h , GC tracking until the conversion of raw materials is complete, cooling down. Underpressure distillation removes solvent cyclohexanol (solvent has no residue), obtains yellow oily liquid, and nuclear magnetic detection product structure is determined to be phenethylamine ( figure 1 ), crude product yield 98%.

[0050] Alkaline hydrolysis operation:

[0051] After re-dissolving the above liquid with 200 mL ethylene glycol diethyl ether, add 40.4 g (0.303 mol) of NaOH aqueous solution (30 wt %), heat to 220 ° C, and sample GC after 5 h to analyze the complete transformation of the intermediate. After cooling down, first add 300 mL of water to wash, and then extract with 2×200 mL of ethyl acetate. After the organic phas...

Embodiment 2

[0053] Decarboxylation operation:

[0054] In a 0.5L pressure-resistant reactor, dissolve 33.04g of racemic phenylalanine (0.2mol) in 150mL of n-butanol, add 0.64g (0.007mol) of cyclohexenone, and fill the reactor with N 2 to 0.3Mpa, stir evenly, then raise the temperature to 120°C, continue heating for 24 hours, and basically stop the conversion after GC tracking the conversion rate of the raw material is 86.5%. After cooling down to stop the reaction, the reaction solution was transferred to vacuum distillation to remove the solvent n-butanol (5% solvent residue), and the crude product yield was 82%.

[0055] Alkaline hydrolysis operation:

[0056] The above-mentioned system after removal of the solvent was directly dissolved with 150 mL of glycerin (glycerol), and 27.2 mL (0.204 mol) of NaOH aqueous solution (30 wt %) was added, heated to 200 ° C, and after 10 hours, the system was sampled by GC to analyze that there was no phenylethylamine residue in the system. After co...

Embodiment 3

[0059] Decarboxylation operation:

[0060] In a 250mL glass bottle, dissolve 16.52g of D-phenylalanine (0.1mol) into 150mL of cyclohexanol, add 0.24g (0.0025mol) of cyclohexenone, stir well, then raise the temperature to 160°C, and continue heating for 6h , GC tracked complete conversion of raw materials. After the temperature was lowered to stop the reaction, the reaction solution was transferred to vacuum distillation to remove the solvent (2% solvent remained), and the crude product yield was 95%.

[0061] Alkaline hydrolysis operation:

[0062] The above solvent-removed system was directly dissolved in 150 mL of ethylene glycol diethyl ether, 23.5 mL (0.105 mol) of KOH aqueous solution (25 wt%) was added, and heated to 250 ° C. After 3 hours, a sample was taken by GC to analyze that there was no phenylethylamine residue in the system. After cooling down, first dilute with 300mL methyl ethyl ketone and 300mL water, separate the organic phase, and remove the methyl ethyl k...

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Abstract

The invention discloses a method for preparing bio-based 2-phenylethanol. Phenylalanine used as raw material undergoes a decarboxylation reaction to obtain a key intermediate phenethylamine, and the intermediate is subjected to an alkali hydrolysis reaction to obtain 2-phenylethanol. The method of the invention adopts a high-efficiency synthesis process and the cheap and easily available raw material to prepare the bio-based 2-phenylethanol only through two steps of reaction, so the conversion process is concise, and the method has a good industrial amplification prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a preparation method of bio-based 2-phenylethanol, in particular to a preparation method of bio-based 2-phenylethanol using phenylalanine as a raw material. Background technique [0002] 2-Phenylethyl alcohol is an alcohol with a soft rose fragrance, which exists in many flowers and plants. It can be used in combination with other spices to create a variety of fragrance types such as clove, hyacinth, and lily of the valley. It is widely used in daily chemicals and food and beverages. In addition, 2-phenylethanol is a highly effective fungicide and is also used in the pharmaceutical industry. [0003] At present, there are two types of 2-phenylethanol products on the market: natural extraction and synthesis. [0004] Because its content in plants is very low, its output is very small, its price is high, and its natural extracts are far from meeting the needs of consumers. Therefo...

Claims

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Application Information

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IPC IPC(8): C07C33/22C07C29/00C07C211/27C07C209/68
CPCC07C29/00C07C209/68C07C211/27C07C33/22
Inventor 牟通王漭赵晶李俊平王静胡展黎源
Owner WANHUA CHEM GRP
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