Check patentability & draft patents in minutes with Patsnap Eureka AI!

Recovery method for chiral amine resolution reagent

A technology for splitting reagents and chiral amines, which is applied in the field of recovery and application of chiral amine splitting reagents, can solve the problems of unreported chiral amine recovery and application, and achieves the advantages of reducing emissions, realizing recycling, and saving production costs. Effect

Active Publication Date: 2015-06-10
APPLE FLAVOR & FRAGRANCE GRP
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

How to realize the recycling of chiral amines in the process of preparing related chiral lactones has not yet been reported

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] recycling part

[0016] Dissolve 50.00 grams (1.25 moles) of sodium hydroxide in 500 milliliters of water in a 1000 milliliter three-necked flask, add 136.2 grams (0.80 moles) of racemic gamma-decalactone dropwise at 60°C, and Stirring was continued for 2 hours. After cooling to room temperature, 50% dilute sulfuric acid was added dropwise to adjust the pH value to 4.00-5.00. Extract and separate the organic layer, and extract twice with ethyl acetate. The organic layers were combined, and an appropriate amount of methanol was added, followed by 48.4 g (0.40 mol) of (S)-(-)-α-phenylethylamine. The solution was cooled at -15 to -30°C for 24 hours to obtain 68.70 g of light white crystals, optically active chiral ammonium salt A. The crystalline filtrate was concentrated to obtain about 150 g of residue, which was chiral ammonium salt B with low optical activity.

[0017] The two chiral ammonium salts A and B are dissolved in an appropriate amount of water, and 50% di...

Embodiment 2

[0026] recycling part

[0027] Dissolve 50.0 grams (1.25 moles) of sodium hydroxide in 500 milliliters of water in a 1000 milliliter three-necked flask, add 147.5 grams (0.8 moles) of racemic γ-undecalactone dropwise at 60°C, and Stirring was continued for 2 hours. After cooling to room temperature, dilute hydrochloric acid was added dropwise to adjust the pH to 5.0. Extract and separate the organic layer, and extract twice with ethyl acetate. Combine the organic layers, add an appropriate amount of methanol, and then add 48.4 (0.4 mol) (R)-(+)-α-phenylethylamine. The solution was cooled at -15 to -30°C for 17 hours to obtain 113.12 g of light white crystals, optically active chiral ammonium salt A. The crystalline filtrate was concentrated to obtain about 140 g of residue, which was chiral ammonium salt B with low optical activity.

[0028] The two chiral ammonium salts A and B are respectively dissolved in appropriate amount of water, and dilute hydrochloric acid is adde...

Embodiment 3

[0037] recycling part

[0038] Dissolve 50.00 grams (1.25 moles) of sodium hydroxide in 500 milliliters of water in a 1000 milliliter three-necked flask, add 158.65 grams (0.8 moles) of racemic γ-dodecanolide dropwise at 60°C, and Stirring was continued for 2 hours. After cooling to room temperature, dilute phosphoric acid was added dropwise to adjust the pH to 5.0. Extract and separate the organic layer, and extract twice with ethyl acetate. Combine the organic layers, add an appropriate amount of methanol, and then add 48.4 g (0.4 mol) of (S)-(-)-α-phenylethylamine. The solution was refrigerated at 10-0°C for 24 hours to obtain 98.93 g of light white crystals, optically active chiral ammonium salt A. The crystalline filtrate was concentrated to obtain about 130.00 g of residue, which was chiral ammonium salt B with low optical activity.

[0039] Dissolve the two chiral ammonium salts A and B in an appropriate amount of water, and add dilute phosphoric acid dropwise under...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a recovery method for a chiral amine resolution reagent. Recovery of the chiral amine resolution reagent is realized by alkalization, extraction, drying and distillation of an aqueous layer during a process for obtaining a chiral lactone by hydrochlorination of hydroxy acid ammonium, in full consideration of a process for preparing optical active gamma-lactone spice by using a chemical resolution method, so that production cost for the optical active gamma-lactone spice prepared by the chemical resolution method can be greatly saved, recycling use of resources is fully realized, discharge of nitrogen-containing waste is reduced, and feasibility for industrial production of the chiral gamma-lactone spice is provided. The chiral amine reagent effectively recycled by reduced pressure distillation is (R)-(+)-alpha-phenyl-ethylamine and (S)-(-)-alpha-phenyl-ethylamine. The optical purity of the recycled chiral amine is not changed, a recovery rate of the recycled chiral amine is 50.00%-75.00%; and the recycled chiral amine can be used in resolution reactions, without influencing resolution results.

Description

technical field [0001] The present invention relates to the recovery method of chiral amine resolution reagent, especially chiral amine reagent is (R)-(+)-α-phenylethylamine and (S)-(-)-α-phenylethylamine Amine recovery method. Background technique [0002] γ-lactone is rich in milky and fruity aroma, has the characteristics of long-lasting fragrance, mellow aroma and aroma-enhancing effect. It is extremely rich in fruits, beverages, and daily foods, so it is an important aroma raw material. They are widely used in the preparation of food flavors and daily chemical flavors, and are one of the products in high demand among spices. Since γ-lactone contains chiral carbon, it has the dextrorotary form of R and the levorotatory form of S. The γ-lactones obtained by general chemical synthesis methods are all racemates. [0003] Because gamma-lactone and butyl-lactone in natural products in nature are mainly chiral pure, the aroma of chiral lactone is stronger and purer than tha...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/27C07C209/86
Inventor 冯黎茅富燕马继红
Owner APPLE FLAVOR & FRAGRANCE GRP
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com