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

Process for manufacture of high purity d-(-)-n,n-diethyl-2-(alpha-naphthoxy) propionamide

一种二乙基丙酰胺、二甲基甲酰胺的技术，应用在制备高纯度D--N领域，能够解决繁琐、大量溶剂、成本高昂等问题

Active Publication Date: 2010-03-24
UNITED PHOSPHORUS LTD
View PDF5 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The steps of these resolution methods are complex and cumbersome, and the resolution reagents used are expensive
These resolution methods also require large amounts of solvent, resulting in high cost

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

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process for manufacture of high purity d-(-)-n,n-diethyl-2-(alpha-naphthoxy) propionamide
  • Process for manufacture of high purity d-(-)-n,n-diethyl-2-(alpha-naphthoxy) propionamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] This embodiment will illustrate the method of the present invention step by step.

[0073] Step I: Preparation of (L)-(+)-2-chloropropionyl chloride from (L)-(-)-2-chloropropionic acid.

[0074] (L)-(-)-2-Chloropropionic acid (108.5 g, 98% chiral purity, 1.0 mole) was placed in a three-neck round bottom kettle, and dimethylformamide (5 ml ). The temperature of the reactant was raised to 55°C, and thionyl chloride (178.5 g, 98% purity, 1.5 mole) was added slowly, and the reaction temperature was maintained at 55°C-57°C during the addition.

[0075] The reaction was monitored by gas chromatography using a DB-5 column. The reaction was complete within 7 hours. During this process, the HCl and SO produced 2 The gas is absorbed with a scrubber containing dilute sodium hydroxide solution. After the reaction is completed, HCl and SO in the scrubber 2 Absorption of gas ceases. Using a 30-cm fractionating column to distill (L)-(+)-2-chloropropionyl chloride liquid under a...

Embodiment II

[0089] Purification of the highly pure D-(-)-N,N-diethyl-2-(α-naphthyloxy)propionamide obtained at the end of step III to a higher purity product with higher chemical and chiral purity .

[0090] This example describes the purification of the high purity product obtained in Example I.

[0091] To the brown solid material obtained at the end of step III of Example I was added 600.0 g of a mixture of isopropanol:water (70:30 v / v) and heated to 60°C-64°C under continuous stirring. Continue heating and stirring until the high-purity product is completely dissolved. Stirring was continued at this temperature for 45 minutes. The product was first cooled to room temperature, then continued to cool to 10°C-12°C and maintained at this temperature for 3-4 hours. The crystalline solid was filtered off, rinsed with cold hexane, and the crystalline solid was placed under vacuum for 3 hours. The higher purity product (690 g) was obtained at the end of Step IV as a crystalline off-white ...

Embodiment III

[0094] Step I and step II are the same as embodiment I.

[0095] Step III: Preparation of D-(-)-N,N diethyl-2-(α-naphthyloxy)propionamide.

[0096] α-Naphthol (1230 g, 8.45 moles, 99% purity) and 1446 g (8.37 moles) of the amide obtained in step II of Example I in toluene (2000 g) were charged into a 3 liter round bottom kettle. The mixture was stirred, and aqueous sodium hydroxide solution (1534 g, 18.41 moles, 48%) was added dropwise to the reactant at 55-57°C.

[0097] After the addition was complete, the reaction was heated to reflux at about 95°C. As reflux begins, sodium chloride begins to separate out. Continue to reflux for 6-7 hours until the α-naphthol content is less than 1% according to the GC area, the reaction is complete.

[0098] The reaction mixture was cooled to 50°C, at which temperature 1400 ml of water were added. The reactants were stirred at this temperature for 45 minutes, and the aqueous phase was separated, which was lighter in color than the orga...

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

According to one aspect of the present invention there is provided a substantially high purity D-(-)-N,N-diethyl-2-(alpha-naphthoxy)propionamide and a process for the manufacture of substantially higher purity D-(-)-N,N-diethyl-2-(alpha-naphthoxy) propionamide having chemical purity near about or above 95%, and chiral purity near about or more than 97%. According to another aspect of the inventionis to provide an agrochemical compositions containing highly pure optically active D-(-)-N,N-diethyl-2- (alpha-naphthoxy)propionamide.

Description

technical field [0001] The present invention relates to the method for preparing high-purity D-(-)-N, N-diethyl-2-(alpha-naphthyloxy)propionamide (herbicide), especially by L-2-halopropionic acid or Preparation of (s)-(-)-2-halopropionic acid. The present invention also provides agrochemical compositions containing optically active D-(-)-N,N-diethyl-2-(α-naphthyloxy)propionamide in high purity. Background technique [0002] N,N-diethyl-2-(α-naphthyloxy)propionamide is known as napropamide, the racemic mixture of which is usually sold under the trade name "napropamide". It is used for pre-emergence control of annual narrow-leaved and broad-leaved weeds in many crops and plantations. [0003] The propionamide group of napropamide has a hydrogen atom, a methyl group, a naphthyloxy moiety and a formamide group on the second carbon atom, thereby forming a chiral center. The molecule [Scheme I] can thus exist as two chiral stereoisomers: the D or (R), and the L or (S)-isomer. ...

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 Applications(China)
IPC IPC(8): A01N37/18C07C233/00C07C235/00
CPCC07C231/12C07C235/20C07C231/02A01N37/18C07C235/06C07C233/05
Inventor 拉吉尼坎塔·杰得夫·什罗夫拉吉尼坎塔·维克拉姆·什罗夫普拉首塔姆·娜仁扎·卡瑞姆贝卡
Owner UNITED PHOSPHORUS LTD
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