Continuous prepn. of amine

A technology of carboxamide and cyclopropylamine, applied in the preparation of organic compounds, rearrangement reaction preparation, chemical instruments and methods, etc., can solve problems such as difficult continuous mode, low space-time yield, and no method for Hoffman reaction

Inactive Publication Date: 2004-05-26
EASTMAN CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] As can be seen from the above methods, the known preparation of amines via the Hofmann reaction requires several complex process steps in order to avoid side reactions
These methods are difficult to perform in a continuo...

Method used

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  • Continuous prepn. of amine
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  • Continuous prepn. of amine

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Experimental program
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preparation example Construction

[0022] The present invention provides a continuous process for the preparation of amines utilizing the Hofmann reaction of carboxamides and alkaline hypohalites. We have found that by utilizing two reaction zones, measuring the concentration of at least one component of the first reaction mixture from the first reaction zone and using the measurement to control the flow of at least one reactant to the first reaction zone In such a way that the feed rate, thereby achieving the desired conversion or concentration of the reaction components, the Hofmann reaction can be performed continuously in an efficient and economical manner. The term "component" or "reaction component", as used herein, means any starting material, reactant, product, intermediate, present in a reaction mixture, in any process stream, or in any process equipment, solvents, or by-products. Non-limiting examples of components or reaction components that may be present in the first reaction mixture include: a so...

Embodiment

[0057] Example

[0058] 2 variable speed peristaltic pumps (Cole-Parmer U-77912-00, Cole-Parmer, Vernon Hills, IL) were connected by polytetrafluoroethylene (PTFE) hoses (with 4 mm PTEE tubing at the top of the reactor). Connect the outlet of the mixer to the mixer and use a 7.9 mm ID hose (LIS 17  C-FLEX  Pipe, Cole-Parmer U-06424-25, Cole-Parmer, Vernon Hills, IL) was equipped with a continuous production unit for cyclopropylamine; the mixer consisted of a Y-shaped fitting of 8 mm (3 / 8 inch) OD glass , with a 2mm stirring rod inserted and held at the "Y" connection. The connection between the 4mm PTFE tubing and the 7.9mm ID tubing was completed using a short section of the 7.9mm ID tubing as filler between the 4mm PTFE tubing and the larger bore L / S 17 tubing. The mixer was magnetically stirred throughout the reaction and was connected to the first reactor with a minimum practicable length of 7.9 mm ID tubing. The first reactor representing a plug flow reactor consis...

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PUM

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Abstract

Disclosed is a process for the preparation of amines by continuously feeding a carboxamide, aqueous alkaline hypohalite, and aqueous alkaline hydroxide to a first reaction zone to form a N-halocarboxamide, measuring the concentration of at least one reaction component in the effluent from the first reaction zone, and using the result of that measurement to control the feed rate of at least one of the feed components of to achieve at least 90% conversion of the carboxamide in the first reaction zone. The effluent from the first reaction zone is fed continuously to a second reaction zone where it further reacts to form an aqueous solution of an amine. The effluent from the second reaction zone may be fed continuously to a distillation column. The process is particularly useful for the preparation of cyclopropylamine.

Description

technical field [0001] The present invention relates to a process for the preparation of amines. More particularly, the present invention relates to a continuous process for the preparation of amines by the reaction of basic hypohalites with carboxamides. Background technique [0002] Amines are important intermediates for the preparation of liquid crystal polymers, agrochemicals, and pharmaceutical compounds. Although many simple aliphatic and aromatic amines are accessible by efficient, low-cost methods such as reductive amination, displacement of halides with ammonia, or amination of alcohols, many are synthetically difficult, sterically hindered, or More reactive amines are prepared from their corresponding carboxamides by Hofmann reactions. These more complex amines are particularly useful in the production of agrochemical and pharmaceutical compounds. For example, cyclopropylamine is particularly useful as an agrochemical and pharmaceutical intermediate, and is prod...

Claims

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Application Information

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IPC IPC(8): C07C209/58C07C211/35
CPCC07C2101/02C07C209/58C07C2601/02C07C211/35
Inventor J·R·佐勒N·L·布查南E·C·沙基D·L·特里尔S·P·贝尔纳
Owner EASTMAN CHEM CO
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