Process for producing N-substituted aziridine compound

Details Process for producing N-substituted aziridine compound Process for producing N-substituted aziridine compound

1992-02-20

1993-07-27

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548968, C07D20306

Patent

active

052311899

DESCRIPTION:

BRIEF SUMMARY
DETAILED DESCRIPTION OF THE INVENTION

1. Technical Field
The present invention relates to a novel process for producing an N-substituted aziridine compound by a gas-phase intramolecular dehydration reaction of an N-substituted alkanolamine in the presence of a catalyst. Since N-substituted aziridine compounds are cyclic amines each having a heterocyclic three-membered ring of large distortion and have both ring-opening reactivity and reactivity as an amine, they are very useful as various intermediates or as a raw material for amine type polymers or crosslinking agents.
2. Background Art
The following processes are known for production of N-substituted aziridine compounds. These conventional techniques, however, have the problems as mentioned below.
(a) A process which comprises converting an N-substituted ethanolamine to its ester with sulfuric acid and treating the ester with a concentrated alkali to give rise to ring closure to produce an N-substituted aziridine (U.S. Pat. No. 1,177,297). Using large amounts of auxiliary raw materials, the process gives a low productivity and produces, as by-products derived from the auxiliary raw materials, large amounts of inorganic salts of low utility value.
(b) A process which comprises conducting an intramolecular dehydration reaction of an N-substituted ethanolamine with diethoxytriphenylphospholan to convert said amine to an N-substituted aziridine compound [Journal of Organic Chemistry 51, (1986), 95-97]. The process cannot be employed as a practical process, because diethoxytriphenylphospholan is very expensive and moreover its recovery and reuse is impossible.
(c) A process which comprises subjecting aziridine to an addition reaction with an epoxy group-containing compound such as ethylene oxide to produce an N-substituted aziridine (U.S. Pat. No. 3,166,590). In the process, the epoxy compound adds successively to the produced N-substituted aziridine, causing an addition reaction. Hence, it is necessary to use aziridine in a considerable excess; even after such a measure, there are unavoidably formed by-products to which 2 to 3 moles of the epoxy compound have been added, lowering the yield of desired product. In the process, it is also necessary ordinarily to add an alkali in order to prevent aziridine from being polymerized; however, the addition of the alkali causes the polymerization of the epoxy compound, which is a contradiction. Hence, the production operation is carried out while a point of compromise is found out between the safety aspect and the polymerization control aspect.
(d) A process which comprises dimerizing ethyleneimine with an alkali metal catalyst to produce 1-(2-aminoethyl)aziridine (U.S. Pat. No. 3,502,654). In the process, the catalyst is a very dangerous alkali metal and, moreover, aziridine dimers and higher polymers are formed as by-products making the yield of desired product relatively low.
When it is intended to produce, in particular, an N-substituted aziridine compound whose substituent has a functional group such as hydroxyl group, amino group, acyl group or the like, any of the above processes makes the reaction complex and produces various by-products.
Thus, any of the above processes is not at all satisfactory viewed from the standpoint of industrial production.
The object of the present invention is to solve the above-mentioned problems and provide a novel process for producing an N-substituted aziridine compound from an N-substituted alkanolamine at a high selectivity at a high efficiency without using any auxiliary raw material.


DISCLOSURE OF THE INVENTION

The present inventors made study on a novel process for production of N-substituted aziridine compound. As a result, the present inventors found that an N-substituted aziridine compound can be produced at a high selectivity by subjecting an N-substituted alkanolamine to an intramolecular dehydration reaction in a gas phase in the presence of a catalyst. The finding has led to the completion of the present invention. The present invention resides in a process for p

REFERENCES:
patent: 3502654 (1970-03-01), Young
patent: 4841060 (1989-06-01), Hino et al.

Affiliated with

Also associated with

Rating

Process for producing N-substituted aziridine compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing N-substituted aziridine compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing N-substituted aziridine compound will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2343132