Premium
A novel and stable hydroxylamine salt generated from betaine hydrochloride and its application in the synthesis of cyclohexanone oxime
Author(s) -
Ren Xiaoliang,
Yang Qiusheng,
Wang Shufang,
Guan Congcong,
Zhang Dongsheng,
Ding Xiaoshu,
Wang Yanji
Publication year - 2021
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.6719
Subject(s) - chemistry , hydroxylamine , betaine , cyclohexanone , hydroxylamine hydrochloride , hydrochloride , oxime , organic chemistry , salt (chemistry) , yield (engineering) , catalysis , materials science , metallurgy
BACKGROUND Hydroxylamine (NH 2 OH) is an important chemical raw material, which is widely used in large‐scale synthesis of cyclohexanone oxime (COX) for nylon 6 manufacture. At present, inorganic acids are usually employed to stabilize NH 2 OH to form solid hydroxylamine salts. However, most of these hydroxylamine salts suffer from the problems of serious equipment corrosion, environmental pollution and difficult recovery of the inorganic acids. To address these issues, herein, a novel betaine hydrochloride hydroxylamine (BHA) was formulated and applied for the production of COX. RESULTS The structure of BHA was identified using experimental analysis and density functional theory calculation. During the synthesis of COX from cyclohexanone (CYC), the BHA exhibited much higher reactivity than that of traditional NH 2 OH·HCl. Moreover, oximation reaction of CYC and BHA can also be conducted in CH 3 CN solution. And an almost 100% yield of COX was obtained under the conditions of 30 °C, 0.5 h and 1:1 molar ratio of BHA to CYC. Furthermore, the betaine hydrochloride released from BHA can be easily separated and recycled after the reaction, achieving a green route for the synthesis of COX. CONCLUSIONS A novel BHA was successfully prepared. It shows great advantage for use as an eco‐friendly and green carrier of NH 2 OH for preparing COX and forming a virtuous cycle. © 2021 Society of Chemical Industry (SCI).