Title:
METHOD FOR CO-PRODUCING ADIPIC ACID AND CYCLOHEXANONE OXIME FROM CYCLOHEXANE
Document Type and Number:
WIPO Patent Application WO/2022/174628
Kind Code:
A1
Abstract:
The invention relates to a method for co-producing adipic acid and cyclohexanone oxime from cyclohexane. The method comprises: (1) subjecting cyclohexane and NO x to oxidation nitration to generate adipic acid, nitrocyclohexane, a nitrogen oxide and byproduct-A, and then separating same to obtain crude adipic acid and nitrocyclohexane; (2) subjecting the obtained nitrocyclohexane and hydrogen to catalytic hydrogenation to generate cyclohexanone oxime and a small amount of cyclohexylamine, and separating same to obtain crude cyclohexanone oxime and cyclohexylamine, wherein the cyclohexylamine can be directly used as a byproduct or continuously converted into cyclohexanone oxime; and (3) partially oxidizing the cyclohexylamine obtained in the previous step with molecular oxygen to obtain an oxidation reaction product composed of cyclohexanone oxime, byproduct-B and possibly unconverted cyclohexylamine, and then, without separation, or after firstly separating out part or all of the water in the oxidation reaction product, subjecting the oxidation reaction product to a hydrogenation and amination reaction, or first a hydrogenation reaction and then an amination reaction, or only a hydrogenation reaction under the action of a catalyst, and then separating same to obtain the cyclohexanone oxime. The method can realize high-selectivity co-production of adipic acid and cyclohexanone oxime, and has a short process flow, low equipment investment, and low material consumption, energy consumption and cost.
Inventors:
LUO HE'AN (CN)
YOU KUIYI (CN)
JIAN JIAN (CN)
LIU PINGLE (CN)
NI WENJIN (CN)
AI QIUHONG (CN)
YOU KUIYI (CN)
JIAN JIAN (CN)
LIU PINGLE (CN)
NI WENJIN (CN)
AI QIUHONG (CN)
Application Number:
PCT/CN2021/130661
Publication Date:
August 25, 2022
Filing Date:
November 15, 2021
Export Citation:
Assignee:
UNIV XIANGTAN (CN)
International Classes:
C07C51/27; C07C249/10; C07C55/14; C07C251/44
Foreign References:
| CN112939765A | 2021-06-11 | |||
| CN103288626A | 2013-09-11 | |||
| CN111253281A | 2020-06-09 | |||
| CN101781217A | 2010-07-21 | |||
| GB908757A | 1962-10-24 | |||
| US2223493A | 1940-12-03 | |||
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| CN101781217B | 2013-05-29 | |||
| CN111530465A | 2020-08-14 |
Other References:
MAO LIQIU, LÜ XING, LI GUANGHONG, YIN DULIN, YOU KUIYI, LUO HE’AN: "Hydrogenation of nitrocyclohexane to cyclohexanone oxime catalyzed by Pd/C", CHEMICAL INDUSTRY AND ENGINEERING PROGRESS, vol. 28, no. 6, 30 June 2009 (2009-06-30), XP055959775, ISSN: 1000-6613, DOI: 10.16085/j.issn.1000-6613.2009.06.008
JIAN JIAN, YOU KUIYI, LUO AND AN: "Single-stage Preparation of Adipic Acid at High Selectivity from Selective Catalytic Oxidation of Cyclohexene with NO2", PROCEEDINGS OF THE 9TH NATIONAL CONFERENCE ON ENVIRONMENTAL CATALYSIS AND MATERIALS OF CHINA: CONFERENCE ON ENVIRONMENTAL CATALYSIS AND MATERIALS FOR SUPPORTING RAPID DEVELOPMENT OF TWO-TYPE SOCIETY, 20 November 2015 (2015-11-20), pages 121 - 121, XP055959778
HILLS P.R. ET AL.: "Radiation-initiated nitrosation of cyclohexane", INTERNATIONAL JOURNAL OF APPLIED RADIATION AND ISOTOPES, vol. 12, no. 3-4, 9 October 2002 (2002-10-09), XP024719080, ISSN: 0020-708X, DOI: 10.1016/0020-708X(61)90067-9
MATSUMOTO YOHEI, KURIYAMA MASAMI, YAMAMOTO KOSUKE, NISHIDA KOYO, ONOMURA OSAMU: "Metal-Free Synthesis of Adipic Acid via Organocatalytic Direct Oxidation of Cyclohexane under Ambient Temperature and Pressure", ORGANIC PROCESS RESEARCH & DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 9, 21 September 2018 (2018-09-21), US , pages 1312 - 1317, XP055959784, ISSN: 1083-6160, DOI: 10.1021/acs.oprd.8b00196
RAJASANKARTHOMAS, J. AM. CHEM. SOC., 1999
YUAN ET AL., ORGANIC PROCESS R&D, 2004
LVRENLIU, APPLIED CATALYSIS A, 2012
JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 160, 2000, pages 393 - 402
J.OF CATALYSIS, vol. 83, 1983, pages 487 - 490
JIAN JIAN, YOU KUIYI, LUO AND AN: "Single-stage Preparation of Adipic Acid at High Selectivity from Selective Catalytic Oxidation of Cyclohexene with NO2", PROCEEDINGS OF THE 9TH NATIONAL CONFERENCE ON ENVIRONMENTAL CATALYSIS AND MATERIALS OF CHINA: CONFERENCE ON ENVIRONMENTAL CATALYSIS AND MATERIALS FOR SUPPORTING RAPID DEVELOPMENT OF TWO-TYPE SOCIETY, 20 November 2015 (2015-11-20), pages 121 - 121, XP055959778
HILLS P.R. ET AL.: "Radiation-initiated nitrosation of cyclohexane", INTERNATIONAL JOURNAL OF APPLIED RADIATION AND ISOTOPES, vol. 12, no. 3-4, 9 October 2002 (2002-10-09), XP024719080, ISSN: 0020-708X, DOI: 10.1016/0020-708X(61)90067-9
MATSUMOTO YOHEI, KURIYAMA MASAMI, YAMAMOTO KOSUKE, NISHIDA KOYO, ONOMURA OSAMU: "Metal-Free Synthesis of Adipic Acid via Organocatalytic Direct Oxidation of Cyclohexane under Ambient Temperature and Pressure", ORGANIC PROCESS RESEARCH & DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 9, 21 September 2018 (2018-09-21), US , pages 1312 - 1317, XP055959784, ISSN: 1083-6160, DOI: 10.1021/acs.oprd.8b00196
RAJASANKARTHOMAS, J. AM. CHEM. SOC., 1999
YUAN ET AL., ORGANIC PROCESS R&D, 2004
LVRENLIU, APPLIED CATALYSIS A, 2012
JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 160, 2000, pages 393 - 402
J.OF CATALYSIS, vol. 83, 1983, pages 487 - 490
Attorney, Agent or Firm:
XIANGTAN HUIZHI PATENT AGENCY (GENERAL PARTNERSHIP) (CN)
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