Metal-Free Synthesis of Adipic Acid via Organocatalytic Direct Oxidation of Cyclohexane under Ambient Temperature and Pressure

被引：15

作者：

Matsumoto, Yohei ^{[1
]}

Kuriyama, Masami ^{[1
]}

Yamamoto, Kosuke ^{[1
]}

Nishida, Koyo ^{[1
]}

Onomura, Osamu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2018年 / 22卷 / 09期

关键词：

adipic acid; metal-free reaction; oxidation; organocatalysis; radical; ONE-STEP CONVERSION; N-HYDROXYPHTHALIMIDE; MOLECULAR-OXYGEN; AEROBIC OXIDATION; NITRIC-ACID; HIGHLY EFFICIENT; SELECTIVE OXIDATION; CATALYTIC-OXIDATION; TEREPHTHALIC ACID; CARBON NANOTUBES;

D O I：

10.1021/acs.oprd.8b00196

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A direct metal-free approach for the production of adipic acid from cyclohexane is reported. The use of N-hydroxyphthalimide (NHPI) as a catalyst in the presence of HNO3/TFA enables the direct oxidation of cyclohexane to yield adipic acid under ambient temperature and pressure via a simple procedure. This reaction proceeds through an initial oxidation of cyclohexane to cyclohexanone oxime and cyclohexanone followed by a second oxidation of these intermediates to adipic acid. NHPI plays a crucial role in both oxidation steps to achieve a high yield and selectivity for adipic acid.

引用

页码：1312 / 1317

页数：6

共 57 条

[1] Nanoclusters of Cu(II) supported on nanocrystalline W(VI) oxide: a potential catalyst for single-step conversion of cyclohexane to adipic acid [J].

Acharyya, Shankha S. ;

Ghosh, Shilpi ;

Bal, Rajaram .

GREEN CHEMISTRY, 2015, 17 (06) :3490-3499

[2] Hydroxylamines as oxidation catalysts: Thermochemical and kinetic studies [J].

Amorati, R ;

Lucarini, M ;

Mugnaini, V ;

Pedulli, GF ;

Minisci, F ;

Recupero, F ;

Fontana, F ;

Astolfi, P ;

Greci, L .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1747-1754

[3] Synthesis and characterization of nitrated [60]fullerene derivatives [J].

Anantharaj, V ;

Bhonsle, J ;

Canteenwala, T ;

Chiang, LY .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (01) :31-36

[4] Aerobic oxidation of benzyl alcohols catalyzed by aryl substituted N-hydroxyphthalimides.: Possible involvement of a charge-transfer complex [J].

Annunziatini, C ;

Gerini, MF ;

Lanzalunga, O ;

Lucarini, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3431-3438

[5] Innovative direct synthesis of adipic acid by air oxidation of cyclohexane [J].

Bonnet, Didier ;

Ireland, Tania ;

Fache, Eric ;

Simonato, Jean-Pierre .

GREEN CHEMISTRY, 2006, 8 (06) :556-559

[6]

BOUGHRIET A, 1985, NOUV J CHIM, V9, P651

[7]

Brown H.C., 1955, Determination of Organic Structures by Physical Methods, P567, DOI DOI 10.1016/B978-1-4832-3166-2.50018-4

[8] INDUSTRIAL-PRODUCTION AND USE OF ADIPIC ACID [J].

CASTELLAN, A ;

BART, JCJ ;

CAVALLARO, S .

CATALYSIS TODAY, 1991, 9 (03) :237-254

[9]

Cavani F., 2009, SUSTAINABLE IND PROC, P331

[10] Oxidation of cyclohexane, cyclohexanone, and cyclohexanol to adipic acid by a non-HNO3 route over Co/Mn cluster complexes [J].

Chavan, SA ;

Srinivas, D ;

Ratnasamyi, P .

JOURNAL OF CATALYSIS, 2002, 212 (01) :39-45

← 1 2 3 4 5 6 →