104810-18-6Relevant articles and documents
Iron(II) and copper(II) phthalocyanine-catalyzed synthesis of 2-nitro-4-methylsulfonylbenzoic acid under mild conditions
Huang, Cheng,Liu, Rui,Zhang, Caiting,Cheng, Qipeng,Zhu, Hongjun
, p. 1587 - 1594 (2017)
Abstract : A novel method was?developed?to produce 2-nitro-4-methylsulfonylbenzoic acid (NMSBA) from the oxidation of 2-nitro-4-methylsulfonyltoluene (NMST) by oxygen catalyzed by iron(II) phthalocyanine (FePc) and copper(II) phthalocyanine (CuPc). The order of activity for oxidation of NMST was found to be: FePc > CuPc. Meanwhile, major reaction parameters such as concentrations of catalyst and NaOH, reaction temperature and oxygen pressure have been investigated. Through optimization of the reaction parameters, the highest yield of NMSBA and conversion of NMST (up to 53%, 89.3%, respectively) were achieved with oxygen (2.0 MPa), FePc (1.0×10-4molL-1), NaOH (0.6molL-1), in methanol at 55°C for 8 h. A plausible mechanism for this catalytic process is proposed which involved deprotonation and radical pathways. Graphical Abstract: A novel method to produce 2-nitro-4-methylsulfonylbenzoic acid (NMSBA) from the oxidation of 2-nitro-4-methylsulfonyltoluene (NMST) by oxygen catalyzed by iron(II) phthalocyanine (FePc) and copper(II) phthalocyanine (CuPc) has been developed. The reaction parameters and mechanism were studied. The catalytic system will be readily applicable to large-scale production of NMSBA. [Figure not available: see fulltext.].
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Davey,Gwilt
, p. 204,206 (1950)
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Kinetics and mechanism of the oxidation of substituted benzaldehydes by benzyltrimethylammonium chlorobromate
Raju, V. Sitarama,Sharma, Pradeep K.,Banerji, Kalyan K.
, p. 3322 - 3325 (2000)
The oxidation of 35 monosubstituted benzaldehydes by benzyltrimethylammonium chlorobromate (BTMACB) in aqueous acetic acid leads to the formation of the corresponding benzoic acids. The reaction is first order with respect to both benzaldehyde and BTMACB. The reaction failed to induce the polymerization of acrylonitrile. There is no effect of benzyltrimethylammonium chloride or potassium bromide on the reaction rate. The oxidation of [2H]benzaldehyde (PhCDO) indicated the presence of a substantial kinetic isotope effect. The effect of solvent composition indicated that the reaction rate increases with an increase in the polarity of the solvent. The rates of oxidation of meta- and para-substituted benzaldehydes were correlated in terms of Charton's triparametric LDR equation, whereas the oxidation of ortho-substituted benzaldehydes was correlated with the tetraparametric LDRS equation. The oxidation of para- substituted benzaldehydes is more susceptible to the delocalization effect, whereas the oxidation of ortho-and meta-substituted compounds displayed a greater dependence on the field effect. The positive value of η suggests the presence of an electron-deficient reaction center in the rate-determining step. The reaction is subjected to steric hindrance by the ortho substituents.
An efficient and mild procedure for the preparation of benzoic acids via oxidation of aromatic carbonyl compounds by employing N-bromoimides and mercuric acetate system
Anjum, Amena,Srinivas
, p. 900 - 901 (2001)
Aromatic carbonyl compounds are efficiently converted into the corresponding benzoic acids under mild reaction conditions by employing N-bromoimide and mercuric acetate in good to excellent yields. This procedure works efficiently at room temperature for aromatic aldehydes as well as aromatic ketones to give the corresponding benzoic acids.
Manganese dioxide and N-hydroxyphthalimide. An effective catalytic system for oxidation of nitrotoluenes with molecular oxygen
Yang, Guanyu,Zheng, Liwen,Wu, Guanghui,Lin, Xuesong,Song, Maoping
, p. 2445 - 2448 (2007)
The inexpensive manganese dioxide has been proven to be an efficient auxiliary for oxidizing N-hydroxyphthalimide (NHPI) to form the phthalimide N-oxyl radical via reduction and reoxidation. The combination of manganese dioxide and NHPI could catalyze effectively the oxidation of nitrotulenes by molecular oxygen. Thus, the oxidation of p-nitrotoluene with molecular oxygen (0.4 MPa) in the presence of manganese dioxide (10 mol%) and NHPI (10 mol%) in acetic acid at 110° for 4 h proceeded with 97 % conversion, and gave p-ni-trotoluene in 89 % isolated yield.
Pd(II) porphyrins: Synthesis, singlet oxygen generation and photoassisted oxidation of aldehydes to carboxilic acids
Pandey, Vijayalakshmi,Jain, Drishti,Pareek, Nitesh,Gupta, Iti
, (2020)
The synthesis and spectral studies of A3B and A2B2 type porphyrins and their Pd(II) complexes are reported. The meso-positions on porphyrin macrocycle are substituted with pentafluorophenyl and N-butylcarbazole or triphenylamine groups. Pd(II) porphyrins displayed decent phosphorescence ～670 nm and are able to produce singlet oxygen by type II pathway, after photoirradiation. The calculated singlet oxygen quantum yields for Pd(II) porphyrins are (ΦΔ = 30%–63%). The catalytic application of Pd(II) porphyrins towards photoassisted aerobic oxidation of aromatic aldehydes to carboxylic acids is demonstrated.
Mild and efficient method for oxidative deprotection of trimethylsilyl ethers mediated by tetraethylammonium superoxide
Raghuvanshi,Singh
, p. 1371 - 1374 (2007)
Oxidative deprotection of trimethylsilyl ethers to their corresponding carbonyl compounds has been achieved under the mild reaction conditions of in situ generated tetraethylammonium superoxide. Copyright Taylor & Francis Group, LLC.
Nanoparticle-supported and magnetically recoverable organic-inorganic hybrid copper(ii) nanocatalyst: A selective and sustainable oxidation protocol with a high turnover number
Rathore, Puran Singh,Patidar, Rajesh,Thakore, Sonal
, p. 41111 - 41121 (2014)
A magnetically recoverable copper-based nanocatalyst was prepared from inexpensive starting materials. With a particle size between 20 to 30 nm, it was shown to catalyze the oxidation of benzylic alcohols. The catalyst exhibited a high turnover number (TON) and excellent selectivity. The catalyst was characterized by several techniques, such as XRD, HR-TEM, SAED, EDS, FT-IR, VSM, and BET surface area. Factors affecting the reaction parameters, such as the substrate to oxidant molar ratio, weight of the catalyst, reaction time, etc., were investigated in detail. The reusability of the catalyst was examined by conducting repeat experiments with the same catalyst; it was observed that the catalyst displayed no significant changes in its activity even after seven cycles for the aerobic, as well as for the peroxide, oxidation of benzyl alcohol. Furthermore, the heterogeneous nature, easy recovery, and reusability, makes the present protocol highly beneficial for addressing environmental concerns and industrial requirements. This journal is
The catalytic performance of Preyssler's anion, [NaP5W 30O110]14-, in the oxidation of benzyl alcohols
Bamoharram, Fatemeh F.,Roshani, Mina,Heravi, Majid M.,Safaie, Shahla
, p. 2833 - 2841 (2006)
Under mild conditions, monosubstituted benzyl alcohols were oxidized to benzaldehydes and benzoic acids in the presence of sodium 30- tungstopentaphosphate (Preyssler's anion), [NaP5W30O 120]14-, and hydrogen peroxide as an oxidant. This polyanion with high hydrolytic stability (pH = 0-12), high thermal stability, and high acidic strength shows good activities. The effects of various parameters on the yield of the products, including a catalyst type, a nature of the substitutents, and temperature, were studied. Comparison between Keggin's heteropolyacids, H3[PW12O40], H 3[PMo12O40], H4[SiW 12O40], and H4[SiMo12O 40], and Preyssler's anion shows that this polyanion reacts similar to Keggin's acids whitout any degradation of the structure. Copyright Taylor & Francis Group, LLC.
Efficient palladium-catalysed carbonylative and Suzuki-Miyaura cross-coupling reactions with bis(di-tert-butylphosphino)-o-xylene
McNulty, James,Nair, Jerald J.,Sliwinski, Marcin,Robertson, Al J.
, p. 2342 - 2346 (2009)
The use of the ligand bis(di-tert-butylphosphino)-o-xylene (dtbpx) in palladium-catalysed carbonylative and Suzuki-Miyaura cross-coupling reactions is described. Aryl and vinyl halides readily entered into the carbonylative catalytic cycle affording carboxylic acids, amides as well as primary, secondary and tertiary esters, respectively, in good yields. Aryl iodides, bromides and chlorides gave high yields of biphenyl products upon reaction with both activated and unactivated boronic acids.
Oxidation of nitrotoluenes with air using N-hydroxyphthalimide analogues as key catalysts
Sawatari, Naoko,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 2053 - 2056 (2003)
Nitrotoluenes are efficiently oxidized with air to the corresponding nitrobenzoic acids by the use of N-acetoxyphthalimide (NAPI) as a key catalyst. Thus, p- and m-nitrotoluenes under 10 atm of air in the presence of NAPI combined with Co(OAc)2 (0.5 mol%) and Mn(OAc)2 (0.05 mol%) at 130°C afforded p- and m-nitrobenzoic acids in 81 and 92% yields, respectively. o-Nitrotoluene was oxidized to o-nitrobenzoic acid in 51% yield by the aid of NO2.
Chromium(VI) Based Oxidants; II. Zinc Dichromete Trihydrate: A Versatile and Mild Reagent for the Oxidation of Organic Compounds
Firouzabadi, H.,Sardarian, A. R.,Moosavipour, H.,Afshari, G. M.
, p. 285 - 288 (1986)
Zinc dichromate trihydrate is an easily prepared, stable, and cheap reagent for the efficient oxidation of organic compounds in aprotic solvents at room temperature.
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Chattaway,Coulson
, (1928)
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Kinetics and mechanism of liquid-phase catalytic ozonation of nitrotoluenes
Galstyan
, p. 362 - 366 (2006)
The kinetics of catalytic oxidation of nitrotoluenes with ozone was studied. It was shown that the introduction of transition metal salts into the system makes it possible to prevent almost completely the ozonolysis of the aromatic ring and to direct the process towards methyl-group oxidation yielding benzoic acids. A mechanism of the process that explains the experimental findings was proposed. Nauka/Interperiodica 2006.
Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions
Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang
, p. 319 - 330 (2021/10/29)
The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.
Continuous production method of benzoic acid derivative
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Paragraph 0032-0034, (2021/11/14)
The invention relates to the technical field of preparation of benzoic acid derivatives. The invention particularly relates to a continuous production method of a benzoic acid derivative. The continuous reaction device is characterized by comprising a small-diameter sleeve, wherein the small-diameter sleeve is sleeved with a large-diameter sleeve, and a small pipeline is arranged between the small-diameter sleeve and the large-diameter sleeve, and a plurality of small holes are arranged on the small pipeline. The small-diameter casing is rotated, the large-diameter casing is fixed, and the reaction liquid composed of the nitric acid and the toluene derivative is between a small-diameter casing pipe and a large-diameter casing pipe.
