100-21-0Relevant articles and documents
Highly efficient conversion of aldehydes to carboxylic acid in the presence of platinum porphyrin sensitizers, air and sunlight
Hajimohammadi, Mahdi,Mofakham, Hamid,Safari, Nasser,Manesh, Anahita Mortazavi
, p. 93 - 100 (2012)
A variety of aromatic and aliphatic aldehydes were oxidized to the corresponding carboxylic acids in the presence of platinum porphyrin, sunlight and air in acetonitrile solvent under mild conditions. Nitrobenzaldehydes were found to be very efficient 1O2 scavengers that quench the formation of acids from any aldehyde in the presence of free-base porphyrin sensitizers. However, nitrobenzaldehydes were converted to the corresponding acids in the presence of platinum porphyrins. The platinum porphyrins are very good and efficient catalysts for a wide range of applications in the aerobic conversion of aldehydes to acids.
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Toland et al.
, p. 5423,5426 (1958)
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Strickland,Bell
, p. 7,9 (1961)
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Novel oxidation of toluenes catalyzed by reusable vanadyl(IV) sulfate under mild conditions with molecular oxygen
Nakai, Takeo,Iwai, Toshiyuki,Mihara, Masatoshi,Ito, Takatoshi,Mizuno, Takumi
, p. 2225 - 2227 (2010)
Efficient oxidation system using reusable vanadyl(IV) sulfate catalyst was established. Toluenes were easily oxidized under molecular oxygen (0.1 MPa) at 100 °C catalyzed by vanadyl(IV) sulfate to afford the corresponding benzoic acids in excellent yields. The recovered catalyst could be reused without loss of activity.
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Hay,Blanchard
, p. 1306,1314 (1965)
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Emerson et al.
, p. 1839,1844 (1951)
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Selectively Upgrading Lignin Derivatives to Carboxylates through Electrochemical Oxidative C(OH)?C Bond Cleavage by a Mn-Doped Cobalt Oxyhydroxide Catalyst
Zhou, Hua,Li, Zhenhua,Xu, Si-Min,Lu, Lilin,Xu, Ming,Ji, Kaiyue,Ge, Ruixiang,Yan, Yifan,Ma, Lina,Kong, Xianggui,Zheng, Lirong,Duan, Haohong
, p. 8976 - 8982 (2021)
Oxidative cleavage of C(OH)?C bonds to afford carboxylates is of significant importance for the petrochemical industry and biomass valorization. Here we report an efficient electrochemical strategy for the selective upgrading of lignin derivatives to carboxylates by a manganese-doped cobalt oxyhydroxide (MnCoOOH) catalyst. A wide range of lignin-derived substrates with C(OH)-C or C(O)-C units undergo efficient cleavage to corresponding carboxylates in excellent yields (80–99 %) and operational stability (200 h). Detailed investigations reveal a tandem oxidation mechanism that base from the electrolyte converts secondary alcohols and their derived ketones to reactive nucleophiles, which are oxidized by electrophilic oxygen species on MnCoOOH from water. As proof of concept, this approach was applied to upgrade lignin derivatives with C(OH)-C or C(O)-C motifs, achieving convergent transformation of lignin-derived mixtures to benzoate and KA oil to adipate with 91.5 % and 64.2 % yields, respectively.
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Carnelley
, (1877)
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Dehydro-aromatization of cyclohexene-carboxylic acids by sulfuric acid: Critical route for bio-based terephthalic acid synthesis
Wang, Fei,Tong, Zhaohui
, p. 6314 - 6317 (2014)
A novel dehydro-aromatization reaction under mild reaction conditions was successfully developed using sulfuric acid as a cost-effective and efficient oxidant. This reaction simplified the synthesis of terephthalic acid (TA, an important aromatic monomer precursor) from biomass-derived isoprene and acrylic acid.
9,10-Dihydroanthracene auto-photooxidation efficiently triggered photo-catalytic oxidation of organic compounds by molecular oxygen under visible light
Chen, Mengke,Deng, Youer,Fu, Zaihui,Hu, Wenwei,Jiang, Dabo,Liu, Yachun,Mao, Feng,Su, Anqun,Yang, Bo,Zhang, Chao
, (2020)
The development of mild and efficient process for the selective oxidation of organic compounds by molecular oxygen (O2) can be one of the key technologies for synthesizing oxygenates. This paper discloses an efficient and mild synthesis protocol for the O2-involved ethylbenzene (EB) photooxidation triggered by 910-dihydroanthracene (DHA) auto- photooxidation in acetone under visible light illumination, which can achieve 87.7 percent EB conversion and 99.5 percent acetylacetone (ACP) selectivity under ambient conditions. Also, 62.9 percent EB conversion and 96.3 percent ACP selectivity is obtained in air atmosphere. Furthermore, this protocol has a good adaptability for the photooxidation of other organic substrates such as tetrahydronaphthalene, diphenylmethane, toluene, cyclohexane, cyclohexene, alcohol, methylfuran and thioether to their corresponding oxygenates. A series of control and quenching tests, combined with EPR spectra, suggest that the photo-excited DHA can transfer its photo-electron to O2 to yield a superoxide radical anion (O2??), then DHA is preferentially oxidized to anthraquinone (AQ) by the active O2?? owing to its high reactivity. Finally, the in situ generated AQ as an active photo-catalyst can achieve the photooxidation of EB and other organic compounds by O2. The present photo-autoxidation protocol gives a good example for the O2-based selective oxidation of inert hydrocarbons under mild conditions.
Selective aerobic oxidation of para-xylene in sub- and supercritical water. Part 3: Effects of geometry and mixing in laboratory scale continuous reactors
Pérez, Eduardo,Thomas, Morgan L.,Housley, Duncan,Hamley, Paul A.,Fraga-Dubreuil, Joan,Li, Jun,Lester, Edward,Poliakoff, Martyn
, p. 11289 - 11294 (2016)
In this paper we report a strong dependence of the observed performance of the catalyst on the geometry and the configuration of laboratory scale reactors in the continuous aerobic oxidation of p-xylene in supercritical water. Small differences, such as t
New crystalline modification of terephthalic acid
Sledz, M.,Janczak, J.,Kubiak, R.
, p. 77 - 82 (2001)
The new crystalline modification of terephthalic acid can be obtained either from the commercially available triclinic modification by heating at 250 deg C or directly by a thermal hydrolysis of p-dicyanobenzene. It crystallises in a monoclinic system, space group C2/m with a = 8.940(2), b = 10.442(2), c = 3.790(1) Angstroem, V = 353.7(2) Angstroem3, β = 91.21(3) deg and Z = 2. Both carboxyl groups of terephthalic acid are coplanar with the phenyl ring. The molecules in the crystal are linked through the hydrogen bonds in the carboxyl groups into infinite chains. The orientational disorder is observed in the carboxyl groups. The structure of the monoclinic form is compared with the structure of both the triclinic modification.
Production of Terephthalic Acid from Corn Stover Lignin
Song, Song,Zhang, Jiaguang,G?zayd?n, G?kalp,Yan, Ning
, p. 4934 - 4937 (2019)
Funneling and functionalization of a mixture of lignin-derived monomers into a single high-value chemical is fascinating. Reported herein is a three-step strategy for the production of terephthalic acid (TPA) from lignin-derived monomer mixtures, in which redundant, non-uniform substitutes such as methoxy groups are removed and the desired carboxy groups are introduced. This strategy begins with the hydro-treatment of corn-stover-derived lignin oil over a supported molybdenum catalyst to selectively remove methoxy groups. The generated 4-alkylphenols are converted into 4-alkylbenzoic acids by carbonylation with carbon monoxide. The Co-Mn-Br catalyst then oxidizes various alkyl chains into carboxy groups, transforming the 4-alkylbenzoic acid mixture into a single product: TPA. For this route, the overall yields of TPA based on lignin content of corn stover could reach 15.5 wt %, and importantly, TPA with greater than 99 % purity was obtained simply by first decanting the reaction mixture and then washing the solid product with water.
Introducing nanocrystalline CeO2 as heterogeneous environmental friendly catalyst for the aerobic oxidation of para-xylene to terephthalic acid in water
Deori, Kalyanjyoti,Gupta, Dinesh,Saha, Basudeb,Awasthi, Satish K.,Deka, Sasanka
, p. 7091 - 7099 (2013)
CeO2 nanoparticles exposed in (100) and (111) surfaces have been synthesized and explored as a heterogeneous catalyst for the first time in the oxidation of para-xylene to terephthalic acid. The synthesis and catalysis reaction was environmenta
Ruzicka,Stoll
, p. 271 (1924)
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Sensemann,Stubbs
, p. 1129 (1931)
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Carboxylation of Benzoic Acid Using Cyclodextrin as Catalyst
Hirai, Hidefumi,Mihori, Hisashi
, p. 1523 - 1526 (1992)
Benzoic acid is found to undergo carboxylation by warming with carbon tetrachloride in aqueous alkali in the presence of copper powder with β-cyclodextrin as catalyst.The reaction under mild conditions gives terephthalic acid in good yield with high selec
Solvent free oxidation of primary alcohols and diols using thymine iron(iii) catalyst
Al-Hunaiti, Afnan,Niemi, Teemu,Sibaouih, Ahlam,Pihko, Petri,Leskelae, Markku,Repo, Timo
, p. 9250 - 9252 (2010)
In this study, we developed an efficient and selective iron-based catalyst system for the synthesis of ketones from secondary alcohols and carboxylic acids from primary alcohol. In situ generated iron catalyst of thymine-1-acetate (THA) and FeCl3 under solvent-free condition exhibits high activity. As an example, 1-octanol and 2-octanol were oxidized to 1-octanoic acid and 2-octanone with 89% and 98% yields respectively.
Catalytic oxidation of alkyl aromatics using a novel silica supported Schiff base complex
Chisem, Ian C.,Rafelt, John,Shieh, M. Tantoh,Chisem, Janet,Clark, James H.,Jachuck, Roshan,Macquarrie, Duncan,Ramshaw, Colin,Scott, Keith
, p. 1949 - 1950 (1998)
A new heterogeneous catalyst based on a chemically modified mesoporous silica gel and possessing immobilised chromium ions has been prepared and successfully applied to the aerial oxidation of alkyl aromatics at atmospheric pressure and in the absence of solvent.
One-step synthesis of terephthalic acid from benzene in water using cyclodextrin as catalyst
Shiraishi, Yukihide,Tashiro, Shigetoshi,Toshima, Naoki
, p. 828 - 829 (2000)
The one-pot synthesis of terephthalic acid from benzene has been achieved by treatment with tetrachloromethane, copper powder, and an aqueous sodium hydroxide solution using cyclodextrin as a catalyst at 30 °C under nitrogen in 46 mol% yield with 100% selectivity.
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Fichter,Meyer
, p. 285 (1925)
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Holtz
, p. 1166 (1971)
Furan Carboxylic Acids Production with High Productivity by Cofactor-engineered Whole-cell Biocatalysts
Zhang, Xue-Ying,Wang, Xin,Li, Nan-Wei,Guo, Ze-Wang,Zong, Min-Hua,Li, Ning
, p. 3257 - 3264 (2020)
Furan carboxylic acids are useful chemicals in various industries. In this work, biocatalytic production of furan carboxylic acids was reported with high productivities by cofactor-engineered Escherichia coli cells. NADH oxidase (NOX) was introduced into E. coli harboring aldehyde dehydrogenases (ALDHs) to promote intracellular NAD+ regeneration, thus significantly enhancing ALDH-catalyzed oxidation. These engineered biocatalysts were capable of efficient aerobic oxidation of a variety of aromatic aldehydes. More importantly, they exhibited high substrate tolerance toward toxic furans. E. coli co-expressing vanillin dehydrogenase and NOX (E. coli_CtVDH1_NOX) enabled efficient oxidation of 250 mM of 5-hydroxymethylfurfural (HMF) to 5-hydroxymethyl-2-furancarboxylic acid (HMFCA), providing a productivity of 3.7 g/L h. With E. coli_CtVDH2_NOX as catalyst, up to 240 mM of furfural and 5-methoxymethylfurfural (MMF) could be smoothly oxidized. 2-Furoic acid (FCA, 227 mM) and 5-methoxymethyl-2-furancarboxylic acid (MMFCA, 287 mM) were produced in fed-batch synthesis, providing the productivities of 2.0 and 5.6 g/L h, respectively.
Ogata et al.
, p. 6005 (1957)
Selective oxidation of para-xylene to terephthalic acid by μ3-oxo-bridged Co/Mn cluster complexes encapsulated in zeolite-Y
Ratnasamy,Chavan,Srinivas
, p. 409 - 419 (2001)
Novel, solid catalysts of μ3-oxo-bridged Co/Mn cluster complexes were prepared and their catalytic properties (in the "neat" state and when encapsulated in zeolite Y) in the selective oxidation of paraxylene to terephthalic acid with oxygen wer
Stepwise benzylic oxygenation via uranyl-photocatalysis
Hu, Deqing,Jiang, Xuefeng
supporting information, p. 124 - 129 (2022/01/19)
Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.
Photoinduced FeCl3-Catalyzed Alkyl Aromatics Oxidation toward Degradation of Polystyrene at Room Temperature?
Zhang, Guoxiang,Zhang, Zongnan,Zeng, Rong
supporting information, p. 3225 - 3230 (2021/09/28)
While polystyrene is widely used in daily life as a synthetic plastic, the subsequently selective degradation is still very challenging and highly required. Herein, we disclose a highly practical and selective reaction for the catalytically efficient oxidation of alkyl aromatics (including 1°, 2°, and 3° alkyl aromatics) to carboxylic acids. While dioxygen was used as the sole terminal oxidant, this protocol was catalyzed by the inexpensive and readily available ferric compound (FeCl3) with irradiation of visible light (blue LEDs) under only 1 atmosphere of O2 at room temperature. This system could further facilitate the selective degradation of polystyrene to benzoic acid, providing an important and practical tool to generate high-value chemical from abundant polystyrene wastes.
Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst
Mittal, Rupali,Kumar, Amit,Awasthi, Satish Kumar
, p. 11166 - 11176 (2021/03/31)
Herein, catalytic application of a metal-free sulfonic acid functionalized reduced graphene oxide (SA-rGO) material is reported for the synthesis of both carboxylic acids and their bioisosteres, 5-substituted-1H-tetrazoles. SA-rGO as a catalytic material incorporates the intriguing properties of graphene oxide material with additional benefits of highly acidic sites due to sulfonic acid groups. The oxidation of aldehydes to carboxylic acids could be efficiently achieved using H2O2as a green oxidant with high TOF values (9.06-9.89 h?1). The 5-substituted-1H-tetrazoles could also be effectively synthesized with high TOF values (12.08-16.96 h?1). The synthesis of 5-substituted-1H-tetrazoles was corroborated by single crystal X-ray analysis and computational calculations of the proposed reaction mechanism which correlated well with experimental findings. Both of the reactions could be performed efficiently at gram scale (10 g) using the SA-rGO catalyst. SA-rGO displays eminent reusability up to eight runs without significant decrease in its productivity. Thus, these features make SA-rGO riveting from an industrial perspective.