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Cas Database

65-85-0

65-85-0

Identification

  • Product Name:Benzoic acid

  • CAS Number: 65-85-0

  • EINECS:200-618-2

  • Molecular Weight:122.123

  • Molecular Formula: C7H6O2

  • HS Code:2916.31

  • Mol File:65-85-0.mol

Synonyms:Carboxybenzene;Tenn-Plas;Salvo liquid;Unisept BZA;Benzoic acid, tech.;Benzeneformic acid;Salvo, liquid;Solvo, powder;Acide benzoique;Benzoic acid (JP14/USP);Retarder BA;Solvo powder;Benzoic acid tech.;Benzoic acid nat.;Benzoic Acid, Crystal, Reagent;Benzoic Acid, Reagent Special;2,40 DECADIENAL;Benzoic Acid [65-85-0];Benzoesaeure;Benzoic acid /Natural;Benzoic acid (MDS);Benzyl acid;Retardex;Benzenemethanoic acid;phenylformic acid;Benzenecarboxylic acid;HA 1 (acid);Benzoesaeure GV;E 210;582-25-2;Dracylic acid;Benzoic acid (7CI,8CI,9CI);Benzoesaeure GK;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn, ToxicT, IrritantXi

  • Hazard Codes:Xn,T,Xi

  • Signal Word:Danger

  • Hazard Statement:H315 Causes skin irritationH318 Causes serious eye damage H372 Causes damage to organs through prolonged or repeated exposure

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . Dust may be irritating to nose and eyes. At elevated temperatures, fumes may cause irritation of eyes, respiratory system, and skin. (USCG, 1999) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/

  • Fire-fighting measures: Suitable extinguishing media If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Behavior in Fire: Vapor from molten benzoic acid may form explosive mixture with air. Concentrated dust may form explosive mixture. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: protective clothing and face shield. Sweep spilled substance into covered plastic containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. Cover with soda ash or sodium bicarbonate. Mix and add water.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. The bulk material should be stored in well-closed container in a cool dry place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Benzoic Acid
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  • Product Description:Benzoic Acid Zone Refined (number of passes:20) >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
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Relevant articles and documentsAll total 3240 Articles be found

Redox Cascades and Making of a C-C Bond: 1,2-Benzodiazinyl Radicals and a Copper Complex of a Benzodiazine

Mondal, Sandip,Bera, Sachinath,Ghosh, Prasanta

, (2019)

Two 1,2-benzodiazinyl radicals, cinnolinyl radicals by name, were successfully isolated by cascade routes using 1,4-naphthoquinone as a precursor. Reaction of 1,4-naphthoquinone with hydrazine hydrate promotes a (5e + 5H+) redox cascade affording benzo[g]naphtho[1,2-c]cinnolinyl-7,12,14-trione (Cn·) in 69% yields, while the similar reaction with 2-hydrazinopyridine is a (7e + 7H+) oxidative cascade and furnishes N-pyridinecinnolinyl radical (PyCn·). The cascades are composed of C-N and C-C bond making reactions. The neutral even alternate arenes are always diamagnetic; thus, the isolation of Cn· and PyCn· is a breakthrough. The Cn·/Cn- and PyCn·/PyCn- redox couples are reversible, and the reaction of Cn· with [CuI(PPh3)3Cl] in the presence of hydrazine hydrate and Et3N affords a Cn- complex of copper(I), [(Cn-)CuI(PPh3)2] (1). Similar to phenalenyl radical, PyCn· exists in three redox states, PyCn+PyCn·, and PyCn-, in a smaller potential range (-0.30 V to -0.60 V vs Fc+/Fc couple) and can be used as an oxidant as well as a reductant. PyCn· acts as a catalyst for the oxidative cleavages of benzil to benzoic and 2,2′-pyridil to picolinic acids in methanol in the presence of air. The molecular and electronic structures of Cn·PyCn·, and 1·1/2MeOH were confirmed by single crystal X-ray crystallography, EPR spectroscopy, and DFT calculations.

Kinetics and Mechanism of the Oxidation of Aromatic Aldehydes by Pyridinium Fluorochromate

Agarwal, Sarswati,Chowdhury, Kakuli,Banerji, Kalyan K.

, p. 5111 - 5113 (1991)

Kinetics of oxidation of a number of ortho-, meta-, and para-substituted benzaldehydes by pyridinium fluorochromate (PFC), in dimethyl sulfoxide, were studied.The main product of oxidation is the corresponding benzoic acid.The reaction is first order with

Study of a benzoylperoxy radical in the gas phase: Ultraviolet spectrum and C6H5C(O)O2 + HO2 reaction between 295 and 357 K

Roth,Chakir,Ferhati

, p. 10367 - 10379 (2010)

This work reports the ultraviolet absorption spectrum and the kinetic determinations of the reactions 2C6H5C(O)O2 → products (I) and C6H5C(O)O2 + HO 2 → C6H5C(O)O2H + O2 (IIa), → C6H5C(O)OH + O3 (IIb), → C6H5C(O)O + OH + O2 (IIc). Experiments were performed using a laser photolysis technique coupled with UV-visible absorption detection over the pressure range of 80-120 Torr and the temperature range of 293-357 K. The UV spectrum was determined relative to the known cross section of the ethylperoxy radical C2H5O2 at 250 nm. Kinetic data were obtained by simulating the temporal behavior of the UV absorption at 245-260 nm. At room temperature, the rate constant value of reaction I (cm3 . molecule-1 . s-1) was found to be kI ) (1.5 ± 0.6) × 10-11. The Arrhenius expression for reaction II is (cm3 . molecule-1 . s -1) kII(T) ± (1.10 ± 0.20) × 10 -11 exp(364 ± 200/T). The branching ratios βO3 and βOH, respectively, of reactions IIb and IIc are evaluated at different temperatures; βO3 increases from 0.15 ± 0.05 at room temperature to 0.40 ± 0.05 at 357 K, whereas βOH remains constant at 0.20 ± 0.05. To confirm the mechanism of reaction II, a theoretical study was performed at the B3LYP/6-311++G(2d,pd) level of theory followed by CBS-QB3 energy calculations.

-

O'Brien,Niemann

, p. 1386,1388 (1957)

-

Highly efficient activated carbon loaded TiO2 for photo defluoridation of pentafluorobenzoic acid

Ravichandran,Selvam,Swaminathan

, p. 89 - 96 (2010)

The activated carbon loaded TiO2-P25 catalysts were prepared and characterized by diffuse reflectance spectra (DRS), FT-IR, scanning electron micrograph (SEM), X-ray diffraction (XRD) and BET surface area analysis. The photocatalytic efficiency

-

Chalfont et al.

, p. 367 (1967)

-

Effect of pyridine and tribenzylamine on the hydrolysis kinetics of benzoyl chloride in water-dioxane system

Batiha, Mohammad A.,Chizhova, Elena A.,Batiha, Marwan M.,Al-Makhadmeh, Leema A.,Rawadieh, Saleh,Alqasaimeh, Muawia,Marashli, Abdullah

, p. 1888 - 1890 (2017)

The aim of this paper was to study the effect of tribenzylamine and pyridine on the kinetics of the hydrolysis reaction of benzoyl chloride in water-dioxane solution. The benzoyl chloride and water initial concentrations were 0.005 and 1 mol/L, respectively. While, the initial concentrations of pyridine and tribenzylamine varied in the range of 0.005-0.02 mol/L and 0.007-0.014 mol/L, respectively. It was found that the addition of tribenzylamine to benzoyl chloride hydrolysis reaction has no catalytic effect and hence the rate constant can be calculated using a first-order rate equation. In the presence of pyridine, reaction obeyed second-order rate. The relationship between the reaction rate constant and pyridine initial concentration was found to be linear with a rate constant of 0.752 × 10–3 min–1.

James,Weissberger

, p. 2040 (1937)

COMPONENTS OF THE GALLS ON THE LEAVES OF PONGAMIA GLABRA: STRUCTURES OF PONGAGALLONE-A AND PONGAGALLONE-B

Gandhidasan, Rathinasamy,Neelakantan, Sthanusubramania,Raman, Pathai Venkateswara,Devaraj, Savithri

, p. 281 - 284 (1987)

The chemical examination of the galls present on the infected leaves of the plant Pongamia glabra has yielded, in addition to a number of known compounds, two new prenylated β-diketones, pongagallone-A and pongagallone-B.Evidence for their structures is presented. Key Word Index--Pongamia glabra; Leguminosae; pongagallone-A; pongagallone-B; β-diketones.

Preparation and Characterization of Destructible Surfactants

Jaeger, David A.,Frey, Moira R.

, p. 311 - 315 (1982)

Surfactants have been designed and prepared specifically for the application of surfactant-based media to organic synthesis.Condensation of 5-chloro-2-pentanone with 1,2-dodecanediol (3) yielded 2-methyl-2-(3-chloropropyl)-4-decyl-1,3-dioxolane (6), which on reaction with quinuclidine and pyridine gave 1--1-azoniabicyclooctane chloride (1) and 1-pyridinium chloride (2a), respectively.Ketal-based surfactants 1 and 2a are stable under neutral and basic conditions but readily hydrolyze under acidic conditions to 1-(4-oxopentyl)-1-azoniabicyclooctane chloride (4) and 1-(4-oxopentyl)pyridinium chloride (5), respectively, and diol 3.In catalysis of the potassium permanganate oxidation of piperonal to piperonylic acid and the aqueous sodium hydroxide hydrolysis of α,α,α-trichlorotoluene to benzoic acid, surfactants 1 and 2a are about as effective as cetyltrimethylammonium bromide.

Gardner,Hodgson

, p. 1819 (1909)

Boron triiodide-N-N-diethylaniline complex: A new reagent for cleaving esters

Kabalka,Narayana,Reddy

, p. 1793 - 1798 (1992)

Boron triiodide N,N-diethylaniline complex was used for the hydrolysis, transesterification, and aminolysis of esters.

Biocompatible Ionic Liquid Based on Curcumin as Fluorescence Probe for Detecting Benzoyl Peroxide without the Interference of H2O2

Zhu, Qiu-Hong,Yuan, Wen-Li,Zhang, Lei,Zhang, Guo-Hao,He, Ling,Tao, Guo-Hong

, (2019)

Accurate estimation of the level of benzoyl peroxide (BPO) is of considerable significance because of its threat to humanity and environment. Several research efforts have been devoted to the detection of BPO by fluorescent method with high sensitivity and selectivity. However, it remains challenging to eliminate the interference of H2O2 due to its similar properties to BPO. In this work, the first demonstration of fluorescent and colorimetric probe for specific detection of BPO without the disturbance of H2O2 was achieved by curcumin-based ionic liquid (CIL) that possesses simple fabrication, good biocompatibility, and low cost. The fluorescence quenches and emission peak blue-shifts once the probe selectively interacts with BPO, whereas the other possible interfering agents, including H2O2, do not have this phenomenon. The probe CIL exhibits prominent sensitivity for BPO sensing and enables the detection limit at levels as ultralow as 10 nM. The local detection of BPO in practical samples is realized by visualization using a portable device derived from CIL-based liquid atomizer.

On cyanopigment synthesis. 3. Constitution of pigment by condensation of N, N-dimethylthiopropionamide-S-phenacylbromid with salicyladehyde

Yamaguchi

, p. 997 - 1002 (1968)

-

Prenylated benzoylphloroglucinols and xanthones from the leaves of garcinia oblongifolia with antienteroviral activity

Zhang, Hong,Tao, Ling,Fu, Wen-Wei,Liang, Shuang,Yang, Yi-Fu,Yuan, Qing-Hong,Yang, Da-Jian,Lu, Ai-Ping,Xu, Hong-Xi

, p. 1037 - 1046 (2014)

An acetone extract of the leaves of Garcinia oblongifolia showed antiviral activity against enterovirus 71 (EV71) using a cytopathic effect inhibition assay. Bioassay-guided fractionation yielded 12 new prenylated benzoylphloroglucinols, oblongifolins J-U (1-12), and five known compounds. The structures of 1-12 were elucidated by spectroscopic analysis including 1D- and 2D-NMR and mass spectrometry methods. The absolute configurations were determined by a combination of a Mosher ester procedure carried out in NMR tubes and ECD calculations. Compared to ribavirin (IC50 253.1 μM), compounds 1, 4, and 13 exhibited significant anti-EV71 activity in vitro, with IC50 values of 31.1, 16.1, and 12.2 μM, respectively. In addition, the selectivity indices of these compounds were 1.5, 2.4, and 3.0 in African green monkey kidney (Vero) cells, respectively.

-

Menger et al.

, p. 3803 (1975)

-

-

Fokin,A.V. et al.

, (1975)

-

-

Briner,Demolis,Paillard

, (1932)

-

Kinetics and mechanism of oxidation of benzohydrazide by bromate catalyzed by vanadium(IV) in aqueous acidic medium

Shewale,Phadkule,Gokavi

, p. 151 - 159 (2008)

The reaction between benzohydrazide and potassium bromate catalyzed by vanadium(IV) was studied under pseudo-first-order condition keeping large excess of hydrazide concentration over that of the oxidant. The initiation of the reaction occurs through oxidation of the catalyst vanadium(IV), VO2+, to vanadium(V), VO2+, which then reacts with hydrazide to give N,N′-diacylhydrazine and benzoic acid as the products. The order in [H+] is found to be two, and its effect is due to protonation and hydrolysis of oxidized form of the catalyst to form HVO3. The oxidized form of the catalyst, VO2+, forms a complex with the protonated hydrazide as evidenced by the occurrence of absorption maxima at 390 nm. The rate of the reaction remains unaffected by the increase in the ionic strength. The activation parameters were determined, and data support the mechanism. The detailed mechanism and the rate equation are proposed for the reaction.

-

Hey et al.

, p. 1477 (1967)

-

ELECTRON-TRANSFER MEDIATED PHOTOOXYGENATION OF BIPHENYL AND ITS DERIVATIVES IN THE PRESENCE OF Mg(ClO4)2

Mizuno, Kazuhiko,Ichinose, Nobuyuki,Tamai, Toshiyuki,Otsuji, Yoshio

, p. 5823 - 5826 (1985)

The 9,10-dicyanoanthracene-sensitized photooxygenation of biphenyl and its derivatives in the presence of Mg(ClO4)2 in acetonitrile brought about the oxidative cleavage of benzene nucleus to give benzoic acid and its derivatives.

Facile synthesis of polystyrene/gold composite particles as a highly active and reusable catalyst for aerobic oxidation of benzyl alcohol in water

Li, Yunxing,Gao, Yan,Yang, Cheng,Sha, Shengsheng,Hao, Jiefu,Wu, Yan

, p. 24769 - 24772 (2014)

PS/Au composite particles have been synthesized facilely based on a thermodynamic effect. More significantly, the PS/Au composite particles can catalyze the aerobic oxidation of benzyl alcohol remarkably under mild conditions (1 atm, air as oxidant, Ksub

-

Briner,Lardon

, p. 1062,1066 (1936)

-

-

Klimenko

, (1911)

-

Catalytic and inhibitory effects of β-cyclodextrin on the hydrolysis of benzoic anhydride

Brandao, Tiago A.S.,Dal Magro, Jacir,Chiaradia, Louise D.,Da Graca Nascimento, Maria,Nome, Faruk,Tato, Jose V.,Yunes, Rosendo A.

, p. 370 - 375 (2004)

The hydrolysis of benzoic anhydride (Bz2O) in the presence of β-cyclodextrin (β-CD) was studied in aqueous solution as a function of pH, temperature and ionic strength, at 25°C. The experimental rate constant versus pH profiles show that, in the region of spontaneous water reaction (pH 3.0-6.5), β-CD inhibits the reaction and the isotope effect (k H2O/kD2O = 4.7) indicates that the rate determining step of the reaction corresponds to the water-catalyzed nucleophilic attack of water on the carbonyl group of Bz2O. Conversely, whereas inhibition is observed at pH 6.0, catalysis of the hydroxide ion reaction is observed at pH 8.0 and it is found that the activation entropy is responsible for the catalytic phenomena in the basic hydrolysis of benzoic anhydride. Copyright 2004 John Wiley & Sons, Ltd.

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Gladyshev,E.N. et al.

, p. 25 - 29 (1975)

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Hydrolysis of several substituted methyl benzoates in the aqueous solution

Steinberg,Lena

, p. 965 - 969 (1995)

The hydrolysis of several ring substituted methyl benzoates was investigated in aqueous solution over a pH range of 3-10. Both the pH dependence (at pH5) and the variation of hydrolysis rates with ring substitution are consistent with a mechanism involving the addition of hydroxide ion to the ester carbonyl group. Extrapolation of the rate data to a pH and temperature that would be consistent with soil and groundwater (pH 8, 10 degrees C) indicate that these esters could have hydrolysis half lives from several months to several years in the environment. (Authors)

ACID-CATALYZED HYDROLYSIS OF BENZOYLHYDRAZINE IN SULFURIC ACID

Zarakhan, N. G.,Borisova, E. N.,Nechaev, P. P.,Zaikov, G. E.

, (1981)

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Novel oxo-peroxo molybdenum(VI) complexes incorporating 8-quinolinol: Synthesis, structure and catalytic uses in the environmentally benign and cost-effective oxidation method of methyl benzenes: Ar(CH3), (n = 1, 2)

Bandyopadhyay, Ratna,Biswas, Sudeb,Guha, Subhadra,Mukherjee, Alok K.,Bhattacharyya, Ramgopal

, p. 1627 - 1628 (1999)

A hitherto unknown distorted pentagonal bipyramidal complex, [MoO(O2)(QO)2], very efficiently catalyses homogeneous liquid phase oxidation of methylbenzenes, viz. toluene and o- and p-xylenes to benzoic acid, phthalic acid and p-toluic acid respectively, using H2O2 and O2 as oxidants.

-

Dimitrov et al.

, p. 674,676, 678, 679 (1970)

-

-

Ogata et al.

, p. 2707 (1952)

-

Blasdale

, p. 1141,1146 (1903)

-

Williams,Whitaker

, p. 2562,2564 (1968)

-

-

Church

, p. 52 (1862)

-

-

Briner,Biedermann

, p. 213,215 (1933)

-

-

Wall,Claussen

, p. 2812,2813 (1939)

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Kharasch, M. S.,May, E. M.,Mayo, F. R.

, p. 175 - 192 (1938)

Facile synthesis of 2,3-diacetoxyflavanones from 3-aminoflavones

Miyake, Hideyoshi,Nishino, Shouko,Sasaki, Mitsuru

, p. 952 - 953 (2009)

3-Aminoflavone reacts with isopentyl nitrite in acetic acid to give 2,3-diacetoxyflavanone in good yield. 3-Aminoflavone, the starting material, is readily available, and this method is a powerful tool for the synthesis of 2,3-dihydroxyflavanone derivativ

A DITERPENE FROM EUPHORBIA MADDENI

Sahai, R.,Rastogi, R. P.,Jakupovic, J.,Bohlmann, F.

, p. 1665 - 1668 (1981)

Key Word Index - Euphorbia maddeni; Euphorbiaceae; euphornin; jatrophone diterpene. From the anticancer-active CHCl3 extract of the plant Euphorbia maddeni, a polyacylated diterpene of jatrophone type, euphornin, has been isolated and its structure elucidated by physico-chemical methods.

-

Kusnezow,Stepanenko

, (1930)

-

Heavy-Atom Isotope Effects on the Acid-Catalyzed Hydrolysis of Methyl Benzoate

Marlier, John F.,O'Leary, Marion H.

, p. 2175 - 2177 (1981)

-

Zn(II)-to-Cu(II) transmetalation in an amide functionalized complex and catalytic applications in styrene oxidation and nitroaldol coupling

Da Silva, M. Fátima C. Guedes,Karmakar, Anirban,Kuznetsov, Maxim L.,Martins, Luísa M. D. R. S.,Paul, Anup,Pombeiro, Armando J. L.

, (2020)

The mononuclear zinc(II) complex cis-[ZnL2(H2O)2] (1; L = 4-(pyridin-3- ylcarbamoyl)benzoate) was synthesized and characterized. By soaking crystals of 1 in a mixture of DMF-H2O solution containing a slight excess of Cu(NO3)2 × 3H2Oa transmetalation reaction occurred affording the related copper(II) complex trans-[CuL2(H2O)2] (2). The structures of the compounds were authenticated by single crystal X-ray diffraction revealing, apart from a change in the isomerism, an alteration in the relative orientation of the chelating carboxylate groups and of the pyridine moieties. H-bond interactions stabilize both geometries and expand them into two-dimensional (2D) networks. The transmetalation was confirmed by SEM-EDS analysis. Moreover, the thermodynamic feasibility of the transmetalation is demonstrated by density-functional theory (DFT) studies. The catalytic activities of 1 and 2 for the oxidation of styrene and for the nitroaldol (Henry) C-C coupling reaction were investigated. The copper(II) compound 2 acts as heterogeneous catalyst for the microwave-assisted oxidation of styrene with aqueous hydrogen peroxide, yielding selectively (>99percent) benzaldehyde up to 66percent of conversion and with a turnover frequency (TOF) of 132 h-1. The zinc(II) complex 1 is the most active catalyst (up to 87percent yield) towards the nitroaldol (Henry) coupling reaction between benzaldehyde and nitro-methane or -ethane to afford the corresponding β-nitro alcohols. The reaction of benzaldehyde with nitroethane in the presence of 1 produced 2-nitro-1-phenylpropanol in the syn and the anti diastereoisomeric forms, with a considerable higher selectivity towards the former (66:34).

-

Briner,Papazian

, p. 497,503 (1940)

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Carbonylation of bromobenzene in a biphasic medium catalysed by water-soluble palladium complexes derived from tris(3-sulphophenyl)phosphine

Monteil, Fanny,Kalck, Philippe

, p. 45 - 52 (1994)

The hydroxycarbonylation of bromobenzene has been explored in a biphasic medium.Water-soluble (TPPTS = sodium salt of tris(3-sulphophenyl) phosphine) catalyses selectively this carbonylation reaction into benzoic acid.This complex is maintained intact in the presence of an excess of tris(3-sulphophenyl)phosphine salt.Even when a hydrogen donor is added, the reaction is limited to hydroxycarbonylation.The two complexes and have been synthesized.A catalytic cycle is proposed.Key words: Palladium; Carbonylation; Biphatic medium Phosphines; Mechanism

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Nystrom et al.,zit. bei Crompton,Woodruff

, p. 44,46 (1950)

-

-

Briner,de Chastonay

, p. 1904 (1954)

-

-

Ross et al.

, p. 1018 (1969)

-

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Siegel,Lanphear

, p. 942,944 (1979)

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Carboxylic acids from methyl aryl ketones by means of a new composite aerobic oxidation process

Bj?rsvik, Hans-René,Liguori, Lucia,Rodríguez González, Raquel,Vedia Merinero, José Angel

, p. 4985 - 4987 (2002)

A new aerobic oxidation method for conversion of methyl aryl ketones to the corresponding benzoic acids is presented. The method is cheap and environmentally friendly, which also makes it suitable for large scale industrial use. The method affords a yield of >75% with an almost 100% selectivity. Experiments have shown that the process operates following two mechanistic pathways, namely by base-catalysed autoxidation and by single electron transfer processes.

Co/rGO synthesized: Via the alcohol-thermal method as a heterogeneous catalyst for the highly efficient oxidation of ethylbenzene with oxygen

Gao, Lingfeng,Zhuge, Wenyun,Feng, Xue,Sun, Wei,Sun, Xu,Zheng, Gengxiu

, p. 8189 - 8194 (2019)

Co3O4 nanoparticles uniformly dispersed on reduced graphene oxide (Co/rGO) were synthesized by the alcohol-thermal method as a highly efficient catalyst with initiator NHPI for the selective oxidation of ethylbenzene to acetophenone using O2 as a green oxidant. X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), and X-ray photoelectron spectroscopy (XPS) were carried out for chemical, morphological, and size analyses of the nanocomposite. The ensuing catalyst was evaluated for the oxidation of ethylbenzene with a high conversion of 84.1% and an acetophenone selectivity of 96.2% within only 2 h. Moreover, the Co/rGO catalyst showed good recyclability and activity towards the selective oxidation of ethylbenzene. It was revealed that the enhanced catalytic activity of Co/rGO was derived from the interaction of the active Co3O4 center and the graphene support material.

Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water

Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David

, (2021/11/30)

Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

Niu, Kaikai,Shi, Xiaodi,Ding, Ling,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin

, (2021/12/13)

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.

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.

Selective catalytic synthesis of bio-based high value chemical of benzoic acid from xylan with Co2MnO4@MCM-41 catalyst

Fan, Minghui,He, Yuting,Li, Quanxin,Luo, Yuehui,Yang, Mingyu,Zhang, Yanhua,Zhu, Lijuan

, (2021/12/20)

The efficient synthesis of bio-based chemicals using renewable carbon resources is of great significance to promote sustainable chemistry and develop green economy. This work aims to demonstrate that benzoic acid, an important high added value chemical in petrochemical industry, can be selectively synthesized using xylan (a typical model compound of hemicellulose). This novel controllable transformation process was achieved by selective catalytic pyrolysis of xylan and subsequent catalytic oxidation. The highest benzoic acid selectivity of 88.3 % with 90.5 % conversion was obtained using the 10wt%Co2MnO4@MCM-41 catalyst under the optimized reaction conditions (80 °C, 4 h). Based on the study of the model compounds and catalyst's characterizations, the reaction pathways for the catalytic transformation of xylan to bio-based benzoic acid were proposed.

Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading

Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui

, (2021/12/13)

Acceptorless dehydrogenative coupling (ADC) of alcohols and water/hydroxides is an emergent and graceful approach to produce carboxylic acids. Therefore, it is of high demand to develop active and practical catalysts/catalytic systems for this attractive transformation. Herein, we designed and fabricated a series of cyclometallated N-heterocyclic carbene-Ru (NHC-Ru) complexes via ligand tuning of [Ru-1], the superior complex in our previous work. Gratifyingly, gram-scale synthesis of carboxylic acids was efficiently enabled at an ultralow Ru loading (62.5 ppm) in open air. Moreover, effects of distinct ancillary NHC ligands and other parameters on this catalytic process were thoroughly studied, while further systematic studies were carried out to provide rationales for the activity trend of [Ru-1]-[Ru-7]. Finally, determination of quantitative green metrics illustrated that the present work exhibited superiority over representative literature reports. Hopefully, this study could provide valuable input for researchers who are engaging in metal-catalyzed ADC reactions.

Process route upstream and downstream products

Process route

4,4'-benzophenonedicarboxylic acid
964-68-1

4,4'-benzophenonedicarboxylic acid

terephthalic acid
100-21-0

terephthalic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
bei der Kalischmelze;
salicylaldehyde-(<i>O</i>-benzoyl oxime )
3848-37-1

salicylaldehyde-(O-benzoyl oxime )

salicylonitrile
611-20-1

salicylonitrile

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With hydrogenchloride; diethyl ether;
4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one
82301-50-6,82301-53-9,113697-03-3

4-(3-methoxybenzylidene)-2-phenyloxazol-5(4H)-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
Behandeln des Reaktionsprodukts mit alkal. Wasserstoffperoxyd-Loesung;
4-chloro-3-sulfo-benzoic acid

4-chloro-3-sulfo-benzoic acid

sodium formate
141-53-7

sodium formate

isophthalic acid
121-91-5

isophthalic acid

terephthalic acid
100-21-0

terephthalic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
Schmelzen des Kaliumsalzes;
4-bromo-3-sulfo-benzoic acid
154117-60-9

4-bromo-3-sulfo-benzoic acid

sodium formate
141-53-7

sodium formate

isophthalic acid
121-91-5

isophthalic acid

terephthalic acid
100-21-0

terephthalic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
Schmelzen des Kaliumsalzes;
2,2-bis(4-methoxyphenyl)-2-phenylacetonitrile
120264-80-4

2,2-bis(4-methoxyphenyl)-2-phenylacetonitrile

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
bei der Kalischmelze;
Conditions
Conditions Yield
With tert.-butylhydroperoxide; copper(ll) bromide; In acetic anhydride; at 80 ℃;
14%
52%
With hydrogen bromide; oxygen; at 195 - 200 ℃; Gasphase;
With oxygen; sodium bromide; cobalt(II) acetate; at 64.9 ℃; Rate constant; kinetic control and diffusion control;
chloroform
67-66-3,8013-54-5

chloroform

1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione
6327-79-3

1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione

phenylglyoxal hydrate
1074-12-0

phenylglyoxal hydrate

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

p-methoxyphenylglyoxal
1076-95-5

p-methoxyphenylglyoxal

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
bei der Ozonspaltung;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione
6327-79-3

1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione
6327-79-3

1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield

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