scholarly journals Hydrogenation of benzoic acid derivatives over Pt/TiO2 under mild conditions

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Miao Guo ◽  
Xiangtao Kong ◽  
Chunzhi Li ◽  
Qihua Yang
Keyword(s):  
Electron Transfer ◽  
Benzoic Acid ◽  
High Efficiency ◽  
Carboxyl Groups ◽  
Carboxyl Group ◽  
Benzoic Acids ◽  
Catalyst Poisoning ◽  
Benzoic Acid Derivatives ◽  
Mild Conditions ◽  
Transfer Direction

AbstractHydrogenation of benzoic acid (BA) to cyclohexanecarboxylic acid (CCA) has important industrial and academic significance, however, the electron deficient aromatic ring and catalyst poisoning by carboxyl groups make BA hydrogenation a challenging transformation. Herein, we report that Pt/TiO2 is very effective for BA hydrogenation with, to our knowledge, a record TOF of 4490 h−1 at 80 °C and 50 bar H2, one order higher than previously reported results. Pt/TiO2 catalysts with electron-deficient and electron-enriched Pt sites are obtained by modifying the electron transfer direction between Pt and TiO2. Electron-deficient Pt sites interact with BA more strongly than electron-rich Pt sites, helping the dissociated H of the carboxyl group to participate in BA hydrogenation, thus enhancing its activity. The wide substrate scope, including bi- and tri-benzoic acids, further demonstrates the high efficiency of Pt/TiO2 for hydrogenation of BA derivatives.

Electron impact studies. LXXVIII. Rearrangement ions and proximity effects in the 'doubly charged ion' mass spectra of benzoic acid derivatives

1973 ◽  
Vol 26 (1) ◽  
pp. 195 ◽  
Author(s):  
JH Bowie
Keyword(s):  
Benzoic Acid ◽  
Mass Spectra ◽  
General Feature ◽  
Molecular Ions ◽  
Ring System ◽  
Proximity Effects ◽  
Carboxyl Groups ◽  
Benzoic Acids ◽  
Benzoic Acid Derivatives ◽  
Doubly Charged

The technique of Beynon1,2 has been used to determine the ?doubly charged ion? mass spectra of a series of benzoic acid derivatives. A general feature of all spectra is the presence of pronounced M-CO species. The losses of carbon monoxide from the doubly charged molecular ions of m- amino- and m-hydroxy-benzoic acids originate mainly from the carboxyl groups, whereas the predominant loss from benzoic acid involves the aryl ring system. The spectra of anthranilates and salicylates contain peaks produced by characteristic proximity effects.

scholarly journals Pt/TiO2 Catalyzed Hydrogenation of Benzoic Acid with Unprecedented High Activity

2020 ◽  
Author(s):  
Miao Guo ◽  
Xiangtao Kong ◽  
Chunzhi Li ◽  
Qihua Yang
Keyword(s):  
Electron Transfer ◽  
Benzoic Acid ◽  
High Activity ◽  
Aromatic Ring ◽  
Terephthalic Acid ◽  
Phthalic Acid ◽  
Dft Calculation ◽  
Carboxyl Group ◽  
Trimesic Acid ◽  
Transfer Direction

Abstract The hydrogenation of benzoic acid (BA) to corresponding cyclohexanecarboxylic acid has important industry and academia significance, however, the electron deficient aromatic ring and the catalyst “poison” by carboxyl group make BA hydrogenation as one of the most challenging transformations. Herein, we found that Pt NPs deposited on TiO2 were very effective for BA hydrogenation with a record TOF of 4490 h− 1 under 80 oC and 50 bar H2 in hexane, one order higher than the reported results. DFT calculation showed that Pt NPs had a weaker interaction with BA than Ru and Pd NPs commonly used for BA hydrogenation, which improved the toxicity resistance of catalyst to BA. Pt/TiO2 catalysts with electron deficient and electron enriched Pt sites were successfully synthesized by modifying the electron transfer direction between Pt and TiO2. Isotopic experiments suggested the participation of dissociated H from carboxyl group in BA hydrogenation. Consequently, the electron deficient Pt sites with stronger adsorption of BA were more active than electron rich Pt sites in BA hydrogenation. In addition to BA, terephthalic acid, iso-phthalic acid, trimesic acid and other BA derivatives could also be efficiently converted to corresponding aromatic saturated products, demonstrating the wide substrate scope of Pt/TiO2.

scholarly journals 4-[(2-Carboxyethyl)amino]benzoic acid monohydrate

2012 ◽  
Vol 68 (4) ◽  
pp. o1098-o1098 ◽  
Author(s):  
Chunman Jia ◽  
Shangwen Chen ◽  
Wenbing Yuan
Keyword(s):  
Hydrogen Bonds ◽  
Benzoic Acid ◽  
Title Compound ◽  
Organic Molecule ◽  
Organic Molecules ◽  
Carboxyl Groups ◽  
Water Molecules ◽  
Carboxyl Group ◽  
Compound C ◽  
Amino Benzoic Acid

In the title compound, C10H11NO4·H2O, the carboxyl group is twisted at a dihedral angle of 6.1 (3)° with respect to the benzene ring. In the crystal, the organic molecules are linked by pairs of O—H...O hydrogen bonds involving both carboxyl groups, forming zigzag chains propagating along theb-axis direction. The water molecules form [100] chains linked by O—H...O hydrogen bonds. The organic molecule and water chains are cross-linked by N—H...Owaterand Owater—H...O hydrogen bonds, generating (001) sheets.

scholarly journals 4-[1-(4-Chlorophenyl)-3-oxobutylamino]benzoic acid

2007 ◽  
Vol 63 (11) ◽  
pp. o4420-o4421
Author(s):  
B. Narayana ◽  
K. Sunil ◽  
B. K. Sarojini ◽  
H. S. Yathirajan ◽  
Michael Bolte
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Benzoic Acid ◽  
Dihedral Angle ◽  
Title Compound ◽  
Carboxyl Groups ◽  
Carboxyl Group ◽  
Amino Group ◽  
Aromatic Rings ◽  
Compound C

Geometric parameters of the title compound, C17H16ClNO3, are in the usual ranges. The two aromatic rings are almost perpendicular, with a dihedral angle of 89.26 (5)°. The carboxyl group is coplanar with the aromatic ring to which it is attached [dihedral angle = 1.70 (17)°]. The packing involves inversion-symmetric dimers bridged via hydrogen bonding of the carboxyl groups. In addition, there is an N—H...O hydrogen bond between the amino group and the carbonyl O atom.

scholarly journals CYP199A4 catalyses the efficient demethylation and demethenylation of para-substituted benzoic acid derivatives

RSC Advances ◽  
2015 ◽  
Vol 5 (64) ◽  
pp. 52007-52018 ◽  
Author(s):  
Tom Coleman ◽  
Rebecca R. Chao ◽  
John B. Bruning ◽  
James J. De Voss ◽  
Stephen G. Bell
Keyword(s):  
Cytochrome P450 ◽  
Benzoic Acid ◽  
Rhodopseudomonas Palustris ◽  
Cytochrome P450 Enzyme ◽  
Benzoic Acids ◽  
Benzoic Acid Derivatives ◽  
P450 Enzyme

CYP199A4, a cytochrome P450 enzyme from Rhodopseudomonas palustris HaA2, is able to efficiently demethylate a range of benzoic acids at the para-position. It can also catalyse demethenylation reactions.

scholarly journals Assessment of the toxicity of benzoic acid derivatives in the intragastric intake

2020 ◽  
Vol 99 (7) ◽  
pp. 755-760
Author(s):  
Larisa G. Gorokhova ◽  
Nadezhda N. Mikhailova ◽  
Evgeniya V. Ulanova ◽  
Tatyana K. Yadykina
Keyword(s):  
Benzoic Acid ◽  
The Body ◽  
Morphological Data ◽  
Benzoic Acids ◽  
Chemical Production ◽  
Hazard Class ◽  
Chlorobenzoic Acid ◽  
Benzoic Acid Derivatives ◽  
Derivatives Of ◽  
Predominant Effect

Introduction. Benzoic acid and its numerous derivatives are widely used in all areas of chemical production. However, there is no information about the toxic properties of a large number of benzoic acid derivatives. The purpose of the study was to study the toxic properties of several derivatives of benzoic acids in intragastric intake in an experiment.Material and methods. The following derivatives of benzoic acid were studied: 4-chlorobenzoic, 4-methoxybenzoic, p-acetoxybenzoic and 2-methoxy-5-sulfamoylbenzoic acids. The studies were performed on white laboratory rats; toxicity was studied in repeated experiments with the oral administration of substances. The condition of the animals was assessed by integrated parameters, indices of biochemical analyzes of blood serum, morphological data from a study of the liver, kidneys, heart, stomach, pancreas and thyroid glands.\Results. According to toxicometric data, 4-chlorobenzoic acid is classified as moderately hazardous, hazard class III, 4-methoxybenzoic, p-acetoxybenzoic and 2-methoxy-5-sulfamoylbenzoic acids belong to hazard class IV (low hazard). Under the subchronic administration of all the studied compounds, there was a significant increase in urea concentration, aminotransferase activity, and a decrease in catalase activity, most pronounced in poisoning with 4-chlorobenzoic and 4-methoxybenzoic acids. Morphohistological studies confirmed the predominant effect of benzoic acid derivatives on the functioning of the hepatorenal system in the animals exposed to poisoning. Microscopically fatty liver dystrophy was observed, there was a diffuse proliferation of Kupffer cells. In the kidneys, the glomeruli were enlarged in size; the lumen of the Shumlyansky-Bowman’s capsule was narrowed as a result of swelling of the capillary endothelium.Conclusion. Subchronic oral intake of 4-chlorobenzoic, 4-methoxybenzoic, p-acetoxybenzoic, and 2-methoxy-5-sulfamoylbenzoic acids leads to many disorders in the body, which are mainly of a common toxic nature with a predominant effect on the state of the hepatorenal system. The most pronounced organotoxic effect is manifested in the chlorine-containing derivative of benzoic acid - 4-chlorobenzoic acid. Due to the low toxicity of benzoic acids, chronic poisoning in the workplace is unlikely; it is possible only if the technological processes are disrupted.

scholarly journals Free Radical Scavenging Activity of Five Benzoic Acid Derivatives: A Theoretical M06-2X Study

2022 ◽  
Author(s):  
Bienfait Kabuyaya Isamura ◽  
Issofa Patouossa ◽  
Isaac Kaba Elaka ◽  
Aristote Matondo ◽  
Pius Tshimankinda Mpiana
Keyword(s):  
Electron Transfer ◽  
Free Radical ◽  
Benzoic Acid ◽  
Gas Phase ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Free Radical Scavenging ◽  
Basis Set ◽  
Antioxidant Power ◽  
Benzoic Acid Derivatives

The meta hybrid M06-2X functional combined with the 6-311++G(d,p) basis set are used to investigate the antioxidant activity of five benzoic acid derivatives naturally occurring in several plant food: gallic acid, para-hydroxybenzoic acid, protocatechuic acid, syringic acid and vanillic acid. To assess the antioxidant properties of these compounds, three mechanisms of free radicals scavenging are considered, namely the hydrogen atom transfer (HAT), stepwise electron transfer proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) models. The effect of polar environments on the antioxidant power of these compounds is mimicked in water and methanol using the IEF-PCM solvation method. Our findings suggest that HAT is the preferred mechanistic pathway in gas phase, while SPLET is favoured in polar mediums. Protocatechuic and gallic acids are the most active in gas and polar solutions respectively, whereas PHBA is the least active in all the environments considered. The O-H group in para position of the carboxylic group (O3-H for GA and O2-H for the rest) is confirmed to be the most reactive site in gas phase, while in solution it is either of the O1-H site (for PHBA, PCA, SA and VA) or O4-H groups (for GA). The “HOMO-rule” of free radical scavenging ability does not seem to account properly for the antioxidant properties of this set of chemicals.

scholarly journals 2,6-Bis(trifluoromethyl)benzoic acid

2009 ◽  
Vol 65 (6) ◽  
pp. o1217-o1217 ◽  
Author(s):  
John M. Tobin ◽  
Jason D. Masuda
Keyword(s):  
Hydrogen Bonding ◽  
Benzoic Acid ◽  
Title Compound ◽  
Carboxyl Groups ◽  
Dihedral Angles ◽  
Carboxyl Group ◽  
Asymmetric Unit ◽  
Compound C ◽  
Independent Molecules ◽  
Trifluoromethyl Groups

The title compound, C9H4F6O2, contains two molecules in the asymmetric unit, one of which exhibits disorder in both of its trifluoromethyl groups. The dihedral angles between the benzene ring and the carboxyl group are 71.5 (2) and 99.3 (2)° in the two independent molecules. The compound exhibits a catemeric structure resulting from intermolecular O—H...O hydrogen bonding between the carboxyl groups.

Bjerkandera adusta as a source of benzoic acid derivatives targeting 26S proteasome and cathepsins B&L

2019 ◽  
Author(s):  
K Georgousaki ◽  
N Tsafantakis ◽  
S Gumeni ◽  
V González-Menéndez ◽  
G Lambrinidis ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
26S Proteasome ◽  
Bjerkandera Adusta ◽  
Benzoic Acid Derivatives
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