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Cas Database

108-95-2

108-95-2

Identification

  • Product Name:Phenol

  • CAS Number: 108-95-2

  • EINECS:203-632-7

  • Molecular Weight:94.113

  • Molecular Formula: C6H6O

  • HS Code:2907111000

  • Mol File:108-95-2.mol

Synonyms:Carbolic Acid;Benzenol;Phenylic Acid;Hydroxybenzene;Phenic acid;Monohydroxybenzene;Monophenol;Oxybenzene;Phenyl alcohol;Phenyl hydrate;Phenyl hydroxide;Phenylic alcohol;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT,CorrosiveC,FlammableF,HarmfulXn

  • Hazard Codes: T:Toxic;

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H314 Causes severe skin burns and eye damage H331 Toxic if inhaled H341 Suspected of causing genetic defects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. To remove substance use polyethylene glycol 300 or vegetable oil. Refer for medical attention . Wear protective gloves when administering first aid. 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. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention . Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)Will burn eyes and skin. The analgesic action may cause loss of pain sensation. Readily absorbed through skin, causing increased heart rate, convulsions, and death. (USCG, 1999)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)Toxic hazard rating is very toxic: probable oral lethal dose (human) is 50-500 mg/kg. Ingestion of 1 gram has been lethal to humans. Lethal amounts may be absorbed through skin or inhaled. Industrial contact can cause chronic poisoning with kidney and liver damage. Persons affected with hepatic or kidney diseases are at a greater risk. (EPA, 1998) Because of the rapid onset of symptoms, possible increased phenol absorption with dilution, and the potential for development of seizures, activated charcoal (1 g/kg) is preferable to lavage or syrup of ipecac. In vitro studies indicated that activated charcoal efficiently absorbs phenol. A cathartic should be given after oral activated charcoal.

  • 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 be ineffective. 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. Keep run off-water out of sewers and water sources. /Phenol, solid/ Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)Special Hazards of Combustion Products: Unburned vapor is toxic Behavior in Fire: Yields flammable vapors when heated, which will form explosive mixtures with air (USCG, 1999)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)Flammable vapors when heated. Runoff from fire control water may give off poisonous gases and cause pollution. Mixtures of 9-10% phenol in air are explosive. Avoid aluminum chloride/nitrobenzene mixture, peroxodisulfuric acid, peroxomonosulfuric acid and strong oxidizing agents. Decomposes slowly on air contact. Avoid contact with strong oxidizing agents. (EPA, 1998) 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: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Control runoff and isolate discharged material for proper disposal. Approach release from upwind.

  • 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. Provision to contain effluent from fire extinguishing. Separated from strong oxidants and food and feedstuffs. Dry. Well closed. Keep in a well-ventilated room.Phenol should be stored in closed containers in an area which is adequate to ensure that airborne phenol concentrations do not exceed 20 mg/cu m. Conditions shall be controlled to prevent overheating and the buildup of pressure in phenol containers. Storage tanks must be electrically grounded and bonded to transfer lines. Transfer and storage systems shall be designed and operated to prevent blockage by condensed phenol. Open flames are prohibited when drums of phenol are heated to melt the contents. The internal pressure will be vented by placing the drums with the bung up and the bung loosened. The bungs shall be tightened prior to moving or handling drums. Drums, carboys, or other containers of phenol shall be closed while being handled or moved. Transfer from such containers shall be done carefully to avoid splashes, spills, or other possible circumstances by which an employee may come in contact with phenol. Bulk storage facilities shall be designed and constructed to contain any leaks or spills.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 15 Min Ceiling Value: 15.6 ppm (60 mg/cu m), skin.Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 ppm (19 mg/cu m).Biological 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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Relevant articles and documentsAll total 2855 Articles be found

Chlorine-nickel interactions in gas phase catalytic hydrodechlorination: Catalyst deactivation and the nature of reactive hydrogen

Shin, Eun-Jae,Spiller, Andreas,Tavoularis, George,Keane, Mark A.

, p. 3173 - 3181 (1999)

The gas phase hydrodechlorination of chlorobenzene and 3-chlorophenol (where 473 K ≤ T ≤ 573 K) has been studied using a 1.5% w/w Ni/SiO2 catalyst which was also employed to promote the hydrogenation of benzene, cyclohexene and phenol. In the former two instances the catalyst was 100% selective in removing the chlorine substituent, leaving the aromatic ring intact. While the dechlorination of chlorobenzene readily attained steady state with no appreciable deactivation, the turnover of 3-chlorophenol to phenol was characterised by both a short and a long term loss of activity. Chlorine coverage of the catalyst surface under reaction conditions was probed indirectly by monitoring, via pH changes in an aqueous NaOH trap, HCI desorption after completion of the catalytic step. Contacting the catalyst with the chlorinated reactants was found to severely limit and, depending on the degree of contact, completely inhibit aromatic ring reduction although a high level of hydrodechlorination activity was maintained. Hydrogen temperature programmed desorption (TPD) reveals the existence of three forms of surface hydrogen which are tentatively assigned as: (i) hydrogen bound to the surface nickel; (ii) hydrogen at the nickel/silica interface; (iii) spillover hydrogen on the silica support. The effect of chlorine-nickel interactions on the resultant TPD profiles is presented and discussed. The (assigned) spillover hydrogen appears to be hydrogenolytic in nature and is responsible for promoting hydrodechlorination while the hydrogen that is taken to be chemisorbed on, and remains associated with, the surface nickel metal participates in aromatic hydrogenation. Hydrodechlorination proceeds via an electrophilic mechanism, possibly involving spillover hydronium ions. The experimental catalytic data are adequately represented by a kinetic model involving non-competitive adsorption between hydrogen and the chloroaromatic, where incoming chloroaromatic must displace the HCI that remains on the surface after the dechlorination step. Kinetic parameters extracted from the model reveal that chlorophenol has a higher affinity than chlorobenzene for the catalyst surface but the stronger interaction leads to a greater displacement of electron density at the metal site and this ultimately leads to catalyst deactivation.

Redox inactive metal ion promoted C-H activation of benzene to phenol with PdII(bpym): Demonstrating new strategies in catalyst designs

Guo, Huajun,Chen, Zhuqi,Mei, Fuming,Zhu, Dajian,Xiong, Hui,Yin, Guochuan

, p. 888 - 891 (2013)

-

Gordon,Miller,Day

, (1949)

Facile synthesis of CuCr2O4 spinel nanoparticles: A recyclable heterogeneous catalyst for the one pot hydroxylation of benzene

Acharyya, Shankha S.,Ghosh, Shilpi,Adak, Shubhadeep,Sasaki, Takehiko,Bal, Rajaram

, p. 4232 - 4241 (2014)

A facile hydrothermal synthesis method is developed to prepare CuCr2O4 spinel nanoparticle catalysts with sizes between 25-50 nm. A detailed characterization of the material was carried out by XRD, ICP-AES, XPS, EXAFS, SEM, TEM, and TGA. XRD revealed the formation of a CuCr2O4 spinel phase and TEM showed the that particles size was 20-50 nm. The catalyst was highly active for the selective oxidation of benzene to phenol with H2O2. The influence of reaction parameters such as temperature, solvent, substrate to oxidant molar ratio, reaction time, etc. were investigated in detail. The reusability of the catalyst was tested by conducting the same experiments with the spent catalyst and it was found that the catalyst did not show any significant activity loss, even after 5 reuses. A benzene conversion of 72.5% with 94% phenol selectivity was achieved over this catalyst at 80 °C. However, significant H2O2 decomposition occurs on the catalyst, necessitating its usage in five-fold excess.

Baxendale,Magee

, p. 160 (1953)

-

Kharasch et al.

, p. 113,125 (1951)

-

-

Kupferberg

, p. 442 (1877)

-

-

Hale,Britton

, (1928)

-

Debromination of 2,4,6-tribromophenol coupled with biodegradation

Weidlich, Tomas,Prokes, Lubomir,Pospisilova, Dagmar

, p. 979 - 987 (2013)

The application effect of aluminium and their alloys and mixtures with nickel was studied for the complete hydrodebromination of 2,4,6-tribromophenol (TBP) to phenol in aqueous NaOH solution at room temperature. It was found that the Raney Al-Ni alloy can

Mixed-donor N,N,O-tridentate ligands for palladium-catalyzed Suzuki reactions

Zhou, Zhonggao,Du, Ziyi,Hu, Qiaosheng,Shi, Jicheng,Xie, Yongrong,Liu, Yulan

, p. 149 - 153 (2012)

Efficient Suzuki-Miyaura cross-coupling reactions of arylboronic acids with aryl halides catalyzed by Pd/N,N,O-tridentate ligands, using methanol as solvent and K3PO4 as base, afforded the corresponding cross-coupled biaryls in good to excellent yields. Springer Science+Business Media B.V. 2012.

Photocatalytic degradation of 2,4-dichlorophenol with V2O5-TiO2 catalysts: Effect of catalyst support and surfactant additives

Sinirtas, Eda,Isleyen, Meltem,Soylu, Gulin Selda Pozan

, p. 607 - 615 (2016)

Binary oxide catalysts with various weight percentage V2O5 loadings were prepared by solid-state dispersion and the nanocomposites were modified with surfactants. The catalysts were analyzed using X-ray diffraction, diffuse-reflectance spectroscopy, Fourier-transform infrared spectroscopy, scanning electron microscopy, and N2 adsorption-desorption. The photocatalytic activities of the catalysts were evaluated in the degradation of 2,4-dichlorophenol under ultraviolet irradiation. The photocatalytic activity of 50 wt% V2O5-TiO2 (50V2O5-TiO2) was higher than those of pure V2O5, TiO2, and P25. Interactions between V2O5 and TiO2 affected the photocatalytic efficiencies of the binary oxide catalysts. Cetyltrimethylammonium bromide (CTAB) and hexadecyltrimethylammonium bromide (HTAB) significantly enhanced the efficiency of the 50V2O5-TiO2 catalyst. The highest percentage of 2,4-dichlorophenol degradation (100%) and highest reaction rate (2.22 mg/(L·min)) were obtained in 30 min with the (50V2O5-TiO2)-CTAB catalyst. It is concluded that the addition of a surfactant to the binary oxide significantly enhanced the photocatalytic activity by modifying the optical and electronic properties of V2O5 and TiO2.

Synthesis, structural characterization, and catalytic activity of IPrNi(styrene)2 in the amination of aryl tosylates

Iglesias, Maria Jose,Blandez, Juan F.,Fructos, Manuel R.,Prieto, Auxiliadora,Alvarez, Eleuterio,Belderrain, Tomas R.,Nicasio, M. Carmen

, p. 6312 - 6316 (2012)

A novel bis-styrene IPrNi0 derivative has been synthesized from the reaction of Ni(COD)2 and free 1,3-bis(2,6-diisopropylphenyl) imidazolidene (IPr) ligand in the presence of styrene. The complex has been characterized by spectroscopic data as well as by X-ray crystallography. Its catalytic performance in the amination reaction of aryl tosylates is also reported. The catalytic reactions proceed in a very selective manner, affording moderate to high yields of cross-coupling products in short reaction times at 110 °C.

Spectroscopic and QM/MM investigations of Chloroperoxidase catalyzed degradation of orange G

Zhang, Rui,He, Qinghao,Huang, Yi,Wang, Xiaotang

, p. 1 - 9 (2016)

Chloroperoxidase (CPO), a heme-thiolate protein, from Caldariomyces fumago catalyzes a plethora of reactions including halogenation, dismutation, epoxidation, and oxidation. Although all CPO-catalyzed reactions go through a common intermediate, compound I, different mechanisms are followed in subsequent transformations. To understand the mechanism of CPO-catalyzed halide-dependent degradation of orange G, the role of halide and pH was systematically investigated. It is revealed that formation and protonation of compound X, a long-sought after hypochlorite heme adduct intermediate existed during CPO-catalyzed halide-dependent reactions, significantly lowers the reaction barrier and increases the efficiency of CPO-catalyzed orange G degradation. The extremely acidic optimal reaction pH suggests the protonation of a residue, presumably, Glu 183 in CPO catalysis. Halide dependent studies showed that Kcat is higher in the presence of Br- than in the presence of Cl-. The degradation products of orange G indicate the cleavage at a single position of orange G, demonstrating a high regioselectivity of CPO-catalyzed degradation. Based on our kinetic, NMR and QM/MM studies, the mechanism of CPO-catalyzed orange G degradation was proposed.

Evidence for HOOO radicals in the formation of alkyl hydrotrioxides (ROOOH) and hydrogen trioxide (HOOOH) in the ozonation of C - H bonds in hydrocarbons

Cerkovnik, Janez,Erzen, Evgen,Koller, Joze,Plesnicar, Bozo

, p. 404 - 409 (2002)

Low-temperature ozonation of cumene (1a) in acetone, methyl acetate, and tert-butyl methyl ether at -70° C produced the corresponding hydrotrioxide, C6H5C(CH3)2OOOH (2a), along with hydrogen trioxide, HOOOH. Ozonation of triphenylmethane (1b), however, produced only triphenylmethyl hydrotrioxide, (C6H5)3COOOH (2b). These observations, together with the previously reported experimental evidence, seem to support the "radical" mechanism for the first step of the ozonation of the C - H bonds in hydrocarbons, i.e., the formation of the caged radical pair (R??OOOH), which allows both (a) collapse of the radical pair to ROOOH and (b) the abstraction of the hydrogen atom from alkyl radical R? by HOOO? to form HOOOH. The B3LYP/6-311++G(d,p) (ZPE) calculations revealed that HOOO radicals are considerably stabilized by forming intermolecularly hydrogen-bonded complexes with acetone (BE = 8.55 kcal/mol) and dimethyl ether (7.04 kcal/mol). This type of interaction appears to be crucial for the relatively fast reactions (and the formation of the polyoxides in relatively high yields) in these solvents, as compared to the ozonations run in nonbasic solvents. However, HOOO radicals appear to be not stable enough to abstract hydrogen atoms outside the solvent cage, as indicated by the absence of HOOOH among the products in the ozonolysis of triphenylmethane. The decomposition of alkyl hydrotrioxides 2a and 2b involves a homolytic cleavage of the RO-OOH bond with subsequent "in cage" reactions of the corresponding radicals, while the decomposition of HOOOH is most likely predominantly a "pericyclic" process involving one or more molecules of water acting as a bifunctional catalyst to produce water and singlet oxygen (Δ1O2).

Solvent-Induced Single Crystal-Single Crystal Transformation of an Interpenetrated Three-Dimensional Copper Triazole Catalytic Framework

Wang, Ying,Meng, Shan-Shan,Lin, Peng-Xiang,Xiao, Yi-Wei,Ma, Qing-Qing,Xie, Qiong,Chen, Yuan-Yuan,Zhao, Xiao-Jun,Chen, Jun

, p. 4069 - 4071 (2016)

The 2-fold interpenetrated 3D framework 1 can be solvent-induced to noninterpenetrated framework 1′ in a reversible single crystal-single crystal transformation fashion. In addition, 1′ represents the first catalyst based on triazole to catalyze the aerobic homocoupling of various substituted arylboronic acids.

2,2,6,6-Tetramethylpiperidine-1-Oxyl-promoted hydroxylation of benzene to phenol over a vanadium-based catalyst using molecular oxygen

Chen, Jiaqi,Gao, Shuang,Li, Jun,Lue, Ying

, p. 1446 - 1451 (2011)

Rapid benzene hydroxylation was achieved using a reaction system that consisted of a vanadium-based catalyst, ascorbic acid, and 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) with molecular oxygen as the oxidant. The hydroxyl radicals that form by a Fento

Photo-Fries rearrangement of 1-pyrenyl esters

Maeda, Hajime,Akai, Tomomi,Segi, Masahito

, p. 4377 - 4380 (2017)

Photo-Fries rearrangement reactions of 1-pyrenyl esters were investigated. Photoreaction of 1-pyrenyl benzoate in benzene generates 1-hydroxy-2-pyrenyl phenyl ketone along with 1-pyrenol. The exceptionally down field 1H NMR chemical shift of OH proton in the photoproduct indicates the existence of intramolecular hydrogen bonding. Photorearrangements of analogs that have electron-withdrawing or electron-releasing group on the phenyl ring, and related heteroaromatic carboxylates also take place to form the corresponding ketones. However, photoreactions of 1-pyrenyl aliphatic carboxylate esters do not occur. The results of spectroscopic and theoretical studies suggest the mechanistic pathway for this process is initiated by homolytic C–O bond cleavage in an aroyl group localized 1(π → π?) excited state of the 1-pyrenyl esters. The radical pair generated in this fashion then undergoes in-solvent-cage coupling to yield the 1-hydroxy-2-pyrenyl aryl ketone selectively.

Electrochemical dechlorination of 4-chlorophenol to phenol

Cheng, I. Francis,Fernando, Quintus,Korte, Nic

, p. 1074 - 1078 (1997)

We have hypothesized that hydrogen gas intercalated in a palladium lattice is the powerful reducing agent that reductively dechlorinates chlorinated organic compounds that are adsorbed on the surface of palladized electrodes. We have shown that dechlorination of 4-chlorophenol to phenol occurs rapidly on palladized carbon cloth or palladized graphite electrodes. The reactions on the palladized carbon cloth and graphite depend on the adsorption of the chlorinated organic compound on the carbon surface and the reaction with hydrogen at the palladium/carbon interface. Palladium was much more effective in promoting the dechlorination reaction than platinum, probably because of its ability to intercalate hydrogen in its lattice.

Selective enzymatic hydrolysis of phenolic acetates

Basavaiah,Raju

, p. 467 - 473 (1994)

Phenolic acetates are selectively hydrolyzed in the presence of alkyl acetates, methyl esters and cinnamates with pig liver acetone powder (PLAP).

Direct hydroxylation of benzene to phenol over pyridine-modified vanadium-substituted heteropoly acid under microwave condition

Liu,Hou

, p. 2683 - 2685 (2014)

Direct oxidation of benzene to phenol over Py3PMo11V and hydrogen peroxide as the oxidant under microwave irradiation. Pyridine(Py)- modified vanadium substituted heteropoly acid (Py3PMo11V) with Keggin structur

Vanadium oxyacetylacetonate grafted on UiO-66-NH2 for hydroxylation of benzene to phenol with molecular oxygen

Wang, Weitao,Li, Na,Tang, Hao,Ma, Yangmin,Yang, Xiufang

, p. 113 - 120 (2018)

V/UiO-66-NH2 was prepared by the vanadium oxyacetylacetonate grafted on UiO-66-NH2. The catalytic performance of V/UiO-66-NH2 was investigated for the hydroxylation of benzene to phenol using O2. It can give the

Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction

Keivanloo, Ali,Fakharian, Mahsa,Nabid, Mohammad Reza,Amin, Amir Hossein

, p. 151 - 160 (2019)

Abstract: A novel, simple, and efficient protocol is described for the synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via the one-pot reaction of phenol or 2-naphthol derivatives, propargyl bromide, and N-alkyl-3-chloroquinoxaline-2-amines in the presence of palladium catalyst. This one-pot reaction is carried out in the absence of any copper salt at room temperature. The reaction product is dependent on the nature of the base used. The use of morpholine, as the base, affords the final cyclized product, and triethylamine only gives the coupling product. Graphical abstract: [Figure not available: see fulltext.].

Bronsted acid-functionalized choline chloride-butane sultone for the catalytic decomposition of cumene hydroperoxide to phenol

Padma priya,Rajarajeswari

, (2018)

Abstract: Choline chloride and 1,4-butane sultone were combined to obtain a sulphonic acid-functionalized ionic liquid. The structural properties of the ionic liquid were evaluated with AT-IR, NMR, mass and elemental analysis. The Bronsted acidity of the

Dramatic Effects Caused by Alkali Metal Salts on Hydrolytic Reaction Rates of Diaryl Ethers in Aqueous Solutions at High Temperatures (250 and 315 deg C)

Katritzky, Alan R.,Balasubramanian, Marudai,Siskin, Michael

, p. 1233 - 1234 (1992)

Variations in hydrolysis rates indicate that alkali metal halides and sodium sulfate behave as salts of strong bases and weak acids at high temperatures.

Long-Lived Photoexcited State of a Mn(IV)-Oxo Complex Binding Scandium Ions That is Capable of Hydroxylating Benzene

Sharma, Namita,Jung, Jieun,Ohkubo, Kei,Lee, Yong-Min,El-Khouly, Mohamed E.,Nam, Wonwoo,Fukuzumi, Shunichi

, p. 8405 - 8409 (2018)

Photoexcitation of a MnIV-oxo complex binding scandium ions ([(Bn-TPEN)MnIV(O)]2+-(Sc(OTf)3)2) in a solvent mixture of trifluoroethanol and acetonitrile (v/v = 1:1) resulted in formation of the long-l

Iron oxide mediated direct C-H arylation/alkylation at α-position of cyclic aliphatic ethers

Singh, Parvinder Pal,Gudup, Satish,Ambala, Srinivas,Singh, Umed,Dadhwal, Sumit,Singh, Baldev,Sawant, Sanghapal D.,Vishwakarma, Ram A.

, p. 5852 - 5854 (2011)

We report a new and efficient iron oxide catalyzed cross-coupling reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and α-hydrogen bearing cyclic aliphatic ethers via activation of C(sp3)-H. This is the first example of iron oxide mediated direct C-C bond formation without expensive or toxic ligands.

Trapping hydrogen sulfide (H2S) with diselenides: The application in the design of fluorescent probes

Peng, Bo,Zhang, Caihong,Marutani, Eizo,Pacheco, Armando,Chen, Wei,Ichinose, Fumito,Xian, Ming

, p. 1541 - 1544 (2015)

Here we report a unique reaction between phenyl diselenide-ester substrates and H2S to form 1,2-benzothiaselenol-3-one. This reaction proceeded rapidly under mild conditions. Thiols could also react with the diselenide substrates. However, the resulted S-Se intermediate retained high reactivity toward H2S and eventually led to the same cyclized product 1,2-benzothiaselenol-3-one. Based on this reaction two fluorescent probes were developed and showed high selectivity and sensitivity for H2S. The presence of thiols was found not to interfere with the detection process.

Pathways and kinetics of anisole pyrolysis studied by NMR and selective 13C labeling. Heterolytic carbon monoxide generation

Tsujino, Yasuo,Yasaka, Yoshiro,Matubayasi, Nobuyuki,Nakahara, Masaru

, p. 124 - 132 (2012)

By applying 13C and 1HNMR spectroscopy the pyrolysis of site-selectively 13C-enriched (H313CO 12C6H5) and normal anisole compounds was studied in the dark at 0.001-1.0M (M, mol dm-3) and at 400-600°C (supercritical conditions). Conversion of the 13C-labeled methyl group was confined to the methoxy-originated fragments, 13CO and 13CH4, and the reactive intermediate, H13CHO. The normal phenyl group, 12C6H5-was converted to benzene, 12C6H6 and phenol, 12C6H 5OH without ring disintegration. The pyrolysis consists of two elementary steps: (1) the ratedetermining unimolecular ether-bond fission (k1) to generate the fragmented product C6H6 and energized intermediate H 13CHO* through the intramolecular proton transfer from the methoxy group to the phenyl, and (2) the fast bimolecular disproportionation (k2) through the intermolecular proton/hydride transfer from H 13CHO* to H313COC6H 5 to produce 13CO, 13CH4, and C 6H5OH. CO is generation by the heterolytic (ionic) mechanism in contrast to the homolytic (radical) one via the phenoxy radical intermediate (C6H5O?) in the literature despite the agreement of the rate constant (k1) and the activation energy.

Reductive dechlorination of 2,4-dichlorophenol by Pd/Fe nanoparticles prepared in the presence of ultrasonic irradiation

Zhao, Deming,Li, Min,Zhang, Dexing,Baig, Shams Ali,Xu, Xinhua

, p. 864 - 871 (2013)

Palladium/Iron (Pd/Fe) nanoparticles were prepared by using ultrasound strengthened liquid phase reductive method to enhance dispersion and avoid agglomeration. The dechlorination of 2,4-dichlorophenol (2,4-DCP) by Pd/Fe nanoparticles was investigated to understand its feasibility for an in situ remediation of contaminated groundwater. Results showed that 2,4-DCP was first adsorbed by Pd/Fe nanoparticles, then quickly reduced to o-chlorophenol (o-CP), p-chlorophenol (p-CP), and finally to phenol (P). The induction of ultrasound during the preparation of Pd/Fe nanoparticles further enhanced the removal efficiency of 2,4-DCP, as a result, the phenol production rates increased from 65% (in the absence of ultrasonic irradiation) to 91% (in the presence of ultrasonic irradiation) within 2 h. Our data suggested that the dechlorination rate was dependent on various factors including Pd loading percentage over Fe0, Pd/Fe nanoparticles availability, temperature, mechanical stirring speed, and initial pH values. Up to 99.2% of 2,4-DCP was removed after 300 min reaction with these conditions: Pd loading percentage over Fe 0 0.3 wt.%, initial 2,4-DCP concentration 20 mg L-1, Pd/Fe dosage 3 g L-1, initial pH value 3.0, and reaction temperature 25 °C. The degradation of 2,4-DCP followed pseudo-first-order kinetics reaction and the apparent pseudo-first-order kinetics constant was 0.0468 min -1.

Factors affecting sonolytic degradation of sulfamethazine in water

Gao, Yu-Qiong,Gao, Nai-Yun,Deng, Yang,Gu, Jin-Shan,Gu, Yu-Liang,Zhang, Dong

, p. 1401 - 1407 (2013)

In this study, the major factors affecting sonolytic degradation of sulfamethazine (SMT), a typical pharmaceutically active compound, in water were evaluated. The factors tested included two operational parameters (i.e. initial SMT concentration and ultrasonic power), three dissolved gases (i.e. Ar, O 2 and N2), five most frequently found anions in water (NO3-,Cl-,SO42-,HCO3-andBr-), ferrous ion (Fe 2+), and four alcohols (methanol, ethanol, isopropyl alcohol, tert-butyl alcohol). Typically, the degradation rate was increased with the increasing initial SMT concentration and power. The degradation rate was accelerated in the presence of argon or oxygen, but inhibited by nitrogen. Effects of anions on the ultrasonic treatment were species-dependent. The SMT degradation rate was slightly inhibited by NO3-,Cl-,and,SO42- but significantly improved by HCO3-andBr-. The negative effects of alcohols acted as hydroxyl radicals scavengers with the following order: tert-butyl alcohol > isopropyl alcohol > ethanol > methanol. The synergetic effect of ferrous ion was mainly due to production of additional hydroxyl radicals (·OH) through Fenton chemistry. LC/MS/MS analysis indicated that the degradation of SMT by ultrasonic irradiation is mainly ascribed to ·OH oxidation. Of interest, although the SMT could be rapidly degraded by ultrasonic irradiation, the degradation products were rarely mineralized. For example, ~100% of 180 μM SMT was decomposed, but only 8.31% TOC was reduced, within 2 h at an irradiation frequency of 800 kHz and a power of 100 W. However, the products became much biodegradable (BOD 5/COD was increased from 0.04 to 0.45). Therefore, an aerobic biological treatment may be an appropriate post-treatment to further decompose the SMT degradation products.

Efficient visible-light-induced photocatalytic activity on gold-nanoparticle-supported layered titanate

Ide, Yusuke,Matsuoka, Mizuki,Ogawa, Makoto

, p. 16762 - 16764 (2010)

The visible-light-induced photocatalytic conversion of aqueous benzene to phenol on Au-nanoparticle-supported layered titanate was accelerated when the reaction was conducted in the presence of aqueous phenol.

Ether Cleavage Re-Investigated: Elucidating the Mechanism of BBr3-Facilitated Demethylation of Aryl Methyl Ethers

Kosak, Talon M.,Conrad, Heidi A.,Korich, Andrew L.,Lord, Richard L.

, p. 7460 - 7467 (2015)

One of the most well-known, highly utilized reagents for ether cleavage is boron tribromide (BBr3), and this reagent is frequently employed in a 1:1 stoichiometric ratio with ethers. Density functional theory calculations predict a new mechanistic pathway involving charged intermediates for ether cleavage in aryl methyl ethers. Moreover, these calculations predict that one equivalent of BBr3 can cleave up to three equivalents of anisole, producing triphenoxyborane [B(OPh)3] prior to hydrolysis. These predictions were validated by gas chromatography analysis of reactions where the BBr3:anisole ratio was varied. Not only do we confirm that sub-stoichiometric equivalents may be used for ether demethylation, but the findings also support our newly proposed three cycle mechanism for cleavage of aryl methyl ethers.

Preparation of salicylic nitrile through direct catalytic dehydration of salicylamide with immobilized phosphoric acid as catalyst

Yao, Shu-Feng,Cai, Zhao-Sheng,Huang, Xu-Juan,Song, Lan-Xuan

, p. 1082 - 1086 (2020)

Salicylic nitrile was prepared through direct catalytic dehydration of salicylamide under high temperature using immobilized phosphoric acid as catalyst. The catalytic performances of different catalysts were evaluated according to the analytic results of

Temperature dependence of binding and catalysis for human serum arylesterase/paraoxonase

Debord, Jean,Bollinger, Jean-Claude,Harel, Michel,Dantoine, Thierry

, p. 72 - 77 (2014)

The influence of temperature upon the hydrolysis of phenyl acetate, catalysed by purified human serum arylesterase/paraoxonase (E. C. 3.1.8.1), was studied in the temperature range 10 C-40 C by spectrophotometry in TRIS buffer, pH 8.0, using both initial rate analysis and progress curve analysis. The kinetic parameters (catalytic constant kcat; Michaelis constant Km; product inhibition constant Kp) were determined by nonlinear regression. All parameters increased with temperature, but the ratios kcat/Km and Kp/Km remained practically constant. Binding of both substrate and reaction product (phenol) was exothermic. A negative entropic term accounted for about 50% of the enthalpy change for both the binding and catalytic steps. Thermodynamic analysis suggested that: (1) the rate-limiting step is the nucleophilic attack of the carbonyl group of the substrate by a water molecule, (2) the active site is preorganized with no induced fit, (3) the enzyme-bound calcium plays an important role in stabilizing both the substrate and the transition state. The practical implications of these results are discussed.

Cu(II) catalyzed reaction between phenyl hydrazine and toluidine blue - dual role of acid

Jonnalagadda,Nattar

, p. 271 - 276 (1999)

The detailed kinetics of Cu(II) catalyzed reduction of toluidine blue (TB+) by phenyl hydrazine (Pz) in aqueous solution is studied. Toluidine white (TBH) and the diazonium ions are the main products of the reaction. The diazonium ion further decomposes to phenol (PhOH) and nitrogen. At low concentrations of acid, H+ ion autocatalyzes the uncatalyzed reaction and hampers the Cu(II) catalyzed reaction. At high concentrations, H+ hinders both the uncatalyzed and Cu(II) catalyzed reactions. Cu(II) catalyzed had stoichiometry similar to the uncatalyzed reaction, Pz+2 TB++H2O = PhOH+2 TBH+2 H++N2. Cu(II) catalyzed reaction occurs possibly through ternary complex formation between the unprotonated toluidine blue and phenyl hydrazine and catalyst. The rate coefficient for the Cu(II) catalyzed reaction is 2.1×104 M-2 s-1. A detailed 13-step mechanistic scheme for the Cu(II) catalyzed reaction is proposed, which is supported by simulations.

BASE AND ACID CATALYZED REACTIONS OF PHENYLAZO 1-NAPHTHYL ETHER, A NEW REACTIVE DIAZOETHER. REPLY TO THE KEKULE'S MECHANISM FOR THE DIAZO COUPLING REACTION

Tezuka, Takahiro,Sasaki, Katsunori,Ando, Setsuo

, p. 4427 - 4430 (1987)

The base and acid catalyzed reactions of phenylazo 1-naphthyl ether (5) yielded biphenyl (8) and 1-naphthol (9) as major products accompanied with 4-phenylazo- (6) and 2-phenylazo-1-naphthols (7).All of our observations do not support the Kekule's diazo coupling mechanism.

UV-controlled shape memory hydrogels triggered by photoacid generator

Feng, Wei,Zhou, Wanfu,Zhang, Shidong,Fan, Yujiao,Yasin, Akram,Yang, Haiyang

, p. 81784 - 81789 (2015)

Light-induced shape memory polymers represent a class of stimuli-responsive materials that can recover their permanent shapes from temporarily trapped ones upon exposure to light illumination. Although much effort has been devoted to developing various light-responsive shape memory polymers, fabrication of such a light-responsive shape memory hydrogel still remains a challenge compared to neat polymers in their dry state. Herein, we developed a facile and general strategy to endow conventional hydrogel systems with ultraviolet (UV)-controlled shape memory performance simply using a photoacid generator (PAG) as a trigger. The process involves shape fixity through coordination interaction between imidazole groups and metal ions, and shape recovery by switching off the complexation via PAG photolysis reaction which leads to the protonation of imidazole groups. Furthermore, this convenient strategy is proved to be applicable to other pre-existing hydrogels such as a boronate ester cross-linked melamine-poly(vinyl alcohol) (PVA) hydrogel. We believe this method could provide a new opportunity with regard to the design and practical application of light-controlled shape memory hydrogels.

-

Gibby,Waters

, p. 2643,2646 (1932)

-

Catalytic dechlorination of chlorophenols in water by palladium/iron

Liu, Yihui,Yang, Fenglin,Yue, Po Lock,Chen, Guohua

, p. 1887 - 1890 (2001)

Three isomer chlorophenols, o-, m-, p-chlorophenol, were dechlorinated by palladium/iron powder in water through catalytic reduction. The dechlorinated reaction is believed to take place on the surface site of the catalyst in a pseudo-first-order reaction. The reduction product for all the three isomers is phenol. The dechlorination rate increases with increase of bulk loading of palladium due to the increase of both the surface loading of palladium and the total surface area. The molecular structure also has an effect on the dechlorination rate. For conditions with 0.048% Pd/Fe, the rate constants are 0.0215, 0.0155 and 0.0112min-1 for o-, m-, p-chlorophenol, respectively. Almost complete dechlorination is achieved within 5h. Copyright

Polarographic behavior and determination of 1,1-dimethyl-3-phenyltriazene

Ignjatovic, Ljubisa M.,Barek, Jiri,Zima, Jiri,Markovic, Dragan A.

, p. 1229 - 1243 (2007)

Polarographic behavior of the genotoxic substance 1,1-dimethyl-3- phenyltriazene was investigated and optimum conditions were found for its determination by sampled direct current polarography and differential pulse polarography at a static mercury drop electrode in the concentration range from 1 × 10-4 to 1 × 10-7 mol l-1. It was established that for reduction of the triazene group four electrons are required resulting in the formation of amino and hydrazo compound. The resulting products were identified, and the reduction pathway was proposed.

Photochemical Reactions in the Benzophenone/tert-Butyl Alcohol/Oxygen System. Some Unexpected Results

Gramain, Jean-Claude,Remuson, Roland

, p. 1120 - 1122 (1985)

-

Preparation of phenolic compounds by decarboxylation of hydroxybenzoic acids or desulfonation of hydroxybenzenesulfonic acid, catalysed by electron rich palladium complexes

Nunez Magro, Angel A.,Eastham, Graham R.,Cole-Hamilton, David J.

, p. 4683 - 4688 (2009)

Phenolic compounds can be prepared by catalytic decarboxylation of 4-hydroxybenzoic acid or desulfonation of 4-hydorxybenzene sulfonic acid. Palladium complexes are shown to be highly active in the decarboxylation reaction, but complexes of platinum or ru

Stable N-functionalised 'pincer' bis carbene ligands and their ruthenium complexes; synthesis and catalytic studies

Danopoulos, Andreas A.,Winston, Scott,Motherwell, William B.

, p. 1376 - 1377 (2002)

Deprotonation of 2,6-bis(arylimidazolium)pyridine dibromide with KN(SiMe3)2 gave thermally stable 2,6-bis(arylimidazol-2-ylidene)pyridine, which was further used to prepare ruthenium 'pincer' complexes; the latter show catalytic activity in transfer hydrogenation of carbonyl compounds.

Approaches to the Preparation of Silyl Cations

Wang, Naelong,Hwu, Jih Ru,White, Emil H.

, p. 471 - 475 (1991)

-

Ionic-liquid-functionalized polyoxometalates for heterogeneously catalyzing the aerobic oxidation of benzene to phenol: Raising efficacy through specific design

Long, Zhouyang,Zhou, Yu,Ge, Weilin,Chen, Guojian,Xie, Jingyan,Wang, Qian,Wang, Jun

, p. 1590 - 1596 (2014)

By combining nitrile-tethered pyridinium-based ionic liquid dication with the polyoxometalate anion of Keggin H5PMo10V2O40 (PMoV2) through precipitation in aqueous solution, an organic-inorganic hybri

Pyrolysis and oxidation of anisole near 1000 K

Pecullan,Brezinsky,Glassman

, p. 3305 - 3316 (1997)

Experiments near 1000 K have revealed the thermal decomposition of anisole to proceed exclusively via homolysis of the O-CH3 bond. The anisole decay was observed to be first order even in the presence of oxygen. The distribution of reaction intermediates was virtually independent of equivalence ratio, φ ≡ ([anisole]/[O2])/([anisole]/[O2]) stoichiometric. Phenol, cresols, methylcyclopentadiene, and CO were major products. Minor species included benzene, cyclopentadiene, ethane, and methane. Trace yields of ethene, toluene, and naphthalenes were observed under all conditions; trace C2-C4 species including acetylene, allene, and 1,3-butadiene were observed only in the oxidation experiments. Oxidation occurs preferentially through methylcyclopentadiene. A multichannel reaction scheme is proposed involving the formation of a chemically activated adduct from phenoxy and methyl. The complex reacts to form primarily cresols and methylcyclopentadiene + CO either directly or subsequent to stabilization. A kinetic model for anisole pyrolysis has been developed to predict the disappearance of anisole and the production of reaction intermediates. Excellent agreement is obtained between experimental data and model predictions of anisole, CO, methylcyclopentadiene, and total phenolics.

Hydroxylation of benzene to phenol by molecular oxygen over an organic-inorganic hybrid catalyst: Schiff base manganese complex attached to molybdovanadophosphoric heteropolyacid

Zhou, Changjiang,Wang, Jun,Leng, Yan,Ge, Hanqing

, p. 120 - 125 (2010)

The organic-inorganic hybrid catalyst L-Mn-PMoV was prepared simply by combining a schiff base Mn complex (L-Mn, L: N,N-disalicylidene-1, 6-hexanediamine) with the Keggin-structured molybdovanadophosphoric heteropolyacid (PMoV). The proposed composition and structure of the catalyst were evidenced by TG, elemental analysis, FT-IR, and UV-Vis characterizations. Its catalytic performance was evaluated in the direct hydroxylation of benzene to phenol by molecular oxygen with ascorbic acid as the reducing agent. Various reaction parameters were changed to attain the optimal conditions. The hybrid catalyst has a formula [{Mn(C20H22N2O 2)(Cl)}2(H4PMo11VO40)], with the two terminal oxygen atoms in the PMoV Keggin structure coordinately linked to the two Mn(III) ions in two L-Mn units, respectively. It exhibits a remarkably enhanced yield to phenol compared to the pure PMoV due to the synergy effect between the Schiff-base manganese complex and PMoV. Graphical Abstract: [Figure not available: see fulltext.]

Synthetic and kinetic aspects of nickel-catalysed amination of allylic alcohol derivatives

Bricout, Herve,Carpentier, Jean-Francois,Mortreux, Andre

, p. 1073 - 1084 (1998)

The design of efficient nickel-based catalytic systems for coupling of diethylamine (1) with esters and ether derivatives of allyl alcohol (2a-c) and related allyl-substituted compounds (4a-e) is reported. Special attention is paid to solvent and salt effects on catalytic activities and kinetic profiles for the formation of allyllamines. The results are discussed in terms of the influence of some reaction parameters (polarity, ion exchange processes, substrate) on the rate determining step of the catalytic cycle.

Active species formed in a Fenton-like system in the medium of triethylammonium acetate ionic liquid for hydroxylation of benzene to phenol

Hu, Xiaoke,Zhu, Liangfang,Wang, Xueqin,Guo, Bin,Xu, Jiaquan,Li, Guiying,Hu, Changwei

, p. 41 - 49 (2011)

High-valent iron(IV)-oxo species was proved to be the main oxidizing species for hydroxylation of benzene to phenol by a Fenton-like reagent in triethylammonium acetate ionic liquid via UV-vis and ESI-MS characterization, while hydroxyl radical was excluded by detailed investigations. It was found that the formation of hydroxyl radical was prohibited by the reduction of redox potential of Fe(III)/Fe(II) couple in triethylammonium acetate medium, leading to a decreased over-oxidation of benzene than that in aqueous solution. The reaction mechanisms for hydroxylation of benzene, as well as for over-oxidation of phenol by iron(IV)-oxo species were proposed. The latter is partly prohibited by the hydrogen-bond interaction between as-produced phenol and acetate anion of the ionic liquid.

-

Stieglitz,Brown

, p. 1277,1278, 1279 (1922)

-

Steady-state kinetic analysis of human cholinesterases over wide concentration ranges of competing substrates

Mukhametgalieva, Aliya R.,Lushchekina, Sofya V.,Aglyamova, Aliya R.,Masson, Patrick

, (2021/10/22)

Substrate competition for human acetylcholinesterase (AChE) and human butyrylcholinesterase (BChE) was studies under steady-state conditions using wide range of substrate concentrations. Competing couples of substates were acetyl-(thio)esters. Phenyl acetate (PhA) was the reporter substrate and competitor were either acetylcholine (ACh) or acetylthiocholine (ATC). The common point between investigated substrates is that the acyl moiety is acetate, i.e. same deacylation rate constant for reporter and competitor substrate. Steady-state kinetics of cholinesterase-catalyzed hydrolysis of PhA in the presence of ACh or ATC revealed 3 phases of inhibition as concentration of competitor increased: a) competitive inhibition, b) partially mixed inhibition, c) partially uncompetitive inhibition for AChE and partially uncompetitive activation for BChE. This sequence reflects binding of competitor in the active centrer at low concentration and on the peripheral anionic site (PAS) at high concentration. In particular, it showed that binding of a competing ligand on PAS may affect the catalytic behavior of AChE and BChE in an opposite way, i.e. inhibition of AChE and activation of BChE, regardless the nature of the reporter substrate. For both enzymes, progress curves for hydrolysis of PhA at very low concentration (?Km) in the presence of increasing concentration of ATC showed that: a) the competing substrate and the reporter substrate are hydrolyzed at the same time, b) complete hydrolysis of PhA cannot be reached above 1 mM competing substrate. This likely results from accumulation of hydrolysis products (P) of competing substrate and/or accumulation of acetylated enzyme·P complex that inhibit hydrolysis of the reporter substrate.

Aerobic C?C Bond Cleavage Catalyzed by Whole-Cell Cultures of the White-Rot Fungus Dichomitus albidofuscus

Zhuk, Tatyana S.,Babkina, Valeriia V.,Zorn, Holger

, (2021/12/30)

Whole-cell cultures of the basidiomycetous white-rot fungus Dichomitus albidofuscus exhibit varying catalytic activity towards aromatic compounds depending on the growth stage. This study reveals the catalytic behavior of mature whole-cell cultures that effectively catalyze a C?C bond cleavage oxidizing toluene, benzaldehyde and acetophenone to phenol. The reaction products were analyzed by GC-MS and NMR techniques. To exclude the de novo formation of phenol by the fungus, its origin has been proven by bioconversion of benzaldehyde-d5. The key step involves an aerobic Baeyer-Villiger type rearrangement where the incorporation of oxygen into the product was confirmed based on isotope labelling experiments with 18O2. Intermediate esters were not found in reaction mixture presumably due to the detected esterase activity in the mycelium as well as in supernatant of the whole-cell cultures. As a result, the sequence of biocatalytic reactions catalyzed by D. albidofuscus for the degradation of toluene via C?C bond cleavage has been disclosed.

Imidazolium-urea low transition temperature mixtures for the UHP-promoted oxidation of boron compounds

Martos, Mario,Pastor, Isidro M.

, (2022/01/03)

Different carboxy-functionalized imidazolium salts have been considered as components of low transition temperature mixtures (LTTMs) in combination with urea. Among them, a novel LTTM based on 1-(methoxycarbonyl)methyl-3-methylimidazolium chloride and urea has been prepared and characterized by differential scanning calorimetry throughout its entire composition range. This LTTM has been employed for the oxidation of boron reagents using urea-hydrogen peroxide adduct (UHP) as the oxidizer, thus avoiding the use of aqueous H2O2, which is dangerous to handle. This metal-free protocol affords the corresponding alcohols in good to quantitative yields in up to 5 mmol scale without the need of further purification. The broad composition range of the LTTM allows for the reaction to be carried out up to three consecutive times with a single imidazolium salt loading offering remarkable sustainability with an E-factor of 7.9, which can be reduced to 3.2 by the threefold reuse of the system.

Coordination Polymers as a Functional Material for the Selective Molecular Recognition of Nitroaromatics and ipso-Hydroxylation of Arylboronic Acids

Rani, Pooja,Husain, Ahmad,Bhasin,Kumar, Girijesh

, (2021/12/06)

We report the synthesis and structural characterization of two coordination polymers (CPs), namely; [{Zn(L)(DMF)4} ? 2BF4]α (1) and [{Cd(L)2(Cl)2} ? 2H2O]α (2) (where L=N2,N6-di(pyridin-4-yl)naphthalene-2,6-dicarboxamide). Crystal packing of 1 reveals the existence of channels running along the b- and c-axis filled by the ligated DMF and lattice anions, respectively. Whereas, crystal packing of 2 reveals that the metallacycles of each 1D chain are intercalating into the groove of adjacent metallacycles resulting in the stacking of 1D loop-chains to form a sheet-like architecture. In addition, both 1 and 2 were exploited as multifunctional materials for the detection of nitroaromatic compounds (NACs) as well as a catalyst in the ipso-hydroxylation of aryl/heteroarylboronic acids. Remarkably, 1 and 2 showed high fluorescence stability in an aqueous medium and displayed a maximum 88% and 97% quenching efficiency for 4-NPH, respectively among all the investigated NACs. The mechanistic investigation of NACs recognition suggested that the fluorescence quenching occurred via electron as well as energy transfer process. Furthermore, the ipso-hydroxylation of aryl/heteroarylboronic acids in presence of 1 and 2 gave up to 99% desired product yield within 15 min in our established protocol. In both cases, 1 and 2 are recyclable upto five cycles without any significant loss in their efficiency.

An alternative route for the preparation of phenol: Decomposition of cyclohexylbenzene-1-hydroperoxide

Yang, Yufei,Zhang, Yadong

, p. 71 - 80 (2021/09/28)

In this work, a HPW/ZSM-5 catalyst was prepared by impregnating phosphotungstic acid (HPW) with carrier ZSM-5 zeolite and characterized by XRD, SEM, N2 adsorption/desorption isotherm, NH3-TPD, and FT-IR techniques. The catalytic performance of HPW/ZSM-5 was investigated by using the decomposition reaction of cyclohexylbenzene-1-hydroperoxide (CHBHP) to phenol and cyclohexanone. The conversion rate of CHBHP was up to 97.28%. In addition, the reusability test exhibited that the high durability HPW/ZSM-5 as the conversion rate of CHBHP only decreased by 3.11% after five runs. The kinetic study of the decomposition reaction indicated it was a primary reaction. The apparent activation energy of the decomposition reaction was 102.39?kJ·mol–1 in the temperature range of 45–60℃. All results indicate that the HPW/ZSM-5 catalyst has good performance and promising applications in acid catalyzed organic chemistry.

Process route upstream and downstream products

Process route

2-hydroxy-3,5-dinitro-benzoic acid phenyl ester
52040-46-7

2-hydroxy-3,5-dinitro-benzoic acid phenyl ester

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

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

3,5-dinitrosalicylic acid
609-99-4

3,5-dinitrosalicylic acid

Conditions
Conditions Yield
phenyl-(1,1,3-trimethyl-but-2-enyl)-ether
857825-12-8

phenyl-(1,1,3-trimethyl-but-2-enyl)-ether

2,4-Dimethyl-1,3-pentadiene
1000-86-8

2,4-Dimethyl-1,3-pentadiene

Conditions
Conditions Yield
at 160 - 170 ℃;
tris-(4-hydroxy-phenyl)-sulfonium ; chloride
17755-35-0

tris-(4-hydroxy-phenyl)-sulfonium ; chloride

4,4'-Thiodiphenol
2664-63-3

4,4'-Thiodiphenol

Conditions
Conditions Yield
at 260 ℃;
fluorobenzene
462-06-6

fluorobenzene

2-hydroxynitrobenzene
88-75-5,78813-12-4

2-hydroxynitrobenzene

Conditions
Conditions Yield
With sodium persulfate; water; nitrobenzene; at 80 ℃; for 1h; Product distribution;
Conditions
Conditions Yield
With oxygen; magnesium; Product distribution; multistep reaction: 1.) ether; 2.) 100 deg C to 250 deg C at 10 deg C/min;
diethyl ether
60-29-7,927820-24-4

diethyl ether

C<sub>24</sub>H<sub>23</sub>O<sup>(1-)</sup>*Br<sup>(1-)</sup>*Mg<sup>(2+)</sup>

C24H23O(1-)*Br(1-)*Mg(2+)

Diphenylacetaldehyde
947-91-1

Diphenylacetaldehyde

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

1-mesityl-3,3-diphenylpropan-1-one
55800-31-2

1-mesityl-3,3-diphenylpropan-1-one

Conditions
Conditions Yield
With oxygen; Product distribution; from 100 deg C to 250 deg C at rate 10 deg C/min;
ethanol
64-17-5

ethanol

phenyl 2-nitrobenzoate
31042-59-8

phenyl 2-nitrobenzoate

ethyl 2-nitrobenzoate
610-34-4

ethyl 2-nitrobenzoate

Conditions
Conditions Yield
With sodium hydrogen telluride; acetic acid; for 0.5h; Yield given. Yields of byproduct given; Heating;
4-nitro-phenyl diphenyl phosphate
10359-36-1

4-nitro-phenyl diphenyl phosphate

diphenyl hydrogen phosphate
838-85-7

diphenyl hydrogen phosphate

phenyl(p-nitrophenyl)phosphoric acid
793-12-4

phenyl(p-nitrophenyl)phosphoric acid

Conditions
Conditions Yield
With (ZnCR)2(ClO4)3(OH); In water; acetonitrile; at 25 ℃; Rate constant; other reagents;
ethylbenzene
100-41-4,27536-89-6

ethylbenzene

1-phenylethyl hydroperoxide
3071-32-7

1-phenylethyl hydroperoxide

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

acetophenone
98-86-2

acetophenone

Conditions
Conditions Yield
With oxygen; potassium stearate; bis(acetylacetonate)nickel(II); at 120 ℃; Product distribution; oxidation in the presence of lithium stearate; effect of fixed valence metal salts on the oxidation of ethylbenzene with Ni(acac)2 catalyst;
With N,N,N,N,N,N-hexamethylphosphoric triamide; oxygen; bis(acetylacetonate)nickel(II); at 120 ℃; for 7.5h; Product distribution; Rate constant; other reagents, times;
With oxygen; Ni(NO3)2*18-crown-6; at 120 ℃; Further Variations:; Catalysts; Kinetics;
With bis(acetylacetonate)nickel(II); oxygen; at 120 ℃; Further Variations:; Reagents; Kinetics;
phenyl propionate
637-27-4,132899-52-6

phenyl propionate

1-(2-Hydroxy-phenyl)-propan-1-on
610-99-1

1-(2-Hydroxy-phenyl)-propan-1-on

4-hydroxypropiophenone
70-70-2

4-hydroxypropiophenone

Conditions
Conditions Yield
With β‐cyclodextrin; In water; at 25 ℃; for 1h; Product distribution; Quantum yield; Irradiation; various times, effect of oxygen, without cyclodextrin;
9.16%
16.49%

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