cas 3006-96-0, 4-(Hydroxymethyl)benzoic acid

Articles about 3006-96-0Total 74 be found

Article title
Article abstract
Author
Journal number and time
Download

One-step highly selective oxidation of p-xylene to 4-hydroxymethylbenzoic acid over Cu-MOF catalysts under mild conditions
p-Xylene, a cheap industrial raw material, is mainly used to synthesize terephthalic acid. However, p-xylene was oxidized rarely to other oxygen-containing derivatives. On the other hand, current methods for synthesis of 4-hydroxymethylenzoic acid suffer from multistep reactions, long reaction time, high temperature, high pressure, and lower selectivity. In this work, p-xylene was directly oxidized into 4-hydroxymethylbenzoic acid using Cu-MOF as the catalyst, acetonitrile as the solvent, and 30% H2O2 as the oxidant under mild conditions. Very high selectivity (99.2%) of 4-hydroxymethylbenzoic acid and good substrate conversion (85.5%) of p-xylene were achieved at 30 °C for 5 h. Fast hot catalyst filtration experiments proved that Cu-MOF acted as a heterogeneous catalyst. It can be reused three times without losing its activity. Under optimized conditions, the selectivity of 4-hydroxymethyl benzoic acid and the conversion of p-xylene were 97.6% and 84.8% even though the experiment was amplified 15-folds. The efficiency of H2O2 was also up to 92.0%. The reaction mechanism was proposed combined with the analysis of XRD, FT-IR and XPS. All data displayed that Cu-MOF shows great potential as a catalyst for highly selective oxidation of stable C–H to high value-added compounds containing two diverse C–O bands under mild conditions. It also opens a new way to use of p-xylene.
Li, Ying,Wu, Mingzhu,Chen, Daomei,Jiang,He, Jiao,Luo,Wang, Wei,Wang, Jiaqiang
(2019)
Read Online

Immobilisation of electroactive macrocyclic complexes within titania films
The 4-carboxyphenyl-appended macrocyclic ligand trans-6,13-dimethyl-6-((4- carboxybenzyl)amino)-11,4,8,11-tetraazacyclotetradecane-6-amine (HL 10) has been synthesised and complexed with CoIII. The mononuclear complexes [Co(HL10)(CN)]2+ and [CoL 10(OH)]+ have been prepared and the crystal structures of their perchlorate salts are presented, where the ligand is bound in a pentadentate mode in each case while the 4-carboxybenzyl-substituted pendent amine remains free from the metal. The cyano-bridged dinuclear complex [CoL 10-μ-NC-Fe(CN)5]2- was also prepared and chemisorbed on titania-coated ITO conducting glass. The adsorbed complex is electrochemically active and cyclic voltammetry of the modified ITO working electrode in both water and MeCN solution was undertaken with simultaneous optical spectroscopy. This experiment demonstrates that reversible electrochemical oxidation of the FeII centre is coupled with rapid changes in the optical absorbance of the film. The Royal Society of Chemistry 2005.
Bernhardt, Paul V.,Kilah, Nathan L.,Meacham, Andrew P.,Meredith, Paul,Vogel, Robert
p. 2508 - 2515
(2005)
Read Online

Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading
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.
Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui
(2021/12/13)

KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols
Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters. This journal is
Li, Xinying,Mi, Tongge,Guo, Wenjing,Ruan, Zhongrui,Guo, Yu,Ma, Yan-Na,Chen, Xuenian
supporting information
p. 12776 - 12779
(2021/12/10)

Direct Heterogenization of the Ru-Macho Catalyst for the Chemoselective Hydrogenation of α,β-Unsaturated Carbonyl Compounds
In this study, a commercially available homogeneous pincer-type complex, Ru-Macho, was directly heterogenized via the Lewis acid-catalyzed Friedel-Crafts reaction using dichloromethane as the cross-linker to obtain a heterogeneous, pincer-type Ru porous organometallic polymer (Ru-Macho-POMP) with a high surface area. Notably, Ru-Macho-POMP was demonstrated to be an efficient heterogeneous catalyst for the chemoselective hydrogenation of α,β-unsaturated carbonyl compounds to their corresponding allylic alcohols using cinnamaldehyde as a model compound. The Ru-Macho-POMP catalyst showed a high turnover frequency (TOF = 920 h-1) and a high turnover number (TON = 2750), with high chemoselectivity (99%) and recyclability during the selective hydrogenation of α,β-unsaturated carbonyl compounds.
Padmanaban, Sudakar,Gunasekar, Gunniya Hariyanandam,Yoon, Sungho
supporting information
p. 6881 - 6888
(2021/03/01)

Nitrogen doped carbon for Pd-catalyzed hydropurification of crude terephthalic acid: Roles of nitrogen species
The purification of crude terephthalic acid was performed by the hydrogenation of 4-carboxybenzaldehyde (4-CBA) over activated carbon (AC) supported Pd catalysts in industry. However, traditional Pd/AC catalysts usually suffer from low hydrogenation activ
Gao, Huanxin,He, Limin,Liu, Zhicheng,Wang, Yangdong,Xie, Zaiku
p. 33646 - 33652
(2021/12/07)

Synthesis, in vitro and in silico anticancer activity of new 4-methylbenzamide derivatives containing 2,6-substituted purines as potential protein kinases inhibitors
A novel class of potential protein kinase inhibitors 7–16 was synthesized in high yields using various substituted purines. The most promising compounds, 7 and 10, exhibited inhibitory activity against seven cancer cell lines. The IC50 values f
Bozhok, Tatyana,Faryna, Aliaksandr,Kalinichenko, Elena,Panibrat, Alesya
(2021/11/30)

Reduction of Aldehydes with Formic acid in Ethanol using Immobilized Iridium Nanoparticles on a Triazine-phosphanimine Polymeric Organic Support
A novel triazine-phosphanimine polymeric organic support (TPA) was synthesized successfully by a controllable one-pot method using melamine (1,3,5-triazine-2,4,6-triamine) and trichlorophosphane (PCl3). The TPA substrate is a material incorporating P and N atoms which can coordinate with metals as a pincer ligand to stabilize them, providing an efficient heterogeneous support to prepare recyclable transition metal catalyst systems. In this study, TPA was used as support to immobilize iridium nanoparticles in the range of ~8 nm on its surface, resulting in the generation of a novel iridium nanocatalyst system (INP-TPA-POP). This catalyst system was characterized using different microscopic and spectroscopic techniques such as FT-IR, TEM, XPS, XRD, SEM, EDX, elemental analysis, ICP and BET analysis. The INP-TPA-POP nanocatalyst exhibited remarkable activity in reduction of aldehydes to alcohols using formic acids as reducing agent in ethanol as solvent.
Panahi, Farhad,Haghighi, Fatemeh,Khalafi-Nezhad, Ali
(2020/07/06)

Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles
Synthetic immune-stimulatory drugs such as agonists of the Toll-like receptors (TLR) 7/8 are potent activators of antigen-presenting cells (APCs), however, they also induce severe side effects due to leakage from the site of injection into systemic circulation. Here, we report on the design and synthesis of an amphiphilic polymer-prodrug conjugate of an imidazoquinoline TLR7/8 agonist that in aqueous medium forms vesicular structures of 200 nm. The conjugate contains an endosomal enzyme-responsive linker enabling degradation of the vesicles and release of the TLR7/8 agonist in native form after endocytosis, which results in high in vitro TLR agonist activity. In a mouse model, locally administered vesicles provoke significantly more potent and long-lasting immune stimulation in terms of interferon expression at the injection site and in draining lymphoid tissue compared to a nonamphiphilic control and the native TLR agonist. Moreover, the vesicles induce robust activation of dendritic cells in the draining lymph node in vivo.
Wang, Bi,Van Herck, Simon,Chen, Yong,Bai, Xiangyang,Zhong, Zifu,Deswarte, Kim,Lambrecht, Bart N.,Sanders, Niek N.,Lienenklaus, Stefan,Scheeren, Hans W.,David, Sunil A.,Kiessling, Fabian,Lammers, Twan,De Geest, Bruno G.,Shi, Yang
supporting information
p. 12133 - 12139
(2020/08/06)

Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols
A catalytic hydroboration of various ketones and aldehydes can be achieved in the presence of inexpensive and commercially available inorganic salts containing fluoride anion. As a result, the reduction of carbonyl moieties to the corresponding primary and secondary alcohols can be achieved at room temperature under mild conditions.
Kuciński, Krzysztof,Hreczycho, Grzegorz
supporting information
p. 552 - 555
(2020/02/04)

Furan Carboxylic Acids Production with High Productivity by Cofactor-engineered Whole-cell Biocatalysts
Furan carboxylic acids are useful chemicals in various industries. In this work, biocatalytic production of furan carboxylic acids was reported with high productivities by cofactor-engineered Escherichia coli cells. NADH oxidase (NOX) was introduced into E. coli harboring aldehyde dehydrogenases (ALDHs) to promote intracellular NAD+ regeneration, thus significantly enhancing ALDH-catalyzed oxidation. These engineered biocatalysts were capable of efficient aerobic oxidation of a variety of aromatic aldehydes. More importantly, they exhibited high substrate tolerance toward toxic furans. E. coli co-expressing vanillin dehydrogenase and NOX (E. coli_CtVDH1_NOX) enabled efficient oxidation of 250 mM of 5-hydroxymethylfurfural (HMF) to 5-hydroxymethyl-2-furancarboxylic acid (HMFCA), providing a productivity of 3.7 g/L h. With E. coli_CtVDH2_NOX as catalyst, up to 240 mM of furfural and 5-methoxymethylfurfural (MMF) could be smoothly oxidized. 2-Furoic acid (FCA, 227 mM) and 5-methoxymethyl-2-furancarboxylic acid (MMFCA, 287 mM) were produced in fed-batch synthesis, providing the productivities of 2.0 and 5.6 g/L h, respectively.
Zhang, Xue-Ying,Wang, Xin,Li, Nan-Wei,Guo, Ze-Wang,Zong, Min-Hua,Li, Ning
p. 3257 - 3264
(2020/05/25)

Polypyridyl iridium(III) based catalysts for highly chemoselective hydrogenation of aldehydes
Iridium-catalyzed transfer hydrogenation (TH) of carbonyl compounds using HCOOR (R = H, Na, NH4) as a hydrogen source is a pivotal process as it provides the clean process and is easy to execute. However, the existing highly efficient iridium catalysts work at a narrow pH; thus, does not apply to a wide variety of substrates. Therefore, the development of a new catalyst which works at a broad pH range is essential as it can gain a broader scope of utilization. Here we report highly efficient polypyridyl iridium(III) catalysts, [Ir(tpy)(L)Cl](PF6)2 {where tpy = 2,2′:6′,2′'-Terpyridine, L = phen (1,10-Phenanthroline), Me2phen (4,7-Dimethyl-1,10-phenanthroline), Me4phen (3,4,7,8-Tetramethyl-1,10-phenanthroline), Me2bpy (4,4′-Dimethyl-2–2′-dipyridyl)} for the chemoselective reduction of aldehydes to alcohols in aqueous ethanol and sodium formate as the hydride source. The reaction can be carried out efficiently in broad pH ranges, from pH 6 to 11. These catalysts are air stable, easy to prepare using commercially available starting materials, and are highly applicable for a wide range of substrates, such as electron-rich or deficient (hetero)arenes, halogens, phenols, alkoxy, ketones, esters, carboxylic acids, cyano, and nitro groups. Particularly, acid and hydroxy groups containing aldehydes were reduced successfully in basic and acidic reaction conditions, demonstrating the efficiency of the catalyst in a broad pH range with high conversion rates under microwave irradiation.
Pandrala, Mallesh,Resendez, Angel,Malhotra, Sanjay V.
p. 283 - 288
(2019/09/30)

Synthesis, Biological Activities and Docking Studies of Novel 4-(Arylaminomethyl)benzamide Derivatives as Potential Tyrosine Kinase Inhibitors
A number of new compounds containing the 4-(aminomethyl)benzamide fragment as a linker were designed and synthesized, and their biological activities were evaluated as potential anticancer agents. The cytotoxicity activity of the designed compounds was studied in two hematological and five solid cell lines in comparison with the reference drugs. Targeted structures against eight receptor tyrosine kinases including EGFR, HER-2, HER-4, IGF1R, InsR, KDR, PDGFRa, and PDGFRb were investigated. The majority of the compounds showed a potent inhibitory activity against the tested kinases. The analogues 11 and 13 with the (trifluoromethyl)benzene ring in the amide or amine moiety of the molecule were proven to be highly potent against EGFR, with 91% and 92% inhibition at 10 nM, respectively. The docking of synthesized target compounds for nine protein kinases contained in the Protein Data Bank (PDB) database was carried out. The molecular modeling results for analogue 10 showed that the use of the 4-(aminomethyl)benzamide as a flexible linker leads to a favorable overall geometry of the molecule, which allows one to bypass the bulk isoleucine residue and provides the necessary binding to the active center of the T315I-mutant Abl (PDB: 3QRJ).
Kalinichenko, Elena,Faryna, Aliaksandr,Kondrateva, Viktoria,Vlasova, Alena,Shevchenko, Valentina,Melnik, Alla,Avdoshko, Olga,Belko, Alla
(2019/10/03)

Method for copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide
The invention discloses a method for a copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide. According to the method, carbon dioxide is used as a C1 source, copper catalysisis adopted, alkoxide serves as alkali, and a reaction is carried out in an organic solvent; the method is simple in process and easy to implement, and shows wide functional group compatibility; the method allows various arylboronic acids such as monosubstituted or polysubstituted phenylboronic acid, polycyclic aromatic hydrocarbon boronic acid and benzoheterocyclic boronic acid to be converted into corresponding arylcarboxylic acids with considerable yield under mild conditions; and the produced carboxylic acids have important application value, and can be used for deriving a great number of other common chemical substances, such as acyl halide, acid anhydride, ester and amide.
-
Paragraph 0061; 0062

(2019/12/29)

The reductive deaminative conversion of nitriles to alcohols using: Para -formaldehyde in aqueous solution
We report herein, for the first time, the application of para-formaldehyde (pFA) to the reductive deamination of both aliphatic and aromatic nitriles in aqueous solution under transfer hydrogenation conditions. A broad range of primary alcohols have been synthesized selectively with very good to excellent yields under the optimized conditions. The study disclosed that the air-stable, inexpensive and commercially available catalyst [Ru(p-cymene)Cl2]2 acts as the catalyst precursor in this reaction, converting to other more active catalytic species in the presence of pFA, resulting in its degradation to CO2 and H2. Nitriles are also showed to play a dual role in this transformation, both as a substrate and as a ligand, where the dimeric catalyst structures convert to monomeric ones upon the coordination of nitrile molecules.
Tavakoli, Ghazal,Prechtl, Martin H. G.
p. 6092 - 6101
(2019/11/11)

Development of a novel secondary phosphine oxide-ruthenium(II) catalyst and its application for carbonyl reduction
A secondary phosphine oxide-phosphine mixed tridentate ligand and its ruthenium complex have been developed. This complex shows excellent catalytic activity for carbonyl reduction, especially for the reduction of α,β-unsaturated aldehydes. The turnover number and selectivity can reach up to 36500 and 99%, respectively. Control experiments and DFT calculations supported an outer-sphere mechanism during the hydrogenation reaction.
Tan, Xuefeng,Zeng, Weijun,Zhang, Xiaoyong,Chung, Lung Wa,Zhang, Xumu
supporting information
p. 535 - 538
(2018/01/19)

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions
A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.
Huy, Peter H.,Filbrich, Isabel
supporting information
p. 7410 - 7416
(2018/04/30)

Preparation method of 4-chloromethyl benzoyl chloride
The invention discloses a preparation method of 4-chloromethyl benzoyl chloride, wherein the preparation method comprises the steps: (1) a step of undergoing a chlorination reaction of 4-methylebnzenemethanol with chlorine gas under the action of a catalyst dibenzoyl peroxide to prepare a 4-hydroxymethyl trichlorobenzene crude product; (2) a step of undergoing a hydrolysis reaction of the 4-hydroxymethyl trichlorobenzene crude product prepared in the step (1) with water; and (3) a step of undergoing an acylation reaction of the hydrolysis product of the step (2) with excessive oxaloyl chlorideunder the action of a catalyst DMF, to prepare the target product 4-chloromethyl benzoyl chloride. The process has the advantages of easy availability of raw materials, low price, simple operation, fewer side reactions in the whole process, low energy consumption, high product quality, low product cost, and fewer three wastes; the total product yield is 85-90% and the purity is 99% or more.
-
Paragraph 0019; 0027; 0029; 0031; 0033; 0035; 0037

(2018/10/26)

Preparation of TiO2 Nanotube Supported Pd for the Hydrogenation of 4-carboxy-benzaldehyde
Abstract: Mesoporous TiO2 nanotube (TNT) with high surface area was synthesized and used to support palladium. The as prepared Pd/TNT was characterized by different physico-chemical techniques, such as XRD, SEM, TEM, N2 physisorption, CO chemisorption and XPS. The catalytic behavior for the hydrogenation of 4-carboxy-benzaldehyde was evaluated and compared with that of a commercial Pd/C. It was observed that Pd species was highly dispersed on TNT at a nominal 0.5% loading, and mainly existed in a metallic state. In comparison with this commercial Pd/C, the Pd/TNT displayed a better catalytic performance for the conversion of 4-carboxy-benzaldehyde. At 0.6?MPa and 280?°C, the Pd/TNT tended to catalytically convert 4-carboxy-benzaldehyde into more stable benzoic acid via a decarbonylation process. Graphical Abstract: A Pd/TNT with high palladium dispersion was successfully prepared by the wet incipient impregnation using a high surface area TiO2 nanotube support, and the fresh catalyst tended to catalytically convert 4-carboxy-benzaldehyde into more stable benzoic acid in the initial operation stage.
Liu, Jingwei,Du, Wenbin,Li, Zezhuang,Yang, Aiwu
p. 2472 - 2479
(2018/07/13)

Hydrogenolysis of C?O Chemical Bonds of Broad Scope Mediated by a New Spherical Sol–Gel Catalyst
The new spherical sol–gel hybrid material SiliaCat Pd0 selectively mediates the hydrogenolysis of aromatic alcohols, aldehydes, and ketones by using an ultralow catalytic amount (0.1 mol % Pd) under mild reaction conditions. The broad reaction scope as well as the catalyst's superior activity and pronounced stability open the route to green and convenient reductive deoxygenation processes of primary synthetic relevance in chemical research as well as in the fine chemical and petrochemical industries.
Pandarus, Valerica,Ciriminna, Rosaria,Gingras, Geneviève,Béland, Fran?ois,Pagliaro, Mario,Kaliaguine, Serge
p. 80 - 91
(2018/02/09)

A mild method for synthesizing carboxylic acids by oxidation of aldoximes using hypervalent iodine reagents
A mild oxidation method for the conversion of aldoximes to carboxylic acids was developed mediated by hypervalent iodine reagents. This method covers a wide range of functionalized aldoximes and proceeds under mild conditions, utilizing PhI(OH)OTs as an oxidant.
Nakamura, Akira,Kanou, Hodaka,Tanaka, Junki,Imamiya, Akira,Maegawa, Tomohiro,Miki, Yasuyoshi
supporting information
p. 541 - 544
(2018/02/07)

Method for synthesizing 4-(hydroxymethyl)benzoic acid from p-xylene (PX)
The invention discloses a method for synthesizing 4-(hydroxymethyl)benzoic acid by using PX as a raw material. PX is dissolved in an organic solvent and undergoes oxidation reaction with an oxidant under the action of an M-MOF catalyst, after the reaction is completed, post-treatment is performed to obtain 4-(hydroxymethyl)benzoic acid. The metal element M in the M-MOF catalyst is Fe, Cu, Cr, Mn,Cu/Fe, Cu/Cr, Cu/Mn, Fe/Mn, Cr/Fe or Cr/Mn. The raw materials of the method are abundant in sources and low in price; less by-products are generated in the reaction process, the yield is high, and separation is convenient; acid-base neutralization is not needed in the reaction process, and pollution is reduced; and the method of the invention is a one-step reaction and is mild in reaction conditions, short in reaction time, low in pollution, and convenient for industrialized scale-up production. The obtained 4-(hydroxymethyl)benzoic acid can be used for preparing medicines, liquid crystal materials, etc., is widely used and has high value.
-
Paragraph 0036; 0039-0043; 0044-0049

(2018/07/30)

An Efficient Aerobic Oxidation Protocol of Aldehydes to Carboxylic Acids in Water Catalyzed by an Inorganic-Ligand-Supported Copper Catalyst
A method for the aerobic oxidation of aldehydes to carboxylic acids in water by using an inorganic-ligand-supported copper catalyst was developed. This method was performed with the use of atmospheric oxygen as the sole oxidant under extremely mild aqueous conditions, and furthermore, a wide range of aldehydes with various functional groups were tolerated. The copper catalyst could be recycled and used in successive reactions at least six times without any appreciable degradation in performance. This method is operationally simple and avoids the use of high-costing, toxic, air/moisture-sensitive, and commercially unavailable organic ligands. The generality of this method gives it potential to be used on the industrial scale.
Yu, Han,Ru, Shi,Zhai, Yongyan,Dai, Guoyong,Han, Sheng,Wei, Yongge
p. 1253 - 1257
(2018/02/16)

IRIDIUM-BASED CATALYSTS FOR HIGHLY EFFICIENT DEHYDROGENATION AND HYDROGENATION REACTIONS IN AQUEOUS SOLUTION AND APPLICATIONS THEREOF
A series of iridium-based catalysts for dehydrogenation of formic acid, and hydrogenation using formic acid as the hydrogen source, and the process using the catalyst(s) to produce hydrogen gas from formic acid solution, or to reduce aldehydes using formic acid, are disclosed and claimed. More specifically, the present invention relates to a group of pentamethylcyclopentadienyl (Cp*) iridium complexes with different Ν,Ν-bidentate ligands that catalyze dehydrogenation from formic acid, and chemo-selective hydrogenation of aldehydes, in the aqueous solution system in a highly efficient, and long life-time manner.
-
Page/Page column 13; 16-17

(2018/11/22)

Tridentate phosphine ligand, catalyst and preparation method and application thereof
The invention belongs to the field of asymmetric catalysis, and discloses tridentate phosphine ligand which is of a structure of formula I as shown in the specification, wherein R is aryl or substituted aryl. The invention further discloses a catalyst prepared from the ligand. The catalyst is of a structure of formula II as shown in the specification, wherein R is aryl or substituted aryl, and L is mono-phosphine ligand. The invention further discloses application of the catalyst in a catalytic reduction reaction. The invention provides a tridentate phosphine ligand which is novel in structure, and a ruthenium complex of the tridentate phosphine ligand. carbonyl compounds, namely aldehyde and ketone, particularly alpha,beta-unsaturated aldehyde, are reduced by using the ruthenium complex, and very good reaction activity and selectivity are achieved.
-
Paragraph 0070-0072

(2017/12/30)

Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source
A water-soluble highly efficient iridium catalyst is developed for the chemoselective reduction of aldehydes to alcohols in water. The reduction uses formic acid as the traceless reducing agent and water as a solvent. It can be carried out in air without the need for inert atmosphere protection. The products can be purified by simple extraction without any column chromatography. The catalyst loading can be as low as 0.005 mol% and the turn-over frequency (TOF) is as high as 73 800 mol mol-1 h-1. A wide variety of functional groups, such as electron-rich or deficient (hetero)arenes and alkenes, alkyloxy groups, halogens, phenols, ketones, esters, carboxylic acids, cyano, and nitro groups, are all well tolerated, indicating excellent chemoselectivity.
Yang, Zhanhui,Zhu, Zhongpeng,Luo, Renshi,Qiu, Xiang,Liu, Ji-Tian,Yang, Jing-Kui,Tang, Weiping
supporting information
p. 3296 - 3301
(2017/07/28)

Amino acid ruthenium complexes containing double-phosphorus-and its application in the hydrogenation of [...]
The invention belongs to the technical field of organic chemistry, and particularly relates to a bi-phosphorus bi-amino acid containing ruthenium complex and catalysis of the complex to hydrogenation reduction of aldehyde. The complex can be obtained from simple phosphine ligands and amino carboxylate via simple preparation. The ruthenium catalyst efficiently carries out catalytic reduction of the aldehyde to alcohol on the neutrality condition. The catalyst has the advantages of being easy to prepare, high in catalytic efficiency, good in stability and the like, thereby having potential industrial application value.
-
Paragraph 0108; 0109; 0110

(2018/04/01)

Harnessing the Reactivity of Iridium Hydrides by Air: Iridium-Catalyzed Oxidation of Aldehydes to Acids in Water
An iridium-catalyzed oxidation of aldehydes to acids was realized by using air as the oxidant and water as the solvent in the presence of base. Interestingly, the same type of catalysts were also used for the reduction of aldehydes under acidic conditions. A common iridium hydride intermediate is proposed for both redox reactions. The oxidation has a number of advantages such as high yields, great functionality tolerance, and easy purification without chromatography.
Yang, Zhanhui,Luo, Renshi,Zhu, Zhongpeng,Yang, Xuerong,Tang, Weiping
supporting information
p. 4095 - 4098
(2017/11/21)

Ru(II) complexes bearing 2,6-bis(benzimidazole-2-yl)pyridine ligands: A new class of catalysts for efficient dehydrogenation of primary alcohols to carboxylic acids and H2in the alcohol/CsOH system
Mono-cationic Ru(II)-complexes [Ru(L)X(CH3CN)2]?X 1～4 (1, L = 2,6-bis(benzimidazol-2-yl) pyridine (L1), X = Cl; 2, L = L1, X = OTf; 3, L = 2-(N-benzyl-benzimidazole-2-yl)-6-(benzimidazole-2-yl)pyridine (L2), X = Cl; 4, L = 2,6-bis(N-benzyl-benzimidazole-2-yl)pyridine (L3), X = Cl) were prepared and fully characterized. The two acetonitrile ligands of each complex are coordinated to the metal center cis to each other. Complex 2 was also structurally characterized by X-ray crystallography. It was found that complexes 1～4 can catalyze the acceptorless dehydrogenation of primary alcohols to corresponding carboxylic acids and H2in the basic aqueous solution, and the reactivity follows the order 1 = 2 > 4 > 3. Furthermore, complexes 1 or 2 can efficiently catalyze the conversion of various primary alcohols to carboxylic acid in good yields (72%–98%) and high selectivity in an alcohol/CsOH system (1/1, mol/mol). Using an excess amount of alcohol to CsOH results in the formation of the carboxylic acid in higher yield (up to 100%, based on CsOH) and higher turnover numbers (TON ～ 10000) accompanied by the H2evolution. Complexes 1 and 2 can act as a new class of phosphine- and N-heterocycle carbene free Ru(II) complexes for efficient conversion of primary alcohols to carboxylic acids and H2in a homogeneous system.
Dai, Zengjin,Luo, Qi,Meng, Xianggao,Li, Renjie,Zhang, Jing,Peng, Tianyou
p. 11 - 18
(2016/12/16)

An Efficient, Stable and Reusable Palladium Nanocatalyst: Chemoselective Reduction of Aldehydes with Molecular Hydrogen in Water
Palladium nanoparticles (Pd-BNP) stabilized by a binaphthyl-backbone can be efficiently used for the chemoselective reduction of aldehydes in the presence of hydrogen at room temperature in water. The Pd-BNP catalyst is easily recovered and reused for five catalytic cycles. (Figure presented.).
Kotha, Surya Srinivas,Sharma, Nidhi,Sekar, Govindasamy
supporting information
p. 1694 - 1698
(2016/10/13)

Dehydrogenative Synthesis of Carboxylic Acids from Primary Alcohols and Hydroxide Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex
Primary alcohols have been reacted with hydroxide and the ruthenium complex [RuCl2(IiPr)(p-cymene)] to afford carboxylic acids and dihydrogen. The dehydrogenative reaction is performed in toluene, which allows for a simple isolation of the products by precipitation and extraction. The transformation can be applied to a range of benzylic and saturated aliphatic alcohols containing halide and (thio)ether substituents, while olefins and ester groups are not compatible with the reaction conditions. Benzylic alcohols undergo faster conversion than other substrates, and a competing Cannizzaro reaction is most likely involved in this case. The kinetic isotope effect was determined to be 0.67 using 1-butanol as the substrate. A plausible catalytic cycle was characterized by DFT/B3LYP-D3 and involved coordination of the alcohol to the metal, β-hydride elimination, hydroxide attack on the coordinated aldehyde, and a second β-hydride elimination to furnish the carboxylate.
Santilli, Carola,Makarov, Ilya S.,Fristrup, Peter,Madsen, Robert
p. 9931 - 9938
(2016/11/02)

Processes for making hydroxymethylbenzoic acid compounds
This invention relates to hydrogenation processes for making hydroxymethylbenzoic acid compounds. More specifically, this invention relates to hydrogenation processes in the presence of tertiary amide solvent compounds, as well as compositions that can re
-
Page/Page column 10; 11; 12

(2016/12/26)

Moisture-Tolerant Frustrated Lewis Pair Catalyst for Hydrogenation of Aldehydes and Ketones
In this paper, we report on the development of a bench-stable borane for frustrated Lewis pair catalyzed reduction of aldehydes, ketones, and enones. The deliberate fine-tuning of structural and electronic parameters of Lewis acid component and the choice of Lewis base provided for the first time, a moisture-tolerant FLP catalyst. Related NMR and DFT studies underpinned the unique behavior of this FLP catalyst and gave insight into the catalytic activity of the resulting FLP catalyst.
Gy?m?re, ádám,Bakos, Mária,F?ldes, Tamás,Pápai, Imre,Domján, Attila,Soós, Tibor
p. 5366 - 5372
(2015/09/15)

Preparation and hydrosilylation activity of a molybdenum carbonyl complex that features a pentadentate bis(imino)pyridine ligand
Attempts to prepare low-valent molybdenum complexes that feature a pentadentate 2,6-bis(imino)pyridine (or pyridine diimine, PDI) chelate allowed for the isolation of two different products. Refluxing Mo(CO)6 with the pyridine-substituted PDI ligand, PyEtPDI, resulted in carbonyl ligand substitution and formation of the respective bis(ligand) compound ( PyEtPDI)2Mo (1). This complex was investigated by single-crystal X-ray diffraction, and density functional theory calculations indicated that 1 possesses a Mo(0) center that back-bonds into the π-orbitals of the unreduced PDI ligands. Heating an equimolar solution of Mo(CO) 6 and the phosphine-substituted PDI ligand, Ph2PPrPDI, to 120 °C allowed for the preparation of (Ph2PPrPDI)Mo(CO) (2), which is supported by a κ5-N,N,N,P,P-Ph2PPrPDI chelate. Notably, 1 and 2 have been found to catalyze the hydrosilylation of benzaldehyde at 90°C, and the optimization of 2-catalyzed aldehyde hydrosilylation at this temperature afforded turnover frequencies of up to 330 h-1. Considering additional experimental observations, the potential mechanism of 2-mediated carbonyl hydrosilylation is discussed.
Pal, Raja,Groy, Thomas L.,Bowman, Amanda C.,Trovitch, Ryan J.
supporting information
p. 9357 - 9365
(2014/11/12)

Air-stable gold nanoparticles ligated by secondary phosphine oxides for the chemoselective hydrogenation of aldehydes: Crucial role of the ligand
The synthesis of air-stable and homogeneous gold nanoparticles (AuNPs) employing tert-butyl(naphthalen-1-yl)phosphine oxide as supporting ligand is described via NaBH4 reduction of a Au(I) precursor, [(tert-butyl(naphthalen-1-yl)phosphine oxide)AuCl]2. This highly reproducible and simple procedure furnishes small (1.24 ± 0.16 nm), highly soluble nanoparticles that are found to be highly active catalysts for the hydrogenation of substituted aldehydes, giving high conversions and chemoselectivities for a wide variety of substrates. In addition to catalytic studies the role of the novel stabilizer in the remarkable activity and selectivity exhibited by this system was interrogated thoroughly using a wide range of techniques, including ATR FT-IR, HRMAS NMR, XPS, and EDX spectroscopy. In particular, isotopic labeling experiments enabled us to probe the coordination mode adopted by the SPO ligand bound to the nanoparticle surface by ATR FT-IR spectroscopy. In combination with a series of control experiments we speculate that the SPO ligand demonstrates ligand-metal cooperative effects and plays a seminal role in the heterolytic hydrogenation mechanism.
Cano, Israel,Chapman, Andrew M.,Urakawa, Atsushi,Van Leeuwen, Piet W. N. M.
supporting information
p. 2520 - 2528
(2014/03/21)

Electrophilicity and nucleophilicity of commonly used aldehydes
The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.
Pratihar, Sanjay
p. 5781 - 5788
(2014/07/22)

DIELS-ALDER REACTIONS CATALYZED BY LEWIS ACID CONTAINING SOLIDS: RENEWABLE PRODUCTION OF BIO-PLASTICS
The present disclosure is related to silica-based Lewis acid catalysts, being essentially devoid of strong Br?nsted acid character, and their ability to effect the [4+2] cycloaddition and dehydrative aromatization of dienes and dienophiles containing oxygenated substituents to form substituted benzene products. In some embodiments, the processes comprise contacting biomass-derived substrates with ethylene to form terephthalic acid and its derivatives.
-
Paragraph 0190; sheet 7

(2015/01/06)

Synthesis of terephthalic acid via Diels-Alder reactions with ethylene and oxidized variants of 5-hydroxymethylfurfural
Terephthalic acid (PTA), a monomer in the synthesis of polyethylene terephthalate (PET), is obtained by the oxidation of petroleum-derived p-xylene. There is significant interest in the synthesis of renewable, biomass-derived PTA. Here, routes to PTA starting from oxidized products of 5- hydroxymethylfurfural (HMF) that can be produced from biomass are reported. These routes involve Diels-Alder reactions with ethylene and avoid the hydrogenation of HMF to 2,5-dimethylfuran. Oxidized derivatives of HMF are reacted with ethylene over solid Lewis acid catalysts that do not contain strong Br?nsted acids to synthesize intermediates of PTA and its equally important diester, dimethyl terephthalate (DMT). The partially oxidized HMF, 5-(hydroxymethyl)furoic acid (HMFA), is reacted with high pressure ethylene over a pure-silica molecular sieve containing framework tin (Sn-Beta) to produce the Diels-Alder dehydration product, 4-(hydroxymethyl)benzoic acid (HMBA), with 31% selectivity at 61% HMFA conversion after 6 h at 190°C. If HMFA is protected with methanol to form methyl 5-(methoxymethyl)furan-2-carboxylate (MMFC), MMFC can react with ethylene in the presence of Sn-Beta for 2 h to produce methyl 4-(methoxymethyl) benzenecarboxylate (MMBC) with 46% selectivity at 28% MMFC conversion or in the presence of a pure-silica molecular sieve containing framework zirconium (Zr-Beta) for 6 h to produce MMBC with 81% selectivity at 26% MMFC conversion. HMBA and MMBC can then be oxidized to produce PTA and DMT, respectively. When Lewis acid containing mesoporous silica (MCM-41) and amorphous silica, or Br?nsted acid containing zeolites (Al-Beta), are used as catalysts, a significant decrease in selectivity/yield of the Diels-Alder dehydration product is observed.
Pacheco, Joshua J.,Davis, Mark E.
p. 8363 - 8367
(2014/06/24)

Identification of a marine NADPH-dependent aldehyde reductase for chemoselective reduction of aldehydes
A putative aldehyde reductase gene from Oceanospirillum sp. MED92 was overexpressed in Escherichia coli. The recombinant protein (OsAR) was characterized as a monomeric NADPH-dependent aldehyde reductase. The kinetic parameters Km and kcat of OsAR were 0.89 ± 0.08 mM and 11.07 ± 0.99 s-1 for benzaldehyde, 0.04 ± 0.01 mM and 6.05 ± 1.56 s-1 for NADPH, respectively. This enzyme exhibited high activity toward a variety of aromatic and aliphatic aldehydes, but no activity toward ketones. As such, it catalyzed the chemoselective reduction of aldehydes in the presence of ketones, as demonstrated by the reduction of 4-acetylbenzaldehyde or the mixture of hexanal and 2-nonanone, showing the application potential of this marine enzyme in such selective reduction of synthetic importance.
Li, Guangyue,Ren, Jie,Wu, Qiaqing,Feng, Jinhui,Zhu, Dunming,Ma, Yanhe
p. 17 - 22
(2013/05/08)

Catalytic oxidation of aromatic hydrocarbons by mono-oxido- alkoxidovanadium(V) complexes of ONNO donor ethylenediaminebis(phenolate) ligands
Two oxidovanadium(V) complexes, [VVO(L1)(OMe)] (1) and [VVO(L2)(OMe)] (2), with ONNO donor ethylenediamine-bis(phenolate) ligands (H2L1 and H2L2) have been readily synthesized by the reaction between the ligand precursors and VOSO4·5H2O in MeOH, and characterized by physico-chemical techniques and single crystal X-ray diffraction studies. Both complexes 1 and 2 are hexa-coordinated with a pseudo-octahedral geometry in an N2O4 coordination environment and are found to catalyze the oxidation of toluene to benzoic acid and isomers of xylene to the corresponding hydroxy acids, with turnover numbers (TON) over 200, except for o-xylene. On changing the ligand fragments and coordination geometry around the metal centre there is an improvement in the catalytic efficiency, selectivity and also TON of the reaction as compared with the previously reported systems. The reactions were monitored using 51V NMR spectroscopy. Based on mass spectra analysis and 51V NMR studies, the mechanism of the catalytic process has been proposed, employing the formation of oxido-hydroperoxido/hydroxido-peroxido [V(ONNO)(O)(OOH)] ? [V(OH)(ONNO)(O2)] intermediates.
Debnath, Mainak,Dutta, Arpan,Biswas, Surajit,Das, Kalyan Kumar,Lee, Hon Man,Vícha, Jan,Marek, Radek,Marek, Jaromir,Ali, Mahammad
p. 189 - 198
(2013/10/22)

NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes
This publication describes a highly selective oxidation of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent.
Moehlmann, Lennart,Ludwig, Stefan,Blechert, Siegfried
p. 602 - 607
(2013/04/24)

Investigation of the substrate range of CYP199A4: Modification of the partition between hydroxylation and desaturation activities by substrate and protein engineering
The cytochrome P450 enzyme CYP199A4, from Rhodopseudomonas palustris HaA2, can efficiently demethylate 4-methoxybenzoic acid. It is also capable of oxidising a range of other related substrates. By investigating substrates with different substituents and ring systems we have been able to show that the carboxylate group and the nature of the ring system and the substituent are all important for optimal substrate binding and activity. The structures of the veratric acid, 2-naphthoic acid and indole-6-carboxylic acid substrate-bound CYP199A4 complexes reveal the substrate binding modes and the side-chain conformational changes of the active site residues to accommodate these larger substrates. They also provide a rationale for the selectivity of product oxidation. The oxidation of alkyl substituted benzoic acids by CYP199A4 is more complex, with desaturation reactions competing with hydroxylation activity. The structure of 4-ethylbenzoic acid-bound CYP199A4 revealed that the substrate is held in a similar position to 4-methoxybenzoic acid, and that the C β C-H bonds of the ethyl group are closer to the heme iron than those of the Cα (3.5 vs. 4.8 A?). This observation, when coupled to the relative energies of the reaction intermediates, indicates that the positioning of the alkyl group relative to the heme iron may be critical in determining the amount of desaturation that is observed. By mutating a single residue in the active site of CYP199A4 (Phe185) we were able to convert the enzyme into a 4-ethylbenzoic acid desaturase. Engineering a P450 desaturase: The substrate range of CYP199A4 from Rhodopseudomonas palustris was investigated. The partition between the hydroxylation and desaturation activities of 4-ethylbenzoic acid was studied by changing the substrate and by mutation. The activity of CYP199A4 with 4-ethylbenzoic acid was changed to a desaturase by a single mutation at F185. Copyright
Bell, Stephen G.,Zhou, Ruimin,Yang, Wen,Tan, Adrian B. H.,Gentleman, Alexander S.,Wong, Luet-Lok,Zhou, Weihong
p. 16677 - 16688
(2013/03/28)

Selective aerobic oxidation of para-xylene in sub- and supercritical water. Part 1. Comparison with ortho-xylene and the role of the catalyst
The selective, continuous, aerobic oxidations of para-xylene (pX) and ortho-xylene (oX) were performed in an identical fashion in supercritical water. The xylenes were oxidized without a catalyst and with hydrobromic acid, cobalt(ii) and manganese(ii) bromide catalysts. The conversions and yields to phthalic acid (OA) from oX were always significantly higher than those for terephthalic acid (TA) from pX. The formation of CO2 was significantly higher for pX than oX despite the higher conversions to oX. These results are unexpected because the literature teaches that thermal and catalytic decarboxylation is much higher for OA than TA. The superior yields from oX are consistent with a lower steady-state concentration of hydroxyl radicals, OH due to the internal, concerted attack of the peroxides with the oX methyl group. This mechanism forms the phthalide directly from o-tolualdehyde (oTOL) which is consistent with the observation that ortho-toluic acid (OTA) is much lower in oX than para-toluic acid, PTA, in pX oxidation. This mechanism also lowers the steady-state concentration of aromatic acids consistent with the observed lower benzoic acid and CO2 yields. Overall, the results suggest that the metal catalysts can play more than one role, thereby opening up the opportunity for discovering new catalytic synergies which are explored in our next paper, Part 2 of this series.
Perez, Eduardo,Fraga-Dubreuil, Joan,Garcia-Verdugo, Eduardo,Hamley, Paul A.,Thomas, W. Barry,Housley, Duncan,Partenheimer, Walt,Poliakoff, Martyn
experimental part
p. 2389 - 2396
(2011/10/13)

CATALYST, USE THEREOF AND PROCESS FOR HYDROGENATING ARYL ALDEHYDES
This invention provides a catalyst and the use thereof and a process for hydrogenating carboxyaryl aldehydes with selectivity to hydroxyalkylaryl monocarboxylic acids. The catalyst comprises iridium.
-
Page/Page column 22-26

(2011/04/25)

Domino rhodium/palladium-catalyzed dehydrogenation reactions of alcohols to acids by hydrogen transfer to inactivated alkenes
The combination of the d8 RhI diolefin amide [Rh(trop2N)(PPh3)] (trop2N=bis(5-H-dibenzo-[a, d]cyclohepten-5-yl)amide) and a palladium heterogeneous catalyst results in the formation of a superior catalyst system for the dehydrogenative coupling of alcohols. The overall process represents a mild and direct method for the synthesis of aromatic and heteroaromatic carboxylic acids for which inactivated olefins can be used as hydrogen acceptors. Allyl alcohols are also applicable to this coupling reaction and provide the corresponding saturated aliphatic carboxylic acids. This transformation has been found to be very efficient in the presence of silica-supported palladium nanoparticles. The dehydrogenation of benzyl alcohol by the rhodium amide, [Rh]N, follows the well established mechanism of metal-ligand bifunctional catalysis. The resulting amino hydride complex, [RhH]NH, transfers a H2 molecule to the Pd nanoparticles, which, in turn, deliver hydrogen to the inactivated alkene. Thus a domino catalytic reaction is developed which promotes the reaction R-CH 2-OH+NaOH+ 2 alkene→R-COONa+2 alkane.
Trincado, Monica,Gruetzmacher, Hansjorg,Vizza, Francesco,Bianchini, Claudio
supporting information; experimental part
p. 2751 - 2757
(2010/06/17)

Facile synthesis of second-generation dendrons with an orthogonal functional group at the focal point
Facile synthesis of second-generation dendrons with an aldehyde, epoxy, or t-Boc group at the focal point and nine carboxylic acid groups at the periphery is reported. The scheme includes a coupling of the first-generation dendrons and a two-step, one-pot reaction that proceeds through a Boc deprotection and in situ conjugation at the focal point.
Cheedarala, Ravi Kumar,Sunkara, Vijaya,Park, Joon Won
body text
p. 1966 - 1980
(2009/10/24)

Fluorous TBAF: A convenient and selective reagent for fluoride-mediated deprotections
(Chemical Equation Presented) A fluorous analogue of TBAF has been developed for its use in the clean removal of silicon-derived protecting groups. Purification of the crude mixtures by fluorous solid-phase extractions allowed alcohols, amines, and carboxylic acids to be obtained in high purity, with no need of chromatographic separations. The moderate reactivity of fluorous TBAF was exploited in selective deprotections of several bifunctional molecules.
Fustero, Santos,Sancho, Amador Garcia,Acena, Jose Luis,Sanz-Cervera, Juan F.
supporting information; experimental part
p. 6398 - 6401
(2009/12/06)

Process for the Production of High Purity Aromatic Carboxylic Acids Using a Benzoic Acid and Water Solvent for Oxidation and Purification
A process is disclosed for producing at least one high purity aromatic carboxylic acid by oxidizing an aromatic feedstock with oxygen in a reaction medium comprising the aromatic feedstock, a promoter, a heavy metal catalyst, and a solvent which comprises
-
Page/Page column 4-6

(2008/12/07)

CuCl catalyzed selective oxidation of primary alcohols to carboxylic acids with tert-butyl hydroperoxide at room temperature
Direct oxidation of primary alcohols to the corresponding carboxylic acids is performed highly efficiently at room temperature with anhydrous tert-butyl hydroperoxide in the presence of a catalytic amount of easily available CuCl under ligand free conditions in acetonitrile. Benzylic alcohols are more reactive than aliphatic alcohols, and these benzylic alcohols are selectively oxidized to the corresponding acids in the presence of aliphatic alcohols such as 1-octanol and 1-decanol.
Mannam, Sreedevi,Sekar
p. 2457 - 2460
(2008/09/20)

Interaction of secondary amines with aromatic aldehydes-efficient method for synthesis of the functionalized heterocyclic amines
A method is proposed for the benzylation of secondary heterocyclic amines with functionalized derivatives of benzaldehyde in the presence of formic acid under conditions close to amination according to the Leuckart-Wallach reaction.
Ignatovich,Gusak,Chernikhova,Kozlov,Koroleva
p. 1540 - 1543
(2008/09/20)

Staged countercurrent oxidation
A process for oxidation with oxygen of at least one aromatic hydrocarbon having oxidizable, substituents that maximizes the utilization of oxygen without reduction in the quality of the carboxylic acid products produced by means of a stagewise countercurr
-
Page/Page column 6-12

(2008/06/13)