505-48-6Relevant articles and documents
Depolymerization of Hydroxylated Polymers via Light-Driven C-C Bond Cleavage
Nguyen, Suong T.,McLoughlin, Elizabeth A.,Cox, James H.,Fors, Brett P.,Knowles, Robert R.
supporting information, p. 12268 - 12277 (2021/08/23)
The accumulation of persistent plastic waste in the environment is widely recognized as an ecological crisis. New chemical technologies are necessary both to recycle existing plastic waste streams into high-value chemical feedstocks and to develop next-generation materials that are degradable by design. Here, we report a catalytic methodology for the depolymerization of a commercial phenoxy resin and high molecular weight hydroxylated polyolefin derivatives upon visible light irradiation near ambient temperature. Proton-coupled electron transfer (PCET) activation of hydroxyl groups periodically spaced along the polymer backbone furnishes reactive alkoxy radicals that promote chain fragmentation through C-C bond β-scission. The depolymerization produces well-defined and isolable product mixtures that are readily diversified to polycondensation monomers. In addition to controlling depolymerization, the hydroxyl group modulates the thermomechanical properties of these polyolefin derivatives, yielding materials with diverse properties. These results demonstrate a new approach to polymer recycling based on light-driven C-C bond cleavage that has the potential to establish new links within a circular polymer economy and influence the development of new degradable-by-design polyolefin materials.
A direct synthesis of carboxylic acidsviaplatinum-catalysed hydroxycarbonylation of olefins
Schneider, Carolin,Franke, Robert,Jackstell, Ralf,Beller, Matthias
, p. 2703 - 2707 (2021/05/05)
The platinum-catalysed hydroxycarbonylation of olefins is reported for the first time. Using a combination of PtCl2/2,2′-bis(tert-butyl(pyridin-2-yl)phosphanyl)-1,1′-binaphthalene (Neolephos) in the presence of sulfuric acid [0.6 M] in acetic acid selective carbonylation of terminal aliphatic olefins proceeds to good yields and selectivities to the corresponding carboxylic acids. Comparing the reactivity of different butenes (iso- andn-butenes), the terminal olefin can be selectively carbonylated.
Synthesis of Dicarboxylic Acids from Aqueous Solutions of Diols with Hydrogen Evolution Catalyzed by an Iridium Complex
Fujita, Ken-ichi,Toyooka, Genki
, (2020/07/13)
A catalytic system for the synthesis of dicarboxylic acids from aqueous solutions of diols accompanied by the evolution of hydrogen was developed. An iridium complex bearing a functional bipyridonate ligand with N,N-dimethylamino substituents exhibited a high catalytic performance for this type of dehydrogenative reaction. For example, adipic acid was synthesized from an aqueous solution of 1,6-hexanediol in 97 % yield accompanied by the evolution of four equivalents of hydrogen by the present catalytic system. It should be noted that the simultaneous production of industrially important dicarboxylic acids and hydrogen, which is useful as an energy carrier, was achieved. In addition, the selective dehydrogenative oxidation of vicinal diols to give α-hydroxycarboxylic acids was also accomplished.
A mild reaction conditions of the catalytic oxidation of cyclooctane new method (by machine translation)
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Paragraph 0017-0018; 0021-0022; 0031-0032, (2019/03/28)
A cyclooctane catalytic oxidation method, said method comprising: the metal porphyrin, cyclooctane mixing, at a temperature of 80 - 120 °C, O2 The pressure 0.6 - 2 mpa reaction under the condition of 2 - 48 H-, after processing reaction liquid, separating the oxidation product [...], cyclooctanol, ring octanone; the invention relates to a new method of cyclooctane catalytic oxidation reaction temperature is low, the catalyst amount is less, but in order to O2 As the oxidizing agent, environmental protection, cyclooctane can be the highly selective oxide cyclooctanol, ring octanone and [...], the catalytic oxidation of cyclooctane new method also has the simple operation, does not use an organic solvent, ring octanone selectivity and the like. (by machine translation)
Colloidal tectonics for tandem synergistic Pickering interfacial catalysis: Oxidative cleavage of cyclohexene oxide into adipic acid
Yang, Bingyu,Leclercq, Lo?c,Schmitt, Véronique,Pera-Titus, Marc,Nardello-Rataj, Véronique
, p. 501 - 507 (2019/01/10)
Supramolecular preorganization and interfacial recognition can provide useful architectures for colloidal building. To this aim, a novel approach, based on colloidal tectonics involving two surface-active particles containing both recognition and catalytic sites, has been developed for controlling the formation and the properties of Pickering emulsions. This was illustrated by the combination of dodecyltrimethylammonium phosphotungstate nanoparticles, [C12]3[PW12O40], and silica particles functionalized with alkyl and sulfonic acid groups, [Cn/SO3H]@SiO2. The interfacial self-assembly occurs by the penetration of the alkyl chains of [Cn/SO3H]@SiO2 into the [C12]3[PW12O40] supramolecular porous structure constituted of polar and apolar regions. The emulsions were used as a non-nitric acid route for adipic acid synthesis from the one-pot oxidative cleavage of cyclohexene oxide with aqueous H2O2. The catalytic performance was significantly boosted due to the synergistic interactions between the particles.
Metal-Free Synthesis of Adipic Acid via Organocatalytic Direct Oxidation of Cyclohexane under Ambient Temperature and Pressure
Matsumoto, Yohei,Kuriyama, Masami,Yamamoto, Kosuke,Nishida, Koyo,Onomura, Osamu
supporting information, p. 1312 - 1317 (2018/09/25)
A direct metal-free approach for the production of adipic acid from cyclohexane is reported. The use of N-hydroxyphthalimide (NHPI) as a catalyst in the presence of HNO3/TFA enables the direct oxidation of cyclohexane to yield adipic acid under ambient temperature and pressure via a simple procedure. This reaction proceeds through an initial oxidation of cyclohexane to cyclohexanone oxime and cyclohexanone followed by a second oxidation of these intermediates to adipic acid. NHPI plays a crucial role in both oxidation steps to achieve a high yield and selectivity for adipic acid.
Silver(I)-Catalyzed Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage
Zhou, Zhong-Zhen,Liu, Mingxin,Lv, Leiyang,Li, Chao-Jun
supporting information, p. 2616 - 2620 (2018/02/13)
The oxidative cleavage of 1,2-diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6, Pb(OAc)4, and KMnO4, generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)-catalyzed oxidative cleavage of 1,2-diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.
Highly efficient oxidative cleavage of alkenes and cyanosilylation of aldehydes catalysed by magnetically recoverable MIL-101
Nourian, Maryam,Zadehahmadi, Farnaz,Kardanpour, Reihaneh,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj
, (2017/09/06)
The catalytic activity of magnetically recoverable MIL-101 was investigated in the oxidation of alkenes to carboxylic acids and cyanosilylation of aldehydes. MIL-101 was treated with Fe3O4 and the prepared catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, N2 adsorption measurements, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy and inductively coupled plasma analysis. The catalytic active sites in this heterogeneous catalyst are Cr3+ nodes of the MIL-101 framework. This heterogeneous catalyst has the advantages of excellent yields, short reaction times and reusability several times without significant decrease in its initial activity and stability in both oxidation and cyanosilylation reactions. Its magnetic property allows its easy separation using an external magnetic field.
Method for preparing acid through oxidating alcohols or aldehydes by oxygen
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Paragraph 0051; 0052; 0053; 0054; 0094; 0095; 0096-0099, (2017/09/29)
The invention provides a method for preparing acid through oxidating alcohols or aldehydes by using oxygen or oxygen in air as an oxidant. The method comprises the steps: oxidating the alcohols or aldehydes to produce the acid at room temperature in an organic solvent in a manner of taking ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidyl nitrogen oxide (TEMPO) and an inorganic halide as catalysts and taking the oxygen or air as an oxidant, and oxidating diols to produce lactone; or, carrying out a reaction on the aldehydes, which serve as a raw material, under neutral conditions by taking ferric nitrate as a catalyst, and oxidating the aldehydes to produce the acid and peroxy acid. The method has the advantages that the method is environmentally friendly, the cost is low, the yield is high, the atomic economical efficiency is high, the compatibility of substrate functional groups is good, the reaction conditions are mild, a reaction scale can be enlarged, and the like, so that the method is suitable for being applied to industrial production.
The aliphatic dicarboxylic acid compound (by machine translation)
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Paragraph 0040; 0049; 0050, (2017/08/02)
PROBLEM TO BE SOLVED: To obtain an aliphatic dicarboxylic acid compound industrially useful as a monomer for high molecular compounds in a high yield and good selectivity under mild conditions.SOLUTION: An aliphatic cyclic hydrocarbon compound such as cyclohexane is efficiently oxidized into an aliphatic dicarboxylic acid compound by oxidizing the aliphatic cyclic hydrocarbon compound with nitric acid or a nitrate, in the presence of trifluoroacetic acid and an N-hydroxyimide compound. When an aliphatic cyclic hydrocarbon compound having a symmetric structure is adopted as a raw material, the obtained aliphatic dicarboxylic acid compound is single.
