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79-11-8Relevant articles and documents
Study on Gas-phase mechanism of chloroacetic acid synthesis by catalysis and chlorination of acetic acid
Xue, Jian-Wei,Zhang, Jian-Peng,Wu, Bo,Li, Fu-Xiang,Lv, Zhi-Ping
, p. 475 - 480 (2014)
The process of acetic acid catalysis and chlorination for synthesizing chloroacetic acid can exist in not only gas phase but also liquid phase. In this paper, the gas-phase reaction mechanism of the synthesis of chloroacetic acid was studied. Due to the high concentration of acetic acid and the better reaction mass transfer in the liquid-phase reaction, the generation amount of the dichloroacetic acid was higher than that in the gas-phase reaction. Under the solution distillation, the concentration of acetyl chloride, whose boiling point is very low, was very high in the gas phase, sometimes even up to 99 %, which would cause the acetyl chloride to escape rapidly with the hydrogen chloride exhaust, so that the reaction slowed down. Therefore, series reactions occured easily in the gas-phase reaction causing the amount of the dichloroacetic acid to increase.
Synthesis of monochloroacetic acid from ethylene chlorohydrin
Svetlakov,Nikitin,Nikolaeva
, p. 1530 - 1530 (2003)
The possibility of preparing monochloroacetic acid by oxidation of ethylene chlorohydrin with nitric acid was examined.
Microwave synthesis of chloroacetic acid with various cocatalysts in acetic anhydride catalyzing method
Song, Guo-Qiang,Wang, Li-Sheng,Li, Fu-Xiang
, p. 3923 - 3926 (2014)
In this paper, we introduce a method of synthesizing chloroacetic acid using acetyl chloride as catalyst and anhydrous ferric chloride, ferric chloride hexahydrate, zinc chloride and concentrated sulfuric acid (98 % H 2SO4) as cocatalysts respectively with a variable frequency microwave oven as heater. From investigating the influences of cocatalysts in reaction, we draw a optimal condition that the yield and selectivity of chloroacetic acid are 98.11 and 98.58 % respectively when adding 0.4 g FeCl3 in mixture after reacting 3.5 h and in comparable with the corresponding percentages, 96.9 and 96.87 %, with 0.7 g ZnCl2 adding, the adding amount of 1.5 g 98 % H2SO4 result in a little lower percentages of 95.71 and 95.61 % correspondingly. We have speculated the cocatalytic mechanisms in chlorination.
Reductive dechlorination of trichloroacetic acid (TCAA) by electrochemical process over Pd-In/Al2O3 catalyst
Liu, Yanzhen,Mao, Ran,Tong, Yating,Lan, Huachun,Zhang, Gong,Liu, Huijuan,Qu, Jiuhui
, p. 13 - 21 (2017)
Electrochemical reduction treatment was found to be a promising method for dechlorination of Trichloroacetic acid (TCAA), and acceleration of electron transfer or enhancement of the concentration of atomic H* significantly improve the electrochemical dechlorination process. Bimetallic Pd-based catalysts have the unique property of simultaneously catalyzing the production of atomic H* and reducing target pollutants. Herein, a bimetallic Pd–In electrocatalyst with atomic ratio of 1:1 was evenly deposited on an Al2O3 substrate, and the bimetallic Pd-In structure was confirmed via X-ray photoelectron spectroscopy (XPS). Electrochemical removal of trichloroacetic acid (TCAA) by the Pd-In/Al2O3 catalyst was performed in a three-dimensional reactor. 94% of TCAA with the initial concentration of 500?μg?L?1 could be degraded within 30?min under a relatively low current density (0.9?mA?cm?2). In contrast to the presence of refractory intermediates (dichloroacetic acid (DCAA)) found in the Pd/Al2O3 system, TCAA could be thoroughly reduced to monochloroacetic acid (MCAA) using Pd-In/Al2O3 catalysts. According to scavenger experiments, an electron transfer process and atomic H* formation function both existed in the TCAA reduction process, and the enhanced indirect atomic H* reduction process (confirmed by ESR signals) played a chief role in the TCAA removal. Moreover, the synergistic effects of Pd and In were proven to be able to enhance both direct electron transfer and indirect atomic H* formation, indicating a promising prospect for bimetallic electrochemical reduction treatment.
Solution Dynamics of Hybrid Anderson-Evans Polyoxometalates
Salazar Marcano, David E.,Lentink, Sarah,Moussawi, Mhamad A.,Parac-Vogt, Tatjana N.
supporting information, p. 10215 - 10226 (2021/05/31)
Understanding the stability and speciation of metal-oxo clusters in solution is essential for many of their applications in different areas. In particular, hybrid organic-inorganic polyoxometalates (HPOMs) have been attracting increasing attention as they combine the complementary properties of organic ligands and metal-oxygen nanoclusters. Nevertheless, the speciation and solution behavior of HPOMs have been scarcely investigated. Hence, in this work, a series of HPOMs based on the archetypical Anderson-Evans structure, δ-[MnMo6O18{(OCH2)3C-R}2]3-, with different functional groups (R = -NH2, -CH3, -NHCOCH2Cl, -NCH(2-C5H4N) {pyridine; -Pyr}, and -NHCOC9H15N2OS {biotin; -Biot}) and countercations (tetrabutylammonium {TBA}, Li, Na, and K) were synthesized, and their solution behavior was studied in detail. In aqueous solutions, decomposition of HPOMs into the free organic ligand, [MoO4]2-, and free Mn3+ was observed over time and was shown to be highly dependent on the pH, temperature, and nature of the ligand functional group but largely independent of ionic strength or the nature of the countercation. Furthermore, hydrolysis of the amide and imine bonds often present in postfunctionalized HPOMs was also observed. Hence, HPOMs were shown to exhibit highly dynamic behavior in solution, which needs to be carefully considered when designing HPOMs, particularly for biological applications.
Catalytic Oxidative Cracking of Benzene Rings in Water
Shimoyama, Yoshihiro,Ishizuka, Tomoya,Kotani, Hiroaki,Kojima, Takahiko
, p. 671 - 678 (2019/01/08)
Efficient degradation of harmful benzene rings in water is indispensable for achieving a clean water environment. We report herein unprecedented catalytic oxidative benzene cracking (OBC) in water using a ruthenium(II)-aqua complex having an N-heterocyclic carbene ligand as a catalyst and a cerium(IV) salt as a sacrificial oxidant under mild conditions. The OBC reactions produced carboxylic acids such as formic acid, which can be converted to dihydrogen directly from the OBC solution using a rhodium(III) catalyst with adjustment of the solution pH to 3.3. The OBC reactions can be applied to monosubstituted benzene derivatives such as ethylbenzene, chlorobenzene, and benzoic acid. Initial rates of the OBC reactions showed a linear relationship in the Hammett plot with a negative slope, indicating the electrophilicity of a Ru(III)-oxyl complex as the reactive species in the catalytic OBC reaction. Also, we discuss a plausible mechanism of the catalytic OBC reactions based on the kinetic analysis and the product stoichiometry for the OBC reaction of nonvolatile sodium m-xylene sulfonate. The addition of an electrophilic radical to the aromatic ring to form arene oxide/oxepin is proposed as the initial step of the OBC reaction.
Reaction of Lithium Acylate α-Carbanions with Carbon Tetrachloride
Zorin,Zaynashev,Zorin
, p. 42 - 46 (2019/04/27)
Metalation of acetic, butanoic, or 2-methylpropanoic acid with lithium diisopropylamide in tetrahydrofuran under argon gave the corresponding lithium acylate α-carbanions which reacted with carbon tetrachloride at 20–25°C for 2 h to afford butanedioic acid or its 2,3-diethyl and 2,2,3,3-tetramethyl derivatives, as well as the corresponding α-chlorocarboxylic acids and chloroform. A radical mechanism was proposed for the formation of dicarboxylic and α-chlorocarboxylic acids.
A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids
Monticelli, Serena,Urban, Ernst,Langer, Thierry,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 1001 - 1006 (2019/01/30)
The homologation of carbon dioxide with stable, (enantiopure) magnesium carbenoids constitutes a valuable method for preparing α-halo acid derivatives. The tactic features a high level of chemocontrol, thus enabling the synthesis of variously functionalized analogues. The flexibility to generate magnesium carbenoids through sulfoxide-, halogen- or proton- Mg exchange accounts for the wide scope of the reaction. (Figure presented.).
Preparation method of alpha-chloro carboxylic acid
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Paragraph 0058; 0059, (2018/04/26)
The invention discloses a preparation method of alpha-chloro carboxylic acid. According to the preparation method, amino acids are dissolved into hydrochloric acid to form a homogeneous solution; thenobtained homogeneous solution and a sodium nitrite water solution are simultaneously pumped into a mixing valve through an injection pump A and an injection pump B of a micro-channel reaction apparatus; after the solutions are fully mixed, the mixed solution is pumped into a micro reactor of the micro-channel reaction apparatus to carry out reactions at a constant flowing speed, and the flow-outliquid namely alpha-chloro carboxylic acid is collected. The provided method realizes the continuous production of alpha-chloro carboxylic acid; furthermore, the product quality is good, the operationis simple, the using amount of raw materials is little, the process is safe, the method is green and environmentally friendly, energy is saved, the efficiency is high, and thus the method is suitablefor industrial production.
METHOD OF INDUSTRIALLY PRODUCING MONOCHLOROACETIC ACID
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Page/Page column 12-14, (2018/02/03)
A method of producing monochloroacetic acid (MCAA) has been disclosed encompassing (a) a stage of the direct chlorination of acetic acid with chlorine and (b) a stage of recovery of the catalyst in the form of acid chlorides from the reaction mixture before (c) a hydrodehalogenation stage characterized by the fact that the chlorination process (a) is conducted at the boiling temperature of the mixture under a pressure of 0 - 1.0 barg, in an excess of acetic acid with respect to the dosed chlorine gas, while the heat from the reaction is taken off mainly through the evaporation of volatile components of the mixture, followed by their condensation in the reflux condenser above the reactor and the return to the chlorination reaction, after which the reaction mixture containing monochloroacetic acid, acetic acid, dichloroacetic acid and optionally acid chlorides which are present in the mixture and, optionally, anhydrides of these acids, is feed to the vacuum distillation process (b), which is conducted continuously in the distillation column in a vacuum of 0 to 500 mbar from which volatile components of the mixture, mainly acid chlorides, as well as some acetic acid and some monochloroacetic acid are taken off as distillate and returned to the chlorination process as a result of which the catalyst of the chlorination is almost completely recovered.