109-78-4Relevant academic research and scientific papers
Liquid-Phase Hydration of Acrylonitrile to Acetamide over the Copper-Nickel Alloy Catalysts
Sugiyama, Kazuo,Miura, Hiroshi,Watanabe, Yoshichika,Ukai, Yasunori
, p. 1579 - 1584 (1987)
The liquid-phase hydration of acrylonitrile to acrylamide has been examined over various metal catalysts at 75 deg C.Five metal elements - Cu, Ag, Fe, Co, and Ni - showed the catalytic conversion of acrylonitrile.The Cu and Ag catalysts gave the acrylamide with a 100 percent selectivity, while the other metals, Fe, Co, and Ni, yielded three products: acrylamide, ehylene cyanohydrin, and bis(2-cyanoethyl) ether.The alloying of Cu and Ni led to an increse in the formation of acrylamide with keeping the high selectivity to acrylamide.Especially, Cu-Ni alloys, with a range of 20-70 percent Cu in their bulk composition, were much more active catalysts than Cu.The maximum yield of acrylamide was obtained on the Cu-Ni alloy catalysts was observed, although such a retardation occurred on the Cu catalyst surface.The maximum synergistic effect was observed over the alloy with the surface component ratio of Cu to Ni of 4; this effect was discussed.
Kinetics and Mechanism of Nitrile Hydration Catalized by Unhindered Hydridobis(phosphine)platinum(II) Complexes. Regioselective Hydration of Acrylonitrile
Jensen, Craig M.,Trogler, William C.
, p. 723 - 729 (1986)
The reaction between trans-PtHCl(PR3)2 (R = Me and Et) and 1 equiv of NaOH in 50-50 water/acetonitrile solutions yields a species that catalyzes the hydrolysis of acetonitrile to acetamide at rates of 178 and 70 mol/(mol of catalyst h) for the R = Me and Et derivatives, respectively, at 80 deg C.These catalysts remain active for days and give as many as 6000 turnovers.The PMe3 derivate catalyzes hydrolysis of acrylonitrile but exhibits low regioselectivity between the olefin and nitrile functionalities at 80 deg C; at 25 deg C, it hydrates 21 mol of acetonitrile/(mol of catalyst h) and regioselectively (97percent) hydrates 6.1 mol of acrylonitrile/(mol of catalyst h) to acrylamide.The catalytic intermediates, +, +, and PtH(NHC(O)Me)(PEt3)2, have been intercepted and stereoscopically characterized and their interconversions demonstrated.Execpt at low hydroxide concentrations, the rates of catalysis were independent of hydroxide concentration, and proton transfer from solvating water to coordinated N-carboxamido, rather than nucleophilic attack of hydroxide on coordinated nitrile, limits the rate.Rate constants of ca. 8 and ca. 20 s-1 were determined for the proton-transfer process for the PEt3 and PMe3 systems, respectively.A kinetic isotope effect of 3.4 was observed in reactions using D2O.Adjusting the catalytic solutions to pH 8.5 resulted in a linear hydroxide dependence, and rate constants of 4.9 +/ -0.3 and 7.0 +/- 0.4E3 M-1s-1 were measured for nucleophilic attack of hydroxide on coordinated acetonitrile for the PEt3 and PMe3 systems, respectively.Deuterium labeling experiments using trans-PtDCl(PMe3)2 to catalyze acrylonitrile hydration showed that olefin hydration proceeds through a coordinated olefin intermediate and, unlike nitrile hydration, involves a reductive elimination step in the catalytic cycle.
SELECTIVE HYDRATION OF ACRYLONITRILE ON METAL OXIDE CATALYSTS
Miura, Hiroshi,Sugiyama, Kazuo,Kawakami, Soichiro,Aoyama, Toshiyuki,Matsuda, Tsuneo
, p. 183 - 186 (1982)
The selective hydration of acrylonitrile to form acrylamide has been studied on several metal oxide catalysts.MnO2, CuO and Co3O4 catalysts were found to be active and selective.Catalytic activities were strongly affected by the method of preparation.Hydration activity of MnO2 was related to the amount of phenol adsorption.
Development of 3-methoxy-4-benzyloxybenzyl alcohol (MBBA) resin as polymer-supported synthesis support: Preparation and benzyl ether cleavage by DDQ oxidation
Huang, Qiang,Zheng, Bao-Zhong,Long, Quan
, p. 203 - 207 (2010)
3-Methoxy-4-benzyloxybenzyl alcohol (MBBA) resin was synthesized by a two-step sequence under microwave irradiation involving the reaction of commercially available Merrifield resin with vanillin, followed by reduction with sodium borohydride. MBBA resin was treated with bromides in the presence of sodium hydride to afford the corresponding resin-bound benzyl ethers. Cleavage of the resin-bound benzyl ethers from the MBBA resin was carried out using 2,3-dichloro-5,6-dicyanobenzoqunone (DDQ) to give the corresponding alcohols in good yields. Moreover, the recovery, regeneration, and reuse of this polymer support could be achieved easily. MBBA resin can be developed as a kind of solid-phase synthesis bead of alcohols. Indian Academy of Sciences.
Preparation method of 3-aminopropanol
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Paragraph 0064; 0065, (2020/05/05)
The invention relates to a preparation method of 3-aminopropanol, wherein the preparation method comprises the following steps: (1) carrying out a reaction on acrylonitrile with benzyl alcohol under the catalysis of a base catalyst, and separating the obtained reaction solution to obtain 3-benzyloxypropionitrile; and (2) in a liquid-phase reaction system in the presence of a hydrogenation catalyst, carrying out a hydrogenation reaction on the 3-benzyloxypropionitrile, separating the obtained reaction liquid to obtain 3-aminopropanol, and recycling the obtained by-product toluene as an extractant in the step (1).
Method used for producing 3-hydroxypropionic acid
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Paragraph 0037; 0045-0047, (2019/12/08)
The invention belongs to the technical field of chemistry, and more specifically provides a method used for producing 3-hydroxypropionic acid. The method comprises following steps: 1, under catalyst effect, hydrogen cyanide and ethylene oxide are reacted to generated 3-hydroxypropionitrile; 2, an acid is added into the 3-hydroxypropionitrile prepared using step 1 for hydrolysis, and 3-hydroxypropionic acid and an inorganic slat are generated through reaction; 3, a reaction solution obtained in step 2 is subjected to continuous chromatography separation to obtain 3-hydroxypropionic acid and aninorganic salt solution, and the inorganic salt solution is subjected to concentration to obtain a by-product. According to the method, continuous chromatography method is adopted to process the 3-hydroxypropionitrile hydrolysis reaction solution, so that the amounts of waste water, waste gas, and waste residue can be reduced effectively, high content of the target product is obtained at high yield, and production cost is reduced.
Method for catalytically synthesizing 3-hydroxylpropionitrile from hydrocyanic acid and epoxyethane
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Paragraph 0030; 0031; 0032; 0033; 0034; 0035; 0036-0048, (2017/07/20)
The invention relates to a method for catalytically synthesizing 3-hydroxylpropionitrile from hydrocyanic acid and epoxyethane. An activated alumina immobilized boron trifluoride and 1,2-pentanediol complex is used for catalyzing a reaction between hydrocyanic acid and epoxyethane so as to synthesize 3-hydroxylpropionitrile. By the method, during the reaction, a reaction mixture is not required to be neutralized with a large volume of acid, and the generation of a large amount of inorganic salts is absent, so that the reaction has the atom economy of 100%; the reaction route is short, the number of operating steps is small, and the product separation is easy, so that the reaction is simple and convenient in operation; and hydrocyanic acid in a system is free of risk of numerous overflowing under the condition of low-temperature reaction, so that the reaction is safe in operation.
Efficient and rapid synthesis of phenolic analogs of 4-phenylbutanoic acid using microwave-assisted Michael addition as a key reaction
Iida, Hirokazu,Akatsu, Yusuke,Mizukami, Kazushi,Natori, Sho,Matsukawa, Minako,Takahashi, Kie
supporting information, p. 581 - 585 (2016/07/06)
ABSTRACT: The addition of phenols to acrylonitrile in the presence of aqueous benzyltrimethylammonium hydroxide or tetramethylammonium hydroxide under microwave irradiation yielded the corresponding Michael adducts. The obtained adducts were easily transformed to phenolic analogs of 4-phenylbutanoic acids via the hydrolysis of nitrile groups.
Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids
Claes, Laurens,Matthessen, Roman,Rombouts, Ine,Stassen, Ivo,De Baerdemaeker, Trees,Depla, Diederik,Delcour, Jan A.,Lagrain, Bert,De Vos, Dirk E.
, p. 345 - 352 (2015/01/30)
The oxidative decarboxylation of amino acids to nitriles was achieved in aqueous solution by in situ halide oxidation using catalytic amounts of tungstate exchanged on a [Ni,Al] layered double hydroxide (LDH), NH4Br, and H2O2 as the terminal oxidant. Both halide oxidation and oxidative decarboxylation were facilitated by proximity effects between the reactants and the LDH catalyst. A wide range of amino acids was converted with high yields, often > 90%. The nitrile selectivity was excellent, and the system is compatible with amide, alcohol, and in particular carboxylic acid, amine, and guanidine functional groups after appropriate neutralization. This heterogeneous catalytic system was applied successfully to convert a pro-tein-rich byproduct from the starch industry into useful biobased N-containing chemicals.
Ruthenium-catalyzed aerobic oxidative decarboxylation of amino acids: A green, zero-waste route to biobased nitriles
Claes, Laurens,Verduyckt, Jasper,Stassen, Ivo,Lagrain, Bert,De Vos, Dirk E.
supporting information, p. 6528 - 6531 (2015/04/14)
Oxidative decarboxylation of amino acids into nitriles was performed using molecular oxygen as terminal oxidant and a heterogeneous ruthenium hydroxide-based catalyst. A range of amino acids was oxidized in very good yield, using water as the solvent. This journal is
