109-77-3Relevant articles and documents
Infrared Spectrum of Matrix-Isolated Hexamethylenetetramine in Ar and H2O at Cryogenic Temperatures
Bernstein, Max P.,Sanford, Scott A.,Allamandola, Louis J.,Chang, Sherwood
, p. 12206 - 12210 (1994)
The infrared spectra of hexamethylenetetramine (HMT) isolated in an argon matrix at 12 K, frozen in H2O at temperatures from 12 to 200 K, and as a pure solid, are reported.The results of ultraviolet photolysis of matrix-isolated HMT and HMT frozen in H2O ice are also presented, and implications for infrared astronomy and astrochemistry are discussed.Furthermore, a simple technique for incorporating large nonvolatile organic molecules into a matrix is described.
Cyanocarbon Acids: Direct Evidence That Their Ionization Is Not an Encounter-Controlled Process and Rationalization of the Unusual Solvent Isotope Effects
Hojatti, M.,Kresge, A. J.,Wang, W.-H.
, p. 4023 - 4028 (1987)
The rate of exchange of the acidic hydrogen of tert-butylmalononitrile was examined by using as a tracer, and the process was found not to be inhibited by hydronium ions in dilute aqueous hydrochloric acid solutions.This rules out the Swain-Grunwald mechanism for this reaction under these conditions.The bromination of malonitrile was investigated under conditions where reprotonation of the dicyanomethyl carbanion and its reaction with bromine occur at comparable rates, and the bromination reaction was found to have a specific rate twice that for reprotonation.Reprotonation therefore cannot be a diffusion-controlled process, and malonitrile is not a "normal" acid.The unusually large solvent kinetic isotope effects found for these cyanocarbon acid ionization reactions are explained by postulating that the transferring hydrogen and its positive charge are becoming associated with a solvent cluster rather than with a single water molecule.The thermodynamic acidity constant of malonitrile was determined to be 11.41 in aqueous solution at 25 deg C.
Hydrolysis study of fluoroorganic and cyano-based ionic liquid anions - Consequences for operational safety and environmental stability
Steudte, Stephanie,Neumann, Jennifer,Bottin-Weber, Ulrike,Diedenhofen, Michael,Arning, Juergen,Stepnowski, Piotr,Stolte, Stefan
, p. 2474 - 2483 (2012)
The hydrolytic stability of ionic liquid anions is a key property with regard to their technical applicability and environmental stability. From a technical point of view hydrolytic processes may lead to reduced durability, diminished technical performance and reduced operational safety in that corrosive and/or toxic hydrolysis products are formed. On the other hand, susceptibility to hydrolytic processes is advantageous where environmental stability and persistency are concerned, since hydrolysis is the most important abiotic degradation pathway in the environment. We investigated the hydrolytic stability of the most common ionic liquid anions, dicyanimide [N(CN) 2]-, tricyanmethanide [C(CN)3]-, tetracyanidoboranate [B(CN)4]-, bis(trifluoromethylsulphonyl)imide [(CF3SO2) 2N]-, trifluorotris(pentafluoroethyl)phosphate [(C 2F5)3PF3]- and 1,1,2,2-tetrafluoroethanesulphonic acid [H(C2F4)SO 3]-, as a function of pH (1, 7, 9 and 13) and temperature. The results show that there was no difference in hydrolytic stability as recorded for 1-ethyl-3-methylimidazolium (IM12) or for the alkali cations. All the anions were stable under neutral and slightly basic conditions (half-lives at 25 °C ?1 year). In strongly acidic and basic solutions, however, B(CN)4-, (CF3SO2)2N -, (C2F5)3PF3- and H(C2F4)SO3- were hydrolytically stable, whereas N(CN)2- and C(CN)3- were not. The kinetics of hydrolysis were recorded and Arrhenius plots were generated for the latter two anions. In addition, their hydrolysis pathways and the resulting products were identified via mass spectrometry. The cytotoxicity of hydrolysed IL solutions towards the mammalian cell line IPC-81 and the identified hydrolysis products (pure compounds) was investigated for a first estimate of their toxicological properties.
Preparation method of malononitrile and malononitrile prepared by preparation method
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Paragraph 0056-0103, (2021/05/01)
The invention relates to the technical field of chemical synthesis methods, particularly to a malononitrile preparation method and malononitrile prepared thereof. The malononitrile preparation method comprises the following steps: mixing cyanoacetamide, a catalyst and a solvent, heating, refluxing, and introducing phosgene to synthesize malononitrile, wherein the mass ratio of the cyanoacetamide to the catalyst to the solvent is (2.5-3.5):(0.005-0.02):(7.5-10.5), the solvent is any one of dichloromethane, dichloroethane or methylbenzene, and the catalyst is any one or more of diethylamine, N,N-dimethylformamide or pyridine. According to the invention, cyanoacetamide is adopted to synthesize malononitrile in one step under the action of phosgene, wherein the required raw materials are cheap and easy to obtain, the synthetic reaction steps are few, harsh conditions are avoided, the operation is simple, stable and good in controllability, and the yield of the prepared malononitrile can reach 93% or above and is far higher than that of malononitrile obtained through other process schemes; and the preparation method is low in three-waste treatment cost, and has objective economic benefit.
Malononitrile preparation method and malononitrile prepared thereof
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Paragraph 0056-0095; 0103, (2020/08/02)
The invention relates to the technical field of chemical synthesis methods, in particular to a malononitrile preparation method and malononitrile prepared thereof. The malononitrile preparation methodcomprises the following steps that cyanoacetamide, a catalyst and a solvent are mixed, heated, refluxed and introduced with phosgene, and malononitrile is synthesized, wherein the mass ratio of the cyanoacetamide to the catalyst to the solvent is (2.5-3.5):(0.005-0.02):(7.5 to 10.5); the solvent is any one of dichloromethane, dichloroethane or methylbenzene; and the catalyst is any one or more ofdiethylamine, N, N-dimethylformamide or pyridine. According to the invention, cyanoacetamide is adopted to synthesize malononitrile in one step under the action of phosgene; the method has the advantages of cheap and easily available required raw materials, few synthesis reaction steps, no harsh conditions, simple operation, stability and good controllability, the yield of the prepared malononitrile can reach 93% or above and is far higher than that of other process schemes, and the preparation method has the advantages of low three-waste treatment cost and objective economic benefits.
Preparation method of malononitrile
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Paragraph 0044-0051, (2020/07/24)
The invention discloses a preparation method of an important organic synthesis raw material malononitrile, which comprises the following steps: performing a reaction on chloroacetonitrile and hydrogencyanide as raw materials in a tubular reactor, and separating the reaction product by condensation and negative pressure distillation to obtain the malononitrile. The method has the advantages of mild reaction conditions, simple separation and purification process, high product yield and purity, energy saving, environmental protection and low cost.
Synthetic method of malononitrile
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Paragraph 0011-0030, (2020/01/08)
The invention belongs to the technical field of organic synthesis, and provides a malononitrile synthesis method. The synthetic method comprises the following steps: adding dichloromethane and sodiumcyanide into a reaction kettle at a molar ratio of (1: 1)-(3: 1), slowly adding a catalyst into the reaction kettle under stirring and heating conditions, controlling the temperature in the reaction kettle to be 90 DEG C, and carrying out thermal preservation reaction for 5-9 hours after feeding is finished; after the reaction is finished, adding deionized water into an obtained reaction product to wash an organic phase for a plurality of times, separating out the organic phase, drying the organic phase, and rectifying to obtain malononitrile; wherein the catalyst is a composition of aluminumtrichloride and tetrabutylammonium bromide. According to the method, the malononitrile product is directly synthesized by taking cheap dichloromethane as a raw material through a one-step method, theprocess route is simple, and the cost is low.
Synthesis method of malononitrile
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Paragraph 0038-0041, (2019/02/06)
The invention discloses a synthesis method of malononitrile. Metal hydride and dihalomethane are used as an initial reactant system; under the existence of metal iodate catalysts, a dipolar aprotic solvent is used as a reaction auxiliary agent to prepare a target product of malononitrile. The method has the advantages that through the addition of the reaction auxiliary agent for reaction promotion, the malononitrile hydrolysis or alcoholysis due to polar solvents of water, alcohol and the like can be avoided; high yield and high quality of malononitrile are ensured; the malononitrile with theyield higher than 91.0 percent and the purity higher than 99.3 percent can be obtained.
Synthesis method of malononitrile
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Paragraph 0029; 0030; 0031; 0032; 0033; 0034; 0035-0053, (2018/05/16)
The invention relates to the technical field of malononitrile synthesis, and particularly discloses a synthesis method of malononitrile. The synthesis method of the malononitrile comprises the following steps: performing mixing treatment on a solvent, cyanoacetamide, phosphoryl chloride and solid phosgene to obtain suspension, heating to 50 to 90 DEG C, and performing heat-preservation reaction toobtain a malononitrile solution; performing heating distillation treatment on the malononitrile solution, recycling the solvent and the phosphoryl chloride to obtain a distillation residue; performing vacuum reduced pressure distillation treatment on the distillation residue to obtain the malononitrile. The synthesis method of the malononitrile has the advantages of simple process, convenient operation and low cost; the phosphoryl chloride and the solid phosgene are adopted as a mixed dehydrating agent, so that the yield and the quality of a product are greatly improved, and production of solid wastes is avoided.
Corresponding amine nitrile and method of manufacturing thereof (by machine translation)
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Paragraph 0136; 0137; 0140, (2018/07/15)
The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.
