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Cas Database

75-05-8

75-05-8

Identification

  • Product Name:Acetonitrile

  • CAS Number: 75-05-8

  • EINECS:200-835-2

  • Molecular Weight:41.0525

  • Molecular Formula: C2H3N

  • HS Code:2926.90 Oral rat LD50: 2460 mg/kg

  • Mol File:75-05-8.mol

Synonyms:Acetonitrilecluster;Cyanomethane;Ethanenitrile;Ethyl nitrile;Methane, cyano-;Methanecarbonitrile;Methyl cyanide;Methyl cyanide (MeCN);NSC 7593;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF, HarmfulXn, IrritantXi, ToxicT

  • Hazard Codes: F:Flammable;

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH302 Harmful if swallowed H312 Harmful in contact with skin H319 Causes serious eye irritation H332 Harmful if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Artificial respiration may be needed. No mouth-to-mouth artificial respiration. Refer immediately for medical attention. See Notes. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention. If swallowed Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer immediately for medical attention. Exposure to 160 ppm for 4 hours causes flushing of the face and a feeling of constriction in the chest; 500 ppm for brief periods is irritating to the nose and throat. Severe exposures cause irritability, skin eruptions, confusion, delirium, convulsions, paralysis, and death due to central nervous system depression. (USCG, 1999) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bog-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Cyanide and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Foam, carbon dioxide, dry chemical Special Hazards of Combustion Products: Toxic vapors are generated when heated Behavior in Fire: Vapor heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. ACCIDENTAL RELEASE MEASURES. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.; Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Keep in a well-ventilated room. Separated from acids, bases, strong oxidants and food and feedstuffs. Well closed.Protect containers against physical damage. Outdoor or detached storage is preferable. Separate from any sources of ignition and combustible materials. Storage room should be well-ventilated.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10-hour Time-Weighted Average: 20 ppm (34 mg/cu m)Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 345 Articles be found

Ammoxidation of Ethanol to Acetonitrile over Molecular Sieves

Kulkarni, S. J.,Rao, R. Ramachandra,Subrahmanyam, M.,Rao, A. V. Rama

, p. 273 - 274 (1994)

For the first time, we report the ammoxidation of ethanol over crystalline, microporous silica-aluminophosphate and Y zeolite with >99.0 and 40.0percent m/m yields of acetonitrile respectively.

Vibrational Overtone Activation of the Isomerization of Methyl Isocyanide

Hassoon, Salah,Rajapakse, Nandani,Snavely, Deanne L.

, p. 2576 - 2581 (1992)

The photoisomerization of methyl isocyanide to form acetonitrile induced by excitation into the fourth (ca. 1 kcal/mol above the activation barrier) and fith (ca. 8 kcal/mol above the barrier) C-H stretch vibrational overtones is reported.The ratio of the collisional deactivation rate constant to be unimolecular rate coefficient, k(ε), was determined by a Stern-Volmer analysis plotting the inverse apparent rate constant against the total pressure.The unimolecular rate coefficients increase monotonically with increasing excitation energies across the rotational band contours.The experimental k(ε) agree with RRKM calculated values.The Stern-Volmer plots are nonlinear at low pressure: the fourth overtone excitation shows negative curvature (decreasing slope with increasing pressure) and the fifth overtone shows positive curvature (increasing slope with increasing pressure).The magnitude and direction of this curvature agree well with the calculated Stern-Volmer plots in earlier work using a master equation simulation.In these vibrational overtone activation studies, the collisional deactivation efficiency of argon is 0.3 of that of the self-collider.

Cationic Titanium(IV) Complexes via Halide Abstraction from : Crystal and Molecular Structure of 3*2MeCN

Willey, Gerald R.,Butcher, Mark L.,McPartlin, Mary,Scowen, Ian J.

, p. 305 - 310 (1994)

Treatment of (cp=η5-C5H5) with SbCl5 as chloride abstractor in acetonitrile provided hexachloroantimonate(V) salts of (1+), (2+) and (3+) respectively.With 1:1 stoichiometry red-brown crystals of 1 are obtained and with 1:2 stoichiometry light blue crystals of 2 2.Complete removal of chloride ion from requires a six-fold excess of SbCl5 when purple-blue crystals of 3 3 can be isolated.These products were characterised by analytical and spectroscopic (IR, 1H NMR) data and, in the case of 3, by a crystal structure determination.Proton NMR studies indicate the presence of intermediate halide-bridged species in solution during the sequential halide abstractions 1 --> 2 --> 3.Crystals of complex 3, obtained as the bis(solvate) from recrystallisation in acetonitrile, are monoclinic and X-ray structural analysis confirmed the formulation.The crystal structure a=19.650(4), b=19.182(4), c=12.958(3) Angstroem, β=91.612(3) deg, Z=4, R=0.0386, R'=0.0406> shows discrete cations and anions and a pseudo-octahedral co-ordination sphere for the Ti(IV).A significant trans influence of the cyclopentadienyl ligand affects Ti-N bond lengths in the complex.

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Lynn, K. R.,Yankwich, P. E.

, p. 3220 - 3223 (1961)

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Structure, stability, and generation of CH3CNS

Krebsz, Melinda,Hajgato, Balazs,Bazso, Gabor,Tarczay, Gyoergy,Pasinszki, Tibor

, p. 1686 - 1693 (2010)

The unstable acetonitrile N-sulfide molecule CH3CNS has been photolytically generated in inert solid argon matrix from 3,4-dimethyl-1,2,5- thiadiazole by 254-nm UV irradiation, and studied by ultraviolet spectroscopy and mid-infrared spectroscopy. The molecule is stable in the matrix to 254-nm UV irradiation, but decomposes to CH3CN and a sulfur atom when broad-band UV irradiation is used. Chemiluminescence due to S2 formation from triplet sulfur atoms was detected on warming the matrix to ~20-25K. The ground-state structure and potential uni- and bimolecular reactions of CH3CNS are investigated using B3LYP, CCSD(T), and MR-AQCC quantum-chemical methods. CH3CNS is demonstrated to be stable under isolated conditions at room temperature, i.e. in the dilute gas phase or in an inert solid matrix, but unstable owing to bimolecular reactions, i.e. in the condensed phase. CSIRO 2010.

An unusual coordination mode of acetylide ligands: synthesis of tetranuclear copper(I) complexes containing μ3-η1acetylide ridging ligands. Crystal structure of 3-η1-CCPh)-(Ph2Ppy-P)>4 (Ph2Ppy=2-(diphenylphosphine)pyridine)

Gamasa, Pilar M.,Gimeno, Jose,Lastra, Elena,Solans, Xavier

, p. 277 - 286 (1988)

The preparation and properties of novel tetranuclear copper(I) complexes of the type CR)(L-L)4 (L-L = 2-(diphenylphosphine)pyridine (Ph2Ppy) R = tBu, Ph; L-L = bis(diphenylphosphino)methane (dppm), R = Ph are described.The crystal structure of 3-η1-CCPh)(Ph2Ppy-P)>4 has been determined by X-ray diffraction.Crystals are monoclinic, space group C2/c with Z=4 in a unit cell of dimensions a 14.859(3), b 24.405(4), c 23.279(4) Angstroem and β 95.35(2) deg; refinement gave R = 0.056 for 3586 reflections with I>=2.5?(I).The molecule consists of a tetrahedral cluster of copper atoms bearing four μ3-η1 phenylacetylide and four monodentate P-bonded 2-(diphenylphosphine)pyridine ligands (Ph2Ppy-P).IR, 1H and 31P-NMR data are discussed.

Ground-state rotational spectrum of CH3NC...HCN and the nature of hydrogen bonds involving triply-bonded carbon

Legon, A. C.,Thorn, J. C.

, p. 449 - 458 (1992)

The ground state rotational spectra of the hydrogen-bonded species CH3NC...HCN and CH3NC...DCN have been studied using the technique of pulsed-nozzle Fourier-transform microwave spectroscopy.The spectra were of the symmetric top type and their analysis led to the rotational constants B0 = 969.0435(4) MHz and 964.7530(5) MHz for the parent and deuterated molecule, respectively.The centrifugal distortion constants, DJ and DJK, were established to be 0.369(7) kHz for CH3NC...HCN, and 0.356(8) kHz and 39.4(2) kHz for the deuterium species, while the corresponding (14)N-nuclear coupling constants were χ(14N) = -4.23(11) MHz and -4.5(1) MHz.Analysis of the centrifugal constants DJ using a model of C3v symmetry with the atoms arranged in the order H3CNC...HCN gave the quadratic force constant associated with stretching of the hydrogen bond as 9.3(1) N m-1 and 9.7(1) N m-1 in CH3NC...HCN and CH3NC...DCN, respectively.The distances in these isotopomers between the carbon nuclei adjacent to the hydrogen bond r(C...C), were found to be 3.433(3) Angstroem and 3.420(3) Angstroem, when using a model that compensates for the contributions of the intermolecular bending modes to the zero-point motion.

Ammoxidation of ethylene over low and over-exchanged Cr-ZSM-5 catalysts

Ayari,Mhamdi,álvarez-Rodríguez,Guerrero Ruiz,Delahay,Ghorbel

, p. 132 - 140 (2012)

Catalytic performances of Cr-ZSM-5 catalysts (5 wt.% of Cr, Si/Al = 26), prepared by solid-state reaction and aqueous exchange, from Cr nitrate and Cr acetate precursors, were evaluated in the selective ammoxidation of ethylene into acetonitrile in the temperature range 425.500 °C. Catalysts were characterized by chemical and thermal analysis, XRD, N2 physisorption, 27Al MAS NMR, TEM, UV-vis DRS, Raman, DRIFTS and H2-TPR. Characterization results shown that solid-state exchange was favorable for Cr2O3 formation, while exchanging chromium in aqueous phase led, essentially, to Cr(VI) species. Catalysts were actives and selectives in the studied reaction, and among them, those, prepared from aqueous exchange, exhibited the highest acetonitrile yields (23±0.5%, at 500 °C). Improved catalytic properties can be correlated with the chromium species nature. In fact, mono/di-chromates and/or polychromate species, sited in the charge compensation positions, were definitively shown, as being, the active sites. Furthermore, during solid-state reaction, the agglomeration of Cr2O3 oxide should be avoided since these species inhibit the catalyst activity.

Lynn,Yankwich

, p. 790 (1961)

A double decker type complex: Copper(I) iodide complexation with mixed donor macrocycles via [1:1] and [2:2] cyclisations

Kang, Yunji,Park, In-Hyeok,Ikeda, Mari,Habata, Yoichi,Lee, Shim Sung

, p. 4528 - 4533 (2016)

19-membered and a 38-membered macrocycles obtained as a mixture via respective [1:1] and [2:2] cyclisations were separated and their coordination behaviours with copper(I) iodide were investigated. One of the notable products isolated is a tetranuclear bis(macrocycle) complex with the larger macrocycle adopting a double decker type structure. Furthermore, removal of the lattice solvent molecules in the above complex in air motivates the displacement of the double decker units along the a-axis by sliding in a single-crystal-to-single-crystal manner.

Synthesis and ligand-based mixed valency of cis- and trans-CrIII(X4SQ)(X4Cat)(L)n (X = Cl and Br, n = 1 or 2) complexes: Effects of solvent media on intramolecular charge distribution and ligand dissociation of CrIII(X4SQ)3

Chang, Ho-Chol,Mochizuki, Katsunori,Kitagawa, Susumu

, p. 4444 - 4452 (2002)

The treatment of CrIII(X4SQ)3 (SQ = o-semiquinonate; X = Cl and Br) with acetonitrile affords trans CrIII(X4SQ)- (X4Cat)(CH3CN)2 (X = Cl (1) and Br (2)). In the presence of 2,2′-bipyridine (bpy) or 3,4,7,8-tetramethyl-1,10-phenanthrene (tmphen), the reaction affords CrIII(X4SQ)(X4Cat)(bpy) ·nCH3CN (X = Cl, n = 1 (3); X = Br, n = 0.5 (4)) or CrIII(X4SQ)(X4Cat)(tmphen) (X = Cl (5) and Br (6)), respectively. All of the complexes show a ligand-based mixed-valence (LBMV) state with SQ and Cat ligands. The LBMV state was confirmed by the presence of the interligand intervalence charge-transfer band. Spectroscopic studies in several solvent media demonstrate that the ligand dissociation included in the conversion of CrIII(X4SQ)3 to 1-6 occurs only in solvents with relatively high polarity. On the basis of these results, the effects of solvent media were examined and an equilibrium, CrIII(X4SQ)3 ? CrIII(X4BQ)(X4SQ)(X4Cat) (BQ = o-benzoquinone), is proposed by assuming an interligand electron transfer induced by solvent polarity.

Picosecond Kinetics by Exchange Broadening in the Infrared and Raman. 3. CH3CN.IBr

Cohen, Benyamin,Weiss, Shmuel

, p. 3974 - 3976 (1984)

Spectra of the ν2 and ν3+ν4 bands of CH3CN in the presence of IBr and in CCl4 solution were measured over a range of temperatures.The spectra could be analyzed to reveal the kinetics of the CH3CN + IBr CH3CN.IBr reaction, in the picosecond range.Association and dissociation rate constants were determined and, from them, activation energies and entropies.

A reaction pathway for the ammoxidation of ethane and ethylene over Co-ZSM-5 catalyst

Li, Yuejin,Armor, John N.

, p. 495 - 502 (1998)

The ammoxidation of ethane and ethylene to acetonitrile was studied over a Co-ZSM-5 catalyst with an emphasis on the reaction pathway. We found that the adsorption of ammonia on Co-ZSM-5 is stronger than that on H-ZSM-5. CzH4 adsorption is weak and readily desorbs below 300°C. While the adsorption of C2H3N (a reaction product) is very strong in He, its desorption is accelerated with the presence of NH3. With a specially designed temperature programmed experiment (reaction between the adsorbed NH3 and gaseous C2H4/O2/He mixture), we observed C2H5NH2 as a reactive intermediate, and this intermediate was demonstrated to be readily converted to C2H3N under the ammoxidation reaction conditions. A detailed pathway is offered, whereby C2H4 is thought to add on an adsorbed NH3, forming an adsorbed ethylamine which is subsequently dehydrogenated to form C2H3N. We further speculate that an oxidative environment N2 comes from N-N pairing between the adsorbed NH3 and an amine (both on a single Co2+ site).

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Schneider,Rabinovitch

, p. 4215,4217 (1962)

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Thompson, H. W.

, p. 344 - 352 (1941)

ENERGY TRANSFER IN THE INFRARED LASER-INDUCED REACTION OF METHYL ISOCYANIDE

Shultz, M. J.,Yam, L. M.,Tricca, Robert E.

, p. 1884 - 1888 (1989)

Experimental results are presented for the infrared laser-induced isomerization of methyl isocyanide to acetonitrile in the presence of several bath gases: Ar, O2, CO2, CH4, C2H6, C2H5CN, C2H5NC, and di-tert-butyl peroxide (DTBP).For all addends except DTBP, increasing the bath gas pressure results in a decrease in acetonitrile yield due to collosional deactivation of the methyl isocyanide.The efficiency of this collosional deactivation is related to the heat capacity and to the vibrational mode distribution of the buffer gas.Ethyl isocyanide as a buffer gas shows an enhanced suppression of the acetonitrile yield due to moderation of the radical channel for the reaction.DTBP, on the other hand, increases the acetonitrile yield and lowers the threshold for massive isomerization due to its generation of methyl radicals.

-

Hammer,Swann

, p. 325 (1949)

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Effect of phosphorus-oxygen compounds on structural, acidic, and catalytic properties of γ-alumina in the acetic acid ammonolysis reaction

Galanov,Sidorova

, p. 387 - 391 (2014)

The effect of a promoter on the acidic and catalytic properties of aluminum oxide in the reaction of acetic acid ammonolysis has been studied. It has been shown that the promotion of γ-Al2O3 with phosphorus-oxygen compounds results in a change in the porous structure, an increase in the concentration of acid sites, and site strength redistribution, thereby enhancing the activity and selectivity of the catalyst. The change in the acid properties of γ-Al2O3 surface has a significant effect on the second stage of the process, the dehydration of acetamide.

Acetonitrile Formation from Ethylene and Ammonia over Zn2+ and Cd2+ Exchanged Y-zeolites

Takahashi, Nobuo,Minoshima, Hiroshi,Iwadera, Hiroyuki

, p. 1323 - 1324 (1994)

Zn2+ and Cd2+ exchanged Y-zeolites are found to be active for acetonitrile formation from ethylene and ammonia.Their catalytic activities are much higher than that on Al2O3, which has been known to be an active catalyst for this reaction.

Interdependence of Fluence and Pressure in the Laser-Induced Isomerization of Methyl Isocyanide

Shultz, M. J.,Tricca, Robert E.,Yam, Loretta M.

, p. 58 - 61 (1985)

The infrared laser-induced isomerization of methyl isocyanide has previously been shown to exhibit a marked pressure dependence; large-scale isomerization occurs when threshold conditions have been exceeded.In this work the wavelength and fluence dependence of the pressure threshold have been investigated.It has been determined that threshold conditions reflect a balance between the average level of excitation and the sample pressure.The multiphoton spectrum and the treshold as a function of wavelength have been determined and both reflect the structure of the linear absorption spectrum, indicating that the effective anharmonicity is small.In addition, the earlier conclusion that the threshold is not due to a laser-triggered, thermal explosion is corroborated.

Laser photochemistry and transient Raman spectroscopy of silyl-substituted Fischer-type carbene complexes

Rooney, A. Denise,McGarvey, John J.,Gordon, Keith C.,McNicholl, Ruth-Anne,Schubert, Ulrich,Hepp, Wolfgang

, p. 1277 - 1282 (1993)

Pulsed laser irradiation of the silyl-substituted carbene complexes (CO)5W=C(XR)SiPh3 (XR = NC4H8 (1); = OEt (2)) in various solvents has been investigated using transient absorbance and time-resolved resonance Raman scattering as monitoring techniques. Irradiation of (1) in noncoordinating or weakly-coordinating solvents at 355 nm within the ligand field absorption band results in the rapid formation, within the laser pulse duration, of a permanent photoproduct. Saturation of the irradiated solution with CO results in regeneration of the starting complex 1. IR and Raman spectral data suggest that the photoproduct is the internally stabilized 16-electron species (CO)4W=C(NC4H8)SiPh3. The observations are discussed in relation to the previously reported formation of the same 16-electron species by thermolysis of 1. When the irradiation is carried out in CH3CN as solvent, UV-visible evidence suggests formation of the photosubstituted species (CO)4(CH3CN)W=C(NC4H8)SiPh 3. No photoactivity, either transient or permanent, is seen in any solvent when the irradiation is carried out at 416 nm, a wavelength which falls within the MLCT absorption region of 1. When the ethoxy-substituted carbene complex 2 is irradiated in either the LF or MLCT absorption regions a transient species forms rapidly, within the laser pulse duration, and decays on a time scale of several μs, with a lifetime dependent on solvent polarity but independent of CO concentration in solution. Time-resolved resonance Raman studies in which the sample is photolyzed at 355 nm and probed by means of a delayed pulse at 406 nm show the formation and decay of a transient consistent with the flash photolysis results. The data are interpreted in terms of photoinduced anti-syn isomerization of 2 about the Ccarbene-O bond.

Radiolytic Studies of Ruthenium Oxo-Acetato Trinuclear Complexes in Acetonitrile

Imamura, Taira,Sumiyoshi, Takashi,Takahashi, Kenta,Sasaki, Yoichi

, p. 7786 - 7791 (1993)

Redox reactions of the ruthenium(III,III,III) and ruthenium(III,III,II) trinuclear cluster complexes PF6 and Ru3(μ3-O)(μ-CH3COO)6(py)3, (Ru(333) and Ru(332), respectively) in acetontrile were studied by pulse radiolysis.Irradiation of deaerated Ru(333) acetonitrile solutions induced one-electron reduction of the trinuclear Ru(333) center by the acetonitrile radical anion, CH3CN(*-), to Ru(332).When Ru(332) was used as a parent complex, irradiation afforded Ru(322).The yield of CH3CN(*-) was evaluated to be 0.21 μmol J-1.In aerated solutions, Ru(333) was competitively reduced by CH3CN(*-) with a rate constant of 6.1 x 1010 M-1 s-1 and the superoxide ion, O2(-), with a rate constant of 3.5 x 109 M-1 s-1 at 14 deg C.Ru(332) once produced decayed to regenerate Ru(333) in 100-300 μs after the electron-pulse irradiation.Oxidation of Ru(332) by the peroxyl radical, (*)OCH2CN, to Ru(333) with a rate constant of 2.7 x 109 M-1 s-1 was confirmed.The whole reaction scheme for the radiation-induced processes is discussed.

Experimental and ab Initio Theoretical Study of the Kinetics of Rearrangement of Ketene Imine to Acetonitrile

Doughty, Alan,Bacskay, George B.,Mackie, John C.

, p. 13546 - 13555 (1994)

When heated by reflected shock waves to temperatures between 1400 and 1700 K at pressures of approximately 12-15 atm, mixtures of acetonitrile in argon (0.4-7 mol percent) exhibit strong banded absorption in the ultraviolet region between 320 and 250 nm.The carrier of the absorption spectrum is ketene imine, H2C=C=NH.Time-resolved spectra of ketene imine have been recorded with exposure times between 100 and 200 μs using a charge-coupled device (CCD) with an imaging spectrograph.Through the use of the technique of pixel binning, temporal profiles of formation and equilibration of ketene imine have been obtained with a time resolution of 24 μs.The rearrangement of ketene imine acetonitrile has been studied using ab initio quantum chemical techniques.The calculations predict the rate-determining step in the rearrangement process to be the 1,2-hydrogen transfer of the imine hydrogen to the adjacent carbon atom to produce vinyl nitrene.With the aid of the ab initio results, the experimental rate data for the reaction ketene imine -> acetonitrile have been extrapolated to the high-pressure limit, yielding the rate constant expression k = 1013.4(+/-0.5) exp(-294(+/-14) kJ mol-1/RT) s-1.

Structural characterization of tris(pyrazolyl)hydroborato and tris(2-pyridylthio)methyl lithium compounds: Lithium in uncommon trigonal pyramidal and trigonal monopyramidal coordination environments

Chakrabarti, Neena,Sattler, Wesley,Parkin, Gerard

, p. 235 - 246 (2013)

X-ray diffraction reveals that the molecular structures of the tris(pyrazolyl)hydroborato and tris(2-pyridylthio) methyl lithium compounds, [TpBut, R]Li (R = H, Me) and [κ4-Tptm]Li, respectively exhibit threecoordinate trigonal pyram

One Step Synthesis of Acetonitrile from Ethanol via Ammoxidation over Sb-V-P-O/Al2O3 Catalyst

Reddy, Benjaram M.,Manohar, Basude

, p. 234 - 235 (1993)

Selective synthesis of acetonitrile in one step from ethanol by ammoxidation is reported, for the first time, using alumina supported and antimony promoted vanadium phosphorus oxide catalyst.

Mitchell,Ashby

, p. 161,162 (1945)

Thermal Explosions of Methyl Isocyanide in Spherical Vessels

Clothier, P. Q. E.,Glionna, M. T. J.,Pritchard, H. O.

, p. 2992 - 2996 (1985)

An improved set of measurements, including a wide variety of consistency tests, on the thermal explosion of methyl isocyanide in spherical vessels from 0.3 to 12.6 L at 350 deg C is presented.We also report an accidental explosion which took place with liquid methyl isocyanide at room temperature.

Lynn,Yankwich

, p. 53 (1961)

Lynn, K. R.,Yankwich, P. E.

, p. 1719 - 1720 (1960)

Mild temperature palladium-catalyzed ammoxidation of ethanol to acetonitrile

Hamill, Conor,Driss, Hafedh,Goguet, Alex,Burch, Robbie,Petrov, Lachezar,Daous, Muhammad,Rooney, David

, p. 261 - 267 (2015)

The ammoxidation of ethanol is investigated as a renewable process for the production of acetonitrile from a bio-feedstock. Palladium catalysts are shown to be active and very selective (>99%) to this reaction at moderate to low temperatures (150-240 °C), with acetonitrile yields considered a function of Pd morphology. Further investigations reveal that the stability of these catalysts is influenced by an unselective product, and that any deactivation observed is reversible. Interpretation of this deactivation allows operating conditions to be defined for the stable, high yielding production of acetonitrile from ethanol.

Conversion of methane to acetonitrile over GaN catalysts derived from gallium nitrate hydrate co-pyrolyzed with melamine, melem, or g-C3N4: the influence of nitrogen precursors

Chen, Chi-Liang,Chen, Chin-Han,Huang, Ai-Lin,Lee, Jyh-Fu,Lin, Yu-Chuan,Trangwachirachai, Korawich

, p. 320 - 331 (2022/01/19)

Co-pyrolyzing gallium nitrate hydrate and melamine, melem, or g-C3N4 generates gallium nitride (GaN) for the conversion of methane to acetonitrile (AcCN). The solid-state-pyrolysis-made GaN catalysts exhibited better activity than commercial GaN. Among the as-prepared catalysts, GaN made by using g-C3N4 with a N/Ga ratio of 2 (i.e., GaN-(C3N4)-(2)) was the most attractive: a high initial methane conversion (28.2%), a high initial AcCN productivity (151 μmol gcat?1 min?1), and a 6 h accumulated AcCN yield (5816 μmol gcat?1) were obtained at 700 °C with a space time of 3000 mLCH4?gcat?1?h?1. GaN-(C3N4)-(2) had finely dispersed GaN crystals and enriched amorphous CN species (e.g., sp2 N and C N groups), and both are important in promoting the methane conversion rate. GaN agglomeration, coke deposition, and depleted CN species contributed to the deactivation of the catalyst, and a nitridation–activation process could rejuvenate the activity partially. The analysis of the structure–activity correlation revealed that the accumulated AcCN yield had an inverse trend with respect to the crystallite size of GaN and the sp3/sp2 ratio of the N environment.

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

Hui, Yu,Luo, Qingsong,Qin, Yucai,Song, Lijuan,Wang, Hai,Wang, Liang,Xiao, Feng-Shou

, p. 2164 - 2172 (2021/09/20)

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.

Reactivity of vanadyl pyrophosphate catalyst in ethanol ammoxidation and β-picoline oxidation: Advantages and limitations of bi-functionality

Tabanelli, Tommaso,Mari, Massimiliano,Folco, Federico,Tanganelli, Federico,Puzzo, Francesco,Setti, Laura,Cavani, Fabrizio

, (2021/04/23)

This study investigates the catalytic activity of vanadyl pyrophosphate (VPP) for both gas-phase ethanol ammoxidation to acetonitrile and β-picoline oxidation to nicotinic acid. Both reactions may be alternative processes to the industrial technologies used to produce these two chemicals. The reaction networks were investigated, also by feeding possible intermediates; in-situ DRIFT spectroscopy was used to monitor the interaction of ethanol and ammonia with the catalyst. VPP bi-functionality features played an important role in the two reactions; specifically, acidity was detrimental either because it catalyzed undesired reactions, such as ethanol dehydration to ethylene during ethanol ammoxidation, or because it caused a strong interaction with reactants – especially those containing N atoms, ammonia and β-picoline – thus giving rise to some surface saturation phenomena which inhibited the consecutive reactions leading to the final desired compounds, acetonitrile and nicotinic acid. The co-feeding of steam helped product desorption, thus enhancing selectivity in β-picoline oxidation.

Redox-Induced Structural Reorganization Dictates Kinetics of Cobalt(III) Hydride Formation via Proton-Coupled Electron Transfer

Kurtz, Daniel A.,Dhar, Debanjan,Elgrishi, Noémie,Kandemir, Banu,McWilliams, Sean F.,Howland, William C.,Chen, Chun-Hsing,Dempsey, Jillian L.

supporting information, p. 3393 - 3406 (2021/03/08)

Two-electron, one-proton reactions of a family of [CoCp(dxpe)(NCCH3)]2+ complexes (Cp = cyclopentadienyl, dxpe = 1,2-bis(di(aryl/alkyl)phosphino)ethane) form the corresponding hydride species [HCoCp(dxpe)]+ (dxpe = dppe (1,2-bis(diphenylphosphino)ethane), depe (1,2-bis(diethylphosphino)ethane), and dcpe (1,2-bis(dicyclohexylphosphino)ethane)) through a stepwise proton-coupled electron transfer process. For three [CoCp(dxpe)(NCCH3)]2+ complexes, peak shift analysis was employed to quantify apparent proton transfer rate constants from cyclic voltammograms recorded with acids ranging 22 pKa units. The apparent proton transfer rate constants correlate with the strength of the proton source for weak acids, but these apparent proton transfer rate constants curiously plateau (kpl) as the reaction becomes increasingly exergonic. The absolute apparent proton transfer rate constants across both these regions correlate with the steric bulk of the chelating diphosphine ligand, with bulkier ligands leading to slower kinetics (kplateau,depe = 3.5 × 107 M-1 s-1, kplateau,dppe = 1.7 × 107 M-1 s-1, kplateau,dcpe = 7.1 × 104 M-1 s-1). Mechanistic studies were conducted to identify the cause of the aberrant kPTapp-ΔpKa trends. When deuterated acids are employed, deuterium incorporation in the Cp ring is observed, indicating protonation of the CoCp(dxpe) species to form the corresponding hydride proceeds via initial ligand protonation. Digital simulations of cyclic voltammograms show ligand loss accompanying initial reduction gates subsequent PCET activity at higher driving forces. Together, these experiments reveal the details of the reaction mechanism: reduction of the Co(III) species is followed by dissociation of the bound acetonitrile ligand, subsequent reduction of the unligated Co(II) species to form a Co(I) species is followed by protonation, which occurs at the Cp ring, followed by tautomerization to generate the stable Co(III)-hydride product [HCoCp(dxpe)]+. Analysis as a function of chelating disphosphine ligand, solvent, and acid strength reveals that the ligand dissociation equilibrium is directly influenced by the steric bulk of the phosphine ligands and gates protonation, giving rise to the plateau of the apparent proton transfer rate constant with strong acids. The complexity of the reaction mechanism underpinning hydride formation, encompassing dynamic behavior of the entire ligand set, highlights the critical need to understand elementary reaction steps in proton-coupled electron transfer reactions.

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

Mayer, Robert J.,Hampel, Nathalie,Ofial, Armin R.

supporting information, p. 4070 - 4080 (2021/01/29)

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

Process route upstream and downstream products

Process route

acetamide
60-35-5

acetamide

phosphorus pentachloride
10026-13-8,874483-75-7

phosphorus pentachloride

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
acetimidoyl bromide; hydrobromide
20203-78-5

acetimidoyl bromide; hydrobromide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
at 25 ℃;
acetimidoyl iodide; hydriodide
92276-99-8

acetimidoyl iodide; hydriodide

hydrogen iodide
10034-85-2

hydrogen iodide

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
2,2-dimethyl-3-phenyl-2H-azirine
14491-02-2

2,2-dimethyl-3-phenyl-2H-azirine

methyl-3 phenyl-1 aza-2 butadiene-1,3
51209-53-1

methyl-3 phenyl-1 aza-2 butadiene-1,3

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
at 600 ℃; under 0.750075 Torr; Inert atmosphere;
35%
51%
10%
3-phenyl-4,4-dimethyl-5-oxo-2-isoxazoline
51942-54-2

3-phenyl-4,4-dimethyl-5-oxo-2-isoxazoline

2,2-dimethyl-3-phenyl-2H-azirine
14491-02-2

2,2-dimethyl-3-phenyl-2H-azirine

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
at 600 ℃; under 7.50075E-05 - 0.000750075 Torr;
44%
16%
14%
benzyl ethyl ketone
1007-32-5

benzyl ethyl ketone

acetic acid
64-19-7,77671-22-8

acetic acid

benzonitrile
100-47-0

benzonitrile

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
With aluminum (III) chloride; sodium nitrite; In N,N-dimethyl-formamide; at 120 ℃; for 3h; Schlenk technique;
91 %Chromat.
4-hydroxy-3-methyl-4-phenylisoxazoline-5-one
80490-51-3

4-hydroxy-3-methyl-4-phenylisoxazoline-5-one

Benzoylformic acid
611-73-4

Benzoylformic acid

acetonitrile
75-05-8,26809-02-9

acetonitrile

Conditions
Conditions Yield
With 2,6-dichloro-benzonitrile; In benzene; for 0.5h; Heating;
70%
Conditions
Conditions Yield
at 650 ℃; under 7.50075E-05 - 0.000750075 Torr;
40%
40%
at 600 ℃; Mechanism; 700 deg C;
β-Propiolactone
57-57-8

β-Propiolactone

3-Methylpyridine
108-99-6

3-Methylpyridine

ethanol
64-17-5

ethanol

acetic acid
64-19-7,77671-22-8

acetic acid

acrylonitrile
107-13-1,25014-41-9

acrylonitrile

7-deazahypoxanthine
3680-71-5

7-deazahypoxanthine

acetonitrile
75-05-8,26809-02-9

acetonitrile

propiononitrile
107-12-0

propiononitrile

Conditions
Conditions Yield
With oxygen; at 400 ℃; for 5.55556E-05h; under 760.051 Torr; Temperature; Inert atmosphere; Pyrolysis; Gas phase; Flow reactor;
Conditions
Conditions Yield
at 400 ℃; for 5.55556E-05h; under 760.051 Torr; Temperature; Inert atmosphere; Pyrolysis; Gas phase; Flow reactor;

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