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Cas Database

107-13-1

107-13-1

Identification

  • Product Name:Acrylonitrile

  • CAS Number: 107-13-1

  • EINECS:203-466-5

  • Molecular Weight:53.0635

  • Molecular Formula: C3H3N

  • HS Code:29261000

  • Mol File:107-13-1.mol

Synonyms:Acrylonitrile(8CI);Acrylon;Carbacryl;Cyanoethene;Cyanoethylene;Fumigrain;NSC 6362;Propenenitrile;VCN;Ventox;Vinyl cyanide;2-Propenenitrile;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,ToxicT,DangerousN

  • Hazard Codes:F,T,N,Xn

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH301 Toxic if swallowed H311 Toxic in contact with skin H315 Causes skin irritation H318 Causes serious eye damage H317 May cause an allergic skin reaction H331 Toxic if inhaled H335 May cause respiratory irritation H350 May cause cancer H411 Toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. See Notes. In case of skin contact First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . It is classified as very toxic. Probable oral lethal dose for human is 50-500 mg/kg (between 1 teaspoon and 1 oz.) for a 70 kg (150 lb.) person. Irritant skin dose -- 500 mg. Toxic concentrations have been reported at 16 ppm/20 min. Acute toxicity is similar to that due to cyanide poisoning, and the level of cyanide ion in blood is related to the level of poisoning. Inhalation or ingestion results in collapse and death due to tissue anoxia (lack of oxygen) and cardiac arrest (heart failure). (EPA, 1998) Severe acute inhalations should be treated like cyanide poisoning. The first priority is to establish adequate ventilation (100% oxygen) and circulation, since cyanide antidotes are theoretically useful but clinically unproven in acrylonitrile poisoning.

  • Fire-fighting measures: Suitable extinguishing media Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Fight fire from protected location or maximum possible distance. Materials are too dangerous to health to expose fire fighters. A few whiffs of vapor could cause death or vapor or liquid could be fatal on penetrating the fire fighter's normal full protective clothing. The normal full protective clothing and breathing apparatus available to the average fire department will not provide adequate protection against inhalation or skin contact with these materials. Explosion hazard is moderate. It is flammable and explosive at normal room temperatures. Can react violently with strong acids, amines, strong alkalis. Vapors may travel considerable distance to source of ignition and flash back. Dilute solutions are also hazardous (flash point of a solution of 2 percent in water is 70F). When heated or burned, toxic hydrogen cyanide gas and oxides of nitrogen are formed. Avoid strong acids, amines, alkalis. Incompatible with strong oxidizers (especially bromine) copper and copper alloys. Unstable, moderate hazard is possible when it is exposed to flames, strong acids, amines and alkalis. May polymerize spontaneously in the container, particularly in absence of oxygen or on exposure to visible light. If polymerization occurs in containers, there is a possibility of violent rupture. (EPA, 1998) 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. Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Ventilation. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Remove solutions containing acrylonitrile by vacuum cleaning to prevent an increase in airborne concentrations.

  • 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. Separated from strong oxidants, strong bases and food and feedstuffs. Cool. Keep in the dark. Ventilation along the floor. Store only if stabilized.PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10-hour Time-Weighted Average: 1 ppm. Skin.Recommended Exposure Limit: 15 Minute Ceiling Value: 10 ppm. Skin.NIOSH considers acrylonitrile to be a potential occupational carcinogen.NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.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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  • Manufacture/Brand:TRC
  • Product Description:Acrylonitrile(1mg/mLinMethanol)
  • Packaging:5x1mL
  • Price:$ 250
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Acrylonitrile (stabilized with MEHQ)
  • Packaging:25ML
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Acrylonitrile (stabilized with MEHQ)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acrylonitrile ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor
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  • Manufacture/Brand:Sigma-Aldrich
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acrylonitrile solution certified reference material, 5000?μg/mL in methanol
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acrylonitrile ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acrylonitrile solution certified reference material, 5000 μg/mL in methanol
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acrylonitrile (stabilised with hydroquinone monomethyl ether) for synthesis. CAS No. 107-13-1, EC Number 203-466-5., (stabilised with hydroquinone monomethyl ether) for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acrylonitrile (stabilised with hydroquinone monomethyl ether) for synthesis
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Relevant articles and documentsAll total 188 Articles be found

Rate enhancing of carbon dioxide in the reaction of acetonitrile with methanol to acrylonitrile over magnesium oxide catalyst

Lin, Yi Wen,Ishi, Makoto,Ueda, Wataru,Morikawa, Yutaka

, p. 793 - 794 (1995)

Carbon dioxide greatly enhanced the formation of acrylonitrile in the gas-phase reaction of acetonitrile with methanol over magnesium oxide catalyst.The reaction in the presence of carbon dioxide was accompanied by the reaction of methanol with carbon dioxide to give carbon monoxide and water.An adsorbed carbon dioxide species on the basic surface of magnesium oxide seems to afford an active methanol-derived species for the reaction with acetonitrile.

Synthesis of MoVNbTe(Sb)Ox composite oxide catalysts via reduction of polyoxometalates in an aqueous medium

Tsuji, Hideto,Koyasu, Yukio

, p. 5608 - 5609 (2002)

The synthesis of MoVNbTe(Sb)Ox composite oxide catalysts based on the self-organization of polyoxometalates (POMs) was investigated. The catalysts which were synthesized via reduction of POMs by using reducing agents under mild conditions and/followed by calcination in an O2-excluded atmosphere which superior performance for propane (amm)oxidation. It was suggested that the metastable phase formed at an elevated temperature with a specific oxidation state corresponds to the catalytic activity. Copyright

Enantioselective Folding at the Cyclodextrin Surface

Eliseev, Alexey V.,Iacobucci, Guillermo A.,Khanjin, Nikolai A.,Menger, F. M.

, p. 2051 - 2052 (1994)

Spectroscopic and kinetic studies of β-cyclodextrin-linked L- and D-phenylalanine cyanoethyl esters in aqueous solution reveal an unusual intramolecular complexation mode where the hydrophobic portion of the amino acid resides outside the host cavity; L- and D-derivatives show different binding geometries and energies.

Study of the local structure and oxidation state of iron in complex oxide catalysts for propylene ammoxidation

Wu, Li-Bin,Wu, Liang-Hua,Yang, Wei-Min,Frenkel, Anatoly I.

, p. 2512 - 2519 (2014)

Iron molybdate plays a crucial role in the complex oxide catalysts used for selective oxidation and ammoxidation of hydrocarbons but its structural and electronic properties and their changes in the process of the reaction are poorly understood. A combination of Raman, X-ray absorption, and UV-visible spectroscopy was applied to investigate a commercial catalyst as a function of the reaction time. The results show that an iron-containing compound exists predominantly as ferric molybdate in the fresh catalyst, which is reduced progressively in the process of reaction, forming predominantly ferrous molybdate. The irreversible transformation from Fe2(MoO 4)3 to FeMoO4 was accompanied by formation of a small amount of Fe2O3. These two processes observed in our experiment shed light on the deactivation mechanism of this complex catalyst because they have a negative effect on the selectivity and activity. Specifically, they are responsible for the deterioration of the redox couple, blocking the transmission of lattice oxygen, and irreversibly changing the catalyst structure. Based on the results of the combined techniques, a refined procedure has been proposed to develop a more stable and efficient selective oxidation catalyst.

PYROLYSIS OF PROPIONITRILE AND THE RESONANCE STABILISATION ENERGY OF THE CYANOMETHYL RADICAL

Trenwith, Antony B.

, p. 2755 - 2764 (1983)

The pyrolysis of propionitrile has been studied at seven temperatures over the range 789-850 K and pressures between 10 and 100 Torr.Under these conditions the principal reaction products which are formed by essentially homogeneous processes are hydrogen, hydrogen cyanide, methane, ethane, ethene, acetonitrile and acrylonitrile.For short reaction times (A free radical chain mechanism has been proposed which accounts for all the above products.The chain initiating step is the reaction .Measurements of the rate of formation of methane in the subsequent reaction yield the rate expression where Θ = 2.303 RT/cal mol-1.The activation energy leads to D(H3C-CH3CN) = 80.4 +/- 1 kcal mol-1 and a resonance energy of 5.4 +/- 1.4 kcal mol-1 for the cyanomethyl radical.

Ammoxidation of allyl alcohol-a sustainable route to acrylonitrile

Guillon, Cyrille,Liebig, Carsten,Paul, Sebastien,Mamede, Anne-Sophie,Hoelderich, Wolfgang F.,Dumeignil, Franck,Katryniok, Benjamin

, p. 3015 - 3019 (2013)

The ammoxidation of allyl alcohol was demonstrated over antimony-iron oxide catalysts with a Sb/Fe ratio of 0.6 and 1. Both catalysts showed high performance with 83 and 84% yield of acrylonitrile, respectively, whereby the main difference was found in the initial performance. This was ascribed to the in-operando formation of the SbFeO4 mixed oxide on the catalyst surface under reaction conditions, as proven by XPS analysis.

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Kim,Takizama

, p. 356 (1974)

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Catalytic properties of nitrided V/Al/O-mixed oxides in the ammoxidation of propane and new efficient preparation method for the catalysts

Bilde,Janke,Brückner,Millet

, p. 10 - 15 (2012)

V/Al/O oxides have been prepared and tested as catalysts for the ammoxidation of propane into acrilonitrile at 500 °C. The high efficiency of these catalysts, which were partially nitrided under catalytic reaction conditions, is confirmed. The best catalysts characterized by a V/Al ratio around 0.30, exhibited selectivity to acrilonitrile of 51% at 58% conversion. Testing at low conversion showed that propene was the main primary product from propane ammoxidation and that the reaction pathway on these catalysts was similar to that on other efficient catalytic systems. A new method of synthesis based upon the decomposition at low temperature of a mixed ammonium aluminum-vanadium oxalate was developed. It leads to highly active catalysts, which displayed increased selectivity to acrylonitrile. The gain in activity and selectivity was attributed to a better dispersion of vanadium with a higher concentration of isolated vanadium species in the bulk and presumably at the surface of the catalysts.

Regioselective synthesis of 1,2,4-triazol-3(2H)-ones and their 3(2H)-thiones: Kinetic studies and selective pyrolytic deprotection

Al-Awadi, Nouria A.,Ibrahim, Yehia A.,Kaul, Kamini,Dib, Hicham

, p. 50 - 55 (2003)

Selective pyrolytic deprotection of 2-ethyl and 2-cyanoethyl-4-arylidenimino-1,2,4-triazol-3(2H)-ones and their 3(2H)-thiones was studied by flash vacuum pyrolysis. This study is useful in regioselective synthesis of 2-and 4-substituted 1,2,4-triazoles of potential biological applications. The kinetic results and product analysis lend support to a reaction pathway involving a six-membered transition state.

Highly active and selective supported bulk nanostructured MoVNbTeO catalysts for the propane ammoxidation process

Lopez-Medina, R.,Rojas, E.,Banares, M. A.,Guerrero-Perez, M. O.

, p. 67 - 71,5 (2012)

We report a methodology to prepare nanoscaled supported-bulk MoVNbTeO catalysts in which the phases required to obtain an active and selective catalysts are nanoscaled on the surface of a support. Thus, a more economic catalytic material with improved mechanical properties can be obtained. The effect of vanadium content and atmosphere of calcination on the catalytic performance are discussed, and the results of the supported-catalysts are compared with those of bulk catalytic samples, which have been prepared as reference. The best supported catalyst afford ca. 50% acrylonitrile yield with 80% propane conversion at 450 °C. The activity per gram of MoVNbTeO increases fourfold upon stabilization of its nanoparticles.

Role of Promoters on the Acrolein Ammoxidation Performances of BiMoOx

Ghalwadkar, Ajay,Katryniok, Benjamin,Paul, Sébastien,Mamede, Anne-Sophie,Dumeignil, Franck

, p. 431 - 443 (2016)

Ammoxidation of acrolein to acrylonitrile was studied using multicomponent (MC) BiMoOx catalysts in the presence of ammonia and oxygen. The MC catalysts containing bivalent and trivalent metal promoters were found to be highly active and selective to acrylonitrile. The corresponding MC catalysts were characterized by X-ray diffraction, nitrogen physisorption, X-ray photoelectron spectroscopy, ICP-MS and UV-visible diffuse reflectance spectroscopy. It was observed that, among the bivalent cations, the catalysts containing both Co-Ni showed superior performances due to the presence of the metastable β-CoxNi1-xMoO4 phase. The presence of a trivalent cation, and especially of iron, promoted the formation of both the γ-Bi2MoO6 active phase and the active β-phase of bivalent metal molybdate. Further, optimization of the reaction conditions enabled the achievement of a 59 % acrylonitrile yield.

Kinetics and mechanism of liquid-phase thermal decomposition of β-cyanoethyl-N-nitramines

Stepanov,Astakhov,Kruglyakova,Pekhotin

, p. 1256 - 1258 (2002)

Termal decomposition of β-cyanoethyl-N-nitramine in melt is preceded by protonation of the amino nitrogen atom and is accompanied by evolution of nitrogen(I) oxide with formation of acrylonitrile. Thermal decomposition of bis(β-cyanoethyl)-N-nitramine under similar conditions follows a radical mechanism with initial dissociation of the N-N bond. The same mechanism is operative in thermal decomposition of both N-nitramines in a dilute dibutyl phthalate solution.

Propane Versus Ethane Ammoxidation on Mixed Oxide Catalytic Systems: Influence of the Alkane Structure

Guerrero-Pérez, M. Olga,Rojas-García, Elizabeth,López-Medina, Ricardo,Ba?ares, Miguel A.

, p. 1838 - 1847 (2016)

Abstract: Catalysts from three different catalytic systems, Ni–Nb–O, Mo–V–Nb–Te–O and Sb–V–O, have been prepared, characterized, and tested during both ethane and propane ammoxidation reactions, in order to obtain acetonitrile and acrylonitrile, respectively. The catalytic results show that Mo–V–Nb–Te–O and Sb–V–O catalyze propane ammoxidation but are inactive for ethane ammoxidation whereas Ni–Nb–O catalysts catalyze both, ethane and propane ammoxidation. The activity results, and the characterization of fresh and used catalysts along with some data from previous studies, indicate that the ammoxidation reaction mechanism that occurs in these catalytic systems is different. In the case of Mo–V–Nb–Te–O and Sb–V–O, two active sites appear to be involved. In the case of Ni–Nb–O catalysts, only one site seems to be involved, which underlines that the mechanism is different and take place via a different intermediate. These catalysts activate the methyl groups in ethane, on the contrary, neither ethane nor ethylene appear to adsorb on the Mo–V–Nb–Te–O and Sb–V–O active sites. Graphical Abstract: [Figure not available: see fulltext.]

Kinetics of Pyrolysis of the Isomeric Butenenitriles and Kinetic Modeling

Doughty, Alan,Mackie, John C.

, p. 272 - 281 (1992)

Kinetics of pyrolysis of the butenenitrile isomers, cis- and trans-crotonitrile and allyl cyanide, have been studied dilute in argon in a single-pulse shock tube over the temperature range of 1200-1500 K at uniform gas residence times behind the reflected shock of between 650 and 750 μs and at pressures between 18 and 20 atm.Thermal decomposition was preceded by isomerization of the butenenitriles whose rates are coupled with the rates of thermal decomposition.The decomposition was found to follow a free-radical mechanism, with the major chain involving propagation reactions of the cyanomethyl radical to produce acetonitrile and acetylene.Other routes important to the mechanism involve hydrogen atom addition to the butenenitriles.HCN principally arises from this route.A detailed kinetic reaction model is presented to model the experimental reactants and products profiles as a function of temperature.From the modeling and experiment, the following initiation rate constants have been obtained: trans-CH3CH=CHCN -> CH3 + HC=CHCN (k-11 = 1017.45 exp(-96.5/RT) s-1), cis-CH3CH=CHCN -> CH3 + HC=CHCN (k-12 = 1017.53 exp(-98.5/RT) s-1), CH2=CHCH2CN -> H2C=CH + CH2CN (k-13 = 1015.53 exp(-82.6/RT) s-1), where the activation energies are in kcal mol-1.

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Lankhuyzen et al.

, p. 20 (1975)

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High temperature pretreatment of Fe-silicalite for the ammoxidation of propane

Raabová, Kate?ina,Bulánek, Roman,Bad'Urová, Eva

, p. 54 - 59 (2013)

Fe-silicalite with low concentration of iron was used in the study of the activation by high temperature nitridation (in the temperature range from 540 °C to 700 °C). Nitrided materials were characterized by means of FTIR and UV-Vis spectroscopy. It was f

Effects of Polar β Substituents in the Gas-Phase Pyrolysis of Ethyl Acetate Esters

Chuchani, Gabriel,Martin, Ignacio,Hernandez, Jose A. A.,Rotinov, Alexandra,Fraile, German,Bigley, David B.

, p. 944 - 948 (1980)

The rates of the gas phase pyrolysis of six β-substituted ethyl acetates were studied in a static system over the temperature range 319-450 deg C and the pressure range 63-207 mmHg.In seasoned vessels the reactions are homogenous, follow a first-order rate law, and are unimolecular.The temperature dependence of the rate constants is given by the following Arrhenius equations for the compounds indicated: 2-(dimethylamino)ethyl acetate, log k(s-1) = (13.90 +/- 0.30) - (220.4 +/- 3.8) kJ*mol-1 (2.303RT)-1; 2-methoxyethyl acetate, log k(s-1) = (12.04 +/- 0.24) -(203.7 +/- 2.9) kJ*mol1- (2.303RT)-1; 2-(methylthio)ethyl acetae, log k(s-1 = (11.27 +/- 0.39) - (179.0 +/- 4.6) kJ*mol-1 (2.303RT)-1; 2-chloroethyl acetate, log k(s-1) = (12.14 +/- 0.66) - (202.0 +/- 8.4)kJ*mol-1 (2.303RT)-1; 2-fluoroethyl acetate, log k(s-1) = (12.68 +/- 0.60) - (211.2 +/- 7.1) kJ*mol-1 (2.303RT)-1; 2-cyanoethylacetate, Log k(s-1) = (11.51 +/- 0.13) - (171.9 +/- 1.7) kJ*mol-1 (2.303RT)-1.The effect of substituents in the gas-phase elimination of β-substituted ethyl acetates may be grouped in three types.The linear correlation of several -I electron-withdrawing groups along strong ? bonds is presented and discussed.A small amount of anchimeric assistance is proposed in the pyrolysis of the 2-(methyltio)ethyl acetate.The experimental data are consistent with the transition state where the Cα-O bond polarization is the rate-determining process.

Pyrolysis and Photolysis Processes of Pyran and Thiopyran Derivatives

Atalla,Hussein,Badr

, p. 29 - 35 (1997)

Pyrolysis and photolysis of 2-amino-3,5-dicyano-6-phenyl-4H-pyran (1) afford HNCO, acrylonitrile, cinnamonitrile, and 2-hydroxy-3,5-dicyano-6-phenylpyridine. Pyrolysis of 2-carboxyimino-3,5-dicyano-6-phenyl-4H-pyran (2) gives HCN, acrylonitrile, cinnamonitrile and 2-hydroxy-3,5-dicyano-6-phenylpyridine. Furthermore, both pyrolysis and photolysis of 2,6-diamino-3,5-dicyanothiopyran (3a) gives rise to HNCS, acrylonitrile and 6-amino-3,5-dicyano-6-mercaptopyridin. Moreover, comparative studies of pyrolysis and photolysis of 2,6-dicyano-4-arylthiopyran derivatives 3b-d revealed similar results. The similarity of products obtained from pyrolysis and photolysis and the mechanistic implications of these data are discussed.

Tetrakis(2-cyanoethoxy)borate - An alternative to tetracyanidoborate-based ionic liquids

Harloff, Joerg,Karsch, Markus,Lund, Henrik,Schulz, Axel,Villinger, Alexander

, p. 4243 - 4250 (2013)

This study examines the synthesis and properties of salts of the new tetrahedral [B(O-C2H4-CN)4]- anion, which can be synthesized by the reaction of tetrahedral NaBH4 and HO-C2H4

Influence of alumina precursor on the physico-chemical properties of V-Sb-P-W/Al2O3 catalyst studied for the ammoxidation of propane

Pasupulety, Nagaraju,Driss, Hafedh,Zaman, Sharif F.,Alhamed, Yahia Abobakor,Alzahrani, Abdulrahim Ahmed,Daous, Muhammad A.,Petrov, Lachezar

, p. 52 - 62 (2016)

Influence of alumina precursor on active phase formation in V1.0-Sb3.5-P0.5-W1.0/50% Al2O3 catalyst was studied for the ammoxidation of propane in the temperature range of 490-530°C at W/F

-

Zidan et al.

, p. 133,134 - 142 (1978)

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Operando raman study of alumina-supported Sb-V-O catalyst during propane ammoxidation to acrylonitrile with on-line activity measurement

Guerrero-Perez,Banares

, p. 1292 - 1293 (2002)

Operando Raman spectra during propane ammoxidation show partially reversible structural transformations of the active phases as a function of reaction environment.

Ammoxidation of acrolein to acrylonitrile over bismuth molybdate catalysts

Thanh-Binh, Nguyen,Dubois, Jean-Luc,Kaliaguine, Serge

, p. 7 - 12 (2016)

The present work deals with the potentially significant process converting acrolein of green origin to acrylonitrile using mesoporous bismuth molybdate catalysts. The ammoxidation catalysts were characterized by N2 physisorption, X-ray diffraction, and catalytic tests under various conditions at different temperatures, contact times, and reactant molar ratios. The results indicated a catalytic activity proportional to specific surface area, which depends on bismuth molybdate phases, and concentration of oxygen in the gas feed. The selectivity of the catalysts only depends on reaction temperature. ACN selectivity obtained at 350-400 °C was 100% and reduced to 97% at 450 °C.

The Mutual Promotion Effect of Molybdates in Multicomponent Molybdate Catalysts

Kripylo, P.,Hohlstamm, I.,Koppe, J.,Kraak, P.,Rapthel, I.,Hofmann, A.

, p. 699 - 704 (1993)

Multicomponent molybdate catalysts (e.g. of the composition Bi2Fe1.5Co7Cr10Mo19Oy) are produced by coprecipitation, drying and calcination.These catalysts exhibit high activity and selectivity in the ammoxidation of propene to acrylonitrile.The individual molybdates (Co-, Fe- and Cr-molybdate) exhibit no selectivity in the ammoxidation of propene.Therefore a mutual promotion effect of these molybdates exists.The cause of the promotion effect is the formation of the active and selective phase from the β-phase of Co-molybdate by exchange of protons with ions of Fe3+ and Cr3+ from the molybdates of Fe and Cr.The structure of this catalytic active and selective phase is similar to the structure of the β-phase of Co-molybdate.

Kinetics and mechanism of thermal gas-phase elimination of β-substituted carboxylic acids

Al-Awadi,Abdallah,Dib,Ibrahim,Al-Awadi,El-Dusouqui

, p. 5769 - 5777 (2005)

3-Phenoxypropanoic acid (1), 3-(phenylthio)propanoic acid (2), and 4-phenylbutanoic acid (3) were pyrolysed between 520 and 682 K. Analysis of the pyrolysates showed the elimination products to be acrylic acid and the corresponding arene. Pyrolysis of ethyl 3-phenoxypropanoate (4) and its methyl analogue (5), ethyl 3-(phenylthio)propanoate (6) and its methyl counterpart (7), and 3-phenoxypropane nitrile (8) were also investigated between 617 and 737 K. The thermal gas-phase elimination kinetics and product analysis are compatible with a thermal retro-Michael reaction pathway involving a four-membered cyclic transition state.

Looking for heteroaromatic rings and related isomers as interstellar candidates

Lattelais,Ellinger,Matrane,Guillemin

, p. 4165 - 4171 (2010)

Finding complex organic molecules in the interstellar medium (ISM) is a major concern for understanding the possible role of interstellar organic chemistry in the synthesis of prebiotic species. The present interdisciplinary report is a prospective study aimed at helping detection of heteroaromatic compounds or at least of some of their isomers in the ISM. The thermodynamic stabilities of the C4H5N, C4H4O, C4H4S families were calculated using density functional theory (DFT). It was found that pyrrole, furan and thiophene are unambiguously the most stable isomers at the 10-50 K temperatures of the ISM. Several of the less stable isomers were synthesized and flash vacuum thermolysis experiments were performed on these species. Although the detection of pyrrole in the pyrolysis of many compounds has been reported in the literature, we observed that none of its isomers led to pyrrole in these conditions, which suggests that other formation routes are to be considered. On the other hand, these three aromatic compounds present a very high stability, few % been decomposed at 1500 K by flash vacuum thermolysis; these experiments also show a great stability of crotonitrile that is the most stable compound that can be formed in these conditions. The rotational constants, dipole moments and IR frequencies of the low-lying isomers are given to encourage laboratory experiments on these prototype molecules.

Ammoxidation of Propane over Antimony-Vanadium-Oxide Catalysts

Nilsson, Roland,Lindblad, Thomas,Andersson, Arne

, p. 501 - 513 (1994)

Catalysts belonging to the Sb-V-O system were prepared with various Sb/V ratios and were used for propane ammoxidation to acrylonitrile.XRD patterns of freshly prepared samples show those with excess vanadia to consist of V2O5 ans SbVO4, while SbVO4 and α-Sb2O4 are constituents in the samples with a Sb/V ratio above unity.High rate and selectivity for propylene formation at low conversion are characteristic for samples with excess vanadia and considering XRD, Raman, infrared, and XPS results, this is explained by formation of amorphous vanadia spread over the surface of SbVO4.Catalysts with both α-Sb2O4 and SbVO4 phases are the most selective for acrylonitrile formation, a function that is linked to their ability to selectively transform intermediate propylene.XPS data suggests this function to be associated with the formation of suprasurface antimony sites on SbVO4 as a results of migration of antimony from α-Sb2O4 during the catalytic process.Raman and infrared spectral features revealed that compared with SbVO4, the samples with both α-Sb2O4 and SbVO4 are more efficiently reoxidises during propane amoxidation.Rate dependences on the partial pressures of reactants over a sample with excess α-Sb2O4 show that the adsorption of propane is the rate limiting step for propylene formation, and that acrylonitrile and carbon oxides are predominantly formed from the intermediate propylene in routes comprising nonequilibrated steps.Addition of water vapour results in an increase of rate and selectivity for acrylonitrile formation.The kinetic dependences indicate that for acrylonitrile formation it is advantageous in have a feed rich in propane and to use recirculation for obtaining high productivity.

Mechanism of Gas Phase Cyanation of Alkenes and Aromatics

Henis, Neil B. H.,Miller, Larry L.

, p. 2820 - 2823 (1983)

ICN was photolyzed at 254 nm in the gas phase in the presence of 15-20 torr of certain alkenes or aromatics.The products were analyzed by GC-MS.Ethene gave acrylonitrile; propene gave acrylonitrile, allyl cyanide and cis- and trans-1-cyanopropene; 2-methylpropene gave 2 cyanopropene; benzene gave benzonitrile; toluene gave benzonitrile and 2-, 3-, and 4-cyanotoluene.These products are explained by a mechanism involving attack of CN on the organic to give vibrationally excited radicals.These radicals rapidly fragment, producing the major products, or react more slowly in bimolecular processes.The relevance of these results to RF discharge chemistry is discussed.

Structure, activity and selectivity relationships in propane ammoxidation to acrylonitrile on V-Sb oxides: Part 3 modifications during the catalytic reaction and effect of feed composition

Centi, Gabriele,Guarnieri, Francesco,Perathoner, Siglinda

, p. 3391 - 3402 (1997)

The change in surface reactivity up until steady-state behavior is reached in propane ammoxidation of a series of V-Sb-oxide catalysts with Sb : V ratios in the range 1-10 and prepared either by calcination or heat treatment in vacuum at 600°C is reported and analyzed in terms of the change in the structural features of the catalyst determined as a function of the time on stream by IR spectroscopy, X-ray diffraction and chemical analysis data. The results indicate that during the catalytic reaction, V5+ oxide when present, quickly reduces forming a V4+O2/VSbO4 solid solution with an increase in the selectivity to propene, but not to acrylonitrile. An increase in the selectivity and productivity to acrylonitrile occurs when an Sb-rich approximate VSbO4 phase forms ('VSbO4'). This phase, however, is partially metastable, decomposing to 'VSbO4' + Sb2O4 when Sb5+ ions are reduced and not rapidly reoxidized. V5+ ions on the surface of the rutile phase stabilize the Sb-rich 'VSbO4' phase, and catalyze the reoxidation of Sb3+. This side oxidation of ammonia to nitrogen competes for the reduction of these V5+ ions and influences the above redox and solid-state reactions. Therefore, a considerable dependence of the surface reactivity on the feed was observed. The optimal catalytic behavior determined for the series of catalysts studied was found to depend on the feed composition indicating that in the analysis of the structure, activity and selectivity relationships in propane ammoxidation the concentration of reactants in the feed plays a specific important role.

-

Goy, C. A.,Shaw, D. H.,Pritchard, H. O.

, p. 1504 - 1507 (1965)

-

Application of high throughput screening to heterogeneous liquid and gas phase oxidation catalysis

Guram, Anil,Hagemeyer, Alfred,Lugmair, Claus G.,Turner, Howard W.,Volpe Jr., Anthony F.,Weinberg, W. Henry,Yaccato, Karin

, p. 215 - 230 (2004)

The application of combinatorial methods to oxidation catalysis in the liquid and gas phases is described. New lead materials have been discovered for the selective liquid phase oxidation of alcohols to aldehydes/ketones catalyzed by vanadium supported on carbon, for the low temperature CO oxidation/ light off for cold start automotive emissions control over supported noble metals and perovskites, for volatile organic compound (VOC) removal using CoCr oxide catalysts, and for the selective gas phase oxidation of propane to acrylic acid and acrylonitrile using mixed metal oxides. Catalyst discovery libraries were screened in 96-well batch reactors, in a rapid serial scanning mass spectrometer and in a massively parallel microfluidic reactor as primary screens. Promising hits were scaled up in conventional autoclaves or in multi-channel fixed bed secondary/ tertiary screening reactors.

Morimoto

, p. 450,452, 891 (1956)

-

Kawamoto,Nishimura

, p. 1105 (1969)

-

-

Odaira et al.

, p. 4106 (1966)

-

Cobalt(II) complexes of nitrile-functionalized ionic liquids

Nockemann, Peter,Pellens, Michael,Van Hecke, Kristof,Van Meervelt, Luc,Wouters, Johan,Thijs, Ben,Vanecht, Evert,Parac-Vogt, Tatjana N.,Mehdi, Hasan,Schaltin, Stijn,Fransaer, Jan,Zahn, Stefan,Kirchner, Barbara,Binnemans, Koen

, p. 1849 - 1858 (2010)

A series of nitrile-functionalized ionic liquids were found to exhibit temperature-dependent miscibility (thermomorphism) with the lower alcohols. Their coordinating abilities toward cobalt(II) ions were investigated through the dissolution process of cobalt(II) bis(trifluoromethylsulfonyl)-imide and were found to depend on the donor abilities of the nitrile group. The crystal structures of the cobalt(II) solvates [Co(C1C1CNPyr) 2(Tf2N)4] and [Co(C1C 2CNPyr)6][Tf2N]8, which were isolated from ionic-liquid solutions, gave an insight into the coordination chemistry of functionalized ionic liquids. Smooth layers of cobalt metal could be obtained by electrodeposition of the cobalt-containing ionic liquids.

Activation Parameters and Location of the Transition State in the Retro-Diels-Alder Reaction of a 7-Oxabicyclohept-5-ene Derivative

Jenner, G.,Papadopoulos, M.,Rimmelin, J.

, p. 748 - 749 (1983)

-

-

Ham,Stevens

, p. 4638 (1962)

-

-

Mori,Tsuji

, p. 827,828, 832 (1973)

-

Alkylating potential of α,β-unsaturated compounds

Manso, Jose A.,Cespedes Camacho, Isaac F.,Calle, Emilio,Casado, Julio

, p. 6226 - 6233 (2011)

Alkylation reactions of the nucleoside guanosine (Guo) by the α,β-unsaturated compounds (α,β-UC) acrylonitrile (AN), acrylamide (AM), acrylic acid (AA) and acrolein (AC), which can act as alkylating agents of DNA, were investigated kinetically. The following conclusions were drawn: i) The Guo alkylation mechanism by AC is different from those brought about the other α,β-UC; ii) for the first three, the following sequence of alkylating potential was found: AN > AM > AA; iii) A correlation between the chemical reactivity (alkylation rate constants) of AN, AM, and AA and their capacity to form adducts with biomarkers was found. iv) Guo alkylation reactions for AN and AM occur through Michael addition mechanisms, reversible in the first case, and irreversible in the second. The equilibrium constant for the formation of the Guo-AN adduct is Keq (37 °C) = 5 × 10-4; v) The low energy barrier (≈10 kJ mol -1) to reverse the Guo alkylation by AN reflects the easy reversibility of this reaction and its possible correction by repair mechanisms; vi) No reaction was observed for AN, AM, and AA at pH 8.0. In contrast, Guo alkylation by AC was observed under cellular pH conditions. The reaction rate constants for the formation of the α-OH-Guo adduct (the most genotoxic isomer), is 1.5-fold faster than that of γ-OH-Guo. vii) a correlation between the chemical reactivity of α,β-UC (alkylation rate constants) and mutagenicity was found.

-

Costa,Mestroni

, p. 325 (1968)

-

Ammoxidation of Propane on Nickel Antimonates: The Role of Vanadium as Promoter

Cassidy,Pollastri,Trifiro

, p. 55 - 63 (1997)

The catalytic behaviour of Ni-Sb mixed oxides doped by vanadium has been investigated for the ammoxidation of propane and propene to acrylonitrile. The binary nickel antimonates, with 1:1 80%) but they showed no activity in propane ammoxidation till 470°C. The activity/gram and the yield in acrylonitrile (ACN)/gram presented a maximum at Ni:Sb 1:2 due to a balance between the surface area and the doping effect of antimony. With the addition of vanadium to the Ni-Sb system, the activity and productivity of the catalysts were increased markedly, both in propane and propene ammoxidation. The optimum vanadium loading in terms of ACN yield was found for NiSb2O6 to be V:Ni 0.2:1 atomic ratio, a compromise between activity and selectivity. It was found that sites containing vanadium are involved in the selective nitrogen insertion step in propene ammoxidation, as well as in the activation of propane. The ammoxidation of propane is a cleaner reaction than the ammoxidation of propene, as smaller amounts of hydrogen cyanide (HCN) and acetonitrile (AceN) were formed for the same yield of acrylonitrile. X-ray analysis revealed the presence of NiSb2O6 and free αSb2O4 in all samples. In the Ni-Sb vanadium doped oxides the FTIR characterisation showed that up to a V:Ni ratio of 0.2, vanadium species different from V2O5, and very likely interacting with the NiSb2O6, were formed; these species are the ones involved in propane activation. With higher loadings of vanadium, V2O5 species formed which are responsible for the lowering of acrylonitrile selectivity.

Elimination Reactions of β-Cyano Thioethers: Internal Return and the Lifetime of the Carbanion Intermediate

Fishbein, James C.,Jencks, William P.

, p. 5087 - 5095 (1988)

The E1cB elimination reaction of the pentafluorothiophenol adduct of fumaronitrile (3) in water containing 8.3percent Me2SO shows strong buffer catalysis and primary deuterium isotope effects of kH/kD = 4-5.In contrast, hydrogen exchange of the methanethiol adduct of 3 shows little or no buffer catalysis.There is no incorporation of deuterium that gives an inverse solvent isotope effect in the buffer-catalyzed elimination of the thionitrobenzoate adduct of 3 in D2O and H2O, although thiol anion expulsion is partly rate limiting for this reaction.These observations are consistent with internal return of the abstracted proton from the protonated buffer base that is competitive with the expulsion of leaving groups with pKa > 4.The primary deuterium isotope effects for elimination catalyzed by hydroxide ion are kH/kD = 4.9 +/- 0.4, 4.2 +/- 0.1, 4.2 +/- 0.3, and 3.1 +/- 0.1 for the pentafluorothiophenol and thionitrobenzoate adducts of 3, the N-methyl-2-mercaptopyridinium ion adduct of acrylonitrile (1), and the pentafluorothiophenol adduct of chloroacrylonitrile (2), respectively.These isotope effects are significantly larger than values of kH/kD = 2.6 +/- 0.3, 2.2 +/- 0.1, and 2.1 +/- 0.1 for buffer-catalyzed elimination from the adducts of 1 and 3.They are also larger than (1) the primary isotope effects of kH/kD = 2.5 +/- 0.3, 2.3 +/- 0.2, and 2.3 +/- 0.2 for the p-nitrothiophenol adducts of 1 and 3 and the thiophenol adduct of 2 that were obtained from the biphasic kinetics for elimination of these compounds in D2O and (2) the product discrimination isotope effects of ca. 3 for the addition of thiol anions to 1 and 3.These observations are consistent with the formation of an unstable carbanion intermediate that undergoes competitive reprotonation by solvent, k-1, exchange of the abstracted proton with the bulk solvent, ks, and elimination, k2.Ratios of k-1/ks and k-1/k2 that were obtained from the results give values of k-1 ca. 1E11 s-1 and k2 = 1E10-1E13 s-1, assuming a value of ks = 1E11 s-1.Estimated pKa values in aqueous solution include 26.8 for NCCH2CH2SPh, 22.0 for NCCH(Cl)CH2SPhNO2, and 23.2 for NCCH2CH(CN)SCH3.

Propane ammoxidation on Bi promoted MoVTeNbOx oxide catalysts: Effect of reaction mixture composition

Andrushkevich, Tamara V.,Popova, Galina Y.,Chesalov, Yuriy A.,Ischenko, Evgeniya V.,Khramov, Mikhail I.,Kaichev, Vasily V.

, p. 109 - 117 (2015)

MoVTeNbO catalysts were characterized with XRD, XPS, and FTIR techniques and tested in the ammoxidation of propane. Bismuth-modified MoVTeNbO catalysts showed a higher acrylonitrile yield than the base four-component system. The effect of the reaction mixture composition (C3H8, NH3 and O2) on selectivity towards different products was studied at propane conversion above 80%. The favorable effect of bismuth promoter on the selectivity towards acrylonitrile was explained by suppression of acrylonitrile transformation connected with decreasing acidity of the catalyst.

Ammoxidation of propane to acrylonitrile over silica-supported Fe-Bi nanocatalysts

Adams, Richard D.,Alexeev, Oleg S.,Amiridis, Michael D.,Blom, Douglas,Elpitiya, Gaya,Khivantsev, Konstantin

, p. 10 - 16 (2015)

Ammoxidation of propane to acrylonitrile was examined over a Fe3BiOx/SiO2 sample prepared by thermal decarbonylation of [Et4N][Fe3(CO)10(μ3-Bi)] on the surface of mesoporous silica. Catalytic measurements performed at 500 °C showed that this sample yields 49% acrylonitrile selectivity at 36% propane conversion when a 5.5%C3H8/30%O2/11%NH3/He balance reaction mixture was used at a GHSV of 1360 h?1. HRSTEM, EDS, and XPS measurements indicate that mixed Fe3BiO6 oxide particles less than 2 nm in size were formed on the surface of this material under reaction conditions. A Fe/Bi atomic ratio in these particles is approximately 3:1 and the Fe and Bi ions both are in the +3 oxidation state. A Fe-Bi/SiO2 sample prepared by co-impregnation of individual Fe and Bi salts had very low activity and low selectivity for acrylonitrile formation from propane under similar experimental conditions due to larger sizes of particles formed under reaction conditions and enrichment of their surface with Fe.

Influence of the Bulk and Surface Properties on the Performance of Iron-Antimony Catalysts

Burriesci, Nicola,Garbassi, Fabio,Petrera, Michele,Petrini, Guido

, p. 817 - 834 (1982)

The modifications induced in Fe-Sb catalysts by the introduction of an excess of antimony oxide, which is needed in order to obtain highly slective catalysts in the ammonoxidation of propylene to acrylonitrile, were investigated by means of X-ray diffraction (X.r.d.), X-ray photoelectron spectroscopy (X.p.s.) and Moessbauer spectroscopy.More important than increasing the surface Sb:Fe ratio, a promoting effect by an excess of Sb was found to develop during activation through the formation of structurally distorted and defective FeSbO4, which appears to be the active phase.Fe2+ ions are thus introduced into the iron antimonate rutile structure near oxygen vacancies.These vacancies are possibly connected with the adsorption sites for the more strongly bound oxygen species that is responsible for allylic oxidation.

New class of catalysts for the ammoxidation of propane to acrylonitrile over nickel-molybdenum mixed nitrides

Zhang, Huimin,Zhao, Zhen,Xu, Chunming,Duan, Aijun

, p. 36 - 37 (2006)

Nickel-molybdenum mixed nitride catalysts were first reported for the ammoxidation of propane to acrylonitrile. It was found that the mixed nitrides exhibited high activity and selectivity to acrylonitrile. The mixed nitride catalyst with 1.0 of Ni/Mo atomic ratios showed the best catalytic properties for propane ammoxidation. The highest yield of acrylonitrile was 28.5% at the propane conversion of 68.4% at 773 K. Copyright

Crossed beam reaction of cyano radicals with hydrocarbon molecules. III. Chemical dynamics of vinylcyanide (C2H3CN;X 1A') formation from reaction of CN(X 2Σ+) with ethylene, C2H4(X 1Ag)

Balucani, N.,Asvany, O.,Chang, A. H. H.,Lin, S. H.,Lee, Y. T.,Kaiser, R. I.,Osamura, Y.

, p. 8643 - 8655 (2000)

The neutral-neutral reaction of the cyano radical, CN(X 2Σ+), with ethylene, C2H4(X 1Ag), has been performed in a crossed molecular beams setup at two collision energies of 15.3 and 21.0 kJ mol-1 to investigate the chemical reaction dynamics to form vinylcyanide, C2H3CN(X 1A') under single collision conditions. Time-of-flight spectra and the laboratory angular distributions of the C3H3N products have been recorded at mass-to-charge ratios 53-50. Forward-convolution fitting of the data combined with ab initio calculations show that the reaction has no entrance barrier, is indirect (complex forming reaction dynamics), and initiated by addition of CN(X 2Σ+) to the ? electron density of the olefin to give a long-lived CH2CH2CN intermediate. This collision complex fragments through a tight exit transition state located 16 kJ mol-1 above the products via H atom elimination to vinylcyanide. In a second microchannel, CH2CH2CN undergoes a 1,2 H shift to form a CH3CHCN intermediate prior to a H atom emission via a loose exit transition state located only 3 kJ mol-1 above the separated products. The experimentally observed mild sideways scattering at lower collision energy verifies the electronic structure calculations depicting a hydrogen atom loss in both exit transition states almost parallel to the total angular momentum vector J and nearly perpendicular to the C2H3CN molecular plane. Since the reaction has no entrance barrier, is exothermic, and all the involved transition states are located well below the energy of the separated reactants, assignment of the vinylcyanide reaction product soundly implies that the title reaction can form vinylcyanide, C2H3CN, as observed in the atmosphere of Saturn's moon Titan and toward and toward dark, molecular clouds holding temperatures as low as 10 KI. In strong agreement with our theoretical calculations, the formation of the C2H3NC isomer was not observed.

XANES study of the dynamic states of V-based oxide catalysts under partial oxidation reaction conditions

Guerrero-Pérez,López-Medina,Rojas-Garcia,Ba?ares

, p. 210 - 215 (2019)

A XANES study under reaction conditions has been performed with two different V-based catalytic systems, Mo-V-Nb-Te-O and V-Sb-O. For this study, an alumina-supported nanoscaled bulk catalyst has been used. In all cases XANES determined the average vanadium oxidation state during reaction. XANES also demonstrated that the nanosized phases are more dynamic, and able to participate in the redox catalytic cycle without significant changes either in their structure or in the overall vanadium oxidation state. Such a stability is also apparent under oxidizing conditions.

Effect of Fe, Ga, Ti and Nb substitution in ≈sbVO4 for propane ammoxidation

Wickman, Andreas,Andersson, Arne

, p. 110 - 117 (2011)

Substitution in rutile-type ≈SbVO4 was made with Fe 3+ and Ga3+ replacing V3+, and Nb5+ replacing Sb5+. Moreover, preparations with Ti were synthesised where Ti4+ ions substitute for both V4+ and V 3+/Sb5+ pairs. ≈SbVO4-related phases containing Ti together with Fe and Ga were also prepared. The samples were characterised using X-ray diffraction, DRIFT and Raman spectroscopy. The characterisations show the formation of a cation deficient single rutile-type phase. Use of the samples in propane ammoxidation to produce acrylonitrile reveals, compared with the pure ≈SbVO4 phase, that Fe, Ga and Ti substitution in ≈SbVO4 results in lower activity but considerably higher selectivity to acrylonitrile at the same level of propane conversion. Niobium substitution, on the contrary, gives no improved catalytic properties. Correlations are presented between the catalytic and structural properties of the catalysts. It is demonstrated that isolation in the structure of the propane activating V-O. sites in a surrounding of nitrogen inserting Sb-sites results in improved selectivity for acrylonitrile formation.

THE CYANATION OF VINYL HALIDES CATALYZED BY NICKEL(0) COMPLEX GENERATED IN SITU

Sakakibara, Yasumasa,Yadani, Nobuichi,Ibuki, Ichiro,Sakai, Mutsuji,Uchino, Norito

, p. 1565 - 1566 (1982)

Nickel(0) species generated in situ from NiBr2(PPh3)2-Zn-PPh3 catalyzed the formation of unsaturated nitriles from vinyl halides and potassium cyanide.The reaction proceeded under very mild conditions and was stereoselective.

PRODUCTION OF DINITRILES

-

Paragraph 0088-0089, (2022/02/15)

A process for producing dinitrile comprises supplying a C6 organic compound, an oxidizing agent, ammonia and a diluent to a reaction zone to produce a reaction mixture and contacting the reaction mixture in the reaction zone with a heterogeneous catalyst at a temperature from 50 to 200°C to convert at least a portion of the C6 organic compound to dinitrile and water and produce a reaction effluent. At least part of the reaction effluent is supplied to a separation system to separate at least dinitrile and unreacted ammonia from the reaction effluent and additional water is supplied to a portion of the reaction effluent prior to or during separation of unreacted ammonia from the reaction effluent.

METHOD FOR PRODUCING NITRILE

-

Paragraph 0080; 0090; 0093-0094, (2021/02/05)

The present invention provides a method of producing a nitrile from a primary amide, characterized in that the primary amide is subjected to a dehydration reaction in a supercritical fluid in the presence of an acid catalyst. The present invention achieves the object of reducing the corrosion of a reactor and the thermal decomposition of raw materials, as well as provides the effect of improving the reaction rate and nitrile selectivity.

PROCESS FOR PRODUCING UNSATURATED NITRILE

-

Paragraph 0067-0080, (2021/07/31)

A process for producing unsaturated nitrile comprising a reaction step of subjecting hydrocarbon to a vapor phase catalytic ammoxidation reaction in a fluidized bed reactor to produce the corresponding unsaturated nitrile, wherein, in the reaction step, a powder is fed to a dense zone in the fluidized bed reactor using a carrier gas, and a ratio of a linear velocity LV1 of the carrier gas at a feed opening to feed the powder to the fluidized bed reactor to a linear velocity LV2 of a gas in the dense zone (LV1/LV2) is not less than 0.01 and not more than 1200.

Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong

, (2020/12/09)

The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.

INTEGRATED METHODS AND SYSTEMS FOR PRODUCING AMIDE AND NITRILE COMPOUNDS

-

Paragraph 00093, (2020/09/30)

Provided herein are integrated methods and systems for the production of acrylamide and acrylonitrile compounds and other compounds from at least beta-lactones and/or beta-hydroxy amides.

Process route upstream and downstream products

Process route

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

3-dimethylaminopropiononitrile
1738-25-6

3-dimethylaminopropiononitrile

hydrochloride of 3-dimethylaminopropionitrile
18076-02-3

hydrochloride of 3-dimethylaminopropionitrile

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

acrylonitrile

N,N-Dimethyl-4-nitroaniline
100-23-2

N,N-Dimethyl-4-nitroaniline

Conditions
Conditions Yield
In i-Amyl alcohol; at 130 ℃; for 130h; Product distribution;
1.4 g
In i-Amyl alcohol; at 130 ℃; for 130h;
1.4 g
2-cyanoethyl p-nitrophenyl sulfoxide

2-cyanoethyl p-nitrophenyl sulfoxide

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

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

acrylonitrile

Conditions
Conditions Yield
In 1,4-dioxane; at 100 ℃; Rate constant; sealed tube;
1-(2-cyanoethyl)-3-cyanopyridinium bromide
130671-04-4

1-(2-cyanoethyl)-3-cyanopyridinium bromide

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

acrylonitrile

Conditions
Conditions Yield
With potassium hydroxide; potassium chloride; In water; at 25 ℃; Rate constant; Product distribution; Mechanism; other N-(2-cyanoethyl)pyridinium bromides, var. basic media; pH dependence of the velocity const.;
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;
2-chlorpropionitrile
1617-17-0,70886-58-7

2-chlorpropionitrile

cyanide<sup>(1-)</sup>
57-12-5

cyanide(1-)

hydrogen cyanide
74-90-8

hydrogen cyanide

2-methylmalononitrile
3696-36-4

2-methylmalononitrile

methylmalononitrile anion
78232-00-5

methylmalononitrile anion

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

acrylonitrile

Conditions
Conditions Yield
In gas; Rate constant;
C<sub>11</sub>H<sub>14</sub>NOS<sup>(1+)</sup>*BF<sub>4</sub><sup>(1-)</sup>

C11H14NOS(1+)*BF4(1-)

1-methoxy-4-methylsulfanyl-benzene
1879-16-9

1-methoxy-4-methylsulfanyl-benzene

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

acrylonitrile

Conditions
Conditions Yield
With potassium chloride; ethylamine; In water; at 25 ℃; Rate constant; Mechanism; var. β-cyanoethylsulfonium salts, var. primary amines and hydroxide anion; effect of catalyst basicity and leaving group basicity on the rate;
1-Methyl-2-cyano-7-oxabicyclo<2.2.1>hept-5-ene
1727-98-6,56561-73-0,90005-40-6

1-Methyl-2-cyano-7-oxabicyclo<2.2.1>hept-5-ene

2-methylfuran
534-22-5

2-methylfuran

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

acrylonitrile

Conditions
Conditions Yield
In cyclohexane; at 69.9 - 89.9 ℃; under 750.06 Torr; Rate constant;
In dichloromethane; at 69.8 - 101.6 ℃; under 750.06 Torr; Rate constant;
In acetonitrile; at 69.8 - 101.6 ℃; under 750.06 Torr; Rate constant;
In cyclohexane; at 80.1 ℃; under 750.06 - 697556 Torr; Rate constant;
In dichloromethane; at 80.1 ℃; under 750.06 - 708807 Torr; Rate constant;
In acetonitrile; at 80.1 ℃; Rate constant;
In acetonitrile; at 79.9 ℃; Thermodynamic data; ΔH(excit.), ΔG(excit.), ΔS(excit.), ΔV(excit.), log A;
In dichloromethane; at 79.9 ℃; Thermodynamic data; ΔH(excit.), ΔG(excit.), ΔS(excit.), ΔV(excit.), log A;
In cyclohexane; at 79.9 ℃; Thermodynamic data; ΔH(excit.), ΔG(excit.), ΔS(excit.), ΔV(excit.), log A;
2-β-cyanoethyl-1,2,4-triazol-3(2H)-one
537698-45-6

2-β-cyanoethyl-1,2,4-triazol-3(2H)-one

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

acrylonitrile

2,4-dihydro-1,2,4-triazol-3-one
930-33-6,5311-58-0

2,4-dihydro-1,2,4-triazol-3-one

Conditions
Conditions Yield
at 800 ℃; under 0.01 Torr;
4%
43%
4-chlorobenzylidenimino-2-β-cyanoethyl-1,2,4-triazol-3(2H)-one

4-chlorobenzylidenimino-2-β-cyanoethyl-1,2,4-triazol-3(2H)-one

4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

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

acrylonitrile

2,4-dihydro-1,2,4-triazol-3-one
930-33-6,5311-58-0

2,4-dihydro-1,2,4-triazol-3-one

2-β-cyanoethyl-1,2,4-triazol-3(2H)-one
537698-45-6

2-β-cyanoethyl-1,2,4-triazol-3(2H)-one

Conditions
Conditions Yield
at 226.85 ℃; under 0.01 Torr; Further Variations:; Temperatures; Kinetics; Activation energy;
Conditions
Conditions Yield
With aluminum oxide; dihydrogen peroxide; ammonium hydroxide; at 100 ℃; for 1h; Microwave irradiation; Neat (no solvent);

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