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107-13-1 Usage

Description

Acrylonitrile is a colourless, flammable liquid. Its vapours may explode when exposed to an open flame. Acrylonitrile does not occur naturally. It is produced in very large amounts by several chemical industries in the United States, and its requirement and demand are increasing in recent years. Acrylonitrile is a heavily produced, unsaturated nitrile. It is used to make other chemicals such as plastics, synthetic rubber, and acrylic fibres. It has been used as a pesticide fumigant in the past; however, all pesticide uses have been discontinued. This compound is a major chemical intermediate used in creating products such as pharmaceuticals, antioxidants, and dyes, as well as in organic synthesis. The largest users of acrylonitrile are chemical industries that make acrylic and modacrylic fibres and high-impact ABS plastics. Acrylonitrile is also used in business machines, luggage, construction material, and manufacturing of styrene-acrylonitrile (SAN) plastics for automotive, household goods, and packaging material. Adiponitrile is used to make nylon, dyes, drugs, and pesticides. Acrylonitrile-3D-balls

Usage History

On the eve of World War II, it was discovered that acrylonitrile copolymer can improve the oil resistance and solvent resistance of synthetic rubber and people began to be taken it seriously. During the war, it was developed in Germany of the manufacturing process through epoxidation of ethylene, followed by addition with hydrogen cyanide to produce cyanide ethanol, and finally dehydration. It was later developed of addition of hydrogen cyanide to acetylene under the catalysis of cuprous chloride. After 1960, it had been developed of new production process in the Ohio standard oil company, using propylene as raw material for ammoxidation reaction to obtain it. This process has led to great changes in industrial production. Owing to the availability of raw materials and the reduction in the cost, there is a sudden surge in production of acrylonitrile. In 1983, the world's annual output reached 3 million tons, of which the production amount of Ohio standard oil can account for 90%. Acrylonitrile is easy to undergo polymerization, being able to produce polyacrylonitrile fiber (under the trade name of acrylic or bulk). Its short fiber is similar to wool, also known as artificial wool. It feels soft by hand with excellent elasticity. It can co-polymerize with vinyl acetate to generate synthetic fibers (under the commercial name of Austrian Lun). In 1950, it was first put into industrial production by the United States DuPont. The majority of acrylonitrile is used for synthetic fiber with the amount accounting for about 40~60% of the total. With copolymerization with butadiene copolymerization, it can generate oil-resistant nitrile rubber. Acrylonitrile dimerization and hydrogenation can be lead to adiponitrile, with then hydrogenation being able to obtain hexamethylene diamine, which is one of the raw materials of polyamide (nylon 66). The co-polymer of acrylonitrile and butadiene, styrene terpolymer is a high-quality engineering plastics, referred to as ABS resin.

Chemical properties

Acrylonitrile is a clear, colorless to pale-yellow liquid with molecular formula C3H3N and molecular weight of 53.06. The yellowing color is upon exposure to light and indicate photo-alteration to saturate derivate. It is practically odorless, or with a very slight odor that may be describe as sweet, irritating, unpleasant, onion or garlic-like or pungent. Odor can only be detected above PEL. Boiling point of 77.3°C and melting point of ?82 °C. The specific gravity is 0.8004 @ 25 deg C, pH is from 6.0 to 7.5 (5% aqueous solution), vapor density of 1.8 (Air=1), Vapor pressure 109 mm Hg @ 25°C. The Henry law constant is 1.38×10?4 atm cu m/mole @ 25°C.

Food fumigants

In 1941~1942, the German Degesch Gesellsch company recommended to use acrylonitrile as a food fumigant.Toxicity: acrylonitrile is of great toxicity to human with comparable toxicity as hydrocyanic acid. Acrylonitrile is highly toxic to insects, and is the most toxic in the main fumigant for controlling various stored grain pests.Acrylonitrile is used alone or in combination with carbon tetrachloride and has no effect on the germination of many vegetables, grains and flower seeds, but has some damage to maize seeds. The mixture of acrylonitrile and carbon tetrachloride can be used to control the vast majority of stored cereals pests. The results showed that acrylonitrile and carbon tetrachloride, when formulated into mixture in a ratio of 1:1, can be used to control the Phthorimaea operculella Zell occurring in potato under storage without damaging the tubers.Usage method: Because acrylonitrile and carbon tetrachloride are of high boiling point, upon atmospheric fumigation, in order to be quickly evaporated, it was developed of a simple method which uses cotton cord core to pass through the shallow iron disk bottom. During the beginning of the fumigation, inject a liquid fumigant into the dish and then blow the air through the fan to the cotton core until the evaporation is complete.

Uses

Different sources of media describe the Uses of 107-13-1 differently. You can refer to the following data:
1. Acrylonitrile is primarily used in the manufacture of acrylic and modacrylic fibers. It is also used as a raw material in the manufacture of plastics (acrylonitrile-butadiene-styrene and styrene-acrylonitrile resins), adiponitrile, acrylamide, and nitrile rubbers and barrier resins. A mixture of acrylonitrile and carbon tetrachloride was used as a pesticide in the past; however, all pesticide uses have stopped. Acrylonitrile is a commercially important industrial chemical that has been used extensively since 1940s with the rapid expansion of the petrochemical industry.The production of ABS and SAN resins consumes the second largest quantity of acrylonitrile. The ABS resins are produced by grafting acrylonitrile and styrene onto polybutadiene or a styrene–butadiene copolymer and contain about 25 wt% acrylonitrile. These products are used to make components for automotive and recreational vehicles, pipe fittings, and appliances. The SAN resins are styrene–acrylonitrile copolymers containing 25–30 wt% of acrylonitrile. The superior clarity of SAN resin allows it to be used in automobile instrument panels, for instrument lenses and for houseware items (Langvardt, 1985; Brazdil, 1991).
2. Acrylonitrile is used in the production of acrylic fibers, resins, and surface coating; as an intermediate in the production of pharmaceuticals and dyes; as a polymer modifier; and as a fumigant. It may occur in fire-effluent gases because of pyrolyses of polyacrylonitrile materials. Acrylonitrile was found to be released from the acrylonitrile–styrene copolymer and acrylonitrile–styrene–butadiene copolymer bottles when these bottles were filled with food-simulating solvents such as water, 4% acetic acid, 20% ethanol, and heptane and stored for 10 days to 5 months (Nakazawa et al. 1984). The release was greater with increasing temperature and was attributable to the residual acrylonitrile monomer in the polymeric materials.

Chemical Properties

Acrylonitrile is a colorless, flammable liquid. Its vapors may explode when exposed to an open flame. Acrylonitrile does not occur naturally. It is produced in very large amounts by several chemical industries in the United States and its requirement and demand has increased in recent years. The largest users of acrylonitrile are chemical industries that make acrylic and modacrylic fi bers, high impact acrylonitrile-butadiene-styrene (ABS) plastics. Acrylonitrile is also used in business machines, luggage, and construction material, in the manufacturing of styrene-acrylonitrile (SAN) plastics for automotive and household goods, and in packaging material. Adiponitrile is used to make nylon, dyes, drugs, and pesticides.

Production Methods

Acrylonitrile is produced in commercial quantities almost exclusively by the vapor-phase catalytic propylene ammoxidation process developed by Sohio.C3H6 + NH3 + 2/3O2→ C3H3N +3H2OThe one-step, fluid bed Acrylonitrile manufacturing process was developed by scientists of The Standard Oil Company (Sohio), one of INEOS's predecessors in the U.S. in the 1950s. Today, over 95 percent of the world's Acrylonitrile is manufactured using INEOS's exclusive technology.

Definition

ChEBI: Acrylonitrile is a nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an ethenyl group. It is very toxic and irritant but is also a sensitizer. It caused both irritant and allergic contact dermatitis in a production manufacture.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

ACRYLONITRILE produces poisonous hydrogen cyanide gas on contact with strong acids or when heated to decomposition. Reacts violently with strong oxidizing agents (dibenzoyl peroxide, di-tert-butylperoxide, bromine) [Sax, 9th ed., p. 61]. Rapidly ignites in air and forms explosive mixtures with air. Polymerizes violently in the presence of strong bases or acids. Underwent a runaway reaction culminating in an explosion on contact with a small amount of bromine or solid silver nitrate [Bretherick, 5th ed., 1995, p. 404].

Health Hazard

Acrylonitrile is a highly toxic compound, an irritant to the eyes and skin, mutagenic, teratogenic, and causes cancer in test animals.Acrylonitrile is a moderate to severe acute toxicant via inhalation, oral intake, dermal absorption, and skin contact. Inhalation of this compound can cause asphyxia and headache. Firefighters exposed to acrylonitrile have reported chest pains, headache, shortness of breath, lightheadedness, coughing, and peeling of skin from their lips and hands (Donohue 1983). These symptoms were manifested a few hours after exposure and persisted for a few days. Inhalation of 110 ppm for 4 hours was lethal to dogs. In humans, inhalation of about 500 ppm for an hour could be dangerous. The toxicity symptoms in humans from inhaling high concentrations of acrylonitrile were somnolence, diarrhea, nausea, and vomiting (ACGIH 1986).

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.

Contact allergens

Acrylonitrile is a raw material used extensively in industry, mainly for acrylic and modacrylic fibers, acrylonitrile-butadiene-styrene and styrene-acrylonitrile resins, adiponitrile used in nylon’s synthesis, for nitrile rubber, and plastics. It is also used as an insecticide. This very toxic and irritant substance is also a sensitizer and caused both irritant and allergic contact dermatitis in a production manufacturer.

Potential Exposure

Acrylonitrile is used in the manufacture of synthetic fibers, polymers, acrylostyrene plastics, acrylonitrile butadiene styrene plastics, nitrile rubbers, chemicals, and adhesives. It is also used as a pesticide. In the past, this chemical was used as a room fumigant and pediculicide (an agent used to destroy lice).

Carcinogenicity

Acrylonitrile is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

storage

Work with acrylonitrile should be conducted in a fume hood to prevent exposure by inhalation, and splash goggles and impermeable gloves should be worn at all times to prevent eye and skin contact. Acrylonitrile should be used only in areas free of ignition sources. Containers of acrylonitrile should be stored in secondary containers in the dark in areas separate from oxidizers and bases.

Shipping

UN1093 Acrylonitrile, stabilized, Hazard Class 3; Labels: 3 Flammable liquids, 6.1-Poisonous materials

Purification Methods

Wash acrylonitrile with dilute H2SO4 or dilute H3PO4, then with dilute Na2CO3 and water. Dry it with Na2SO4, CaCl2 or (better) by shaking with molecular sieves. Fractionally distil it under N2. It can be stabilised by adding 10ppm tert-butyl catechol. Immediately before use, the stabilizer can be removed by passage through a column of activated alumina (or by washing with 1% NaOH solution if traces of water are permissible in the final material), followed by distillation. Alternatively, shake it with 10% (w/v) NaOH to extract inhibitor, and then wash it in turn with 10% H2SO4, 20% Na2CO3 and distilled water. Dry for 24hours over CaCl2 and fractionally distil under N2 taking fraction boiling at 75.0-75.5oC (at 734mm). Store it with 10ppm tert-butyl catechol. Acrylonitrile is distilled off when required. [Burton et al. J Chem Soc, Faraday Trans 1 75 1050 1979, Beilstein 2 IV 1473.]

Environmental Fate

Acrylonitrile is both readily volatile in air and highly soluble in water. These characteristics determine the behavior of acrylonitrile in the environment. The principal pathway leading to the degradation of acrylonitrile in air is photooxidation, mainly by reaction with hydroxyl radicals (OH). Acrylonitrile may also be oxidized by other atmospheric components such as ozone and oxygen. Very little is known about the nonbiologically mediated transformation of acrylonitrile in water. It is oxidized by strong oxidants such as chlorine used to disinfect water. Acrylonitrile is readily degraded by aerobic microorganisms in water.

Incompatibilities

Acrylonitrile is reactive with, and must be kept away from, strong oxidizers, especially bromine. Use extreme care to keep Acrylonitrile away from strong bases, strong acids, copper, copper alloys, ammonia and amines. Contact with these chemicals can cause a chemical reaction resulting in a fire or explosion. Chemical compatibility should also be determined before Acrylonitrile comes in contact with any other chemical.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration with provision for nitrogen oxides removal from effluent gases by scrubbers or afterburners. A chemical disposal method has also been suggested involving treatment with alcoholic NaOH; the alcohol is evaporatedand calcium hypochlorite added; after 24 hours the product is flushed to the sewer with large volumes of water. Recovery of acrylonitrile from acrylonitrile process effluents is an alternative to disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 107-13-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 107-13:
(5*1)+(4*0)+(3*7)+(2*1)+(1*3)=31
31 % 10 = 1
So 107-13-1 is a valid CAS Registry Number.
InChI:InChI=1/C3H3N/c1-2-3-4/h2H,1H2

107-13-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name acrylonitrile

1.2 Other means of identification

Product number -
Other names Acrylonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Acrylonitrile is primarily used in the manufacture of acrylic and modacrylic fibers. It is also used as a raw material in the manufacture of plastics (acrylonitrile-butadiene-styrene and styrene-acrylonitrile resins), adiponitrile, acrylamide, and nitrile rubbers and barrier resins.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:107-13-1 SDS

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107-13-1Relevant articles and documents

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.

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.

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.

-

Kim,Takizama

, p. 356 (1974)

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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.

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.

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.]

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Lankhuyzen et al.

, p. 20 (1975)

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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.

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

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Zidan et al.

, p. 133,134 - 142 (1978)

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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.

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.

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.

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.

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.

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Kawamoto,Nishimura

, p. 1105 (1969)

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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.

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Ham,Stevens

, p. 4638 (1962)

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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.

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.

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.

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.

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.

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.

PRODUCTION OF DINITRILES

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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.

PROCESS FOR PRODUCING UNSATURATED NITRILE

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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.

PROCESSES FOR STABILIZING ANTIMONY CATALYSTS

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Paragraph 0101-0104, (2020/09/08)

The present disclosure relates to a process for stabilizing an antimony ammoxidation catalyst in an ammoxidation process. The process may comprise providing an antimony ammoxidation catalyst to a reactor; reacting propylene with ammonia and oxygen in the fluidized bed reactor in the presence of the antimony ammoxidation catalyst to form a crude acrylonitrile product; and adding an effective amount of an antimony-containing compound to the antimony ammoxidation catalyst to maintain catalyst conversion and selectivity; wherein the antimony-containing compound has a melting point less than 375°C. The present disclosure also relates to catalyst compositions and additional processes using the antimony ammoxidation catalyst stabilized by an antimony-containing compound.

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