107-13-1 Usage
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
107-13-1Relevant 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.
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.
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.
