Acrylonitrile

Description:

  • Chemical Name: Acrylonitrile
  • Regulatory Name:2-Propenenitrile, Acrylonitrile

  • Molecular formula C3H3N
  • Molecular weight 53.1 g/mol
  • Density 0.81 g/cm3 at 25oC
  • Boiling point 77.3oC
  • Melting point -82oC
  • Vapor pressure 100 torr at 23oC
  • Solubility Soluble in isopropanol, ethanol, ether,acetone, and benzene
  • Conversion factor 1 ppm = 2.17 mg/m3 at 25 oC
  • DOT Label: Flammable Liquid, Poison

The acrylonitrile is a colorless to pale yellow liquid and volatile liquid that is soluble in water and most common organic solvents such as acetone, benzene, carbon tetrachloride, ethyl acetate, and toluene. It melts at 84 degrees C and boils at 77 degrees C. Technical-grade acrylonitrile is more than 99% pure and always contains a polymerization inhibitor. Acrylonitrile is a reactive chemical that polymerizes spontaneously, when heated, or in the presence of a strong alkali unless it is inhibited, usually with ethylhydroquinone. It can explode when exposed to flame. It attacks copper. It is incompatible and reactive with strong oxidizers, acids and alkalis; bromine; and amines. Synonyms for acrylonitrile are AN, acrylonitrile monomer, cyanoethylene, propenenitrile, vinyl cyanide, and VCN.

Lewis structure shown below. In the space provided, draw a 3D hybrid orbital bonding picture of acrylonitrile. Label the hybridization of each atomic orbital. Show overlap of orbitals to give bonds and label the type of bond. Indicate what type of orbital the lone pair is in.

Uses:

Acrylonitrile is produced commercially by propylene ammoxidation, in which propylene,ammonia, and air are reacted by catalyst in a fluidized bed. Acrylonitrile is used primarily as a co-monomer in the production of acrylic and modacrylic fibers. Uses include the production of plastics, surface coatings, nitrile elastomers, barrier resins, and adhesives. It is also a chemical intermediate in the synthesis of various antioxidants, pharmaceuticals, dyes, and surface-active

agents. Formerly, acrylonitrile was used as a fumigant for food commodities, flour milling, and bakery food processing equipment (HSDB, 1994). The annual statewide industrial emissions from facilities reporting under the Air Toxics Hot Spots Act in California based on the most recent inventory were estimated to be 3948 pounds of acrylonitrile (CARB, 2000). US EPA

(1993) reported a mean ambient air concentration of acrylonitrile at four urban locations in the U.S.of 0.66 mg/m3.

Regulation:

In the following text you can see the differents normatives in Sapin and EE.UU.

Spanish normative:

Chemical agents:

Prepared substances and (mixtures or solutions of several substances) chemical.

Dangerous chemical agents:

Those that are able to produce damages on the people, environment or material.

The chemical agents like factors of risk, classification for the dangerous chemical agent commercialization:Law 31/1995 of 8 of November, Prevention of Labor Risks Real Decree 374/2001 of 6 of April, on the protection of the health and security of the workers against the risks related to the chemical agents during the work.

Article 3.

Evaluation of the risks.

  1. The industralist will have to determine, in the first place, if dangerous chemical agents in the work place exist. If thus outside, the risks for the health and security of the workers, originated by these agents are due to evaluate, in accordance with article 16 of the Law of Prevention of Labor Risks and the section 1ª of chapter II of the Regulations of Prevention, considering and analyzing jointly:

a) Its dangerous properties and any other necessary information for the evaluation of the risks, that must facilitate the supplier, or that can be successfully obtained of this one or of any other source of intelligence readily accessible. This information must include the card of security data and, when it comes, the evaluation of the risks for the users, contemplated in the norm on commercialization of dangerous chemical agents.

Article 9. Information and formation of the workers.

d) Access to all list of credits facilitated by the supplier, in agreement the arranged thing in the norm on classification, packaging and labeling of dangerous prepared substances and.

Article 18. The industralist will have to adopt the suitable measures so that the workers receive all the necessary information on the risks for the security and the health that its activity originates, as much the generals of the company, like those of the job.

Article 41. The used chemical agent manufacturers, importers and providers in the work will have to package and to label such so that allows to his conservation and manipulation in conditions of security. 2. In individual, the industralist will have to facilitate to the workers or their representatives, following the criterion settled down in section 1 of article 18 of the Law of Prevention of Labor risks:

By its effects on the environment

By its fisicoquímicas properties

By its toxicológicas properties

By its specific effects on the health

  • Very toxic
  • Toxics
  • Injurious
  • Corrosive
  • Irritating
  • Sensibilizantes
  • Toxics for the reproduction
  • Carcinogénicos
  • Mutagénics
  • Easily inflammable
  • Inflammable
  • Explosives
  • Supporters of combustion
  • Extremely inflammable
  • Dangerous for the environment

Ocupational Safety & Health Administration (OSHA):

Has issued permissible exposure limits for acrylonitrile of 2 ppm; ceiling concentration, which must not be exceeded during any part of the workday, is 10 ppm. OSHA regulates acrylonitrile under the Hazard Communication Standard and as a chemical hazard in laboratories. The Environmental Protection Agency (EPA )regulates acrylonitrile under the Clean Air Act; Clean Water Act; Comprehensive Environmental Response, Compensation, and Liability Act (Superfund); Federal Insecticide, Fungicide, and Rodenticide Act; Resource Conservation and Recovery Act; and Superfund Amendments and Reauthorization Act. According to EPA, acrylonitrile is classified by the EPA as a water priority pollutant, a hazardous air pollutant, and a volatile organic compound.

Under Section 302 of the Emergency Planning and Community Right to Know Act of 1986, acrylonitrile is listed as an Extremely Hazardous Substance and has a threshold planning quantity of 10,000 lbs.

Effects of Human Exposure

Many occupational epidemiology studies have investigated retrospectively the morbidity and mortality of acrylonitrile exposed workers. An increased incidence of lung cancer was associated with acrylonitrile exposure. No significant excess mortality has been observed for any noncarcinogenic endpoint. One early cross-sectional study (Wilson et al., 1948) observed multiple deleterious effects in synthetic rubber manufacturing workers acutely exposed (20 to 45 minutes) to various concentrations of acrylonitrile (16 to 100 ppm, 34.7 to 217 mg/m3). Mucous membrane irritation, headaches, feelings of apprehension, and nervous irritability were observed in the majority of workers. Other less common symptoms observed included low-grade anemia, leukocytosis, and mild jaundice. These effects were reported to subside with cessation of exposure. Human volunteers exposed for a single 8 hour period to acrylonitrile vapors exhibited no deleterious CNS effects at concentrations ranging from 5.4 to 10.9 mg/m3 (2.4 to 5.0 pm) (Jakubowski et al., 1987).

Acrylonitrile disasters:

Location

Year

Date

Origin of accident

Products involved

Number of people

Dead

injured

evacuated

Melbourne (Australia)

1991

21-08

Fire at a chemical store

Phenol, Acrylonitrile

0

0

>1000

Minatitlan (Mexico)

1987

15-12

Process failure

Acrylonitrile

0

>200

>1000

English channel

1988

27-05

The cargo ship "Anne Broere" sinks with c. 248 hl of toxic acrylonitrile.

Acrylonitrile

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