1-Bromopropane

Preparation

Industrial routes to 1-bromopropane involve free-radical additions to the corresponding alkenes. In this way, the anti-Markovnikov product is obtained. Alternatively, npropanol may be substitutively brominated. The latter reaction is also viable laboratory synthesis.

One laboratory technique for substitutive bromination treats propanol with a mixture of hydrobromic and sulfuric acids: :CH3CH2CH2OH + HBr → CH3CH2CH2Br + H2O Alternate synthetic routes include treating propanol with phosphorus tribromide or via a Hunsdiecker reaction with butyric acid.

Applications

Like many other liquid halocarbons, 1-bromopropane finds use as a liquid or gaseous solvent. It is a solvent for adhesives in aerosol glues that glue foam cushions together. It is a solvent in asphalt production, in the aviation industry for maintenance, and in synthetic fiber production. It is a solvent for degreasing plastics, optics and on metal surfaces, to remove soldering residues from electronic circuit boards. It is an aggressive solvent with a Kauri-butanol value of 129 which is similar to 1,1,1-trichloroethane.

It was used in dry-cleaning in the United States, introduced in 2006. It was represented by the FabriSolv and DrySolv products. while perchloroethylene remained the most common solvent in dry cleaning as of 2024. Dry cleaning machines used with 1-Bromopropane were converted PERC machines.

Regulation

In the European Union, 1-bromopropane has been classified as reproductive toxicant per Registration, Evaluation, Authorisation and Restriction of Chemicals, which makes it a "substance of very high concern".

As of January 5, 2022, 1-bromopropane has been added to the United States Clean Air Act list of Hazardous Air Pollutants (HAP).

Since 2007, it has been approved for use under the U.S. EPA's Significant New Alternatives Policy (SNAP) as a suitable replacement for ozone depleting chemicals. In 2013, the U.S. EPA announced that, based on a work plan developed under the Toxic Substances Control Act of 1976, it would begin a full risk assessment of 1-Bromopropane. In December 2022, the U.S. EPA released a revised risk determination from the August 2020 risk evaluation, used to form a proposed risk management rule in July 2024.

The North Carolina Department of Labor's Occupational Safety and Health Division issued a Hazard Alert in 6/2014, as it "is not regulated to protect workers, consumers or the environment".

Safety

In 2003, the American Conference of Governmental Industrial Hygienists (ACGIH) set the time-weighted average threshold limit value for an 8-hour exposure at 10 parts per million (ppm). In 2014, the ACGIH adopted a lower threshold limit value of 0.1 ppm as an 8-hour time-weighted average. The California Occupational Safety and Health Administration set the permissible exposure limit at 5 ppm in 2010. Though symptoms of overexposure can begin within 2 days of exposure, typically long-term exposure is more harmful.

In 2008, the U.S. CDC recommended that use of 1-bromopropane as a replacement for perchloroethylene may require adjustment and modification of equipment, improved ventilation, and use of personal protective equipment.

In 2013, a peer-review panel convened by the U.S. National Toxicology Program unanimously recommended that 1-bromopropane, be classified as reasonably anticipated human carcinogens.

Extended occupational exposure to 1-bromopropane in higher concentrations than recommended has resulted in significant injury to workers in the United States. Its use as a solvent in aerosol glues used to glue foam cushions has been especially controversial. Reported symptoms of overexposure affect the nervous system and include confusion, slurred speech, dizziness, paresthesias, and difficulty walking, unusual fatigue and headaches, development of arthralgias, visual disturbances (difficulty focusing), and muscle twitching. Symptoms may persist over one year. Other symptoms include irritation of mucous membranes, eyes, upper respiratory tract, and skin, as well as transient loss of consciousness. One worker's long-term exposure resulting in neurological damage was covered in the NY Times. Air sampling for the level of 1-bromopropane and monitoring workers' urine for metabolites are both effective at measuring workers' exposure.

Occupational exposure to 1-bromopropane typically occurs through breathing or skin contact; it is easily absorbed into the blood via the skin. Replacing 1-bromopropane with water or acetone-based adhesives is the preferred NIOSH option for controlling occupational exposure, but other options include engineering controls like isolation and ventilation, administrative controls, and PPE that includes respiratory and skin protection. 1-Bromopropane can penetrate most gloves, but not those made of polyvinyl alcohol or laminates.

Animal studies

Animal studies of 1-bromopropane have shown that it is a carcinogen in those models. Rodents exposed to 1-bromopropane developed lung, colon, and skin cancer at higher rates.

Environmental impact

Stratospheric ozone layer damage

Although 1-bromopropane is naturally produced, it is one of the very short-lived substances that depletes ozone. Because 1-bromopropane is so short-lived, its ozone depletion potential (ODP) is dependent on the latitude where it is released. According to the United States Environmental Protection Agency, the ODP is 0.013-0.018 in U.S. latitudes and 0.071-0.100 in tropical latitudes.

References

References

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