He phenanthrene it is a hydrocarbon (it has in its structure carbon and hydrogen) whose physical and chemical properties are studied by organic chemistry. It belongs to the group of so-called aromatic compounds, whose fundamental structural unit is benzene.
The aromatics also include the fused polycyclic compounds, formed by several aromatic rings that share a carbon-carbon (C-C) bond. Phenanthrene is one of these, it has three fused rings in its structure. It is considered an isomer of anthracene, a compound that has its three rings fused in a linear fashion.
It was isolated from anthracene oil from coal tar. It is obtained through the distillation of wood, vehicle emissions, oil spills and other sources.
It is in the environment through cigarette smoke, and in the steroidal molecules it forms the aromatic base of the chemical structure, as shown in the cholesterol molecule.
Index
- 1 Chemical structure
- 2 Physical and chemical properties
- 3 Applications
- 3.1 Pharmacology
- 4 Effects on health
- 5 References
Chemical structure
Phenanthrene has a chemical structure formed by three benzene rings fused together by a carbon-carbon bond.
It is considered an aromatic structure because it complies with Hückle's Law for aromaticity, which says:"A compound is aromatic, if it has 4n + 2 pi (π) delocalized and conjugated (alternating) electrons, with the sigma electrons (σ) of the simple links.
The molecular formula of phenanthrene is C 14 H 10 Its structural formula is as shown in the following image:
When applying Hückel's law to the structure of phenanthrene and taking into account that n corresponds to the number of benzene rings in the structure, it turns out that 4n + 2 = 4 (3) +2 = 16 electrons π. These are seen as double bonds in the molecule.
Physical and chemical properties
-Density 1180 kg / m3; 1.18 g / cm3
-Fusion point 489.15 K (216 ° C)
-Boiling point 613.15 K (340 ° C)
The properties of a compound are the characteristics or qualities that allow it to be differentiated from others. The properties that are measured to a compound are the physical properties and the chemical properties.
Although phenanthrene is the isomeric form of anthracene, its properties are very different, giving phenanthrene greater chemical stability due to the angular position of one of its aromatic rings.
Applications
Pharmacology
Opioid drugs may be of natural origin or derivatives of phenanthrene. Among these are morphine, codeine and thebaine.
The most representative uses of phenanthrene are obtained when it is in an oxidized form; that is, as phenanthrenequinone. In this way it can be used as dyes, medicines, resins, fungicides and in the inhibition of the polymerization of some processes. 9,10-biphenyldicarboxylic acid is used to make polyester and alkyd resin.
Effects on health
Not only phenanthrene, but all polycyclic aromatic hydrocarbons, generally known as PAHs, are toxic and harmful to health. They are found in water, in the soil and in the air as a result of combustion, oil spills or as a product of reactions in the industrial field.
The toxicity increases as their chains with fused benzene rings get larger, although that does not mean that short chain PAHs are not.
From the benzene, which is the fundamental structural unit of these compounds, its high toxicity and mutagenic activity in living beings is already known.
Naphthalene, called against moths, is used to control pests that attack garment fabrics. Anthracene is a microbicide used in the form of pills to counteract the bad odors caused by bacteria.
In the case of phenanthrene, it accumulates in the fatty tissues of living beings, producing toxicity when the individual is exposed to the pollutant for long periods.
In addition to these effects, the following may be named:
- It's fuel.
- After long periods of exposure to phenanthrene, an individual may cough, respiratory dyspnea, bronchitis, respiratory irritation and skin irritation.
- If heated to decomposition, can cause skin and respiratory tract irritation by the emission of dense and suffocating smoke.
- May react with strong oxidants.
- In case of fire that involves this compound, it can be controlled with dry carbon dioxide, halon extinguisher or with water spray.
- It must be stored in cool places, in airtight containers and away from oxidizing substances.
- Personal protective equipment (MMP), covered shoe, long-sleeved apron and gloves should be worn.
- According to the National Institute for Occupational Health and Safety, for handling the compound a half-face mask equipped with anti-fog filters and another specific filter for chemical vapors should be used.
- In case of irritation in the eyes and / or on the skin it is recommended to wash with plenty of water, remove clothing or accessories that are contaminated and, in very serious cases, refer the patient for medical help.
References
- ScienceDirect, (2018), Phenanthrene, recovered, arzo 26 of 2018, sciencedirect.com
- Mastandrea, C., Chichizola, C., Ludueña, B., Sánchez, H., Alvarez, H., Gutiérrez, A., (2005). Polycyclic aromatic hydrocarbons. Risks to health and biological markers, Latin American Clinical Biochemistry Act, vol 39 , 1, scielo.org.ar
- Beyer, H., Wolfgang, W., (1987), Manual of Organic Chemistry, (E-Book), books.google.com.co
- Cheimicalbook, (s.f), Phenanthrene, Phenanthrene Chemical Properties and safety information, Recovered, March 26, 2018, chemicalbook.com
- Fernández, P L., (1996), Pharmacological treatment of pain, opiate drugs derived from phenanthrene, UCM, Madrid, [PDF], ucm.es, revistas.ucm.es
- Cameo Chemicals, (s.f), Phenanthrene, Data Sheet and Safety, Retrieved, March 27, 2018, cameochemicals.noaa.gov
- Morrison, R., Boyd, R., (1998), Organic Chemistry (5th edition), Mexico, Inter-American Educational Fund, S.A de C.V
- Pine, S., Hammond, G., Cram, D., Hendrickson, J., (1982). Química Orgánica, (second edition), Mexico, McGraw-Hill de México, S.A de C.V
- Chemsketch. Software used to write formulas and molecular structures of different chemical compounds. Desktop application.