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ROBERT BURKE

Hydrocarbon derivatives are hydrocarbon compounds such as methane, propane, and benzene, which have had one or more hydrogen atoms removed, or a double bond broken, and atoms of other elements added. Primarily the atoms other than carbon and hydrogen are oxygen, nitrogen, fluorine, chlorine, bromine, and iodine. Hydrocarbon derivatives using these elements make up a large percentage of the hazardous materials encountered in accidents. Hydrocarbon compounds other than the benzene family are generally flammable as a hazard. Hydrocarbon derivatives may be flammable, oxidizers, toxic, corrosive, form explosive peroxides, and may polymerize. Not all hazards fit each family, but there is a family effect and if response personnel recognize the family a compound belongs to, they should be able to identify the hazard. There are ten hydrocarbon derivative functional groups that will be presented, alkyl halide, nitro, amine, peroxide, ether, alcohol, ketone, aldehyde, ester, and organic acid.

Derivative Family General Formula Hazard Alkyl Halide R-X* Toxic-Flammable Nitro R-NO2 Explosive Amine R-NH2 R2-NH R3-N Toxic-Flammable Peroxide R-O-O-R Explosive Oxidizer Ether R-O-R WFR Anesthetic Alcohol R-O-H WFR Toxic Ketone R-C-O-R Flammable Narcotic Aldehyde R-C-H-O WFR Toxic Ester R-C-O-O-R Polymerize Organic Acid R-C-O-O-H Corrosive Toxic Flammable * Can be any of the halogens, fluorine, chlorine, bromine, or iodine.

When a hydrogen atom is removed from a hydrocarbon compound, a radical of that compound is created. Radicals are compounds, which are not complete, so they cannot exist in that form. Radicals must bond with some other element in order to form a complete compound. Methane is an alkane hydrocarbon compound. It contains one carbon and four hydrogen atoms. When one hydrogen atom is removed, methane becomes the "methyl" radical, one carbon and three hydrogen atoms. One bonding spot is open to add another element and create a hydrocarbon derivative compound. When the hydrocarbon compounds were presented in an earlier column prefixes were discussed that were identified with the number of carbons that were in a particular compound. Hydrocarbon derivative compounds use an abbreviated version of those same prefixes. Because the compounds created with the hydrocarbon radicals are different than the hydrocarbon compound from which it originated, the prefix is altered by adding a "yl" to the end of the prefix. For example, "meth" indicates one carbon, when a "yl" is added, "methyl" indicates a one carbon radical of methane. "Eth" is a prefix, which indicates two carbons, "prop" three carbons, "but" four carbons, and "pent" five carbons with single bonds. There generally are not hydrocarbon derivative compounds created from hydrocarbons having six carbon single bonds and higher. The suffix "yl" is added to each of the first five hydrocarbon radicals, so that you have methyl, ethyl, propyl, butyl, and pentyl radicals. Some individual hydrocarbon derivative families use an alternate naming system for radicals having one or two carbons. Those families include aldehydes, esters, and organic acids. The alternate name for "meth" is form and "eth" is "acet".

Hydrocarbon # of Carbons Radical Name Methane One Methyl/Form Ethane Two Ethyl/Acet Propane Three Propyl Butane Four Butyl Pentane Five Pentyl

Radicals can also be created from double bonded alkene hydrocarbon compounds. Remember that the trademark of the alkene family is a compound with hydrogen and carbon and one or more double bonds. There are only two alkenes that are normally used to form radicals; they are the two-carbon ethane and three-carbon propane. Because ethyl and propyl are already used for single bonded compounds, a different system is used for radicals with double bonds. They are "vinyl" for two carbons with a double bond, and "acryl" for three carbons and a double bond. Benzene is also used to form hydrocarbon derivatives. When a hydrogen atom is removed from benzene, the "phenyl" radical is formed. If a hydrogen atom is removed from the methyl radical attached to the benzene ring of toluene, the radical formed is called the "benzyl" radical. The radicals formed from hydrocarbon compounds can be used in any of the hydrocarbon derivative families. The radicals simply indicate the number of carbons present in the compound. The other naming conventions for the actual compounds formed will be discussed within the individual families, as each is different.

Hydrocarbon Compound # of Carbons Radical Name Ethene Two - Double Bond Vinyl Propene Three - Double Bond Acryl Benzene Benzene Ring Phenyl Toluene Benzene Ring - Methyl Benzyl

Each hydrocarbon derivative family will be discussed in detail in the coming months. Subjects covered will be the naming conventions for each family, molecular formulas, structures, and examples of compounds for each family.

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