Editing Creosote (section)

===Alkylation===
[[Alkylation]] occurs when a molecule replaces a hydrogen atom with an alkyl group that generally comes from an organic molecule.<ref>{{cite web |title=Alkylation |website=Dictionary.com |url=https://www.dictionary.com/browse/alkylation |access-date=October 29, 2016}}</ref> Alkyl groups that are found naturally occurring in the environment are [[organometallic chemistry|organometallic]] compounds.<ref name="Connell 2005"/> Organometallic compounds generally contain a methyl, ethyl, or butyl derivative which is the alkyl group that replaces the hydrogen.<ref name="Connell 2005"/> Other organic compounds, such as [[methanol]], can provide alkyl groups for alkylation.<ref name=Bolognini2002/> Methanol is found naturally in the environment in small concentrations, and has been linked to the release from biological decomposition of waste and even a byproduct of vegetation.<ref name=Howard311/> The following reactions are alkylations of soluble compounds found in creosote preservatives with methanol.

====m-Cresol====
[[File:M-cresol reaction with methanol.png|frameless|upright=2.25]]

The diagram above depicts a reaction between m-cresol and methanol where a c-alkylation product is produced.<ref name=Bolognini2002/> The c-alkylation reaction means that instead of replacing the hydrogen atom on the -OH group, the methyl group (from the methanol) replaces the hydrogen on a carbon in the benzene ring.<ref name=Bolognini2002/> The products of this c-alkylation can be in either a para- or ortho- orientation on the molecule, as seen in the diagram, and water, which is not shown.<ref name=Bolognini2002/> [[Isomer]]s of the dimethylphenol (DMP) compound are the products of the para- and ortho-c-alkylation.<ref name=Bolognini2002/> Dimethylphenol (DMP) compound is listed as an aquatic hazard by characteristic, and is toxic with long lasting effects.<ref>{{cite web |title=2,3-Dimethylphenol |website=PubChem Database |publisher=National Center for Biotechnology Information |url=https://pubchem.ncbi.nlm.nih.gov/compound/2_3-dimethylphenol |access-date=April 7, 2019}}</ref>

====Phenol====
[[File:Phenol reaction with methanol.png|frameless|upright=1.5]]

This diagram shows an o-alkylation between phenol and methanol. Unlike the c-alkylation, the o-alkylation replaces the hydrogen atom on the -OH group with the methyl group (from the methanol).<ref name="Balsama et al 1984"/> The product of the o-alkylation is methoxybenzene, better-known as [[anisole]], and water, which is not shown in the diagram.<ref name="Balsama et al 1984"/> Anisole is listed as an acute hazard to aquatic life with long-term effects.<ref>{{cite web |title=Anisole |website=PubChem Database |publisher=National Center for Biotechnology Information |url=https://pubchem.ncbi.nlm.nih.gov/compound/anisole |access-date=April 7, 2019}}</ref>