thumb|upright=1.8|Wood [[railroad ties before (right) and after (left) infusion with creosote, being transported by railcar at a facility of the Santa Fe Railroad, in Albuquerque, New Mexico, in March 1943. This U.S. wartime governmental photo reports that "The steaming black ties in the [left of photo]... have just come from the retort where they have been infused with creosote for eight hours." Ties are "made of pine and fir... seasoned for eight months" [as seen in the untreated railcar load at right]. The wood-tar variety has been used for meat preservation, ship treatment, and such medical purposes as an anaesthetic, antiseptic, astringent, expectorant, and laxative, though these have mostly been replaced by modern formulations.
Varieties of creosote have also been made from both oil shale and petroleum, and are known as oil-tar creosote when derived from oil tar, and as water-gas-tar creosote when derived from the tar of water gas. Creosote also has been made from pre-coal formations such as lignite, yielding lignite-tar creosote, and peat, yielding peat-tar creosote.
Creosote oils
The term creosote has a broad range of definitions depending on the origin of the coal tar oil and end-use of the material.
With respect to wood preservatives, the United States Environmental Protection Agency (EPA) considers the term creosote to mean a pesticide for use as a wood preservative meeting the American Wood Protection Association (AWPA) Standards P1/P13 and P2. The AWPA Standards require that creosote "shall be a pure coal tar product derived entirely from tar produced by the carbonization of bituminous coal."
Currently, all creosote-treated wood products—foundation and marine pilings, lumber, posts, railroad ties, timbers, and utility poles—are manufactured using this type of wood preservative. The manufacturing process can only be a pressure process under the supervision of a licensed applicator certified by the State Departments of Agriculture. No brush-on, spray, or non-pressure uses of creosote are allowed, as specified by the EPA-approved label for the use of creosote.
Two later methods for creosoting wood were introduced after the turn of the century, referred to as empty-cell processes, because they involve compressing the air inside the wood so that the preservative can only coat the inner cell walls rather than saturating the interior cell voids. This is a less effective, though usually satisfactory, method of treating the wood, but is used because it requires less of the creosoting material. The first method, the "Rüping process" was patented in 1902, and the second, the "Lowry process" was patented in 1906. Later in 1906, the "Allardyce process" and "Card process" were patented to treat wood with a combination of both creosote and zinc chloride. Alkyl groups that are found naturally occurring in the environment are organometallic compounds.
Phenol
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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).
Bioaccumulation
Bioaccumulation is the process by which an organism takes in chemicals through ingestion, exposure, and inhalation.
{| class="wikitable"
!Compound
!pKa
!pH of Seawater
!Form (Ionized or Un-Ionized)
|-
|m-cresol
|10.09
| rowspan="6" |8.1
|Un-ionized
|-
|o-cresol
|10.29
|Un-ionized
|-
|p-cresol
|10.30
|Un-ionized
|-
|2-ethylphenol
|10.20
|Un-ionized
|-
|guaiacol
|9.98
|Un-ionized
|-
|phenol
|9.99
|Un-ionized
|}
Each of the compounds in the table above is found in creosote preservatives; all are in the favored un-ionized form. In another study, various species of small fish were tested to see how the exposure time to PAH chemicals affected the fish.
Environmental hazards
Sediment
In aquatic sediments, several reactions can transform the chemicals released by the creosote preservatives into more dangerous chemicals. Most creosote preservative compounds have hazards associated with them before they are transformed. Cresol (m-, p-, and o-), phenol, guaiacol, and xylenol (1,3,4- and 1,3,5-) all are acute aquatic hazards prior to going through chemical reactions with the sediments. Alkylation reactions allows for the compounds to transition into more toxic compounds with the addition of R-groups to the major compounds found in creosote preservatives. Compounds formed through alkylation include: 3,4-dimethylphenol, 2,3-dimethylphenol, and 2,5-dimethylphenol, which are all listed as acute environmental hazards.
See also
- Creolin
- Pentachlorophenol