creosote creosote creosote is a category of carbonaceous chemicals formed by the distillation of various tars and pyrolysis of plant-derived material, such as wood, or fossil fuel. they are typically used as preservatives or antiseptics. 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 … 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" . some creosote types were used historically as a treatment for components of seagoing and outdoor wood structures to prevent rot (e.g., bridgework and railroad ties, see image). samples may be found commonly inside chimney flues, where the coal or wood burns under variable conditions, producing soot and tarry smoke. creosotes are the principal chemicals responsible for the stability, scent, and flavor characteristic of smoked meat; the name is derived from greek κρέας (kreas) 'meat', and σωτήρ (sōtēr) 'preserver'. the two main kinds recognized in industry are coal-tar creosote and wood-tar creosote. the coal-tar variety, having stronger and more toxic properties, has chiefly been used as a preservative for wood; coal-tar creosote was also formerly used as an escharotic, to burn malignant skin tissue, and in dentistry, to prevent necrosis, before its carcinogenic properties became known. 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such medical purposes as an anaesthetic, antiseptic, astringent, expectorant, and laxative, though these have mostly been replaced by modern formulations.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. the use of creosote according to the awpa standards does not allow for mixing with other types of "creosote type" materials—such as lignite-tar creosote, oil-tar creosote, peat-tar creosote, water-gas-tar creosote, or wood-tar creosote. the awpa standard p3 does however, allow blending of a high-boiling petroleum oil meeting the awpa standard p4. the information that follows describing the other various types of creosote materials and its uses should be considered as primarily being of only historical value. this history is important, because it traces the origin of these different materials used during the 19th and early 20th centuries. furthermore, it must be considered that these other types of creosotes – lignite-tar, wood-tar, water-gas-tar, etc. – are not currently being manufactured and have either been replaced with more-economical materials, or replaced by products that are more efficacious or safer. for some part of their history, coal-tar creosote and wood-tar creosote were thought to have been equivalent substances—albeit of distinct origins—accounting for their common name; the two were determined only later to be chemically different. all types of creosote are composed of phenol derivatives and share some quantity of monosubstituted phenols, but these are not the only active element of creosote. for their useful effects, coal-tar creosote relies on the presence of naphthalenes and anthracenes, while wood-tar creosote relies on the presence of methyl ethers of phenol. otherwise, either type of tar would dissolve in water. creosote was first discovered in its wood-tar form in 1832, by carl reichenbach, when he found it both in the tar and in pyroligneous acids obtained by a dry distillation of beechwood. because pyroligneous acid was known as an antiseptic and meat preservative, reichenbach conducted experiments by dipping meat in a dilute solution of distilled creosote. he found that the meat was dried without undergoing putrefaction and had attained a smoky flavor. this led him to reason that creosote was the antiseptic component contained in smoke, and he further argued that the creosote he had found in wood tar was also in coal tar, as well as amber tar and animal tar, in the same abundance as in wood tar. soon afterward, in 1834, friedrich ferdinand runge discovered carbolic acid (phenol) in coal-tar, and auguste laurent obtained it from "phenylhydrate", which was soon determined to be the same compound. there was no clear view on the relationship between carbolic acid and creosote; runge described it as having similar caustic and antiseptic properties, but noted that it was different, in that it was an acid and formed salts. nonetheless, reichenbach argued that creosote was also the active element, as it was in pyroligneous acid. despite evidence to the contrary, his view held sway with most chemists, and it became commonly accepted wisdom that creosote, carbolic acid, and phenylhydrate were identical substances, with different degrees of purity. carbolic acid was soon commonly sold under the name "creosote", and the scarcity of wood-tar creosote in some places led chemists to believe that it was the same substance as that described by reichenbach. in the 1840s, eugen freiherr von gorup-besanez, after realizing that two samples of substances labelled as creosote were different, started a series of investigations to determine the chemical nature of carbolic acid, leading to a conclusion that it more resembled chlorinated quinones and must have been a different, entirely unrelated substance. independently, there were investigations into the chemical nature of creosote. a study by f.k. völkel revealed that the smell of purified creosote resembled that of guaiacol, and later studies by heinrich hlasiwetz identified a substance common to guaiacum and creosote that he called creosol, and he determined that creosote contained a mixture of creosol and guaiacol. later investigations by gorup-besanez, a.e. hoffmann, and siegfried marasse showed that wood-tar creosote also contained phenols, giving it a feature in common with coal-tar creosote. historically, coal-tar creosote has been distinguished from what was thought of as creosote proper—the original substance of reichenbach's discovery—and it has been referred to specifically as "creosote oil". but, because creosote from coal-tar and wood-tar are obtained from a similar process and have some common uses, they have also been placed in the same class of substances, with the terms "creosote" or "creosote oil" referring to either product. wood-tar creosote constituency of distillations of creosote from different woods at different temperatures beech oak pine 200–220 °c 200–210 °c 200–210 °c 200–210 °c monophenols 39.0 %39.0 %55.0 %40.0% guaiacol 19.7 %26.5 %14.0 %20.3% creosol and homologs 40.0%32.1%31.0%37.5% loss 1.3%2.4%. . .2.2% wood-tar creosote is a colourless to yellowish greasy liquid with a smoky odor, produces a sooty flame when burned, and has a burned taste. it is non-buoyant in water, with a specific gravity of 1.037 to 1.087, retains fluidity at a very low temperature, and boils at 205-225 °c. in its purest form, it is transparent. dissolution in water requires up to 200 times the amount of water as the base creosote. this creosote is a combination of natural phenols: primarily guaiacol and creosol (4-methylguaiacol), which will typically constitute 50% of the oil; second in prevalence are cresol and xylenol; the rest being a combination of monophenols and polyphenols. composition of a typical beech-tar creosote phenol c6h5oh 5.2% o-cresol (ch3)c6h4(oh) 10.4% m-cresol and p-cresol (ch3)c6h4(oh) 11.6% 2-ethylphenol c6h4(c2h5)oh 3.6% guaiacol c6h4(oh)(och3) 25.0% 3,4-xylenol c6h3(ch3)2oh 2.0% 3,5-xylenol c6h3(ch3)2oh 1.0% various phenols c6h5oh— 6.2% creosol and homologs c6h3(ch3)(oh)(och3)— 35.0% the simple phenols are not the only active element in wood-tar creosote. in solution, they coagulate albumin, which is a water-soluble protein found in meat, so they serve as a preserving agent, but also cause denaturation. most of the phenols in the creosote are methoxy derivatives: they contain the methoxy group linked to the benzene nucleus (o–ch3). the high level of methyl derivates created from the action of heat on wood (also apparent in the methyl alcohol produced through distillation) make wood-tar creosote substantially different from coal-tar creosote. guaiacol is a methyl ether of pyrocatechin, while creosol is a methyl ether of methyl-pyrocatechin, the next homolog of pyrocatechin. methyl ethers differ from simple phenols in being less hydrophilic, caustic, and poisonous. this allows meat to be successfully preserved without tissue denaturation, and allows creosote to be used as a medical ointment. derivation of wood-tar creosote from resinous woods because wood-tar creosote is used for its guaiacol and creosol content, it is generally derived from beechwood rather than other woods, since it distills with a higher proportion of those chemicals to other phenolics. the creosote can be obtained by distilling the wood tar and treating the fraction heavier than water with a sodium hydroxide solution. the alkaline solution is then separated from the insoluble oily layer, boiled in contact with air to reduce impurities, and decomposed by diluted sulphuric acid. this produces a crude creosote, which is purified by re-solution in alkali, re-precipitation with acid, then redistilled with the fraction passing over between 200° and 225° constituting the purified creosote. when ferric chloride is added to a dilute solution, it will turn green: a characteristic of ortho-oxy derivatives of benzene. it dissolves in sulphuric acid to a red liquid, which slowly changes to purple-violet. shaken with hydrochloric acid in the absence of air, it becomes red, the color changing in the presence of air to dark brown or black. in preparation of food by smoking, guaiacol contributes mainly to the smoky taste, while the dimethyl ether of pyrogallol, syringol, is the main chemical responsible for the smoky aroma. industrial soon after it was discovered and recognized as the principle of meat smoking, wood-tar creosote became used as a replacement for the process. several methods were used to apply the creosote. one was to dip the meat in pyroligneous acid or a water of diluted creosote, as reichenbach did, or brush it over with them, and within one hour the meat would have the same quality of that of traditionally smoked preparations. sometimes the creosote was diluted in vinegar rather than water, as vinegar was also used as a preservative. another was to place the meat in a closed box, and place with it a few drops of creosote in a small bottle. because of the volatility of the creosote, the atmosphere was filled with a vapour containing it, and it would cover the flesh. the application of wood tar to seagoing vessels was practiced through the 18th century and early 19th century, before the creosote was isolated as a compound. wood-tar creosote was found not to be as effective in wood treatments, because it was harder to infuse the creosote into the wood cells, but still experiments were done, including by many governments, because it proved to be less expensive on the market. medical even before creosote as a chemical compound was discovered, it was the chief active component of medicinal remedies in different cultures around the world. in antiquity, pitches and resins were used commonly as medicines. pliny mentions a variety of tar-like substances being used as medicine, including cedria and pissinum. cedria was the pitch and resin of the cedar tree, being equivalent to the oil of tar and pyroligneous acid which are used in the first stage of distilling creosote. he recommends cedria to ease the pain in a toothache, as an injection in the ear in case of hardness of hearing, to kill parasitic worms, as a preventive for infusion, as a treatment for phthiriasis and porrigo, as an antidote for