Turpentine

Turpentine (Gum Turpentine, Spirit of Turpentine, Gum Spirit, Wood Turpentine) 

Uses Turpentine is oleorosin extracted from the plant Pinus. It is a yellowish, opaque, sticky mass with a characteristic odor. It is extensively used in different 

Vegetable turpentine was an ingredient in rubefacients such as Sloan s liniment. Allergic contact dermatitis to turpentine has been thoroughly investigated by Pirila and co-workers (e.g., Pirila et al. 1969). 

Many binders (nitrocellulose derivatives, drying oils, and resins) are hazardous and many pigments and additives contribute hazards, but it is the host of flammable solvents and thinners used, like turpentine, naphtha, toluene. 

Related Terms Alcohol, see Alcohols, p.5 Compound, see Terminology, Compound, p.234 

Flammable liquids, n.o.s., see Flammable Liquids and Class 3, p.96 Flammable solid, inorganic, n.o.s., see Flammable Solids and Division 4.1, p.99 Flammable solid, organic, n.o.s., see Flammable Solids and Division 4.1, p.99 Lacquer base or lacquer chips, nitrocellulose. 

Liquid, see Terminology, Liquid, p.241 Solid, see Terminology, Solid, p.247 Solution, see Terminology, Solutions, p.247 Solvent, see Solvents, p.224 

Coating Solution, Material such as automobile undercoating, drum or barrel lining material, etc., which cannot properly be described as cement, but presents similar hazards during transport. It usually contains flammable solvents. ICAO A2 

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C, b.p. 156 C. The most important of the terpene hydrocarbons. It is found in most essential oils derived from the Coniferae, and is the main constituent of turpentine oil. Contains two asymmetric carbon atoms. The (- -)-form is easily obtained in a pure state by fractionation of Greek turpentine oil, of which it constitutes 95%. Pinene may be separated from turpentine oil in the form of its crystalline nitrosochloride, CioHigClNO, from which the ( + )-form may be recovered by boiling with aniline in alcoholic solution. When heated under pressure at 250-270 C, a-pinene is converted into dipentene. It can be reduced by hydrogen in the presence of a catalyst to form... 

By oxidation with permanganate it forms pinonic acid, C,oH,<503, a monobasic acid derived from cyclobutane. With strong sulphuric acid it forms a mixture of limonene, dipentene, terpinolene, terpinene, camphene and p-cymene. Hydrogen chloride reacts with turpentine oil to give CioHijCl, bomyl chloride, artificial camphor . 

Crude oils appear as liquids of varying viscosities. Their color can range from green (crude from Moonie, Australia) to dark brown (crude from Ghawar, Saudi Arabia). They can have an odor of hydrogen sulfide, turpentine or simply hydrocarbon. 

Chlorine Ammonia, acetylene, alcohols, alkanes, benzene, butadiene, carbon disulflde, dibutyl phthalate, ethers, fluorine, glycerol, hydrocarbons, hydrogen, sodium carbide, flnely divided metals, metal acetylides and carbides, nitrogen compounds, nonmetals, nonmetal hydrides, phosphorus compounds, polychlorobi-phenyl, silicones, steel, sulfldes, synthetic rubber, turpentine... 

Chromic(VI) acid Acetic acid, acetic anhydride, acetone, alcohols, alkali metals, ammonia, dimethylformamide, camphor, glycerol, hydrogen sulflde, phosphorus, pyridine, selenium, sulfur, turpentine, flammable liquids in general... 

Tin(lV) chloride Alkyl nitrates, ethylene oxide, K, Na turpentine... 

Oil-free alkyds Oil from seeds Oil-in-water emulsion Oil laundering Oil length Oil mining Oil of anise Oil of bergamot Oil of eucalyptus Oil oflemon Oil of Olay Oil of Palma Christi Oil of turpentine Oil Orange Oil-pump Oil reclaiming Oil recovery... 

A varnish is often appHed on top of the paint layers. A varnish serves two purposes as a protective coating and also for an optical effect that enriches the colors of the painting. A traditional varnish consists of a natural plant resin dissolved or fused in a Hquid for appHcation to the surface (see Resins, natural). There are two types of varnish resins hard ones, the most important of which is copal, and soft ones, notably dammar and mastic. The hard resins are fossil, and to convert these to a fluid state, they are fused in oil at high temperature. The soft resins dissolve in organic solvents, eg, turpentine. The natural resin varnishes discolor over time and also become less soluble, making removal in case of failure more difficult (see Paint and FINNISH removers). Thus the use of more stable synthetic resins, such as certain methacrylates and cycHc ketone resins, has become quite common, especially in conservation practice. 

Terpenes, specifically monoterpenes, are naturally occurring monomers that are usually obtained as by-products of the paper and citms industries. Monoterpenes that are typically employed in hydrocarbon resins are shown in Figure 2. Optically active tf-limonene is obtained from various natural oils, particularly citms oils (81). a and P-pinenes are obtained from sulfate turpentine produced in the kraft (sulfate) pulping process. Southeastern U.S. sulfate turpentine contains approximately 60—70 wt % a-pinene and 20—25 wt % P-pinene (see Terpenoids). Dipentene, which is a complex mixture of if,/-Hmonene, a- and P-pheUandrene, a- and y-terpinene, and terpinolene, is also obtained from the processing of sulfate Hquor (82). 

A process of polymerization of isomerized a-pinene or turpentine with vinylbenzenes has been disclosed (105). a-Pinene or turpentine is isomerized by flash pyrolysis at 518 5° C in a hot tube reactor to yield a mixture of predominantly dipentene and i7t-alloocimene... 

Hydrocarbons, compounds of carbon and hydrogen, are stmcturally classified as aromatic and aliphatic the latter includes alkanes (paraffins), alkenes (olefins), alkynes (acetylenes), and cycloparaffins. An example of a low molecular weight paraffin is methane [74-82-8], of an olefin, ethylene [74-85-1], of a cycloparaffin, cyclopentane [287-92-3], and of an aromatic, benzene [71-43-2]. Cmde petroleum oils [8002-05-9], which span a range of molecular weights of these compounds, excluding the very reactive olefins, have been classified according to their content as paraffinic, cycloparaffinic (naphthenic), or aromatic. The hydrocarbon class of terpenes is not discussed here. Terpenes, such as turpentine [8006-64-2] are found widely distributed in plants, and consist of repeating isoprene [78-79-5] units (see Isoprene Terpenoids). 

Oxidizing Properties. Nitric acid is a powerful oxidizing agent (electron acceptor) that reacts violentiy with many organic materials (eg, turpentine, charcoal, and charred sawdust) (19,20). The concentrated acid may react explosively with ethanol (qv). Such oxidizing properties have had military appHcation nitric acid is used with certain organics, eg, furfuryl alcohol and aniline, as rocket propellant (see Explosives AND PROPELLANTS). 

Turpentine Oil. The world s largest-volume essential oil, turpentine [8006-64-2] is produced ia many parts of the world. Various species of piaes and balsamiferous woods are used, and several different methods are appHed to obtain the oils. Types of turpentines include dry-distiUed wood turpentine from dry distillation of the chopped woods and roots of pines steam-distilled wood turpentine which is steam-distilled from pine wood or from solvent extracts of the wood and sulfate turpentine, which is a by-product of the production of sulfate ceUulose. From a perfumery standpoint, steam-distilled wood turpentine is the only important turpentine oil. It is rectified to yield pine oil, yellow or white as well as wood spirits of turpentine. Steam-distilled turpentine oil is a water-white mobile Hquid with a refreshing warm-balsamic odor. American turpentine oil contains 25—35% P-pinene (22) and about 50% a-pinene (44). European and East Indian turpentines are rich in a-pinene (44) withHtfle P-pinene (22), and thus are exceUent raw materials... 

In several important cases, new synthetic strategies have been developed into new production schemes. An outstanding example of this is the production of an entire family of terpene derivatives from a-pinene (29), the major component of most turpentines, via linalool (3) (12). Many of these materials had been produced from P-pinene, a lesser component of turpentine, via pyrolysis to myrcene and further chemical processing. The newer method offers greater manufacturing dexibiUty and better economics, and is environmentally friendly in that catalytic air oxidation is used to introduce functionality. 

The main uses of petroleum naphtha fall into the general areas of solvents (diluents) for paints, etc, dry-cleaning solvents, solvents for cutback asphalt, solvents in mbber industry, and solvents for industrial extraction processes. Turpentine, the older, more conventional solvent for paints, has been almost completely replaced by the cheaper and more abundant petroleum naphtha. 

By-Products. There are three stages within the pulping operation at which wood-derived chemicals can be recovered as by-products. Turpentine is obtained from the reHef of gases after an initial steaming of chips in the digester. Better yields of turpentine are obtained from batch digesters than from continuous systems. Pines and firs give the best yields. Turpentine is composed principally of unsaturated bicycHc hydrocarbons, of which ca 90% are a- and P-pinenes and 5—12% other terpenes. 

In the gum rosin process, pine trees are wounded to stimulate the flow of gum. V-shaped slashes are cut through the bark, and the exudate is collected in a bucket below the slash. Production is stimulated by painting sulfuric acid on the slashes. The oleoresin (exudate) is separated by distillation into gum spidts of turpentine and gum rosin. The gum turpentine industry has decreased in importance in the 1990s because it is labor-intensive. The process is carried out in Russia, the People s Repubflc of China, Indonesia, Portugal, Brazil, and Mexico. 

The pyrolysis or carbonization of hardwoods, eg, beech, birch, or ash, in the manufacture of charcoal yields, in addition to gaseous and lighter Hquid products, a by-product tar in ca 10 wt % yield. Dry distillation of softwoods, eg, pine species, for the production of the so-called DD (destmctively distilled) turpentine yields pine tar as a by-product in about the same amount. Pine tar, also called Stockholm tar or Archangel tar, was at one time imported from the Baltic by European maritime countries for the treatment of cordage and ship hulls it was an important article of commerce from the seventeenth to the nineteenth century. The small amount produced in the late twentieth century is burned as a cmde fuel. Charcoal production from hardwoods, on the other hand, has increased in the 1990s years. 

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