Phenols cresylic

Solvent dewaxing removes wax from lubricating oil stocks, promoting crystallization of the wax. Solvents include furfural, phenol, cresylic acid-propane (DuoSol), liquid sulfur dioxide (Eleleanu process), B,B-dichloroethyl ether, methyl ethyl ketone, nitrobenzene, and sulfur-benzene. The process yields de-oiled waxes, wax-free lubricating oils, aromatics, and recovered solvents. 

Solvents used in commercial operations at the present time are furfural, phenol, cresylic acid, Chlorex, nitrobenzene, and sulfur dioxide. The Duosol process utilizes a solvent called Selecto which is a mixture of phenol and cresylic acid. The propane used in the Duosol process precipitates the asphalt (18). 

Contamination of water by phenol or substituted phenols is very often due to industrial activity, because these are commercially very important chemicals. Phenol, cresylic acids, and cresols are used for making phenol-formaldehyde resins and tricesyl phosphates. Phenol, alkylphenol, and polyphenols are important raw materials for a wide variety of organic compounds, dyes, pharmaceuticals, plastizers, antioxidants, etc. Phenols are also present in effluents from coke ovens, blast furnaces, and shale oil processing [1]. 

Creaylol—Cresof—Cresylie acid—Benzylic phenol—Cresylic p/tenof— C H (GH,)OH—198—aceompames phenol in coal- and wo -U, from wbicQ it may be obtained by fractional distiUaticn it is more readily obtained pure from toluene. 

Triaryl phosphates are produced from the corresponding phenols (usually mixtures) by reaction with phosphoms oxychloride, usually in the presence of a catalyst (94—96). They are subsequently distilled and usually washed with aqueous bases to the desired level of purity. Tricresyl phosphate was originally made from petroleum-derived or coal-tar-derived cresyflc acids, ie, cresols, variously admixed with phenol and xylenols. Discovery of the toxicity of the ortho-cresyl isomers led manufacturers to select cresols having very Httle ortho-isomer. 

Phenols react readily with tetraalkoxides to give highly colored (yeUow to orange) titanium tetraphenoxides (6). TYZOR KTM [83897-99-8] is the bis-cresyl titanate derived from TYZOR TBT. The tetracresyl titanate [28503-70-0] is also available commercially. 

Mercaptan extraction is used to reduce the total sulfur content of the fuel. When potassium isobutyrate and sodium cresylate are added to caustic soda, the solubility of the higher mercaptans is increased and they can be extracted from the oil. To remove traces of hydrogen sulfide and alkyl phenols, the oil is pretreated with caustic soda in a packed column or other mixing device. The mixture is allowed to settle and the product water washed before storage. 

Oxygen compounds in crude oils are more complex than the sulfur types. However, their presence in petroleum streams is not poisonous to processing catalysts. Many of the oxygen compounds found in crude oils are weakly acidic. They are carboxylic acids, cresylic acid, phenol, and naphthenic acid. Naphthenic acids are mainly cyclopentane and cyclohexane derivatives having a carboxyalkyl side chain. 

Cresylic acid is a commercial mixture of phenolic compounds including phenol, cresols, and xylenols. This mixture varies widely according to its source. Properties of phenol, cresols, and xylenols are shown in Table 4-5 Cresylic acid constitutes part of the oxygen compounds found in crudes that are concentrated in the naphtha fraction obtained principally from naphthenic and asphaltic-based crudes. Phenolic compounds, which are weak acids, are extracted with relatively strong aqueous caustic solutions. 

Originally cresylic acid was obtained from caustic waste streams that resulted from treating light distillates with caustic solutions to reduce H2S and mercaptans. Currently, most of these streams are hydrodesulfurized, and the product streams practically do not contain phenolic compounds. 

However, cresylic acid is still obtained to a lesser extent from petroleum fractions, especially cracked gasolines, which contain higher percentages of phenols. It is also extracted from coal liquids. 

Organophosphate Ester Hydraulic Fluids. Organophosphate esters are made by condensing an alcohol (aryl or alkyl) with phosphorus oxychloride in the presence of a metal catalyst (Muir 1984) to produce trialkyl, tri(alkyl/aryl), or triaryl phosphates. For the aryl phosphates, phenol or mixtures of alkylated phenols (e.g., isobutylated phenol, a mixture of several /-butylphenols) are used as the starting alcohols to produce potentially very complex mixtures of organophosphate esters. Some phosphate esters (e.g., tricresyl and trixylyl phosphates) are made from phenolic mixtures such as cresylic acid, which is a complex mixture of many phenolic compounds. The composition of these phenols varies with the source of the cresylic acid, as does the resultant phosphate ester. The phosphate esters manufactured from alkylated phenylated phenols are expected to have less batch-to-batch variations than the cresylic acid derived phosphate esters. The differences in physical properties between different manufacturers of the same phosphate ester are expected to be larger than batch-to-batch variations within one manufacturer. 

Duo-Sol A process for separating aromatic from aliphatic hydrocaibons by partition between two solvents. The first solvent (Selecto or Selectox) is a mixture of phenol and cresylic acids the second is liquid propane. Developed by the Max B. Miller Company and licensed by Milwhite Company. 

CP 1309, see Pentachlorophenol CPD-244, see 2-Nittopropane CPD-926, see Dibenzofuran 4-CPPE, see 4-Chlorophenyl phenyl ether p-CPPE, see 4-Chlorophenyl phenyl ether Crag sevin, see Carbaryl Crawhaspol, see Trichloroethylene 2-Cresol, see 2-Methylphenol 4-Cresol, see 4-Methylphenol oCresol, see 2-Methylphenol p-Cresol, see 4-Methylphenol Crestoxo, see Toxaphene Crestoxo 90, see Toxaphene oCresylic acid, see 2-Methylphenol p-Cresylic acid, see 4-Methylphenol oCresyl phosphate, see Tri-ocresyl phosphate Crisalin, see Trifluralin Crisalina, see Trifluralin Crisfuran, see Carbofuran Crisulfan, see a-Endosulfan, p-Endosulfan Crisuron, see Diuron Crolean, see Acrolein Crop rider, see 2,4-D Crotenaldehyde, see Crotonaldehyde Crotilin, see 2,4-D Crotonal, see Crotonaldehyde Crotonic aldehyde, see Crotonaldehyde CRS, see Phenol Crunch, see Carbaryl Cryptogil OL, see Pentachlorophenol CS, see oChlorobenzylidenemalononitrile, Methyl mercaptan... 

Synonyms Cresylic acid tricresol methyl-phenol o-cresol m-crtsoV, p-cresol hydroxytoluene... 

Since before World War II, multimillion pound quantities of cresols have been produced annually in the United States (O Brochta 1949), and domestic production and sales of cresols have steadily increased in recent years. Approximately 57.3 (USITC 1986), 73.3 (USITC 1988), and 82.3 (USITC 1989) million pounds of cresols were produced annually in the United States in 1986, 1987, and 1988, respectively. Respective sales were 56.6 (USITC 1986), 66.8 (USITC 1988), and 72.1 (USITC 1989) million pounds. These production totals include data on the manufacture of cresylic acid and exclude information on cresol production by coke and gas-retort ovens. The commercial mixture of cresol isomers, in which the m-isomer predominates and contains less than 5% phenol, is sometimes referred to as cresylic acid (Windholz et al. 1983). However, cresylic acids generally are composed of cresols, phenols, and xylenols they are defined as those mixtures in which over 50% will boil at temperatures above 204 C (Sax and Lewis 1987). In 1987, the national capacity for producing cresylics was 208 million pounds per year (CMR 1987). Information regarding the production levels of individual isomers and specific mixtures was unavailable. 

At other refineries, only two continuous stills in series are used, but these are of 80—100 plate efficiency and yield pure grades of phenol and 0-cresol and a base mixture of cresols, xylenols, and higher boiling tar acids. The latter are fractionated batchwise to various saleable grades of cresylic acids. 

Fries rearrangement of aromatic formate esters suggests that phenols are the major products (.24) obtained in the reaction. As poly(p-hydroxystyrene) is remarkably clear in the deep UV, it is likely that poly(p-formyloxystyrene) will not suffer from the same problem of photostabilization upon exposure as was the case with poly (p-acetoxystyrene). This expectation was confirmed by our study of the photo-Fries reaction of p-cresyl formate no ortho rearranged product was isolated after reaction while p-cresol and a small amount of starting material were obtained. 

Duosol Process. The Duosol process developed by the Max B. Miller Co. (28) is an outstanding example of commercial adoption of a double solvent extraction process. Patents (27) for this process date from May 1933 and cover numerous aspects of the problem including a variety of paraffinic solvents (ethane, propane, butane, petroleum ether) and naphthenic solvents (wood tar acids, cresols, creosote, and phenol). Present commercial application utilizes propane and Selecto (a mixture of phenol and cresylic acid, normally ranging in composition from 20 to 80% phenol). 

The practical range of operating temperatures is limited on the high side (about 150° F.) by the high vapor pressure of propane and on the low side by the tendency for emulsion formation as wax precipitates or possibly as phenol freezes as in high phenol content Selecto. Operation between these limits provides no difficulty because the solvent power of Selecto can be altered by changing the ratio of phenol to cresylic acid. 

Solvent extraction has become the most widely used method of refining lubricating oils. Selective solvents which extract the less desirable constituents include phenol, furfural, dichloroethyl ether, mixtures of cresylic acid and propane, and liquid sulfur dioxide. Liquid propane precipitates asphaltic constituents and wax and retains the more desirable oil components in solution. Dewaxing may also be accomplished by other solvents such as mixtures of benzene and methyl ethyl ketone. 

Synthetic resins, such as phenolic and cresylic resins (see PHENOLIC RESINS), are the most commonly used friction material binders, and are usually modified with drying oils, elastomer, cardanol [37330-39-5], an epoxy, phosphorus- or boron-based compounds, or even combinations of two. They are prepared by the addition of the appropriate phenol and formaldehyde [50-00-0] in the presence of an acidic or basic catalyst. Polymerization takes place at elevated temperatures. Other resin systems are based on elastomers (see Elastomers, synthetic), drying oils, or combinations of the above or other polymers. 

CRESYLIC ACID (mixture of cresols and phenol) n-Butane Isobutane n-Pentane n-Hexane n-Hept ane... 

Properties of the tar oil products are given in Table 14. The oils change only slightly with change in the retorting temperature sulfur levels are low. The fraction boiling up to 230°C contains 65 wt % of phenols, cresols, and cresylic acids. 

Cresol, Cresylic Acid or Methylphenol (called Kresol or Oxytoluol in Ger), CH3.CgH4.OH mw 108.13, 0 14.79% A coml coal tar product of the middle heavy oil fractions. It contains a mixt of o-, m- p- isomers which may be separated by fractional distillation into two fractions o- and a mixt of m- p-cresols. The props of cresol depend upon the compn proportion of isomers in the mixt. See Kirk Othmer (Ref 5) for more details o Cresol, wh crysts, phenol-like odor, poisonous, mp 30.8°, bp 191°, d 1.048 at 20° sol in ale, eth chlf si sol in w (Refs 1 7). Prepn other props are given in Beil (Ref 1)... 

Cresol (Cresylic Acid, Cresylol, Hydroxytoluene, Methyl Phenol, Oxytoluene, Tricresol)... 

Helferich10 10 and co-workers prepared phenyl /J-D-fructopyranoside, m. p. 173°, [ ]D —210° in water and o-cresyl /J-D-fructopyranoside, m. p. 167-170°, [o]D —233° in water, by the deacetylation of the products obtained by heating /3-D-fructopyranose pentaacetate with phenol and o-cresol, respectively, in the presence of p-toluenesulfonic acid. 

---