Tri chlorophenol

Organic carboxylic acids are commonly found in foods, in the adipate process stream, and as pollutants. Fatty acids are the lipophilic portion of glycerides and a major component of the cell membrane. Phenols are widely used in polymers, as wood preservatives, and as disinfectants. Chloro-phenols such as 4-chlorophenol, two isomeric dichlorophenols, 2,4,6-tri-chlorophenol, three isomeric tetrachlorophenols, and pentachlorophenol were separated on a Dowex (The Dow Chemical Co. Midland, MI) 2-X8 anion exchange resin using an acetic acid-methanol gradient.138... 

Chemical/Physical. An aqueous solution containing chloramine reacted with 2,4,6-tri-chlorophenol to yield the following intermediate products after 2 h at 25 °C 2,6-dichloro-l,4-benzoquinone-4-(A-chloro)imine and 4,6-dichloro-l,2-benzoquinone-2-(A-chloro)imine (Maeda et al., 1987). 

Apak, R. and Hugul, M., Photooxidation of some mono-, di-, and tri-chlorophenols in aqueous solution by hydrogen peroxide/UV combination, /. Chem. Tech. Biotechnol., 67, 221-226, 1996. 

Boyd, E.M., Killham, K. and Meharg, A.A. (2001) Toxicity of mono-, di- and tri-chlorophenols to lux marked terrestrial bacteria, Burkholderia species Rase c2 and Pseudomonas fluorescens. Chemosphere, 43, 157-166. 

Dichlorophenol is produced by chlorination of phenol in a polar solvent such as water or acetic acid at temperatures from 70 to 80 °C to minimize further chlorination (when using non-polar solvents with an excess of chlorine, 2,4,6-tri-chlorophenol is the main reaction product). The crude product is purified by fractional distillation. West European production of 2,4-dichlorophenol is around 20,000 tpa. 2,4-Dichlorophenol is used mainly to produce 2,4-dichlorophenoxy-acetic acid (2,4-D), first used as a herbicide in 1942 and obtained by the reaction of 2,4-dichlorophenol and monochloroacetic acid at 80 to 100 °C and a pH value of 7 to 11. 

Another example is hexachlorophene, 2,2-methylene-bis(3,4,6-tri-chlorophenol), with formula... 

Determination of C -C cai bonyl compounds, phthalic acid alkyl esters, mutagen MX and its geometric isomer E-MX, chlorophenols, organochlorine pesticides (OCPs) - a-, P-, J-, 5-HCH, DDE, DDD, DDT, total isomeric-specific content of polychlorinated byphenyls (PCBs) (tri-, tetra-, penta-, hexa-, hepta-, octachloroisomers) in SCAN and SIM mode was canned out. MDE of procedure for OCPs makes up 0.01-0.1 and PCBs - 0.17-0.38 ng/1 at enrichment factor K = (1.50-4.00)T0. ... 

By the procedure described in the preceding experiment, 30 g (0.11 mole) of tri-phenylphosphine dissolved in 100 ml of acetonitrile is converted to triphenylphosphine dibromide. After the addition of the bromine has been completed, the cooling bath is removed, the flask is set up for vacuum distillation, and the solvent is removed. To the residue is added /7-chlorophenol (10.3 g, 0.08 mole), and the flask is heated at 200° (mantle, wax bath, or sand bath) until HBr ceases to be evolved (about 2 hours). The flask is cooled and the contents are steam distilled affording crude / -chlorobromo-benzene in about 90% yield. Recrystallization from benzene gives the pure product, mp 65-66°. 

Dichlorodibenzo-p-dioxin was prepared from isotopic potassium 2,4-dichlorophenate uniformly labeled with Ullman conditions gave a 20.5% yield. Small amounts of dichlorophenoxy chlorophenol were removed from the product by extraction with sodium hydroxide before purification by fractional sublimation and recrystallization from anisole. Chlorination of 2,7-dichlorodibenzo-p-dioxin in chloroform solution containing trace amounts of FeCls and 12 yielded a mixture of tri-, tetra-, and pentachloro substitution products. Purification by digestion in boiling chloroform, fractional sublimation, and recrystallization from anisole was effective in refining this product to 92% 2,3,7,8-tetrachloro isomer, which also contained 7% of the tri- and 1% of the penta-substituted dibenzo-p-dioxin. Mass spectroscopy was used exclusively to monitor the quality of the products during the synthesis. 

A wide variety of xenobiotics can become cross-linked to naturally occurring humic matter by the action of phenyloxidases. These xenobiotics include phenols (e.g., mono-, di-, and tri-substituted chlorophenols, 2,6-xylenol), and anilines (e.g., 4-chloroaniline, 3,4-dichloroaniline, and 2,6-diethylaniline) [17,160]. 

Soil Under anaerobic conditions, pentachlorophenol may undergo sequential dehalogenation to produce /n-chlorophenol, tetra-, tri-, and dichlorophenols (Kobayashi and Rittman, 1982). In aerobic and anaerobic soils, pentachloroanisole was the major metabolite, with minor quantities of... 

C. Chlorophenols. Chlorophenols have been extensively used since the 1930 s as insecticides, fungicides, mould inhibitors, antiseptics and disinfectants. The annual production volume is estimated to be in the order of 150 000 tons. In the US penta-chlorophenol is the second heaviest in use of all pesticides (38). The most important use of 2,U,6-tri, 2,3,, 6-tetra- and pentachlorophenol (or their salts) is for wood protection. Penta-chlorophenol is also used as a fungicide for slime control in the manufacture of paper pulp and for a variety of other purposes such as in the tanning process of leather and an additive in cutting oils and fluids, paint, glues and out-door textiles. 

Dichlorophenol and 2,4,5-trichlorophenol have been used in the synthesis of phenoxy acid herbicides, including 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-tri-chlorophenoxyacetic acid (2,4,5-T). 2,4,5-Trichlorophenol has also been used as a fungicide and a bactericide. 2,4,6-Trichlorophenol has been used as a pesticide. 2,3,4,6-Tetra-chlorophenol has been used as a fungicide (Lewis, 1993 Verschueren, 1996). Chlorophenols have also been formulated and used as salts in some applications. 

Production and Use of Contaminated Chemicals and Certain Herbicides. CDDs are known trace contaminants of certain chlorinated industrial chemicals like chlorophenols (Buser 1987). CDDs can inadvertently form as by-products during the manufacture of chlorophenols. Since the 1930s, PCP and the tri- and tetrachlorophenols have gained recognition as fungicides, herbicides, insecticides, and precursors in the synthesis of other pesticides. 

In 1888 formaldehyde, the first synthetic fungicide appeared. Unless you count chlorophenol mercury in 1913, little really new happened until 1934 when Tisdale and Williams of DuPont revealed the dialkyldithiocarbamates. They were expensive to make, however, and it was depression days, and so DuPont was skittish about trying to sell them to farmers when copper sulfate could be bought for 6 cents a pound. 

Fig. 4. A-D. Resonance Raman spectra of pyrocatechase complexed with o-fluorophenol (A) o-chlorophenol (B) o-bromophenol (C) o-chlorophenol-4,6-d2 (D). Conditions 647.1 nm excitation, 150-200 mW power, 4 cm-1 slit width, 40-50 mg/mL of enzyme in Tris-acetate pH 8.5 buffer, 4 °C sample temperature. SO - was used as internal standard...

F027 - Discarded unused formulations containing tri-, tetra-, or pentachlorophenol or discarded unused formulations containing compounds derived from these chlorophenols. (This listing does not include formulations containing hexachlorophene synthesized from prepurified 2,4,5-TCP as the sole component.)... 

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