P-Chloro-o-cresol

The effect of sodium hydroxide on p-chloro-o-cresol according to the following equation ... 

Environmental chemicals such as p-nonylphenol (NP), 4-ferf.-octylphenol (OP), 4-ferf.-pentylphenol (TPP), bisphenol-A (BPA), tetrabromobisphenol-A (TBBA), butylbenzylphthalate (BBP), di- -butylphthalate (DBP), butylated hydroxyanisole (BHA), p-chloro-ra-cresol, p-chloro-o-cresol, ds-nonachlor, frans-nonachlor, and the herbicide alachlor [2-chloro-iV-(2,6-diethylphenyl)-N-(methoxymethyl) acetamide] have been discovered to be weakly estrogenic [128,129,137,138]. 

P-chloro-o-cresol is the precursor for the pesticides MCPA (2-methyl-4-chloro-phenoxyacetic acid), MCPP (2-methyl-4-chloro-phenoxy propionic acid) and MCPB (2-methyl-4-chloro-phenoxy butyric acid). MCPP is also known as mecoprop. 

These phenoxy herbicides are very popular in W. Europe and Japan. Total Western European capacity for p-chloro-o-cresol exceeds 21-22,000 tpa. Major producers of PCOC include Coalite Chemicals, UK (9000 tpa) and Rhone-Poulenc (5000 tpa), UK, and BASF (7000 tpa) in Germany. These companies along with Bayer and Chemie Linz, which also produce PCOC in plants with flexible operations are the major producers of the chlorophenoxy carboxylic acid pesticides. 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Preventol CMK, see p-Chloro-/n-cresol Preventol I, see 2,4,5-Trichlorophenol Priltox, see Pentachlorophenol Primary amyl acetate, see Amyl acetate Primary isoamyl alcohol, see Isoamyl alcohol Primary isobutyl alcohol, see Isoamyl alcohol Prioderm, see Malathion Prist, see Methyl cellosolve Profume A, see Chloropicrin Profume R 40B1, see Methyl bromide Prokarbol, see 4,6-Dinitro-o-cresol... 

GC-MS and HPLC analyses of electrolyzed solutions allowed the detection of aromatic intermediates such as p-benzoquinone and nitrobenzene for aniline, 4-chlorocatechol for 4-chlorophenol, 4-chlorophenol, 4-chlorocatechol, hydroquinone, and p-benzoquinone for 4-CPA, 4-chloro-o-cresol, mehylhy-droquinone, and methyl-p-benzoquinone for MCPA, 2,4-dichlorophenol, 4,6-dichlororesorcinol, chlorohydroquinone, and chloro-p-benzoquinone for 2,4-D, and 2,4,5-trichloro-phenol, 2,5-dichlorohydroquinone, 4,6-dichlororesorcinol, and 2,5-dihydroxy-p-benzoquinone for 2,4,5-T. In general, these by-products persisted in solution while the initial pollutant was degraded. 

Pure meto-cresol has been used for manufacture of synthetic musk— musk ambrette, used as a fixative to perfumes, for manufacture of synthetic Thymol and Menthol amd also leather preservative p-chloro-meto-cresol, synthetic pyre-throids, and lastly for manufacture of 2,3,6-trimethylphe-nol—an intermediate for vitamin E. o-Cresol has been used for manufacture of Coumarin and some derivatives which are employed in perfumery as fixative. o-Cresol has also been used for making Novolac and epoxy resins and also for the herbicides based on di-nitro-oAt/io-cresol, etc. In sum, individual cresols have been very successfully converted to important intermediates in the organic chemical synthesis. It is expected that further development work will lead to synthesis of many more organic chemicals of vital importance. While new chemicals using individual cresols are in the pipeline... 

Figure 18.12 Systematic optimization of the separation often phenols (reproduced by permission of Du Pont). Peaks 1 = phenol 2 = p-nitrophenol 3 = 2,4-dinitrophenol 4— o-chlorophenol 5— o-nitrophenol 6 = 2,4-dimethylphenol 7 = 4,6-dinitro-o-cresol S p-chloro-m-cresol 9 = 2,4-dichlorophenol 10 = 2,4, 6-trichlorophenol.

Nipacide MX. See Chloroxylenol Nipacide OPP. See o-Phenyl phenol Nipacide PC. See p-Chloro-m-cresol Nipacide PTAP. See p-t-Amylphenol Nipacide PX, Nipacide PXBP/USP Nipacide PX-R. See Chloroxylenol Nipacide SOPP. See Sodium o-phenylphenate Nipacide TCM30. See2-Thiocyanomethylthiobenzothiazole Nipagin A Potassium. See Potassium ethyl paraben... 

Phenol acetate. See Phenyl acetate Phenol alcohol. See Phenol Phenol, o-allyl-. See 2-Allylphenol Phenol, 2-amino-. See o-Aminophenol Phenol, 3-amino-. See m-Aminophenol Phenol, 4-amino-. See p-Aminophenol Phenol, m-amino. See m-Aminophenol Phenol, 3-amino-2-chloro-6-methyl-. See 5-Amino-6-chloro-o-cresol... 

Sodium hydroxymethylglycinate antimicrobial, disinfectants Sodium o-phenylphenate antimicrobial, disinfection Didecyidimonium bromide antimicrobial, dispersed pigments Methyidibromo glutaronitrile antimicrobial, drilling fluids Coco-1,3-propylene diamine diacetate antimicrobial, emulsions p-Chloro-m-cresol Methyidibromo glutaronitrile... 

Bromo-2-nitropropane-1,3-diol 2-n-Octyl-4-isothiazolin-3-one 10,10-Oxybisphenoxyarsine Sodium o-phenylphenate Zinc pyrithione antimicrobial, latex coatings p-Chloro-m-cresol antimicrobial, latex emulsions Quaternium-15 Tribromosalicylanilide antimicrobial, latex paints 4,5-Dichloro-2-n-octyl-4-isothiazolin-3-one antimicrobial, laundry prods. 

Myristalkonium chloride antimicrobial, leather Sodium o-phenylphenate antimicrobial, leather goods p-Chloro-m-cresol antimicrobial, lipsticks Sodium dehydroacetate antimicrobial, liq. detergents Sodium hydroxymethylglycinate antimicrobial, liq. soaps Chlorhexidine digluconate antimicrobial, make up foundations Willow (Salix alba) bark extract antimicrobial, meat... 

Bromo-2-nitropropane-1,3-diol p-Chloro-m-cresol Dimethyl oxazolidine 10,10 -Oxybisphenoxyarsine 2-Thiocyanomethylthiobenzothiazole antimicrobial, thickeners Dichlorophene Methylenebis (thiocyanate) antimicrobial, timber Sodium o-phenylphenate antimicrobial, tobacco Sorbic acid antimicrobial, toners Willow (Salix alba) bark extract antimicrobial, topical Basic violet 3 3,4,4 -Trichlorocarbanilide antimicrobial, topical anti-infectives Thimerosal... 

Benzyl chloride o-Chloroaniline 2-Chlorophenol Copper Maleic anhydride Quinone Sodium fluorophosphate (Na2POsF) 2,3-Xylenol fungicide, adhesives Diiodomethyl tolylsulfone 3,5-Dimethyl tetrahydro-2-H,1,3,5-thiadiazone-2-thione Hexahydro-1,3,5-triethyl-s-triazine lodopropynyl butylcarbamate Sodium p-chloro-m-cresol... 

Sodium benzoate preservative, deodorants Bromochlorophene Lichen (Usnea barbata) extract Phytosphingosine preservative, detergents o-Phenylphenol 3,4,4 -Trichlorocarbanilide preservative, dextrins Pentachlorophenol preservative, diagnostic medicinals Sodium azide preservative, disinfectants Calcium disodium EDTA preservative, disinfectants hospitals Sodium p-chloro-m-cresol... 

Ammonium benzoate m-Chlorobenzoic acid o-Chlorobenzoic acid p-Chloro-m-cresol Pentachlorophenol Sorbic acid preservative, greases Dilauryl thiodipropionate preservative, gums p-Chloro-m-cresol... 

Halogenation of phenol also leads to phenol derivatives which are much more effective than the starting substance. At the same time, the dissociation constant increases with an increase in the number of halogen atoms, i.e. the acidic character of the phenol derivatives becomes more distinctive. The combination of alkylation and halogenation (the latter with preference in the p-position) has led to microbicides which have attained great practical significance as substances for the protection of materials and disinfection, e.g. p-chloro-o-benzyl phenol, p-chloro-m-cresol, p-chloro-/M-xylenol. 

Phenol derivatives, o-phenylphenol [II, 7.4.1.], p-chloro-m-cresol [II, 7.3.1.] and isopropylcresol [II, 7.2.2.] are intended for use in alkaline environments and are therefore seldom used in cosmetics. All phenols are inactivated by inclusion in micelles which detergents/surfactants (non-ionic and anionic) form in solutions as soon as their concentration exceeds the critical micellization concentration (see Part II, 7. and 18.). 

Figure 15 Decrease in concentration of phenolics in activated sludge (Paulus Genth, 1983). (OPP, u-phenyl-phenol PCMC, p-chloro-m-cresol BP, benzyl-phenol CBP, -chloro-o-benzyl-phenol DC, (2,2 -dihydroxy-5,5 dichloro-)diphenyl methane PCMX, p-chloro-m-...

From the facts there is no foundation for a blanket rejection of phenol derivatives. On the contrary it must be assumed, for many reasons, that it will not be possible to dispense with special phenolics as microbicides for material protection. After all, some of them, such as o-phenylphenol and p-chloro-m-cresol, meet the requirement now expected of such microbicides very satisfactorily. 

Phenols are also often nsed as preservatives. The most commonly used are phenol, o-phenylphenol, p-chloro-m-cresol, o-cymen-5-ol, chlorophene and triclosan, among others. 

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