| | 2,4-Dimethylphenol Chemical Properties |
| Melting point | 22-23 °C(lit.) | | Boiling point | 211-212 °C(lit.) | | density | 1.011 g/mL at 25 °C(lit.) | | vapor pressure | 0.1 mm Hg ( 25 °C) | | refractive index | n20/D 1.538(lit.) | | Fp | 205 °F | | storage temp. | Store below +30°C. | | solubility | 5.0g/l | | form | Liquid | | pka | pK1:10.58 (25°C) | | color | Clear colorless to yellow | | Odor | at 100.00 %. weak smoky roasted dark | | Odor Type | smoky | | explosive limit | 1.4%(V) | | Water Solubility | 0.5 g/100 mL (25 ºC) | | Merck | 14,10082 | | BRN | 636244 | | Henry's Law Constant | 42.8(x 10-6 atm?m3/mol) at 75.9 °C, 74.0 at 88.7 °C, 113.0 at 98.5 °C (VLE circulation still-UV spectrophotometry,
Dohnal and Fenclová, 1995) | | InChIKey | KUFFULVDNCHOFZ-UHFFFAOYSA-N | | LogP | 2.61 | | CAS DataBase Reference | 105-67-9(CAS DataBase Reference) | | NIST Chemistry Reference | Phenol, 2,4-dimethyl-(105-67-9) | | EPA Substance Registry System | 2,4-Dimethylphenol (105-67-9) |
| | 2,4-Dimethylphenol Usage And Synthesis |
| Description | 2,4-dimethylphenol (also named as 2,4-xylenol) is a substituted phenol which occurs naturally. It can be also derived from the cresol fraction of petroleum or coal tars by fractional distillation and extraction with aqueous alkaline solution. It can be used as a feedstock for the production of phenolic antioxidants, disinfectants, solvents, pharmaceuticals, insecticides, fungicides, plasticizers, rubber chemicals, polyphenylene oxide, dyestuffs, wetting agents, and as an additive or constituent of gasolines, lubricants, and cresylic acid. It is an allowed liquid smoke flavoring agent in the EU.
| | Reference |
- J. P. Ghosh, K. E. Taylor, J. K. Bewtra, N. Biswas, Laccase-catalyzed removal of 2,4-dimethylphenol from synthetic wastewater: Effect of polyethylene glycol and dissolved oxygen, Chemosphere, 2008, vol. 71, pp. 1709-1717
- G. W. Holcombe, G. L. Phipps, J. T. Fiandt, Effects of phenol, 2,4-dimethylphenol, 2,4-dichlorophenol, and pentachlorophenol on embryo, larval, and early-juvenile fathead minnows (Pimephales promelas), Archives of Environmental Contamination and Toxicology, 1982, vol. 11, pp. 73-78
- A. Giri, Z. Zelinkova, T. Wenzl, Experimental design-based isotope-dilution SPMEGC/MS method development for the analysis of smoke flavouring products, Food Additives & Contaminants: Part A, 2007, vol. 34, pp. 2069-2084
| | Chemical Properties | 2,4-Dimethylphenol is a clear colorless to yellow liquid or needle crystals. miscible with alcohol and ether, slightly soluble in water.It has a moderate mammalian oral toxicity and is a recognised irritant. | | Physical properties | Colorless solid, slowly turning brown on exposure to air. | | Uses | It is used as a perfuming agent in cosmetic industry. Also used in the production of high-viscosity phosphate esters, as a feedstock for hindered phenol antioxidant and specialty modified phenolic resin manufacture. | | Uses | 2,4-dimethylphenol is a fungicide and disinfectant with a variety of agricultural uses. It is also used in making wetting agent; dyestuffs; phenolic antioxidants; pharmaceuticals; rubber chemicals; lubricant ; gasoline additive and plasticizers. | | Definition | ChEBI: 2,4-xylenol is a member of the class of phenols that phenol substituted by methyl groups at positions 2 and 4. It has a role as a disinfectant and a volatile oil component. It is a member of phenols and an aromatic fungicide. It derives from a hydride of a m-xylene. | | Preparation | synthesis of 2,4-dimethylphenol: 2,4-Dimethylphenol is obtained by sulfonation, salting out, alkali melting and acidification of m-xylene. | | General Description | 2,4-dimethylphenol appears as colorless crystals or clear, dark amber liquid. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | 2,4-Dimethylphenol is a very weak acid (pKa = 10.6) . Incompatible with acid chlorides, acid anhydrides, bases and oxidizing agents. Corrodes steel, brass, copper and copper alloys . | | Health Hazard | 2,4-Dimethylphenol is expected
to be an irritant of the eyes, mucous membranes,
and skin, by analogy to other phenols.
The oral LD50 for rats was 3.2 g/kg; the
dermal LD50 in mice was 1.04 g/kg. | | Fire Hazard | 2,4-Dimethylphenol is probably combustible. | | Safety Profile | Poison by intravenous
and intraperitoneal routes. Moderately toxic
by ingestion and skin contact. Questionable
carcinogen with experimental carcinogenic
data. When heated to decomposition it
emits acrid smoke and irritating fumes. See
also other xylenol entries. | | Carcinogenicity | 2,4-Dimethylphenol was tested for mutagenicity
in the Salmonella microsome preincubation
assay using the standard protocol of the
National Toxicology Program and five strains
of Salmonella; results were negative.
The ACGIH has not established a threshold
limit value (TLV) for 2,4-dimethylphenol. | | Source | Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for
24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method
625. Average 2,4-dimethylphenol concentrations reported in water-soluble fractions of unleaded
gasoline, kerosene, and diesel fuel were 50, 99, and 108 μg/L, respectively. 2,4-Dichlorophenol
may also enter groundwater by leaching from coal tar, asphalt runoff, plastics, and pesticides
(quoted, Verschueren, 1983). | | Environmental fate | Biological. When 2,4-dimethylphenol was statically incubated in the dark at 25 °C with yeast
extract and settled domestic wastewater inoculum, significant biodegradation with rapid
adaptation was observed. At concentrations of 5 and 10 mg/L, 100 and 99% biodegradation,
respectively, were observed after 7 d (Tabak et al., 1981).
Photolytic. 2,4-Dimethylphenol absorbs UV light at a maximum wavelength of 277 nm
(Dohnal and Fenclová, 1995).
Chemical/Physical. Wet oxidation of 2,4-dimethylphenol at 320 °C yielded formic and acetic
acids (Randall and Knopp, 1980). 2,4-Dimethylphenol will not hydrolyze because there is no
hydrolyzable functional group (Kollig, 1993). |
| | 2,4-Dimethylphenol Preparation Products And Raw materials |
| Raw materials | m-Xylene-->2,4-Dimethylphenoxytrimethylsilane-->4-(allyloxy)-m-xylene-->4-Hydroxy-3-methylbenzaldehyde-->2,4-Dimethylbromobenzene | | Preparation Products | 2,4,6-Trimethyliodobenzene-->2,6-Dimethylphenol-->2,5-Dimethylphenol-->Mordant Brown 66-->2-[(DIMETHYLAMINO)METHYL]-4,6-DIMETHYLBENZENOL-->2,4-DIMETHYL-6-IODOPHENOL-->Phenol,2,2'-(phenylmethylene)bis[4,6-dimethyl- |
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