2,6-Xylenol

log Kow= 2.36

2.36

less than 1 mg/mL at 68 °F (NTP, 1992)

Sol in ethyl alcohol, ethyl ether, carbon tetrachloride

Very sol in benzene, chloroform

Sol in hot water

In water, 6.05X10+3 mg/l @ 25 °C.

5.1 x 10 (-2) mol/l, at pH 5.1 and 25 °C.

165 °F (NTP, 1992)

73 °C

73 °C (closed cup)

397 °F at 760 mmHg (NTP, 1992)

203 °C (also reported as 201.030 °C)

201.00 to 203.00 °C. @ 760.00 mm Hg

212 °C

203 °C @760 [mm Hg]

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P264+P265, P270, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Chemical: Phenol, 2,6-dimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Phenol, 2,6-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,6-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 02-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13315

2,6-Dimethylphenol: Does not have an individual approval but may be used under an appropriate group standard

SYMPTOMS: Symptoms of exposure to this compound may include burning sensation, coughing, wheezing, laryngitis, and shortness of breath. Other symptoms may include severe irritation or burning of the eyes and skin; irritation of the respiratory system; dizziness, stomach pain, exhaustion, and coma. It can cause headaches, nausea, and vomiting. It can also cause corrosion of the mucous membranes, upper respiratory tract, skin, and eyes. Affected areas initially show white discoloration, wrinkling, and softening; then become red, brown or black. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi; chemical pneumonitis; and pulmonary edema. Chronic exposure may cause liver or kidney damage.

Irritating to eyes; [HSDB] Safe when used as a flavoring agent in food; [JECFA] Corrosive to tissues; Inhalation may cause laryngeal spasm, edema of the bronchi, and chemical pneumonitis; Chronic exposure may cause liver and kidney damage [CAMEO] Toxic by ingestion, and skin contact; May cause burns; [eChemPortal: ESIS] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and edema; May be absorbed through skin; Effects in high-dose animal studies include general anesthesia, convulsions or effect on seizure threshold, and impaired liver function; [MSDSonline] As the six dimethylphenol isomers and the mixed isomer substance are generally similar in toxicity, a common TLV for these substances is appropriate. . . . In mice, oral exposure to 250 mg/kg/day produced changes in blood parameters including statistically significant decreases in mean corpuscular volume and mean corpuscular hemoglobin concentration (4 and 3% reduction in mean values, respectively. . . . Available data on skin sensitization from exposure to dimethylphenol are mixed but warrant the addition of a DSEN notation. . . . All six dimethylphenol isomers were tested in a mouse local lymph node assay and the results found 2.4, 2,5, and 3,4-dimethylphenol to be positive for skin sensitization. There are no epidemiology studies. In a case report, ingestion of about 250 ml of a mixture of dimethylphenol isomers resulted in CNS depression, hypotension, and death. [ACGIH] See Phenol.

Toxikologische Bewertung 138: 19 (1995). Summary and assessment of 2,6-xylenol.

Environmental Protection Agency EPA/600/8-88/031 p.30 (1987). Health effects assessment for dimethylphenols.

Tucker JD et al; Mutat Res 297 (2): 101-80 (1993). Sister-chromatid exchange: second report of the Gene-Tox Program.

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Xylenols; Xylenols, liquid; Xylenols, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Xylenols; Xylenols, liquid; Xylenols, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Xylenols; Xylenols, liquid; Xylenols, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Xylenols; Xylenols, liquid; Xylenols, solid/

For more DOT Emergency Guidelines (Complete) data for 2,6-DIMETHYLPHENOL (8 total), please visit the HSDB record page.

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute toxicity (Oral) - Category 3

Acute toxicity (Oral) - Category 3

Acute Tox. 3 *

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Chemical Treatability of 2,6-Dimethylphenol; Concentration Process: Biological treatment; Chemical Classification: Phenols; Scale of Study: Unknown; Type of Wastewater Used: Pure compound (one solute in a solvent); Results of Study: 94.3% reduction based on chemical oxygen demand; rate of biodegradation 9 mg chemical oxygen demand/g hr (Activated sludge process).

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

6.0 [mg/m3]

26 [mg/m3]

59 [mg/m3]

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Some data suggesting breakthrough times /for butyl rubber/ of approximately an hour or more. /Aromatic hydroxyl cmpd/

Breakthrough times /for neoprene/ greater than one hour reported by (normally) two or more testers. /Aromatic hydroxyl cmpd/

Breakthrough times /for polyvinyl alcohol/ less (usually significantly less) than one hour reported by (normally) two or more testers. /Aromatic hydroxyl cmpd/

LC50 PIMEPHALES PROMELAS (FATHEAD MINNOW) > 27 MG/L/96 HR /FRESHWATER, FLOW THROUGH BIOASSAY/

LC100 Terahymena pyriformis (ciliate) 2.66 mmole/l/24 hr /Conditions of bioassay not specified/

LC50 Daphnia magna (cladoceran) 11.2 mg/1/48 hr /Static bioassay/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a log Kow of 2.36(2) and a regression-derived equation(3), indicates that 2,6-dimethylphenol is expected to have moderate mobility in soil(SRC). Volatilization of 2,6-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 6.7X10-6 atm-cu m/mole (4). 2,6-Dimethylphenol is not expected to volatilize from dry soil surfaces(3) based upon a vapor pressure of 0.274 mm Hg at 25 °C(4). The rate of biodegradation obtained for 2,6-dimethylphenol in a screening test with an adapted activated sludge seed was 94.3% chemical oxygen demand after 5 days(6). Other dimethylphenols have been reported to degrade within 4 to 14 days from soil(7).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 460(SRC), determined from a log Kow of 2.36(2) and a regression-derived equation(3), indicates that 2,6-dimethylphenol is expected to adsorb very little to suspended solids and sediment in water(SRC). 2,6-Dimethylphenol is expected to volatilize from water surfaces(3,SRC) based upon a Henry's Law constant of 6.7X10-6 atm-cu m/mole(4). Estimated volatilization half-lives for a model river and model lake are 6 days and 49 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 37(3,SRC), from 2,6-dimethylphenol's log Kow(2), suggests bioconcentration in aquatic organisms is moderate(SRC). In humic waters, degradation by the reaction with peroxy radicals should ensue with a half-life on the order of hours(6). 2,6-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Screening studies indicate that a loss of 94.3% chemical oxygen demand was obtained after 5 days(7). In addition, it has been reported that 2,6-dimethylphenol was readily degraded in St. Lawrence River water(8). Biodegradation under anaerobic conditions failed to occur in one study, time unspecified(9) and only 7% degradation occurred after 8 weeks in another study(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,6-dimethylphenol, which has a vapor pressure of 0.274 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,6-dimethylphenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.8 hours(SRC) from its rate constant of 6.60X10-11 cu cm/molecule-sec at 25 °C(3). Atmospheric 2,6-dimethylphenol is known to be removed by rainwater(4). 2,6-Dimethylphenol has an absorption band at 268 nm (water), and a shoulder may extend over 290 nm, thus making it a candidate for direct photochemical degradation(5,6). Night-time degradation in urban areas should occur rapidly through reaction with atmospheric nitrate radicals, as rate constants for this reaction with phenolic compounds are approximately 250 times faster than with hydroxyl radicals(7,SRC).

Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an estimated 2,6-dimethylphenol concn of 12 mg/l(1). 2,6-Dimethylphenol was detected in three samples of shale oil wastewater in the range 0.75-1.7 ug/ml at three different sites at the Rio Blanco Oil Shale Company in Logan, WA and at the Laramie Energy Technology Center, WY(2). 2,6-Dimethylphenol was identified but not quantified in leachate collected from a Swedish municipal landfill in May 1990(3). 2,6-Dimethylphenol was identified as a volatile component from textile floor coverings, concn unknown(4).

2,6-Dimethylphenol

Hepatic

6 x 10 ^-4 mg/kg-day

The Koc of 2,6-dimethylphenol is estimated as 460(SRC), using a log Kow of 2.36(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,6-dimethylphenol is expected to have moderate mobility in soil(SRC). 72.8% and 8% of 2,6-dimethylphenol was adsorbed onto the high clay content, adsorption activated materials Bentone 24 (pH 7.9) and Bentone 18C (pH 7.6), respectively; these values fluctuate as a function of pH(4).

Fine textured soils with appreciable iron oxides (e.g., Molokai clay) are more likely to slow the migration of 2.6-dimethylphenol than clay soils low in iron oxides (e.g, Fanno clay)(1). One study determined that adsorption of dimethylphenols by soils is very time dependent; the percentage of iron oxides and pH were determined to be two of the most important soil properties controlling the adsorption of 2,6-dimethylphenol by mineral soils(2). Laboratory gas-phase sorption/desorption studies for 2,6-dimethylphenol showed that sorption to high clay content soils in the gas phase can be important; the ratio of sorption to organic matter was the same for the two clays studied(2). It was shown that the adsorption and transformation of 2,6-dimethylphenol onto smectite clay surfaces were greatly influenced by the nature of the exchangeable cations Fe, Al, Ca, and Na(3).

URBAN/SUBURBAN: In 1984, a gas phase concn of 2,6-dimethylphenol was detected in 7 of seven rain events in Portland, OR, at concns ranging from 0.009-0.15 ng/cu m; the amount associated with adsorption to particulate matter was <5% of the gas phase concn in every case(1). 2,6-Dimethylphenol was detected at 0.4 ug/cu m in the air outside an oil shale wastewater facility in Logan WA, but not in a nearby undeveloped site(2).

TOXIC BY INGESTION AND SKIN ABSORPTION. /COMMERCIAL MIXTURES/

A case of fatal xylenol ingestion by a long stay mental hospital patient is described. The clinical course was similar to that observed in other phenolic poisonings with active bowel sounds, nausea ad vomiting, severe metabolic acidosis, hypotension and cardiac and renal failure. The formulation of xylenol ingested contains alcohol which would facilitate absorption; due to the dangers of such poisonings care must be exercised as to access and exposure to xylenol sterilising agents.

/SRP/: DIMETHYLPHENOLS OCCUR IN SHALE OIL PROCESS WATER, INDUSTRIAL WASTE WATER, AIRBORNE PARTICULATES, ... AND EVOLUTES FROM WASTE CHEMICAL DUMPS. /DIMETHYLPHENOLS/

2,6-Dimethylphenol's use for the preparation of coal tar disinfectants (1), in the manufacture of artificial resins(1,3), as a constituent of coal tar creosote (0.5 wt%)(2), as a raw material for pesticide manufacture(3), and as a component of automobile and diesel exhaust(4-7) may result in its release to the environment through various waste streams(SRC). In addition, 2,6-dimethylphenol has been released to the atmosphere by the paint industry(7) and via the combustion of phenolic resins and foam insulation used in the construction industry(8). Dimethylphenols, of which 2,6-dimethylphenol is an isomer, are components of disinfectants, solvents, pharmaceuticals, insecticides, fungicides, plasticizers, rubber chemicals, additives to lubricants and gasolines, wetting agents and dyestuffs(9).

Used as an intermediate in organic synthesis; [HSDB]

Intermediate for the manufacture of polyphenylene oxide and modified phenolic resins and phosphate esters used in the production of hydraulic fluids; in halogenation and aminolysis reactions.

Starting materials in the phenolic resins. /Xylenols/

Used in the production of high-viscosity phosphate esters, as a feedstock for hindered phenol antioxidant and specialty modified phenolic resin manufacture. /Xylenol 410/

Used in phosphate esters, alkylated xylenols, antioxidants. /Xylenol 100/

2023: 100,000,000 - <250,000,000 lb

(1977) AT LEAST 9.12X10+8 G

(1981) PROBABLY GREATER THAN 6.81X10+6 G

The insertion of methyl groups into phenol to produce ... xylenols is a commercial process of considerable utility. The process commomly employed is methylation with methyl alcohol over a solid catalyst, generally a modified metal oxide, at temp in the range of 300-450 °C. /Xylenols/

Orthoalkylation of phenol + methanol (coproduced with o-cresol)

Pitt-Consol Xylenol 235 is a synthetic 2,6-xylenol. Homolog distribution, wt%: Ortho cresol, 0.5; 2,6-xylenols, 92; 2,4/2,5 xylenols, 0.5; meta/para cresol, 7.

Grade or purity: 99%

Pitt-Consol Xylenol 410 is a synthetic xylenol blend ... homolog distribution, wt %: 2,6-xylenol, 1; 2,4-xylenol, 42; 2,5-xylenol, 43; 2,3-xylenol group, 14. /Xylenol 410/

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Phenol, 2,6-dimethyl-: ACTIVE

2,6-Dimethylphenol produces 2,6-dimethyl-1,4-phenylene oxide via oxidative coupling polymerization in the prescence of cobalt-containing catalysts of the salcomine type.

Tetra-methyl-bisphenol, a monomer, is produced by condensing acetone with 2,6-dimethylphenol.