Cresol Chemical Properties

Melting point:

-1--2°C

Boiling point:

88-94°C

Density 

1.04

refractive index 

1.5410 to 1.5440

Flash point:

82°C

storage temp. 

Store at R.T.

form 

clear liquid

color 

Colorless to Almost colorless

Odor

Sweet, tarry.

Water Solubility 

1.932 g/100 mL

Merck 

14,2579

Exposure limits

TLV-TWA (skin) for all isomers, 5 ppm (～22 mg/m³ ) (ACGIH, MSHA, and OSHA), 10-hour TWA 2.3 ppm (～10 mg/m³ ) (NIOSH), IDLH 250 ppm (NIOSH).

Dielectric constant

9.0（Ambient）

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

QTWJRLJHJPIABL-UHFFFAOYSA-N

LogP

1.950

CAS DataBase Reference

1319-77-3(CAS DataBase Reference)

EPA Substance Registry System

Cresol (1319-77-3)

Safety Information

Hazard Codes 

T

Risk Statements 

20-24/25-34-52/53-68

Safety Statements 

26-36/37/39-45-61-24/25

RIDADR 

UN 2076 6.1/PG 2

WGK Germany 

1

RTECS 

GO5950000

F 

8-23

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29071219

Hazardous Substances Data

1319-77-3(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Cresol Usage And Synthesis

Description

Professions that involve dealing with the combustion of coal or wood may be exposed to higher levels of cresols than the general population. Environmental tobacco smoke is also a source of cresol exposure. Average cresol concentration may vary between the brand and type of cigarette in a 45-cubic meter chamber after six cigarettes had been smoked (ranged from 0.17 to 3.9 mg m3), although low levels of cresol can be detected in certain foods and tap water, and these do not constitute major sources of exposure for most population. Detectable levels of cresols have been reported in several consumer products including tealeaves, tomatoes, and ketchup as well as butter, oil, and various cheeses. Exposure to children occurs by the same routes that affect adults. Children are likely to be exposed to cresols through inhalation of contaminated air from automobile exhaust, waste incineration, and secondhand smoke.

Chemical Properties

Cresol,a clear amber to red liquid, also known as cresylic acid, methylphenol, and tricresol,is a mixture of three isomers of cresol derived from coaltar and is used in making plastics, ore flotation, refining petroleum, and as a strong antiseptic. Orthocresol is a color less solid with a melting point of 30 °C(86 OF) that is soluble in alcohol,but only slightly soluble in water. It is used in making disinfectants and as a plasticizer. Metacresol is a colorless liquid used in the manufacture of photographic developers,printing inks, and paint removers.It is also used as a leather preservative.The least soluble isomer, paracresol, is a colorless solid and is used in the production of dyes and pharmaceuticals.

Chemical Properties

Cresol consists of a mixture of cresol isomers, predominantly mcresol,and other phenols obtained from coaltar or petroleum.It is a colorless,yellowish to pale brownish-yellow,or pink-colored liquid, with a characteristic odor similar to phenol but more tarlike. An aqueous solution has a pungent taste.

Chemical Properties

Cresol is a mixture of the three isomeric cresols, o-, m-, and p-cresol. Cresols are slightly soluble in water. m-Isomer: Colorless or yellow liquid with characteristic odor.

Uses

Disinfectant, phenolic resins, tricresyl phosphate, ore flotation, textile scouring agent, organic intermediate, manufacture of salicylaldehyde, coumarin, and herbicides, surfactant, synthetic food flavors (para isomer only).

Uses

Cresol is used in disinfectants and fumigants,in the manufacture of synthetic resins, inphotographic developers and explosives.

Uses

Cresols (mixtures of the ortho-, meta-, and para-isomers) are synthesized by sulfonation or oxidation of toluene compounds or can be derived from coal tar and petroleum. Commercial grade crude cresol is generally a mixture of 20% o-cresol, 40% m-cresol, and 30% p-cresol. Phenol and xylenols are often found as minor contaminants. Manufacture of synthetic resins, tricresyl phosphate, salicylaldehyde, coumarin, and herbicides employ cresols. Degreasing compounds in textile scouring, paintbrush cleaners as well as fumigants in photographic developers, and explosives contains cresols. Cresols are also often used as antiseptics, disinfectants, and antiparasitic agents in veterinary medicine. Estimated breakdown of cresol and cresylic acid use is 20% phenolic resins, 20% wire enamel solvents, 10% agricultural chemicals, 5% phosphate esters, 5% disinfectants and cleaning compounds, 5% ore flotation, and 25% miscellaneous purposes. Overall, use of cresols as antimicrobial outweighs any other property.

Production Methods

Cresol may be obtained from coal tar or prepared synthetically by either sulfonation or oxidation of toluene.

Definition

A mixture of isomers obtained from coal tar or petroleum.

General Description

Colorless to yellow liquids with a tarry odor. Flash point 178°F. Insoluble in water. Density 8.7 lb / gal. Poisonous by ingestion and skin absorption and corrosive to skin.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Mixing CRESOL in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, nitric acid, oleum, [NFPA 1991].

Hazard

Irritant, corrosive to skin and mucous membranes, absorbed via skin. Questionable carcinogen.

Health Hazard

LIQUID: Will burn skin and eyes. Harmful if swallowed.

Health Hazard

The toxic actions of cresol are similar tothose of phenol. The para-isomer is somewhat more toxic than the other two isomers.The toxic symptoms are weakness, confu-sion, depression of the central nervous system, dyspnea, and respiratory failure. It isan irritant to the eyes and skin. Skin con-tact can cause burn and dermatitis. Chroniceffects are gastrointestinal disorders, nervousdisorders, tremor, confusion, skin eruptions,oliguria, jaundice, and liver damage. SkinLD50 values in rats for o-, m-, and p-phenolsare 620, 1100, and 750 mg/kg, respectively.
Dietz and Mulligan (1988a,b) have investigated the subchronic toxicity of meta- andpara-cresols in Sprague-Dawley rats after13 weeks of oral gavage. There was noadverse effects from a dose of 50 mg/kg/day.High dose levels of 150 mg/kg/day producedcentral nervous system depression and reduction of body weight gain. p-Cresol was foundto be hepatotoxic and nephrotoxic, inducinga mild anemic effect. The acute toxicity ofmethyl phenols did not show any relationshipto the number or position of methyl groupson the phenol nucleus. In an acute toxicitystudy on Daphnia magna, Devillers (1988)found cresols to be more toxic than phenol,xylenols, and trimethylphenols.

Fire Hazard

Combustible. POISONOUS GASES MAY BE PRODUCED IN FIRE. Flammable toxic vapors given off in a fire. Sealed closed containers can build up pressure if exposed to heat.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Pharmaceutical Applications

Cresol is used at 0.15-0.3% concentration as an antimicrobial preservative in intramuscular, intradermal, and subcutaneous injectable pharmaceutical formulations. It is also used as a preservative in some topical formulations and as a disinfectant. Cresol is not suitable as a preservative for preparations that are to be freeze-dried.

Safety

Reports of adverse reactions to cresol are generally associated with the use of either the bulk material or cresol-based disinfectants, which may contain up to 50% cresol, rather than for its use as a preservative. However, a recent case of cutaneous hypersensitivity reaction to the m-cresol component of an insulin formulation detected via intradermal and patch testing has been reported.
Cresol is similar to phenol although it is less caustic and toxic. However, cresol is sufficiently caustic to be unsuitable for skin and wound disinfection. In studies in rabbits, cresol was found to be metabolized and excreted primarily as the glucuronide.
A patient has survived ingestion of 12g of cresol though with severe adverse effects.
LD50 (mouse, oral): 0.76g/kg
LD50 (rabbit, skin): 2g/kg
LD50 (rat, oral): 1.45g/kg

Potential Exposure

Cresol is used as a disinfectant and fumigant; as an ore flotation agent, and as an intermediate in the manufacture of chemicals, dyes, plastics, and antioxidants. A mixture of isomers is generally used; the concentrations of the components are determined by the source of the cresol.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24-48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray.

Environmental Fate

It acts by disruption of the cell membrane by denaturation of proteins and enzymes of the cell.

storage

Cresol and aqueous cresol solutions darken in color with age and on exposure to air and light. Cresol should be stored in a well-closed container, protected from light, in a cool, dry place.

Shipping

UN2076 Cresols, liquid, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 8-Corrosive material. UN3455 Cresols, solid, Hazard class: 6.1; Labels: 6.1- Poisonous materials, 8-Corrosive material.

Toxicity evaluation

Cresol’s production and use as a solvent, disinfectant, and chemical intermediate in the production of synthetic resins may result in its release to the environment through various waste streams. Cresols are also released to the environment through automobile exhaust and tobacco smoke. Cresols are a group of widely distributed natural compounds formed as metabolites of microbial activity and excreted in the urine of mammals. Cresols occur in various plant lipid and oil constituents. If released to air, an extrapolated vapor pressure range of 0.11–0.299 mm Hg at 25°C for the various isomers indicates cresols will exist solely as a vapor in the ambient atmosphere. Vapor-phase cresols will be degraded in the atmosphere by photochemical reaction and produce hydroxyl radicals. The half-life for this reaction in air is estimated to be 6–9 h. If released to soil, cresols are expected to have high mobility based upon Koc values of 22–49 measured in soil. Volatilization from moist soil surfaces is expected to occur slowly based upon Henry’s Law constants. Cresols are not expected to volatilize from dry soil surfaces based upon the extrapolated vapor pressure range. Cresols biodegrade quickly in soils with half-lives of few days. If released into water, cresols do not adsorb to suspended solids and sediment in the water. Cresols biodegrade quickly in water with half-lives of severaldays to few weeks. Volatilization from water surfaces is expected to occur slowly based upon the range of Henry’s Law constants for the various isomers. Estimated volatilization halflives for a model river and model lake range from 21 to 29 and 235–327 days, respectively. Cresols are not expected to undergo hydrolysis since they lack functional groups that hydrolyze under environmental conditions. Direct photolysis in sunlit surface occurs and products occur at a much slower rate than biodegradation. Log bioconcentration factor values of 1.3 and 1.03 measured in ide and zebrafish respectively suggests that the potential for bioconcentration in aquatic organisms is low.

Incompatibilities

Vapors may form explosive mixture with air. Incompatible with strong acids; oxidizers, alkalies, aliphatic amines; amides, chlorosulfonic acid; oleum. Decomposes on heating, producing strong acids and bases, causing fire and explosion hazard. Liquid attacks some plastics and rubber. Attacks many metals.

Incompatibilities

Cresol has been reported to be incompatible with chlorpromazine. Antimicrobial activity is reduced in the presence of nonionic surfactants.

Waste Disposal

Wastewaters may be subjected to biological treatment. Concentrations may be further reduced by ozone treatment. High concentration wastes may be destroyed in special waste incinerators.

Regulatory Status

Included in the FDA Inactive Ingredients Database (IM, IV, intradermal, and SC injections). Included in parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Cresol(1319-77-3)Related Product Information

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