Diphenylmethan

log Kow = 4.14

4.22

Odor of oranges

Harsh herbaceous odor reminiscent of geranium leaves

1.3421 at 10 °C/4 °C (solid); 1.0008 at 26 °C/4 °C (liquid)

1.008 @25 °C

Orthorhombic needles

Long, colorless needles

Liquid

In water, 14.1 mg/L at 25 °C

In water, 14.5 mg/L

Freely soluble in alcohol, ether, chloroform, hexane, benzene; insoluble in liquid ammonia

>10% in both ethyl ether, ethanol and chloroform.

130 °C

266 °F (130 °C) (CLOSED CUP)

264.5 °C

264.5 °C @760 [mm Hg]

This chemical does not meet GHS hazard criteria for 2.2% (37 of 1665) of reports.

Warning

H400 (93.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1665 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Benzene, 1,1'-methylenebis-

Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

Benzene, 1,1'-methylenebis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,1'-methylenebis- 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)

Status: Active Update: 07-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21882

Diphenylmethane: Does not have an individual approval but may be used under an appropriate group standard

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

6.8 [mg/m3]

74 [mg/m3]

450 [mg/m3]

IN EVENT OF SPILLAGE OR LEAKAGE OF HOT FLUIDS, APPROVED CHEM CARTRIDGE RESPIRATORS OR MASKS SHOULD BE WORN FOR PROTECTION AGAINST VAPORS. SKIN CONTACT WITH TERPHENYLS AND POSSIBLY WITH DIPHENYL AND DERIVATIVES SHOULD BE AVOIDED BY PROPER HANDLING PROCEDURES. CONTAMINATED CLOTHING MUST BE LAUNDERED BEFORE USE. EYE PROTECTION SHOULD BE WORN IF EYE HAZARD EXISTS. /DIPHENYL & DERIVATIVES/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9160(SRC), determined from a structure estimation method(2), indicates that 1,1'-methylenebisbenzene is expected to be immobile in soil(SRC). Volatilization of 1,1'-methylenebisbenzene from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 8.61X10-3 mm Hg(3), and water solubility, 14.1 mg/L(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Biodegradation is expected to be an important fate process in soil. 1,1'-Methylenebisbenzene has been shown to biodegrade readily in river die-away tests(5) and in soil inoculum studies following acclimation(6). A 0% of theoretical BOD using activated sludge in a 2-week Japanese MITI test(7) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9160(SRC), determined from a structure estimation method(2), indicates that 1,1'-methylenebisbenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 8.61X10-3 mm Hg(4), and water solubility, 14.1 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 13 hours and 8 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 116 days if adsorption is considered(6). According to a classification scheme(7), a measured BCF range of 452 to 1190 in catfish(8), suggests bioconcentration in aquatic organisms is high to very high(SRC). Biodegradation is expected to be an important fate process in water. 1,1'-Methylenebisbenzene has been shown to biodegrade readily in river die-away tests(9) and in soil inoculum studies following acclimation(10). A 0% of theoretical BOD using activated sludge in a 2-week Japanese MITI test(8) suggests that biodegradation is not an important environmental fate process in water(SRC). Hydrolysis is not expected to be an important environmental fate process(SRC) since this compound lacks functional groups that hydrolyze under environmental conditions(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,1'-methylenebisbenzene, which has a vapor pressure of 8.21X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. However, monitoring data indicates that 1,1'-methylenebisbenzene is found on particulate matter in the ambient atmosphere(3); the source of atmospheric particulate matter containing 1,1'-methylenebisbenzene may be fly ash from municipal incinerators(4,5). Vapor-phase 1,1'-methylenebisbenzene 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 1.5 days(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(6). Particulate-phase 1,1'-methylenebisbenzene may be removed from the air by wet and dry deposition(SRC). 1,1'-Methylenebisbenzene has a UV absorption band that extends beyond 290 nm(7), therefore, it may be susceptible to direct photolysis by sunlight(SRC).

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the US EPA, 1,1'-methylenebisbenzene was identified in discharges of the following industrial category (frequency of occurrence, median concentration in ppb): timber products (1; 70.9), paint and ink (3; 34.8), printing and publishing (1; 38.5), coal mining (2; 75.7), organics and plastics (10; 356.6), plastics and synthetics (1; 28.6), rubber processing (1; 207.1), pesticides manufacture (1; 281.4), pharmaceuticals (6; 204.7), explosives (2; 40.6), electronics (1; 43.8), oil and gas extraction (1; 43.8), organic chemicals (3; 1183.3), publicly owned treatment works (20; 18.2). The highest effluent concentration was 29,554 ppb in the paint and ink industry(1).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,1'-methylenebisbenzene can be estimated to be 9160(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,1'-methylenebisbenzene is expected to be immobile in soil.

/HUMAN EXPOSURE STUDIES/ A maximization test was carried out on 25 volunteers. The material was tested at a concn of 8% in petrolatum and produced no sensitization.

/SIGNS AND SYMPTOMS/ PROBABLE IRRITANT & CNS DEPRESSION HIGH CONCN.

1,1'-Methylenebisbenzene's production and use in organic synthesis and dyes(1) and in the fragrance industry as both a fixative and scenting agent in soaps(2) may result in its release to the environment through various waste streams(SRC). 1,1'-Methylenebisbenzene is emitted from municipal incinerators in fly ash and may leach from the fly ash in landfills(3).

AEROBIC: When seeded with a soil inoculum, 1,1'-methylenebisbenzene underwent extensive degradation in 40 days, following a 30 day lag(1). 1,1'-Methylenebisbenzene was completely degraded within 5 days in a river die-away test(2); the study found that, in general, 1,1'-methylenebisbenzene compunds having an unsubstituted phenyl ring undergo rapid primary biodegradation(2). 1,1'-Methylenebisbenzene is degraded by microorganisms isolated from sewage, water, soil, and leaves(3-5). Three metabolic pathways have been identified leading to the initial metabolic product 1,1,1',1'-tetraphenyldimethyl ether, phenylacetic acid, and benzhydrol(3). 1,1'-Methylenebisbenzene, present at 100 mg/L, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(6).

Using catfish which were exposed over an 8-week period to 1,1'-methylenebisbenzene concentrations of 0.01 mg/L and 0.1 mg/L, 1,1'-methylenebisbenzene BCF values were measured that ranged from 452 to 1190(1). According to a classification scheme(3), this BCF range suggests the potential for bioconcentration in aquatic organisms is high to very high(SRC).

Urine and feces, and two-hour bile samples from adult male rats dosed with (14)C-diphenylmethane were analyzed for benzhydrol and 2- and 4-hydroxydiphenyl-methane by silica gel GF t.l.c. and (14)C-determination. Mean values of 48.4% and 17.7% of the administered (14)C were present in 24 hr urine and feces, respectively. Benzhydrol and 2- and 4-hydroxydiphenylmethane comprised 3.7%, 0.3% and 4.8% respectively of the (14)C isolated from urine and 3.1%, 0.8%, and 4.8% respectively of the (14)C isolated from feces. Bile samples (2 hr) contained 3.2% of the administered radioactivity. After treatment with beta-glucuronidase/aryl sulphatase, 71.9% of the recovered biliary radioactivity was identified as benzhydrol (37.5%) and 4-hydroxydiphenylmethane (34.4%).

CONVERSION OF DIPHENYLMETHANE TO P-HYDROXYDIPHENYLMETHANE WAS DEMONSTRATED IN RATS GIVEN 900 MG/KG IP; 24 HR URINE CONTAINED 0.37 MMOL OF UNCONJUGATED & 0.06 MMOL OF CONJUGATED P-HYDROXYDIPHENYLMETHANE. FECES CONTAINED 0.06 MMOL MIXT OF CONJUGATED & UNCONJUGATED.

DIPHENYLMETHANE WAS CONVERTED TO P-HYDROXYDIPHENYLMETHANE, DIPHENYLMETHANOL, & DIPHENYL KETONE BY RAT LIVER MICROSOMES.

A STRAIN OF HYDROGENOMONAS WAS ISOLATED BY ELECTIVE CULTURE IN A SOLN CONTAINING DIPHENYLMETHANE (DDT ANALOG) AS SOLE CARBON SOURCE. CONSTITUTIVE ENZYMES EFFECTED OXIDATION & FISSION OF ONE BENZENE RING OR DIPHENYLMETHANE, AND PHENYLACETIC ACID WAS FOUND AS A MAJOR DEGRADATION PRODUCT. SMALL AMOUNTS OF PHENYLGLYOXYLIC ACID & BENZOIC ACID WERE ALSO GENERATED.

Diphenylmethane is hydroxylated in the rabbit and some 15% of the dose is excreted as 4-hydroxydiphenylmethane, which is largely (80-90%) in the free state. Neither the hydrocarbon nor its metabolite is estrogenic. This reaction also occurs in the dog.

Used for organic synthesis; in dyes; in fragrances, flavor compounds, and perfumery; in solvents for cellulose lacquers; in the manufacture of hexachlorophene, benzophenone, and pharmaceuticals; [HSDB] Used in fragrances, dyes, polyesters, and jet fuels; [Ullmann]

Diphenylmethane is used in the fragrance industry both as a fixative and in scenting soaps. It can serve as a synergist for pyrethrin in pesticides and insecticides. Diphenylmethane is recommended as a plasticizer to improve the dyeing properties, as a solvent for dyes, and as a dye carrier for printing with disperse dyes. The addition of diphenylmethane to saturated, linear polyesters improves their thermal stability, and its addition to jet fuels increases their stability and lubricating properties.

Organic synthesis

As a component of solvents for cellulose lacquers.

In the manufacturing of hexachlorophene.

2023: 58,140 lb

(1977) PROBABLY GREATER THAN 2.72X10+6 GRAMS

(1979) PROBABLY GREATER THAN 2.72X10+6 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5191]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Phenol, Benzene, 1,1'-methylenebis-. Aggregated National Production Volume: 1 to < 10 million pounds.

The Friedel-Craft reaction of benzyl chloride with benzene in the presence of aluminum chloride is an important method for production of diphenylmethane ... Other known catalysts of this process are elemental aluminum, iron(III) chloride, antimony pentachloride, zinc chloride-hydrogen chloride and boron fluoride dihydrate. When sulfuric acid is used as a condensation agent diphenylmethane yields are 83% and with polyphosphoric acid yields are over 90%. Condensation of benzene with formaldehyde in presence of 85% sulfuric acid yields 79% diphenylmethane.

Prepared from methylene chloride and benzene with aluminum chloride as catalyst.

Fragrance Ingredients

Cosmetics -> Solvent

All Other Chemical Product and Preparation Manufacturing

Benzene, 1,1'-methylenebis-: ACTIVE