디페닐메탄

디페닐메탄 · 다이페닐메탄 · 다이탄 · 벤젠, 1,1'-메틸렌비스- · 벤질벤젠 · 페닐메틸벤젠 · diphenyl-methan · BENZYLBENZENE

식별자 및 물리적 특성

CAS No.	101-81-5
분자식	C13H12
평균 분자량	168.23 g/mol
단동위원소 질량	168.09390038 g/mol
SMILES	c1ccc(Cc2ccccc2)cc1
InChIKey	CZZYITDELCSZES-UHFFFAOYSA-N
PubChem CID	7580
ChEMBL	CHEMBL1796022
ChEBI	CHEBI:38884
EC No.	202-978-6
DTXSID	DTXSID1041891
현지명	디페닐메탄

화학 및 물리적 성질

XLogP	4.1
극성 표면적	0
수소 결합 공여자 수	0
수소 결합 수용자 수	0
회전 가능 결합 수	2
무거운 원자 수	13
형식 전하	0
복잡도	111
물질 분류	Other Classes -> Aromatic Hydrocarbons
Polymers	Polycyclic aromatic hydrocarbon
화장품	Solvent
SpringerMaterials Properties	13C nuclear magnetic resonance spectrum
향료	Fragrance Ingredient (Diphenylmethane) -> IFRA transparency List
LogP(분배 계수)	log Kow = 4.144.22
냄새	Odor of orangesHarsh herbaceous odor reminiscent of geranium leaves디프로필렌 글리콜 중 10.00%. 달콤한 녹색 젖은 플라스틱 제라늄
밀도	1.3421 at 10 °C/4 °C (solid)1.0008 at 26 °C/4 °C (liquid)1.008 @25 °C1.006 g/mL at 25 °C (lit.)
Color/Form	Orthorhombic needlesLong, colorless needlesLiquid
용해도	In water, 14.1 mg/L at 25 °CIn water, 14.5 mg/LFreely soluble in alcohol, ether, chloroform, hexane, benzeneinsoluble in liquid ammonia>10% in both ethyl ether, ethanol and chloroform.에탄올, 에테르, 벤젠, 클로로포름에 용해됩니다.
인화점	130 °C266 °F (130 °C) (CLOSED CUP)>230 °F
끓는 점	264.5 °C264.5 °C @760 [mm Hg]264 °C (lit.)
녹는점	22-24 °C (lit.)
증기 밀도	5.79 (vs air)
증기압	<1 mm Hg ( 77 °C)
굴절률	n20/D 1.577(lit.)
저장 조건	Store below +30°C.
pKa(산도 계수)	33.5(at 25℃)
물리적 상태	저융점 고체
색상	무색~담황색
비중	1.006
향취 유형	녹색
폭발한계	0.69-8.66%(V)
용해도	14.1mg/L(25℃)
Merck	14,3328
BRN	1904982
헨리 상수	7.7×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
유전율	2.6(26℃)
화장품 원료 기능	용제향기
InChI	1S/C13H12/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1-10H,11H2
InChIKey	CZZYITDELCSZES-UHFFFAOYSA-N
SMILES	C(c1ccccc1)c2ccccc2
LogP(분배 계수)	4.140
NIST	Diphenylmethane(101-81-5)
EPA	Diphenylmethane (101-81-5)

화학적 성질

Colorless to pale yellow low melting solid

안전 및 규제

GHS 분류	This chemical does not meet GHS hazard criteria for 2.2% (37 of 1665) of reports.WarningH400 (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.
규제 정보	Chemical: Benzene, 1,1'-methylenebis-Commission Regulation (EC) No 1565/2000 (Repealed by Com.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/21882Diphenylmethane: Does not have an individual approval but may be used under an appropriate group standard
화재 가능성	DIPHENYL AND ITS DERIVATIVES ARE MODERATELY FLAMMABLE ... DANGER OF FIRE IS NEGLIGIBLE @ AMBIENT TEMP BUT INCR @ HIGH TEMP, WHEN MATERIAL IS DISPERSED IN AIR. /DIPHENYL & DERIVATIVES/
유해성 요약	May cause irritationNo other information available about toxicity in humansOral LD50 (rat) = 2250 mg/kg[MSDSonline]
NFPA Hazard Classification	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.
Hazard Classes and Categories	Aquatic Acute 1 (93.4%)
Critical Temperature and Pressure	Critical temperature: 760 deg Kcritical pressure: 2.71X10+6 Pa
Hazardous Reactivities and Incompatibilities	... Can react with oxidizing material.
소화 절차	/Use/ carbon dioxide /or/ dry chemical /to extinguish fire/.
보관 조건	/DIPHENYL AND ITS DERIVATIVES/ ... MUST BE STORED IN COOL, WELL-VENTILATED PLACE, FAR FROM OPEN FLAMES & AREAS WHERE DANGER OF FIRE EXISTS. /DIPHENYL & DERIVATIVES/
처리 방법	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 qualitypotential migration in soil or watereffects on animal and plant lifeand 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.
Preventive Measures	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.
Protective Action Criteria (PAC)	6.8 [mg/m3]74 [mg/m3]450 [mg/m3]
Personal Protective Equipment (PPE)	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/
생태독성 수치	LC50Species: Leuciscus idus ssp. melanotus (Carp)Concentration: 7500 ug/L for 48 hr /Conditions of bioassay not specified in source examined/ /formulation/
환경 거동	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).
식품 조사 수치	1,1'-Methylenebisbenzene has been detected in the volatile component of baked potato(1).
Effluent Concentrations	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 (170.9), paint and ink (334.8), printing and publishing (138.5), coal mining (275.7), organics and plastics (10356.6), plastics and synthetics (128.6), rubber processing (1207.1), pesticides manufacture (1281.4), pharmaceuticals (6204.7), explosives (240.6), electronics (143.8), oil and gas extraction (143.8), organic chemicals (31183.3), publicly owned treatment works (2018.2). The highest effluent concentration was 29,554 ppb in the paint and ink industry(1).
Soil Adsorption/Mobility	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.
Natural Pollution Sources	1,1'-Methylenebisbenzene has been identified as a component in crude oils(1).
Atmospheric Concentrations	SOURCE DOMINATED: A 1,1'-methylenebisbenzene concentration of 0.59 ng/cu m was detected in the ambient particulate material collected from the atmosphere near the highly industrialized Xigu District, Lanzhou China in March 2003(1).
Human Toxicity Excerpts	/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.
Fish/Seafood Concentrations	1,1'-Methylenebisbenzene was identified, but not quantified, in fish in the Great Lakes(1).
Artificial Pollution Sources	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).
Environmental Biodegradation	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).
Environmental Bioconcentration	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).
수질 위해 등급(WGK)	2
TSCA 등재 상태	TSCA listed
RTECS 번호	DA4976500
운송 번호(UN)	UN3077
독성	LD50 orally in Rabbit: 2250 mg/kg LD50 dermal Rabbit > 5000 mg/kg
관세 코드	29029090
위험 문구(R)	22
위험 표시	Xn
안전 문구(S)	24/25-58-54-44-29
포장분류	III
위험 등급	9Aquatic Acute 1Aquatic Chronic 1
기존화학 물질	KE-23811
자연 발화 온도	905 °F
저장 분류	10 - Combustible liquids
유해 물질 데이터	101-81-5(Hazardous Substances Data)

용도

출처

Has apparently not been reported to occur in nature.

용도

Diphenylmethane, is used as an adhesive chemical composition for making flexible laminates for use in food packaging.

제조 및 합성 방법

제조 방법

By interaction of benzyl chloride and benzene in the presence of an acid cata lyst.