二苯醚

Diphenyl Ether

HCID 7583CAS 101-84-8

基本信息

标准SMILES
c1ccc(Oc2ccccc2)cc1
InChIKey
USIUVYZYUHIAEV-UHFFFAOYSA-N
分子式
C12H10O
平均分子量
170.21 g/mol
单同位素质量
170.07316494

名称与标识

首选名称
Diphenyl Ether
IUPAC
phenoxybenzene
中文名
二苯醚
英文名
Diphenyl ether
分子式
C12H10O
分子量
170.21

名称与别名

DIPHENYL ETHERDiphenyl oxide101-84-8PhenoxybenzenePhenyl etherBenzene, 1,1'-oxybis-DiphenyletherOxybisbenzenePhenyl oxideBiphenyl oxideGeranium crystalsOxydiphenyl
展开更多名称
苯醚联苯醚二苯醚苯基醚苯氧苯氧化二苯氧化二苯基二苯醚CP二苯醚 溶液二苯[基]醚OxydibenzeneFEMA 3667Diphenyl etheether,diphenylDEPHENYL OXIDE
Chemcryl JK-EBBenzene, phenoxy-1,1'-Oxybis(benzene)1,1'-OxybisbenzeneEther, diphenylFEMA No. 3667DTXSID90218473O695R5M1U

数据库标识

CAS
101-84-8、32576-61-7
PubChem CID
7583
DTXSID
DTXSID9021847
ChEMBL
CHEMBL38934
ChEBI
CHEBI:39258
UNII
3O695R5M1U
EC Number
202-981-2
Nikkaji
J3.598J

性质

结构计算性质

XLogP
4.2
极性表面积
9.2 Ų
氢键供体
0
氢键受体
1
可旋转键
2
重原子
13

实验与物化性质

LogP · 3 条

log Kow = 4.21

4.21

4.21

OdorGeranium-like odor
Density · 6 条

1.07 at 80.6 °F (USCG, 1999) - Denser than water; will sink

1.0661 g/cu cm at 30 °C

Percent in saturated air: 0.0028; Density of saturated air: 1.0014 (Air = 1)

Relative density (water = 1): 1.08

1.071-1.075

1.08

Viscosity3.4909X10-3 Pa-sec at melting point
Color/Form · 2 条

Colorless crystals or liquid

Colorless, crystalline solid or liquid (above 82 degrees F)

Solubility · 6 条

Insoluble (NTP, 1992)

In water, 18 mg/L at 25 °C

Soluble in ethanol, ether, benzene, acetic acid; slightly soluble in chloroform

0.018 mg/mL at 25 °C

Solubility in water, g/100ml: 0.002 (very poor)

Insoluble in water, soluble in oils

物理化学性质

熔点
26 °C · 26 °C
沸点
259 °C · 259 °C(lit.)
密度
1.073 g/mL · 1.073 g/mL at 25 °C(lit.)
蒸气密度
5.86 · >5.86 (25 °C, vs air)
蒸气压
1 mm · <1 mm Hg ( 20 °C)
折射率
20 · n20/D 1.579(lit.)

化学性质

无色结晶或液体。具有桉叶油气味。 溶于乙醇、乙醚、苯和冰醋酸,不溶于水、无机酸溶液和碱溶液。在胺类或碱的水溶液中比较稳定,加热时醚键容易断裂,分解成苯酚。例如二苯醚在吡啶中与金属钠或钾一起加热回流,90%以上变成苯酚。Grignard试剂也能使醚键断裂。用无水氯化钴作催化剂时,反应在常温即可进行。与碘化氢一起加热到250℃不发生分解。在乙酸中对氧化铬(CrO3,Cr2O3)也比较稳定。二苯醚与浓硝酸反应时,生成4,4'-二硝基二苯醚。

安全与法规

GHS分类

GHS Classification · 6 条

This chemical does not meet GHS hazard criteria for 0.5% (12 of 2199) of reports.

Warning

H319 (84.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H400 (16.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (10.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard];H411 (78.8%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2199 reports by companies from 45 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 12 of 2199 reports by companies.;There are 44 notifications provided by 2187 of 2199 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危害信息

Regulatory Information · 5 条

Chemical: Benzene, 1,1'-oxybis-

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

Benzene, 1,1'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,1'-oxybis- 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: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14971;Status: Active Update: 07-10-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18130

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

DOT LabelClass 9
Fire Hazards · 2 条

This chemical is combustible. (NTP, 1992)

Combustible.

Fire PotentialCombustible when exposed to heat or flame.
Health HazardsInhalation may cause nausea because of disagreeable odor. Contact of liquid with eyes causes mild irritation. Prolonged exposure of skin to liquid causes reddening and irritation. Ingestion produces nausea. (USCG, 1999)
Hazards Summary · 1 条

. . . industrial experience has shown no evidence that phenyl ether, either as liquid mist or vapor, was a human health hazard under ordinary conditions of manufacture, handling, or use. Controlling workplace concentration below 1 ppm has been recommended to prevent the disagreeable odor and nausea in some workers. Damage to the liver and other organs has been documented in acute feeding studies of experimental animals; LD50 = 4 g/kg for rats and guinea pigs; [ACGIH] An irritant of the eyes and respiratory tract; [ICSC]

安全与防护

Fire Fighting · 2 条

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.;Fire Extinguishing Agents: Dry chemical, carbon dioxide (USCG, 1999)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 条

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth.

First Aid · 2 条

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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash promptly - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: Respiratory support

Safe StorageSeparated from strong oxidants. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection1.0 [ppm]
Fire Fighting Procedures · 4 条

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Dry chemical, carbon dioxide. Water or foam may cause frothing.

毒理信息

Body BurdenAs part of the USEPA's National Human Adipose Tissue Survey (NHATS), diphenyl ether was detected in 40 of 44 composite adipose tissue collected for fiscal year 1982(1).
Target OrgansEyes, skin, respiratory system
Ecotoxicity Values · 5 条

LC50; Species: Daphnia magna (Water Flea) age < or =24 hr; Conditions: freshwater, static, 22 °C, pH 7.4-9.4, dissolved oxygen 6.5-9.1 mg/L; Concentration: 1400 ug/L for 24 hr (95% confidence limit: 1100-1900 ug/L) /> or =80% purity/

LC50; Species: Daphnia magna (Water Flea) age < or =24 hr; Conditions: freshwater, static, 22 °C, pH 7.4-9.4, dissolved oxygen 6.5-9.1 mg/L; Concentration: 670 ug/L for 48 hr (95% confidence limit: 110-1100 ug/L) /> or =80% purity/

LC50; Species: Cyprinodon variegatus (Sheepshead Minnow) age 14-28 dph, juvenile, length 8-15 mm; Conditions: saltwater, static; Concentration: 2400 ug/L for 24 hr (95% confidence limit: 1800-3200 ug/L) /> or =80% purity/

LC50; Species: Cyprinodon variegatus (Sheepshead Minnow) age 14-28 dph, juvenile, length 8-15 mm; Conditions: saltwater, static; Concentration: 2400 ug/L for 48 hr (95% confidence limit: 1800-3200 ug/L) /> or =80% purity/

For more Ecotoxicity Values (Complete) data for DIPHENYL ETHER (6 total), please visit the HSDB record page.

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1950(2), indicates that diphenyl ether is expected to have low mobility in soil(SRC). Volatilization of diphenyl ether from moist soil surfaces may be an important fate process(SRC) given its Henry's Law constant estimated as 2.8X10-4 atm-cu m/mole(SRC) based upon its vapor pressure, 2.25X10-2 mm Hg(3), and water solubility, 18 mg/L(4). Diphenyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.25X10-2 mm Hg at 25 °C(3). A 6.3% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1950(2), indicates that diphenyl ether is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 2.8X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 2.25X10-2 mm Hg(4), and water solubility, 18 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 4 hours and 6 days, respectively(SRC). According to a classification scheme(6), experimental BCF values of 195, 470 and 590, suggest that bioconcentration in aquatic organisms is moderate to high(SRC). A 6.3% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diphenyl ether, which has a vapor pressure of 2.25X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diphenyl ether 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 3 days(SRC), calculated from its rate constant of 9.8X10-12 cu cm/molecule-sec at 25 °C(3). Diphenyl ether contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesDiphenyl ether has been qualitatively detected in the volatile aroma components of roasted beef(1).
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

法规信息

Regulatory Information · 5 条

Chemical: Benzene, 1,1'-oxybis-

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

Benzene, 1,1'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,1'-oxybis- 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: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14971;Status: Active Update: 07-10-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18130

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

TSCA Requirements · 1 条

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Diphenyl oxide is included on this list. Effective date: 4/13/89; Sunset date: 6/30/98.

Atmospheric Standards · 1 条

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diphenyl oxide is produced, as an intermediate or a final product, by process units covered under this subpart.

安全数据

wgk
2
tsca
TSCA listed
毒性
LD50 orally in Rabbit: 2450 mg/kg LD50 dermal Rabbit > 7940 mg/kg
RTECS号
KN8970000
包装类别
III
危险等级
9
毒性防护 · 4 条

毒性GRAS(FEMA)。

急性毒性口服- 大鼠 LD50: 3370 毫克/ 公斤

刺激数据皮肤- 兔子 500 毫克/ 24小时 轻度; 眼睛 -兔子 10 PPM/140小时 中度

职业标准TLV-TWA 7 毫克/ 立方米; STEL 14 毫克/ 立方米

包装储运 · 4 条

爆炸物危险特性与空气混合可爆

可燃性危险特性遇明火、高温、强氧化剂可燃;燃烧排放刺激烟雾

储运特性库房通风低温干燥

灭火剂泡沫、二氧化碳、干粉、砂土、1211

化学与工业

药理信息

Metabolism/Metabolites · 4 条

... In the rabbit no cleavage of the ether linkage /of phenyl ether/ occurs. The major metabolite was the p-hydroxylated ether, which is excreted both unconjugated (15%) and conjugated with glucuronic acid (63%) and sulfuric acid (12%). Another metabolite was also isolated from the rabbit urine and fairly well identified as di(p-hydroxyphenyl) ether.

Subcellular fractions of trout liver homogenate metab diphenyl ether mainly to 4 hydroxy derivates with traces of other compounds including 3 hydroxy derivates and possibly 4,4'-dihydroxy derivates.

The bacterium Sphingomonas sp strain SS3, which utilizes diphenyl ether as source of carbon and energy, was enriched from soil samples of an industrial waste deposit. During diphenyl ether degradation in batch culture experiments, phenol and catechol were produced as intermediates which were then channeled into the 3-oxoadipate pathway. The initial step in the degradation follows the recently discovered mechanism of 1,2-dioxygenation, which yields unstable phenolic hemiacetals from diphenyl ether structures.

Screening of selected fungi proved Cunninghamella echinulata most suitable for research on hydroxylation of biphenyl oxide. The process depended on cultivation conditions and yielded up to 76% 4-hydroxybiphenyl oxide and about 6% 4,4'-dihydroxybiphenyl oxide.

Absorption, Distribution and Excretion · 3 条

The absorption of diphenyl ether after oral uptake is up to 90% in rats and rabbits and is independent of the administered dose. The data on dermal absorption are somewhat conflicting. After semi-occlusive application of 10-1,000 mg/kg to the clipped skin of rats, almost 20% of the dose was absorbed as measured by the amount excreted in urine. However, in a diffusion experiment only 0.3% (rat skin) or 0.2% (human skin) of diphenyl ether penetrated the skin in vitro. The higher absorption in the in vivo experiment may have been caused by the vehicle (diethyl phthalate) and some oral uptake after removal of the occlusion plaster.

After intraperitoneal injection in rats, diphenyl ether was distributed into all organs and tissues within 1 hour with maximum concentrations in liver, lung, kidney and spleen.

... Phenyl ether, when injected into the rabbit, was excreted in the urine as p-hydroxyphenyl phenyl ether and none was excreted as the unchanged ether. /Route not specified/

Cellular LocationsMembrane

用途与制造

Uses · 6 条

Used as a heat transfer medium, Dowtherm A, and as a chemical intermediate for surface active agents and lubricants; [ACGIH]

Perfumery, particularly soaps; heat-transfer medium resins for laminated electrical insulation; chemical intermediate for such reactions as halogenation, acylation, alkylation.

Commonly used dye carrier. /From table/

... Employed as a processing aid in the production of polyesters; several polybromine derivatives of diphenyl ether are used as fire retardants.

... Used in large quantities in soap perfumes. However, its main application is as a heat-transfer medium (eutectic mixture with diphenyl).

For more Uses (Complete) data for DIPHENYL ETHER (6 total), please visit the HSDB record page.

U.S. Imports · 3 条

(1972) 2.74X10+6 G

(1975) 9.17X10+7 G

581,836 lbs (principal US custom districts)

U.S. Production · 6 条

2023: 40,000,000 - <55,000,000 lb;2022: 70,000,000 - <85,000,000 lb;2021: 70,000,000 - <85,000,000 lb;2020: 70,000,000 - <85,000,000 lb

(1972) OVER 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Benzene, 1,1'-oxybis- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzene, 1,1'-oxybis-. Aggregated National Production Volume: 50 to < 100 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzene, 1,1'-oxybis-. National Production Volume: 77,839,277 lb/yr.

Consumption PatternsApproximately 67% is used in making heat-transfer fluids; approximately 100,000 lbs used annually in fragrance products
Consumer UsesNot Known or Reasonably Ascertainable;Fragrance
Industry UsesIntermediate;Fragrance;Heat transferring agent;Processing aids not otherwise specified;Surfactant (surface active agent)
应用领域 · 1 条

用途二苯醚主要用作有机高温载热体组分之一。由二苯醚和联苯按质量比73.5:26.5配制的混合物称导生A。使用温度范围:气相232-399℃,液相21-399℃,工作温度不大于400℃。由二苯醚与甲基联苯组成的混合物称导生LF,凝固点低,在-30℃仍可使用,是低温,低粘度载热体。二苯醚具有香叶和洋海棠的香气,也带有甜橙和洋水仙的香调,在香料行业称为结晶香叶油或人造香叶油。由于二苯醚对碱性较为稳定,多用于调配皂用香精,也常用香叶油的代用品,适于调制花香型分妆品、除臭剂等。该品作为有机合成中间体,用于香料工业、合成树脂和其他有机合成生产。恒温传热介质,气相色谱固定液(最高使用温度100℃,溶剂为丙酮)。 与二苯甲烷共用,香气可较为轻飘,可用于香皂、洗涤剂、日用工业品用的玫瑰、香叶、风信子、香薇、新刈草、檀香等型香精中给以青气。用作传热介质。

制备方法

生产方法由氯苯与苯酚在苛性碱溶液中,以铜为催化剂缩合而得。氢氧化钾、苯酚、氯苯按摩尔比配比1:1.4:1.06混合,加入铜粉,搅拌加热进行缩合反应。反应结束后,用酸处理,分出二苯醚油层,经减压蒸馏得到二苯醚成品。也可将氯苯和苯酚在氢氧化钠溶液中反应。二苯醚的另一工业来源是作为氯苯水解制苯酚时的副产品。用氢氧化钠进行氯苯水解的过程中,约有10%的氯苯转化成二苯醚,有些工艺这个比例可达20%。通过萃取精制即得二苯醚产品。

试剂价格

P0177 · 5G
二苯醚Phenyl Ether — 70元
P0177 · 25G
二苯醚Phenyl Ether — 155元

相关反应

1,226 条

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