基本情報
- 標準SMILES
O=C1CCCC1- InChIKey
BGTOWKSIORTVQH-UHFFFAOYSA-N- 分子式
- C5H8O
- 平均分子量
- 84.12 g/mol
- 単同位体質量
- 84.05751488
概要
Cyclopentanone appears as a clear colorless liquid with a petroleum-like odor. Flash point 87 °F. Less dense than water and insoluble in water. Vapors heavier than air.
名称と識別子
- 優先名称
- Cyclopentanone
- IUPAC
- cyclopentanone
- 現地名
- シクロペンタノン
- 英語名
- Cyclopentanone
- 分子式
- C5H8O
- 分子量
- 84.12
名称と別名
名称をさらに表示
データベース識別子
- CAS
120-92-3- PubChem CID
- 8452
- DTXSID
DTXSID3029154- ChEMBL
CHEMBL18620- ChEBI
CHEBI:16486- UNII
- 220W81TN3S
- EC Number
- 204-435-9
- Nikkaji
- J5.333C
物性
構造計算による物性
- XLogP
- 0.4
- 極性表面積
- 17.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 1
- 回転可能結合数
- 0
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 58.3
実験および物理化学的性質
Density
0.94869 at 68 °F (NTP, 1992) - Less dense than water; will float
0.94869 @ 20 °C/4 °C
Relative density (water = 1): 0.95
0.950-0.960
0.95 @ 20°C
Solubility
Sol in alcohol, acetone, ether
Estimated water solubility of 9175 mg/l
Solubility in water: poor
water; miscible in ether
Miscible at room temperature (in ethanol)
Flash Point
86 °F (NTP, 1992)
87 °F (CLOSED CUP)
26 °C
Boiling Point
267.17 °F at 760 mmHg (NTP, 1992)
130.6 °C AT 760 MM HG
130.00 to 131.00 °C. @ 760.00 mm Hg
131 °C
130-131 °C
130.6 °C @760 [mm Hg]
物理化学的性質
- 融点
- -51 °C · -51 °C (lit.)
- 沸点
- 130 · 130-131 °C (lit.)
- 比重(密度)
- 0.951 g/mL · 0.951 g/mL at 25 °C (lit.)
- 蒸気密度
- 2.97 · 2.97 (vs air)
- 蒸気圧
- 11.5 hPa · 11.5 hPa (20 °C)
- FEMA
- 3910 · 3910 | CYCLOPENTANONE
- 屈折率
- 20 · n20/D 1.437(lit.)
- 闪点
- 87 °F · 87 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 9.18 g/l · 9.18g/l 微溶性
- 外見
- 液体
- 色
- 無色透明~微黄色透明
- 臭い (Odor)
- 楽しい
- においのタイプ
- ミント系
- 由来生物
- synthetic
- 爆発限界(explosive limit)
- 1.6 · 1.6-10.8%(V)
- 水溶解度
- 実質的に不溶
- Merck
- 14 · 14,2743
- JECFA Number
- 1101 · 1101
- BRN
- 605573 · 605573
- Henry's Law Constant
- 1.2 · 1.2×100 mol/(m3Pa) at 25℃, Brockbank (2013)
- Dielectric constant
- 16 · 16.0(-49℃)
- 安定性
- 安定。強力な還元剤、強力な酸化剤、強塩基とは相容れない。
- 主な用途
- フレーバーそして香料
- 化粧品成分の機能
- 香料
- InChI
- 1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2
- InChIKey
- BGTOWKSIORTVQH-UHFFFAOYSA-N
- SMILES
- O=C1CCCC1
- LogP
- 0.7 at · 0.7 at 25℃
- 表面張力
- 33.78 mN/m · 33.78mN/m at 298.15K
- CAS データベース
- 120 · 120-92-3(CAS DataBase Reference)
- NISTの化学物質情報
- Cyclopentanone(120-92-3)
- EPAの化学物質情報
- Cyclopentanone (120-92-3)
化学的性質
化学的特性Cyclopentanone is a colorless liquid with a pleasant, slightly pepperminty odor. It is soluble in water and miscible with common organic solvents. Cyclopentanone has an agreeable, peppermint-like odor. It tends to polymerize in the presence of acids.
安全と法規制
GHS分類
GHS Classification
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P264, P264+P265, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 1.8% (12 of 678) of reports.
Warning
H226 (98.2%): Flammable liquid and vapor [Warning Flammable liquids]
危険有害性情報
Regulatory Information
Chemical: Cyclopentanone
Regulation (EC) No 1334/2008 (amended)
Cyclopentanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclopentanone 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: 29-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13920
Cyclopentanone: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Flammable. Heating will cause rise in pressure with risk of bursting. Gas/air mixtures are explosive.
Health Hazards
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.
Hazards Summary
A skin and eye irritant; A possible respiratory tract irritant; Can be absorbed through skin; [ICSC] Inhalation of high concentrations can cause CNS depression; [HSDB] May cause irritation or burns to skin and eyes; [CAMEO] A skin and eye irritant; [eChemPortal: ESIS] Oral LD50 (mouse) = 1820 mg/kg; Effects in high-dose animal studies include somnolence, coma, and other changes to liver; [RTECS] Safe when used as a flavoring agent; [JECFA]
The major hazards encountered in the use and handling of cyclopentanone stem from its toxicologic properties and flammability. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this peppermint-smelling, water-white liquid may occur from its production and use as an intermediate for pharmaceuticals, biologicals, insecticides, and rubber chemicals. Effects from exposure may include contact burns to the skin and eyes, CNS depression, and suffocation. In activities and situations where over-exposure may occur, wear protective clothing and a positive pressure self-contained breathing apparatus. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes and wash exposed skin thoroughly with soap and water. Contaminated clothing and shoes should be removed and isolated at the site. Cyclopentanone may be ignited by heat, sparks, or flames (flash point: 87 °F, closed cup), and is dangerously reactive with oxidizing materials. Its heavier-than-air vapor may travel to a source of ignition and flash back, or accumulate to explosive concentrations in confined spaces such as sewers. Also, containers of this substance may explode in the heat of a fire. For fires involving cyclopentanone, extinguish with dry chemical, CO2, water spray, fog, or alcohol-resistant foam. Isolate the area for 1/2 mile in all directions if a tank, rail car, or tank truck is involved in the fire. For small spills of cyclopentanone, take up with sand or other noncombustible absorbent and place into containers for later disposal. Large spills should first be diked far ahead of the spill.
Special Reports
OPDYKE DL J; FOOD COSMET TOXICOL 17 (3): 271 (1979). REVIEW WITH 23 REFERENCES ON TOXICITY, INHALATION, IRRITATION, SENSITIZATION, METABOLISM, PHARMACOLOGY & CYTOTOXICITY OF CYCLOPENTANONE.
Savolainer H; Nordic Expert Group for Documentation of Occupational Exposure Limits. Arbetarskyddtyrelsen Publikationsservice, 171 84 Solna, Sweden 33 pp. (1985). Literature survey on cyclohexanone and cyclopentanone as background for discussion of occupational exposure limits.
安全と保護具
Fire Fighting
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
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.
General First Aid:
Isolation and Evacuation
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Immediate precautionary measure
毒性情報
Environmental Fate
TERRESTRIAL FATE: Cyclopentanone is not expected to hydrolyse in soils(1), or undergo photolysis on sunlit soil surfaces due to lack of >290 nm UV adsorption(2). A single 5-day BOD screening test, which utilized activated sludge for inocula, suggests that cyclopentanone will biodegrade rapidly upon acclimation in terrestrial environments(3). An estimated Koc of 30(1) indicates cyclopentanone should have a very high mobility in soil(4). A Henry's Law constant of 1.0X10-5 atm-cu m/mole(5) suggests volatilization of cyclopentanone from moist soils may be an important fate process(1). Based on a vapor pressure of 11.4 mm Hg at 25 °C(6), cyclopentanone should evaporate from dry surfaces, especially when present in high concn such as in spill situations(SRC).
AQUATIC FATE: Cyclopentanone is not expected to hydrolyze(1) or undergo direct photolysis in aquatic systems(2). A single 5-day BOD screening test, which utilized activated sludge for inocula, suggests that cyclopentanone will biodegrade rapidly upon acclimation in natural waters(3). An estimated log bioconcentration factor (log BCF) of -0.05(1) indicates cyclopentanone should not bioconcentrate in aquatic organisms(SRC). An estimated Koc of 30(1) indicates cyclopentanone should not partition from the water column to organic matter contained in sediments and suspended solids(SRC). A Henry's Law constant of 1.0X10-5 atm-cu m/mole at 25 °C(4) indicates that volatilization of cyclopentanone from natural bodies of water should be an important fate process(1). Based on this Henry's Law constant, the volatilization half-life from a model river has been estimated to be 3.5 days(1,SRC). The volatilization half-life from an model pond, which considers the effect of adsorption, has been estimated to be about 40 days(5,SRC).
ATMOSPHERIC FATE: Based on a vapor pressure of 11.4 mm Hg at 25 °C(1), cyclopentanone is expected to exist almost entirely in the vapor phase in ambient air(2). Vapor phase reactions with photochemically produced hydroxyl radicals in the atmosphere have been shown to be important(SRC). A rate constant for cyclopentanone of 2.94X10-12 cu cm/molecule-sec at 25 °C corresponds to an atmospheric half-life of about 5.5 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(3). Direct photolysis in air is not expected to be an important environmental fate process(4).
Signs and Symptoms
Cough. Sore throat.
Redness. Pain.
Redness. Pain.
Effluent Concentrations
Cyclopentanone was detected in 4 of 7 wastewater effluents from energy related processes(1). A groundwater water sample from a coal gasification facility in Hanna, WY contained cyclopentanone at an average concn of 32 ppb; the process water at a coal gasification facility in Gillette, WY contained cyclopentanone at an average concn of 110 ppb; effluent from the gasification of Rosebud coal in Morgantown, WV contained cyclopentanone at an average concn of 56 ppb; and retort water from an in situ shale oil processing facility in Rock Spring, WY contained cyclopentanone at an average concn of 5 ppb(1). Wastewater from coal gasification at the Grand Fork's Energy Technology Center, ND was also reported to contain cyclopentanone at a concn of 0.8 mg/L(2). In addition, wastewater effluent from a shale oil facility in Queensland, Australia was shown to contain cyclopentanone at a concn of 53 mg/L(3).
Human Toxicity Excerpts
/PRODUCES CNS DEPRESSION/ IN HIGH CONCN.
25 MMOLAR CYCLOPENTANONE INCUBATED WITH /HUMAN LUNG FIBROBLAST/ CELLS FOR 30 MIN AT 37 °C SHOWED NO SIGNS OF ACTIVE MEMBRANE DAMAGE.
Artificial Pollution Sources
Cyclopentanone may be released to the environment via effluents at sites where it is produced or used as an intermediate for pharmaceuticals, biologicals, insecticides and rubber chemicals(4). Cyclopentanone is also released to the environment via effluents from the manufacture and use of coal-derived liquid fuels and the disposal of coal liquefaction and gasification waste byproducts(1-3).
Environmental Biodegradation
Pure culture studies showed various isolated species of bacteria(1,2) and yeast(3) were unable to utilize cyclopentanone as a single carbon source. A single 5-day BOD screening test, which utilized activated sludge for inocula, indicates cyclopentanone biodegraded rapidly with acclimation(4). After a 20 day acclimation period. 95.4% COD of an initial concn of 100 mg/L was removed in a closed bottle maintained at 20 °C and a pH of 7.2(4).
Environmental Bioconcentration
Based upon an estimated log kow of 0.24(1), the bioconcentration factor (log BCF) for cyclopentanone has been calculated to be -0.05, from a recommended regression-derived equations(2). This BCF value indicates cyclopentanone should not bioconcentrate in aquatic organisms(SRC).
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- GY4725000
- ridadr
- UN 2245
- hs_code
- 2914 29 00
- risk_code
- 10-36/38
- 化審法
- (9)-2108
- 消防法
- 危険物第4類第二石油類(非水溶性)
- hazard_code
- Xi
- safety_code
- 23
- hazard_class
- 3
- packing_group
- III
- 自然発火温度
- 445 °C
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 120-92-3(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
... MINOR (1-2%) METABOLITES OF CYCLOPENTANONE ... HAVE BEEN DETECTED IN RAT & RABBIT URINE. 2-HYDROXYCYCLOALKYLMERCAPTURIC ACIDS ... WHICH WERE PRESENT AS ... SULFATE ('DOUBLE CONJUGATE') ... PRESUMABLY FORMED BY DEHYDRATION OF CYCLOALKANOLS (MAJOR METABOLITES) TO CYCLOALKENES WITH SUBSEQUENT EPOXIDATION & MERCAPTURATION.
... RABBITS FED ... /CYCLOPENTANONE/ EXCRETED LARGE AMT (MORE THAN HALF THE DOSE) AS CYCLOPENTYL ... GLUCURONIDE ... MINOR AMT OF SULFATE CONJUGATES WERE ALSO PRESENT.
用途と製造
Uses
Used as intermediate for pharmaceuticals, biologicals, insecticides, and rubber chemicals; [Hawley]
INT FOR PHARMACEUTICALS, BIOLOGICALS, INSECTICIDES, & RUBBER CHEMICALS.
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Computer and Electronic Product Manufacturing
Cyclopentanone: ACTIVE
応用分野
解説シクロペンタノンとは、化学式(CH2)4COで表される5員環構造を有する環状ケトンの1つです。 分子量は84.12 g/mol、密度は0.95 g/cm3、融点は-58.2 ℃、沸点は130.6 ℃、CAS番号は120-92-3です。
用途医薬品、殺虫剤、ゴム薬品の合成中間体
天然物の起源Reported found in roasted onion, baked potato, tomato, gruyere cheese, butter, heated chicken, boiled beef, heated pork, roasted pecan, yellow passion fruit juice.
使用Cyclopentanone is used as an intermediate in the synthesis of rubber adhesives, synthetic resins, pharmaceuticals and biologically active compounds. It acts as precursor for the preparation of cyclopentamine and also pentethylcyclanone, cyclopentobarbital. It is a useful laboratory reagent and is used as thinner for epoxies. It can also be used as a solvent in paint and varnish removers and for electronic applications. As a dry cleaning agent, it is used for oil extraction. It is also involved in the preparation of cyclopentanone derivatives like cyclopenylamine and cyclopentanol which find application in the perfume industry.
一般的な説明A clear colorless liquid with a petroleum-like odor. Flash point 87°F. Less dense than water and insoluble in water. Vapors heavier than air.
使用用途シクロペンタノンの使用用途として、医薬品、殺虫剤、ゴム薬品などの合成中間体が挙げられます。ウェーハ製造などの電子材料分野においては、洗浄剤や溶剤としても有用です。 1. 植物由来物質の原料 シクロペンタノン骨格は、ジャスミンから単離された植物ホルモン様物質であるジャスモン酸に含まれているように、さまざまな植物由来物質の構造中に含まれています。このようなホルモンなど、植物にとって不可欠な物質を合成する際にシクロペンタノンは非常に重要な原料です。 2. 香料の原料 上記で述べたジャスモン酸の類縁体であるジヒドロジャスモン酸メチルや2-ブチルシクロペンタノン、2-ヘキシリデンシクロペンタノン、(Z)-3-(2-オキソプロピル)-2-(ペンタ-2-エン-1-イル)シクロペンタノンおよびMagnolioneなどは、各種香料の原料としても重要であり、合成上のとなります。 3. 金属の洗浄剤 シクロペンタノンは金属材料に付着する各種の油、ワックスの洗浄、さらには電子材料分野でのフラックス洗浄剤としても用いられます。あらゆる金属加工油の脱脂洗浄力、各種フラックス、各種ワックスの溶解力、洗浄力が優れていることです。 また、比較的に沸点が低く乾燥性や回収性が優れていたり、蒸留再生をすることで品質が安定し、リサイクル使用が可能であったり、生分解性が良好で毒性が低かったりすることも理由の1つです。
調製方法
製造方法Prepared by heating adipic acid (285 to 295°C) in the presence of barium hydroxide, distilling, ether extraction and then fractionation.
純化方法Shake it with aqueous KMnO4 to remove materials absorbing around 230 to 240nm. Dry it with Linde-type 13X molecular sieves and fractionally distil it. It has also been purified by conversion to the NaHSO3 adduct which, after crystallising four times from EtOH/water (4:1), is decomposed by adding to an equal weight of Na2CO3 in hot H2O. The free cyclopentanone is steam distilled from the solution. The distillate is saturated with NaCl and extracted with *benzene which is then dried (anhydrous K2CO3) and evaporated. The residue is then distilled [Allen, et al. J Chem Soc 1909 1960]. [Beilstein 7 IV 5.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A cyclic ketone that consists of cyclopentane bearing a single oxo substituent.
関連反応
関連ノート
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