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HCID 7967作成日:2026年10月23日

Cyclohexanone

シクロヘキサノン · 3α-シクロヘキサノン · アノン · ケトヘキサメチレン · ナドン · ケトシクロヘキサン · セクストン · ヒトロールO

https://huagongshe.com/ja/chemical/7967

Cyclohexanone の分子構造式

識別子と物理属性

CAS No.108-94-1
分子式C6H10O
平均分子量98.14 g/mol
単同位体質量98.07316494 g/mol
SMILESO=C1CCCCC1
InChIKeyJHIVVAPYMSGYDF-UHFFFAOYSA-N
PubChem CID7967
ChEMBLCHEMBL18850
ChEBICHEBI:17854
EC No.203-631-1
DTXSIDDTXSID6020359
現地名シクロヘキサノン

化学・物理的性質

XLogP0.8
極性表面積17.1
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7
形式電荷0
複雑度68.2
物質分類Flammable agents - 2nd degreeVolatile Organic Compound (VOC)
医薬品Pharmaceuticals -> Listed in ZINC15
SolventsSolvents -> Ketones (<C12)
SpringerMaterials PropertiesCoriolis coupling
香料Fragrance Ingredient (Cyclohexanone) -> IFRA transparency List
農薬Pesticide -> EPA IRIS
LogP(分配係数)Log Kow= 0.81
臭いODOR REMINISCENT OF PEPPERMINT & ACETONE... Peppermint- or acetone-like odor.ペパーミントとアセトンのように。
食品添加物FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
密度0.945 at 68 °F (USCG, 1999) - Less dense than waterwill float0.9421 @ 25 °C/4 °C0.9478 @ 20 °C/4 °CRelative density (water = 1): 0.950.947-0.9500.9421 @25 °C0.947 g/mL at 25 °C (lit.)
香味料EU Flavoring substances
Viscosity2.2 mPa.s (=cP) @ 25 °C
融点-47 °C (lit.)
沸点155 °C (lit.)
蒸気密度3.4 (vs air)
蒸気圧3.4 mm Hg ( 20 °C)
屈折率n20/D 1.450(lit.)
FEMA3909 | CYCLOHEXANONE
引火点116 °F
貯蔵条件Store at +5°C to +30°C.
溶解度90g/リットル150g/L(10℃)
pKa(酸解離定数)17(at 25℃)
外観・状態液体
色APHA: ≤10
pH7 (70g/l, H2O, 20℃)
においのタイプミント系
由来生物synthetic
爆発限界1.1%, 100°F
比熱容量Cp(liquid): 1.86 J/(g·K), at 25℃
JECFA Number1100
Merck14,2726
BRN385735
ヘンリー定数1.2 x 10-5 atmm3/mol at 25 °C (Hawthorne et al., 1985) 6.92 x 10-5 atmm3/mol at 60.00 °C, 10.7 at 70.00 °C, 16.4 at 80.00 °C (headspace-GC, Hovorka et al., 2002)
誘電率18.2(20℃)
安定性安定。可燃性。強力な酸化剤とは相容れない。
主な用途フレーバーそして香料
化粧品成分の機能香料溶媒
InChI1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
InChIKeyJHIVVAPYMSGYDF-UHFFFAOYSA-N
SMILESO=C1CCCCC1
LogP(分配係数)0.86 at 25℃
表面張力33.74mN/m at 298.15K
CAS データベース108-94-1(CAS DataBase Reference)
NISTの化学物質情報Cyclohexanone(108-94-1)
EPAの化学物質情報Cyclohexanone (108-94-1)

化学的特性

シクロヘキサノンは有機化合物でありその分子式はC6H10Oですこの化学物質は透明な油性の液体で軽いアセトンのような臭いが特徴です多くの化学産業や製造プロセスにおいて重要な役割を果たしています

化学的特性

Cyclohexanone is a water-white to slightly yellow liquid with a peppermint-like or acetone-like odor. The Odor Threshold is 0.12 0.24 ppm in air.

安全性と法規制

GHS 分類WarningH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)DangerH226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
規制情報Chemical: CyclohexanoneRegulation (EC) No 1334/2008 (amended)Cyclohexanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanone 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: 02-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15388Cyclohexanone: HSNO Approval: HSR001112 Approved with controlsThe 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.)
その他の安全情報IMAP assessments - Cyclohexanone: Human health tier I assessment
輸送ラベル(DOT)Flammable Liquid
火災危険Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Above 44 °C explosive vapour/air mixtures may be formed.
火災の可能性MODERATE, WHEN EXPOSED TO HEAT OR FLAMECAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS .../CYCLOHEXANONE/ ... SHOULD NOT PRESENT A PROBLEM OF FLAMMABILITY UNLESS HANDLED AT ELEVATED TEMP.
健康有害性Inhalation of vapors from hot material can cause narcosis. The liquid may cause dermatitis. (USCG, 1999)· Inhalation or contact with material may irritate or burn skin and eyes.
有害性の概要Liquid causes first degree burns on short exposure[CHRIS] Animals become stuporous in high-dose inhalation studies and develop liver necrosis after high-dose feeding studies. [ACGIH] [Sanmartin O, et al. Occupational contact dermatitis from cyclohexanone as a PVC adhesive. Contact Dermatitis. 1992 Sep27(3):189-90. No abstract available. Abstract in NIOSHTIC #179644]
輸送番号・ガイド(DOT)1915 127
反応性グループKetones
EC 分類Symbol: XnR: 10-20S: (2)-25
UN 分類UN Hazard Class: 3UN Pack Group: III
Special ReportsOccupational exposure to ketones, including cyclohexanone, is discussed.[NIOSHCriteria Document: Ketones p.1-244 (1978) DHEW Pub. NIOSH 78-173.]44 FR 31866 (6/1/79). The fourth report of the TSCA interagency testing committee to the administrator, EPA concerning cyclohexanone is discussed.Spencer PS et alCrit Rev Toxicol 7 (4): 279-356 (1980). Neurotoxicity of cyclohexanone is discussed.
消火Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Use alcohol-resistant foam, carbon dioxide, powder. In case of fire: keep drums, etc., cool by spraying with water.
応急処置措置Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .
漏出応急措置· 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.
応急処置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:(General first aid procedures)
安全保管Fireproof. Separated from strong oxidants.
暴露管理・個人防護· Wear positive pressure self-contained breathing apparatus (SCBA).Biological Exposure Indices (BEI) [ACGIH] - 1,2-Cyclohexanediol (with hydrolysis) in urine: 80 mg/L (end of shift at end of workweek)Cyclohexanol (with hydrolysis) in urine: 8 mg/L (end of shift)See notations in ACGIH TLVs and BEIs.756.0 [ppm]
消火手順ALCOHOL FOAM, DRY CHEMICAL OR CARBON DIOXIDEIf material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.
保管条件Keep containers closedprohibit open flame. Store in cool and dark plane.
清掃方法Remove all ignition sources. Ventilate area of spill or leak. For small quantities of liquids containing cyclohexanone, absorb on paper towels and place in an appropriate container. Place towels in a safe place (such as a fume hood) for evaporation. Allow sufficient time for evaporation of the vapors so that the hood ductwork is free from cyclohexanone vapors. Burn the paper in a suitable location away from combustible materials.Large quantities of liquids containing cyclohexanone may be absorbed in vermiculite, dry sand, earth, or a similar material and placed in an appropriate container. Cyclohexanone should not be allowed to enter a confined space such as a sewer because of the possibility of an explosion. Cyclohexanone may be collected by vacuuming with an appropriate system. If a vacuum system is used, there should be no sources of ignition in the vicinity of the spill and flashback prevention devices should be provided.Absorb on paper. Evaporate on a glass or an iron dish in hood. Burn the paper.
非火災時の漏出対応Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
処分方法Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U057, F003, must conform with USEPA regulations in storage,transportation, treatment and disposal of waste.Cyclohexanone is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.
漏出処分Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
体内負荷In a study including 42 production workers from a large video tape manufacturing plant and 17 workers from two plastic bag printing plants in Singapore, the mean cyclohexanone level in breath was 1.08 ppm with a range of 0-6.4 ppm(1). Environmental levels of cyclohexanone in the plants ranged from 0.1 to 36.0 ppm, with a mean of 9.04 ppm.
標的器官Eyes, skin, respiratory system, central nervous system, liver, kidneys
生態毒性値LC50 Pimephales promelas (fathead minnow) 527 mg/l 96 hr flow-through bioassay, wt 0.12 g, water hardness 45.5 mg/l CaCO3, temp: 25 +/- 1 °C, pH 7.5, dissolved oxygen greater than 60% of saturation
環境中動態TERRESTRIAL FATE: Cyclohexanone is estimated to be highly mobile in soil(1,3,SRC). In view of its moderate vapor pressure(2) and low adsorption to soil(3), it would be expected to volatilize from surface soil. Although data are lacking, it may also undergo direct photolysis on the soil surface(4). Cyclohexanone is readily biodegradable according to aerobic screening tests(5-12) and therefore would be expected to biodegrade in soil(SRC).AQUATIC FATE: If released in water, cyclohexanone would be slowly lost by volatilization. Its estimated half-lives in a model river and model lake are 4.1 and 33 days, respectively(1,2). Cyclohexanone is readily biodegradable according to aerobic screening tests(6) and in a die-away test performed using microorganisms from river water(3) and therefore, may be expected to biodegrade in natural waters. Adsorption to sediment(2,4) and bioconcentration(2,5) in aquatic organisms should be minimal(2) based upon its high water solubility(4) and low octanol/water partition coefficient(5).ATMOSPHERIC FATE: In the atmosphere, cyclohexanone will degrade by reacting with photochemically-produced hydroxyl radicals. Its estimated half-life resulting from this reaction is 1.3 days(1,2).
有害作用Neurotoxin - Acute solvent syndrome
暴露経路The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact
Signs and SymptomsCough. Sore throat. Dizziness. Drowsiness.MAY BE ABSORBED! Dry skin. Redness.Redness. Pain.Abdominal pain. Burning sensation.irritation eyes, skin, mucous membraneheadachenarcosis, comadermatitisIn Animals: liver, kidney damage
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=108-94-1]
Effluent ConcentrationsIn a comprehensive survey of wastewater from 4,000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, cyclohexanone was identified in discharges of the following industrial category (positive occurrences, median concentration in ppb): leather tanning (4593), iron and steel manufacturing (213.3), nonferrous metals (128.1), paint and ink (534.4), printing and publishing (2149), ore mining (23.1), inorganic chemicals (532.7), plastics and synthetics (2375.8), auto and other laundries (11.2), pharmaceuticals (244.2), explosives (116.8), aluminum (412.9), electronics (411.9), organic chemicals (262.7), and POTWs (1223.5)(1). Maximum effluent concentrations above 1000 ppb were observed in leather tanning (1,927 ppb), inorganic chemicals (10,256 ppb), and plastics and synthetics (2,345 ppb)(1).Wastewater from advanced treatment facilities in Lake Tahoe, CA, Dallas, TX, and Blue Plains, Washington, DC contained cyclohexanone(1). A final effluent grab sample from the Danville, IL POTW collected in June 1980 contained cyclohexanone(2). Wastewaters from processing shale oil have been found to contain cyclohexanone(3,4). It was identified in leachate from a municipal landfill in Ontario, Canada(5). The concentration of cyclohexanone in active compost blower exhaust from a wastewater sludge composting facility was 13 ug/cu m(6).
EPA IRIS InformationCyclohexanone5 mg/kg-day
Medical SurveillanceConsider the points of attack /respiratory system, eyes, skin, central nervous system/ in preplacement and periodic physical examinations.
Soil Adsorption/MobilityThe Koc for cyclohexanone estimated using structure activity relationships (SAR) is 15(1). A Koc of 17 can be estimated from the water solubility, 23,000 mg/L(2), using a recommended regression equation(3). According to a suggested classification scheme(4), these Koc values indicate that cyclohexanone will be highly mobile in soil.
RCRA 要件U057As stipulated in 40 CFR 261.33, when CYCLOHEXANONE, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).When cyclohexanone is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F003), as stated in 40 CFR 261.31, and must be managed according to State and/or Federal hazardous waste regulations.
TSCA 要件Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.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. Cyclohexanone is included on this list.
FIFRA 要件As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cyclohexanone is found on List C. Case No: 3053Pesticide type: insecticideCase Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.Active ingredient (AI): CyclohexanoneAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."Cyclohexanone is exempted from the requirement of a tolerance when used as a solvent or cosolvent in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.Cyclohexanone is exempted from the requirement of a tolerance when used as a solvent or cosolvent accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
大気基準This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). These standards implement Section 111 of the Clean Air Act and are based on the Administrator's determination that emissions from the Synthetic Organic Chemical Manufacturing Industry cause, or contribute significantly to, air pollution which may reasonably be anticipated to endanger public health or welfare. The intended effect of these standards is to require all newly constructed, modified, and reconstructed Synthetic Organic Chemical Manaufacturing Industry process units to use the best demonstrated system of continuous emission reduction for equipment leaks of Volatile Organic Compounds, considering costs, non air quality health and environmental impact and energy requirements. Cyclohexanone is produced, as an intermediate or final product, by process units covered under this subpart. These standards of performance become effective upon promulgation but apply to affected facilities for which construction or modification commenced after January 5, 1981.
CERCLA 報告数量Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2700 kg. The toll free number of the NRC is (800) 424-8802In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
州飲料水ガイドライン(FL) FLORIDA 35,000 ug/l
職業暴露区分(OEB)A
職業暴露限界(OEL)TWA: 25 ppm (100 mg/m3) [skin]
水環境危害等級(WGK)1
生命健康即時危険濃度700 ppm
TSCA 収載状態TSCA listed
RTECS 番号GW1050000
輸送番号(UN)UN 1915
毒性LD50 orally in rats: 1.62 ml/kg (Smyth)
税関コード2914 22 00
危険文句(R)10-20-41-38-20/21/22
化審法(3)-2376 優先評価化学物質
安衛法有機則 第二種有機溶剤等
消防法危険物第4類第二石油類(非水溶性)
危険表示Xn
安全措置(S)25-36/37/39-26
危険等級3Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Flam. Liq. 3Skin Irrit. 2STOT SE 3
包装等級III
自然発火温度788 °F
貯蔵分類3 - Flammable liquids
有害物質データ108-94-1(Hazardous Substances Data)

用途

解説

シクロヘキサノン,cyclohexanone.アノンともいう.環状脂肪族飽和ケトン類の一つ.工業的には,シクロヘキサンの液相空気酸化およびシクロヘキサノールの脱水素で製造される.ハッカのような臭気をもつ無色の液体.融点-45 ℃,沸点155 ℃.0.9421.1.4507.各種有機溶剤および水に可溶.ナイロン原料であるアジピン酸およびε-カプロラクタムの製造中間体.溶剤として用いられる.また,シクロヘキサノンオキシムのベックマン転位によってカプロラクタムが生成する。6-ナイロン,6,6- ナイロンの製造中間体である。

用途

有機合成原料、溶剤。

用途

ナイロン用原料のアジピン酸及びかプロ楽他無の製造、樹脂、ニトロセルロース、ゴム、シェラック樹脂、およびワックス等の溶剤

用途

有機合成原料、溶剤、洗浄剤。

説明

Cyclohexanone, a colorless liquid is a cyclic ketone. It is an important building block for the synthesis of a variety of organic compounds. Majority of the cyclohexanone synthesized is utilized as an intermediate in the synthesis of nylon.Used as a polyvinyl chloride (PVC) solvent, cyclohexanone caused contact dermatitis in a woman manufacturing PVC fluidotherapy bags. Cyclohexanone probably does not cross react with cyclohexanone resin. A cyclohexanone-derived resin used in paints and varnishes caused contact dermatitis in painters.

天然物の起源

Reported present in Cistus labdaniferus.

使用

Cyclohexanone is used in the productionof adipic acid for making nylon; in thepreparation of cyclohexanone resins; and asa solvent for nitrocellulose, cellulose acetate,resins, fats, waxes, shellac, rubber, and DDT..

一般的な説明

A colorless to pale yellow liquid with a pleasant odor. Less dense than water . Flash point 111°F. Vapors heavier than air. Used to make nylon, as a chemical reaction medium, and as a solvent.

使用用途

シクロヘキサノンの主な使用用途は、以下の通りです。 カプロラクタム、アジピン酸、ナイロンの原料 セルロイド、脂肪、ワックス、ゴム、合成樹脂、樹脂ラッカー等の高沸点溶剤 ペンキ、ワニスの剥離剤 特に、6-ナイロン、6,6-ナイロンの原料としての用途が大半を占めます。そのほか、溶媒、または酸化反応の活性化剤として用いられることもあります。

製法・合成法

純化方法

Dry cyclohexanone with MgSO4,CaSO4, Na2SO4 or Linde type 13X molecular sieves, then distil it. Cyclohexanol and other oxidisable impurities can be removed by treatment with chromic acid or dilute KMnO4. More thorough purification is possible by conversion to the bisulfite addition compound, or the semicarbazone, followed by decomposition with Na2CO3 and steam distillation. [For example, equal weights of the bisulfite adduct (crystallised from water) and Na2CO3 are dissolved in hot water and, after steam distillation, the distillate is saturated with NaCl and extracted with Et2O which is then dried (anhydrous MgSO4 or Na2SO4), filtered and the solvent evaporated prior to further distillation.] FLAMMABLE [Beilstein 7 III 14, 7 IV 15.]