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Hexafluoroacetone

Hexafluoroacetone structure

Hexafluoroacetone 

structure
  • CAS No:

    684-16-2

  • Formula:

    C3F6O

  • Chemical Name:

    Hexafluoroacetone

  • Synonyms:

    2-Propanone,1,1,1,3,3,3-hexafluoro-;2-Propanone,hexafluoro-;1,1,1,3,3,3-Hexafluoro-2-propanone;GC 7887;Perfluoroacetone;Hexafluoroacetone;Perfluoro-2-propanone;Hexafluoro-2-propanone;Bis(trifluoromethyl) ketone;1,1,1,3,3,3-Hexafluoroacetone;NSC 202438;Hexafluoropropanone

  • Categories:

    Active Pharmaceutical Ingredients  >  Other Chemical Drugs

Description

generally supplied as liquid under pressure Hexafluoroacetone is a colorless, nonflamma ble poison gas. Musty odor. Shipped as a liquefied com pressed gas.


Hexafluoroacetone is a colorless, toxic, and highly reactive gas. At ambient temperatures, it is likely to generate a considerable amount of vapor. It is an irritant to skin, eyes and mucous membranes and is toxic by ingestion, skin absorption, and inhalation. When heated to high temperatures it emits toxic fluoride fumes. Prolonged exposure of the container to fire or intense heat may cause it to violently rupture and rocket. It is used in the production of other chemicals.|Liquid|COLOURLESS GAS WITH CHARACTERISTIC ODOUR.|Colorless gas with a musty odor.|Colorless gas with a musty odor. [Note: Shipped as a liquefied compressed gas.]


Hexafluoroacetone is a colorless, toxic, and highly reactive gas. At ambient temperatures, it is likely to generate a considerable amount of vapor. It is an irritant to skin, eyes and mucous membranes and is toxic by ingestion, skin absorption, and inhalation. When heated to high temperatures it emits toxic fluoride fumes. Prolonged exposure of the container to fire or intense heat may cause it to violently rupture and rocket. It is used in the production of other chemicals.|Hexafluoroacetone is a ketone that is acetone in which all the methyl hydrogens are replaced by fluoro groups. It is a ketone and a perfluorinated compound.

Hexafluoroacetone Basic Attributes

166.022

166.02

211-676-3

AKU9463N1Y

1057

202438

2420

DTXSID9043778

COLORLESS GAS|Colorless gas [Note: Shipped as a liquefied compressed gas].

2914700090

Characteristics

17.1

1.46

Hexafluoroacetone is a colorless, toxic, and highly reactive gas. At ambient temperatures, it is likely to generate a considerable amount of vapor. It is an irritant to skin, eyes and mucous membranes and is toxic by ingestion, skin absorption, and inhalation. When heated to high temperatures it emits toxic fluoride fumes. Prolonged exposure of the container to fire or intense heat may cause it to violently rupture and rocket. It is used in the production of other chemicals.

1.33 g/cm3 @ Temp: 25 °C

-129 °C

-27 °C

-23.6±20.1 °C

1.248

Reacts

4525 mm Hg ( 21.1 °C)

Relative vapour density (air = 1): 5.7

LD50 (mg/kg) in rats: 190 orally (trihydrate), 670 dermally (sesquihydrate); in mice: 250 i.p., 180 i.v.; in rabbits: 113 dermally (trihydrate) (Kennedy)

Nonflammable Gas, but highly reactive with water & other substances, releasing heat.

MUSTY ODOR BECOMES ACRID IN PRESENCE OF ACIDIC IMPURITIES

HYGROSCOPIC; HIGHLY REACTIVE; REACTS VIGOROUSLY WITH WATER & OTHER SUBSTANCES, RELEASING CONSIDERABLE HEAT|FP: -122 °C|Heat of Formation = 1250 kJ/mol

Reacts with water or water vapor to form a highly acidic product.

Ketones

Water-Reactive

HEXAFLUOROACETONE is incompatible with the following: Water, acids [Note: Hygroscopic (i.e., absorbs moisture from the air); reacts with moisture to form a highly acidic sesquihydrate.] (NIOSH, 2016).

11.81 eV

Nonflammable Gas, but highly reactive with water & other substances, releasing heat.

The gas is heavier than air.

21.51 kJ/mol @ -27.28 °C

Critical pressure = 2.834 MPa

Safety Information

2.3

UN 2420 2.3

3

R60;R14;R23/24/25;R34;R63

S53-S26-S28-S36-S45-S7/9

UC2450000

T:Toxic;

Fireproof if in building. Cool.

P201, P202, P260, P264, P270, P271, P280, P281, P284, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P310, P314, P320, P321, P332+P313, P337+P313, P362, P403+P233, P405, P410+P403, P501

H280

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Water and acids. [Note: Hygroscopic (ie, absorbs moisture from the air); reacts with moisture to form a highly acidic sesquihydrate.]

Kennedy GL Jr; Crit Rev Toxicol 21 (2): 149-70 (1990). Toxicology of fluorine containing monomers. /A toxicological review covering metabolism, acute toxicity, repeated dose toxicity, genetic toxicity, developmental toxicity, carcinogenicity and environmental toxicology/.

Excerpt from ERG Guide 125 [Gases - Corrosive]: Some may burn but none ignite readily. Vapors from liquefied gas are initially heavier than air and spread along ground. Some of these materials may react violently with water. Cylinders exposed to fire may vent and release toxic and/or corrosive gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket. For UN1005: Anhydrous ammonia, at high concentrations in confined spaces, presents a flammability risk if a source of ignition is introduced. (ERG, 2016)|Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.|Reactive - 2nd degree

|Danger|H280 (69.18%): Contains gas under pressure; may explode if heated [Warning Gases under pressure]|P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P403+P233, P405, P410+P403, and P501|Aggregated GHS information provided by 159 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H280: Contains gas under pressure; may explode if heated [Warning Gases under pressure]|P201, P202, P260, P264, P270, P271, P280, P281, P284, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P310, P314, P320, P321, P332+P313, P337+P313, P362, P403+P233, P405, P410+P403, and P501

Excerpt from ERG Guide 125 [Gases - Corrosive]: As an immediate precautionary measure, isolate spill or leak area for at least 100 meters (330 feet) in all directions. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 2420 datasheet. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 1600 meters (1 mile) in all directions; also, consider initial evacuation for 1600 meters (1 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 125 [Gases - Corrosive]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. Do not touch or walk through spilled material. Stop leak if you can do it without risk. If possible, turn leaking containers so that gas escapes rather than liquid. Prevent entry into waterways, sewers, basements or confined areas. Do not direct water at spill or source of leak. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Isolate area until gas has dispersed. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact and to prevent skin from becoming frozen from contact with the liquid or from contact with vessels containing the liquid. Eyes: Wear appropriate eye protection to prevent eye contact with the liquid that could result in burns or tissue damage from frostbite. Wash skin: No recommendation is made specifying the need for washing the substance from the skin (either immediately or at the end of the work shift). Remove: No recommendation is made specifying the need for removing clothing that becomes wet or contaminated. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Quick drench facilities and/or eyewash fountains should be provided within the immediate work area for emergency use where there is any possibility of exposure to liquids that are extremely cold or rapidly evaporating. (NIOSH, 2016)|Wear appropriate eye protection to prevent eye contact.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate personal protective clothing to prevent skin contact. Wear appropriate personal protective clothing to prevent the skin from becoming frozen from contact with the liquid or from contact with vessels containing the liquid.|Wear appropriate eye protection to prevent eye contact. Wear appropriate eye protection to prevent eye contact with the liquid that could result in burns or tissue damage from frostbite.|Quick drench facilities and/or eye wash fountains should be provided within the immediate work area for emergency use where there is any possibility of exposure to liquids that are extremely cold or rapidly evaporating.|(See protection codes)

HIGHLY DANGEROUS; WHEN HEATED, EMITS HIGHLY TOXIC FUMES. /FLUORINE/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.|/GUIDE 125: GASES - CORROSIVE/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Vapors are extremely irritating and corrosive. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control may cause pollution.|/GUIDE 125: GASES - CORROSIVE/ Fire or Explosion: Some may burn, but none ignite readily. Vapors from liquefied gas are initially heavier than air and spread along ground. Some of these materials may react violently with water. Cylinders exposed to fire may vent and release toxic and/or corrosive gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.|/GUIDE 125: GASES - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Many gases are heavier than air and will spread along ground and collect in low or confined areas (sewers, basements, tanks). Keep out of low areas. Ventilate closed spaces before entering.|For more DOT Emergency Guidelines (Complete) data for 1,1,1,3,3,3-HEXAFLUORO-2-PROPANONE (9 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

HIGH /ACUTE/ IRRITATION TO SKIN, EYES & MUCOUS MEMBRANES BY INHALATION & POSSIBLY DERMAL ROUTES. ...

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.1 ppm (0.7 mg/cu m), skin.

Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Remove gas with fine water spray.

Fireproof if in building. Cool.

A harmful concentration of this gas in the air will be reached very quickly on loss of containment.

The substance is severely irritating to the eyes, skin and respiratory tract. Inhalation of this gas may cause lung oedema. Rapid evaporation of the liquid may cause frostbite. The effects may be delayed. Medical observation is indicated.

Animal tests show that this substance possibly causes malformations in human babies. Animal tests show that this substance possibly causes toxic effects upon human reproduction.

STRICT HYGIENE! AVOID EXPOSURE OF (PREGNANT) WOMEN!

Use ventilation, local exhaust or breathing protection.

Cold-insulating gloves. Protective clothing.

Wear safety spectacles, face shield or eye protection in combination with breathing protection.

Toxicity

1,1,1,3,3,3-Hexafluoro-2-propanone is widely used in the synthesis of polymers, medicinals, agriculture chemicals, and as a component of high-performance fluoropolymers and in the manufacture of the solvent 1,1,1,3,3,3-hexafluoro-2-propanol(1). It is also used as a chemical intermediate for hexafluoroisopropanol, polyacrylates used for textile coating, and polyester coatings for textiles; a solvent for acetal resins and polyamides; and a polymer adhesive(2). During 1,1,1,3,3,3-hexafluoro-2-propanone's production and subsequent use in the above products, it may be released to the environment through various waste streams(SRC).

TERRESTRIAL FATE: An estimated Koc of 150(1,SRC), based on an experimental log Kow(2), indicates that 1,1,1,3,3,3-hexafluoro-2-propanone will have moderate mobility in soil(3,SRC). In moist soils, 1,1,1,3,3,3-hexafluoro-2-propanone is expected to vigorously react with water producing 1,1,1,3,3,3-hexafluoro-2,2-propanediol, a stable solid hydrate as well as liquid hydrates(4,5). If released to dry soils, 1,1,1,3,3,3-hexafluoro-2-propanone may quickly volatilize based on a vapor pressure of 5 mm Hg at 25 °C(6,SRC). 1,1,1,3,3,3-Hexafluoro-2-propanone on soil surfaces may photolyse(SRC); this compound decomposes under UV irradiation to trifluoromethyl radicals and carbon monoxide(7).|AQUATIC FATE: 1,1,1,3,3,3-Hexafluoro-2-propanone is expected to vigorously react with water producing 1,1,1,3,3,3-hexafluoro-2,2-propanediol, a stable solid hydrate as well as liquid hydrates(1,2). This is expected to be a major fate process for 1,1,1,3,3,3-hexafluoro-2-propanone in aquatic systems(SRC). An estimated BCF value of 8(4), based on an experimental log Kow(3), indicates that 1,1,1,3,3,3-hexafluoro-2-propanone should not bioconcentrate in aquatic organisms(SRC).|ATMOSPHERIC FATE: Based on a vapor pressure of 5.0 mm Hg at 25 °C(1,SRC), as extrapolated from experimentally derived coefficients, 1,1,1,3,3,3-hexafluoro-2-propanone will exist solely in the vapor phase(2,SRC). 1,1,1,3,3,3-hexafluoro-2-propanone absorbs in the 220 to 400 nm region with a lambda max of 302 nm(2) and may thus directly photolyse(3,SRC). This compound decomposes under UV irradiation to trifluoromethyl radicals and carbon monoxide(3). The rate constant for the vapor-phase reaction of 1,1,1,3,3,3-hexafluoro-2-propanone with photochemically produced hydroxyl radicals has been estimated to be less than 1X10-16 cu cm/molecule-sec at 25 °C(4,SRC) indicating that 1,1,1,3,3,3-hexafluoro-2-propanone is essentially non-reactive and that degradation via hydroxyl radical reaction is not a major fate process for this compound in the atmosphere(SRC).

1,1,1,3,3,3-Hexafluoro-2-propanone reacts readily with nucleophilic reagents(1). 1,1,1,3,3,3-Hexafluoro-2-propanone reacts vigorously with water(2). In water, this compound forms 1,1,1,3,3,3-hexafluoro-2,2-propanediol, a stable solid hydrate. Further addition of water produces liquid hydrates. With ammonia and primary or secondary amines it forms stable 2,2-amino alcohols(1). 1,1,1,3,3,3-Hexafluoro-2-propanone absorbs in the 220 to 400 nm region with a lambda max of 302 nm(3). This compound decomposes under UV irradiation to trifluoromethyl radicals and carbon monoxide(3). Small amounts of CF3CO radical have also been detected in low temperature flash photolysis(3). The rate constant for the vapor phase reaction of 1,1,1,3,3,3-hexafluoro-2-propanone with photochemically produced hydroxyl radicals has been estimated to be less than 1X10-16 cu cm/molecule-sec at 25 °C(4,SRC); this indicates that 1,1,1,3,3,3-hexafluoro-2-propanone is essentially non-reactive and that degradation via hydroxyl radical reaction is not a major fate process for this compound in the atmosphere(SRC).

A BCF of 8 was calculated for 1,1,1,3,3,3-hexafluoro-2-propanone, using an experimental log Kow of 1.46(1) and a recommended regression-derived equation(2,SRC). This BCF value suggests that 1,1,1,3,3,3-hexafluoro-2-propanone will not bioconcentrate in aquatic organisms(2,SRC).

Based on an experimental log Kow of 1.46(1), the Koc of 1,1,1,3,3,3-hexafluoro-2-propanone is estimated as approximately 150 using a regression-derived equation(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that 1,1,1,3,3,3-hexafluoro-2-propanone has moderate mobility in soil(SRC).

The Henry's Law constant for 1,1,1,3,3,3-hexafluoro-2-propanone is estimated as 3.07X10-3 atm-cu m/mole(1,SRC). This indicates that 1,1,1,3,3,3-hexafluoro-2-propanone will volatilize from water surfaces(2,SRC). This compound's rapid rate of hydrolysis(3) indicates that hydrolysis should preclude volatilization in aquatic environments(SRC).

Exposure to 1,1,1,3,3,3- hexafluoro-2-propanone occurs via inhalation and via skin exposure(1).

Drug Information

Most of an injected dose of radiolabeled HFA was excreted by the rat rapidly and unmetabolized in the urine, and no unusual accumulation or retention of HFA occurred in the testes.

Excerpt from ERG Guide 125 [Gases - Corrosive]: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Vapors are extremely irritating and corrosive. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control may cause pollution. (ERG, 2016)

Eye: If eye tissue is frozen, seek medical attention immediately. If tissue is not frozen, immediately and thoroughly flush the eyes with large amounts of water for at least 15 minutes, occasionally lifting the lower and upper eyelids. If irritation, pain, swelling, lacrimation, or photo phobia persist, get medical attention as soon as possible. Skin: If frostbite has occurred, seek medical attention immediately; do NOT rub the affected areas or flush with water. In order to prevent further tissue damage, do NOT attempt to remove frozen clothing from frostbitten areas. If frostbite has NOT occurred, immediately and thoroughly wash contaminated skin with soap and water. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . ON FROSTBITE: rinse with plenty of water, do NOT remove clothes.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

HIGH /ACUTE/ IRRITATION TO SKIN, EYES & MUCOUS MEMBRANES BY INHALATION & POSSIBLY DERMAL ROUTES. HIGH: CAPABLE OF CAUSING DEATH OR PERMANENT INJURY DUE TO EXPOSURES OF NORMAL USE; INCAPACITATING & POISONOUS; REQUIRES SPECIAL HANDLING.

hexafluoroacetone

The substance can be absorbed into the body by inhalation and through the skin.|inhalation, skin absorption, skin and/or eye contact

irritation eyes, skin, mucous membrane, respiratory system; pulmonary edema; liquid: frostbite; In Animals: teratogenic, reproductive effects; kidney injury


Cough. Sore throat. Burning sensation. Laboured breathing. Shortness of breath. Symptoms may be delayed.


MAY BE ABSORBED! Redness. Pain. ON CONTACT WITH LIQUID: FROSTBITE.


Redness. Pain.

Eyes, skin, respiratory system, kidneys, reproductive system

Hexafluoroacetone Use and Manufacturing

Methods of Manufacturing

1,1,1,3,3,3-Hexafluoro-2-propanone is prepared from acetone in low yield by direct fluorination|1,1,1,3,3,3-Hexafluoro-2-propanone is manufactured by perchlorination of acetone, followed by reaction with hydrogen fluoride and a chromium catalyst. Separation of the product from excess hydrogen fluoride requires the use of a hydrogen fluoride acceptor, such as activated sodium fluoride or acetic anhydride.|The rearrangement of hexafluoropropyleneoxide induced by Lewis acids is an attractive new route that avoids the highly toxic sym-dichlorotetrafluoro- and chloropentafluoroacetones.

Uses

Protecting and activating reagent in peptide chemistry; in synthesis of high performance fluoropolymers, pharmaceutical and agricultural chemicals; in 19F NMR. Solvent for polyamides, polyesters, polyacetals, polyols.


Intermediates

AS PRESENTLY AVAIL, ITS PURITY IS AT LEAST 99.5% & COMMONLY EXCEEDS 99.9%.|MINIMUM PURITY 95%.

All other basic organic chemical manufacturing|2-Propanone, 1,1,1,3,3,3-hexafluoro-: ACTIVE|...1,1,1,3,3,3-HEXAFLUOROPROPAN-2-ONE...WAS INTRODUCED IN 1967 BY ALLIED CHEM CORP AS NONSELECTIVE HERBICIDE UNDER CODE NUMBER 'GC-7887'... HEXAFLUOROACETONE IS SUGGESTED FOR CONTROL OF ANNUAL & PERENNIAL WEEDS & OF WOODY PLANTS ON UNCROPPED GROUND... /TRIHYDRATE/

POROUS POLYMERS WERE USED TO SEPARATE WATER-SOL ORG POLLUTANTS BY GAS CHROMATOGRAPHY. CHROMOSORB 104 EFFECTIVELY SEPARATED METHANOL, ACETALDEHYDE, HEXAFLUOROACETONE & ACETIC ACID.|TO DETECT AS LITTLE AS 0.1 PPM (F3C)2CO, AIR IS DRAWN THROUGH SHORT TUBE CONTAINING K2CO3. (F3C)2CO IS ABSORBED AS K SALT OF HEXAFLUOROACETONE HYDRATE. TUBE IS CONNECTED TO IR CELL & HEATED TO 150 °C TO FORM HCF3 (FLUOROFORM) & MEASURED BY ITS ABSORPTION AT 1150 CM.|DETERMINATION OF HEXAFLUOROACETONE IN AIR BY PLASMA CHROMATOGRAPHY WITH UPPER LIMIT OF DETECTION AT 8 PPB.

Fire Hazards -> Reactive - 2nd degree

Computed Properties

Molecular Weight:166.02
XLogP3:1.5
Hydrogen Bond Acceptor Count:7
Exact Mass:165.98533359
Monoisotopic Mass:165.98533359
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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