1,1,3,3,3-Pentafluoro-2-(trifluoromethyl)-1-propene

1.592 g/cu cm at 0 °C

1.6 g/l

1.592

1.5922 @ 0°C

Colorless gas

Gas at room temperature

7 °C

7 °C

44.6 °F

7 °C @760 [mm Hg]

-130 °C

-202 °F

-130 °C

6.3 (Air = 1)

6.3

1740 mm Hg at 25 °C

1740 mmHg

Colorless gas; [ICSC] Colorless gas that is a colorless liquid when stored under its own pressure; [SynQuest Laboratories MSDS]

COLOURLESS GAS.

Colorless, odorless gas at room temp. When heated to decomposition it emits toxic fumes of hydrogen fluoride.

Danger

H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]；H370 (100%): Causes damage to organs [Danger Specific target organ toxicity, single exposure]

P260, P264, P270, P271, P284, P304+P340, P308+P316, P316, P320, P321, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；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.

Heating polytetrafluoroethylene (PTFE) to approximated 425 degrees C releases this toxic gas as a thermal degradation product. The 3 minute LC50 value for rats, rabbits, and mice ranges from 61 to 183 ppm. Poisoned animals have pulmonary and renal hemorrhages. Surviving animals recovered fully and showed no long-term ill effects. [ACGIH] Teflon is the brand name for PTFE. Inhalation of perfluoroisobutylene in high concentrations can cause pneumonitis, pulmonary edema, and death. [ICSC] PFIB is one of the pulmonary agents that could be used as chemical weapons. It is 10 times more toxic than phosgene. [Weinstein, p. 134] Cough, chest pain, dyspnea, fever, and delayed pneumonitis and pulmonary edema have been reported in humans following acute inhalation exposure; [HSDB] Many military vehicles are lined with Teflon (R) and may release PFIB in a fire; [DOD] Extremely toxic by inhalation (pulmonary edema); Evaporating liquid may cause frostbite; [SynQuest Laboratories MSDS] See Polymer fume fever in Diseases.

Acute Tox. 1 (100%)；STOT SE 1 (100%)

Acute toxicity (Inhalation: Gases) - Category 1；Specific target organ toxicity - Single exposure - Category 1 (central nervous system, lung)；Specific target organ toxicity - Repeated exposure - Category 1 (central nervous system)

Acute toxicity (Inhalation: Gases) - Category 1；Specific target organ toxicity - Single exposure - Category 1 (respiratory system)；Specific target organ toxicity - Repeated exposure - Category 1 (respiratory system)

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

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

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

SRP: 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 quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Ventilation, local exhaust, or breathing protection

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

0.01 [ppm]

Ceiling Limit: 0.01 ppm

0.01 ppm as STEL

0.01 ppm [1989]

Perfluoroisobutene, a pyrolysis product of polyetrafluoroethene may cause pulmonary edema and death when inhaled. Oral N-acetylcysteine has shown protection against inhalation of perfluoroisobutene... . Protection against the lethal effects of inhaled perfluoroisobutene has been shown when N-acetylcysteine has been orally administered 4, 6 or 8 hr before gas exposure. Plasma levels of cysteine, glutathione and N-acetylcysteine were increased for up to 7 hr following oral administration of Nac. N-acetylcysteine was not detected in the bronchioalveolar lavage fluid following oral administration. Duration of protection in vivo has been related to the duration of increased thiol levels in the plasma.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1700(SRC), determined from a structure estimation method(2), indicates that perfluoroisobutylene is expected to have slight mobility in soil(SRC). Volatilization of perfluoroisobutylene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 34 atm-cu m/mole(SRC), using a fragment constant estimation method(2). However, volatilization from moist soil is expected to be attenuated by hydrolysis(SRC) because perfluoroisobutylene decomposes rapidly in water(3). Perfluoroisobutylene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1740 mm Hg at 25 °C(3). Biodegradation data for perfluoroisobutylene were not available(SRC, 2015).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,740 (SRC), determined from a structure estimation method(2), indicates that perfluoroisobutylene is expected to adsorb slightly to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 34 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.1 hours and 5.6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by hydrolysis(SRC) because perfluoroisobutylene decomposes rapidly in water(4). Perfluoroisobutylene is reported to decompose rapidly in water via hydrolysis to yield fluorophosgene, which in turn decomposes to yield carbon dioxide and hydrogen fluoride(4). According to a classification scheme(5), an estimated BCF of 46(SRC), from an estimated log Kow of 3.03(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, due to hydrolysis, bioconcentration is not expected to be an important fate process(SRC). Biodegradation data for perfluoroisobutylene were not available(SRC, 2015).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), perfluoroisobutylene, which has a vapor pressure of 1740 mm Hg at 25 °C(2), is expected to exist solely in the gas phase in the ambient atmosphere. Gas-phase perfluoroisobutylene 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 5.7 days(SRC), calculated from its rate constant of 2.8X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Gas-phase perfluoroisobutylene is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 41 days(SRC), calculated from its rate constant of 2.8X10-19 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Based on analogy to a measured nitrate radical rate constant of 3.0X10-15 cu cm/molecule-sec at 25 °C for perfluoropropylene(4), the atmospheric half-life of 2-(diisopropylamino)ethyl methacrylate is estimated to be about 10.7 days(SRC). Gas-phase perfluoroisobutylene is susceptible to hydrolysis in air(5).

IDENTIFICATION AND USE: Perfluoroisobutylene is a colorless gas which is soluble in water. It may be used as a potential chemical warfare agent; etching material for semiconductor fabrication and synthesis of polymeric materials. HUMAN EXPOSURE AND TOXICITY: A harmful concentration of this gas in the air will be reached very quickly on loss of containment. The substance can be absorbed into the body by inhalation. The substance irritates the respiratory tract. Inhalation exposure may cause severe symptoms of pulmonary edema with wheezing, difficulty in breathing, coughing up sputum and bluish discoloration of the skin. Coughing and chest pain may occur initially. However, severe symptoms of pulmonary edema may be delayed for several hours and then become rapidly worse. Overexposure may cause death. This chemical is a human skin, eye, and mucous membrane irritant. Human acute exposures causes marked irritation of conjunctivae, throat, and lungs. Occupational exposure to perfluoroisobutylene is limited but may occur through inhalation at workplaces where it or the polymer, polytetrafluoroethylene (PTFE, Teflon) is produced or used. ANIMAL STUDIES: In an acute study, rats were exposed to perfluoroisobutylene at 0.25 ppm for 4 hours. During exposure, some animals showed hyperpnea, while three of six animals had dyspnea for 3 hours postexposure. Hyperemia, sneezing, dyspnea, and mild responsiveness were also documented in some animals. Rats exposed by inhalation to this chemicalat either 0.24 or 0.49 ppm for 4 hours showed changes in conditioned reflexes, accompanied by an increase in the activity of glutamicoxaloacetic and glutamicpyruvic transaminases in the blood serum. Edema was seen in the lungs. The histopathology of rat lung has been studied after an acute exposure to perfluoroisobutylene at a concentration of 78 ppm for 1.5 minutes. Within 5 minutes of exposure changes to bronchioles and peribronchial alveoli were observed which took the form of alterations to

Using a structure estimation method based on molecular connectivity indices(1), the Koc of perfluoroisobutylene can be estimated to be 1,700(SRC). According to a classification scheme(2), this estimated Koc value suggests that perfluoroisobutylene is expected to have slight mobility in soil.

/SIGNS AND SYMPTOMS/ A harmful concentration of this gas in the air will be reached very quickly on loss of containment. The substance can be absorbed into the body by inhalation. The substance irritates the respiratory tract. Inhalation of this gas may cause lung edema. Exposure may result in death. The effects may be delayed.

/SIGNS AND SYMPTOMS/ This substance is formed as a by-product in tetrafluoroethylene production and during thermal degradation of polytetrafluoroethylene (PTFE/Teflon(R)) at approximateley 425 °C. The symptoms of lung edema often do not become manifest until a few hours have passed and they are aggravated by physical effort. Rest and medical observation are therefore essential. ...

/SIGNS AND SYMPTOMS/ Perfluoroisobutylene is extremely toxic /by/ inhalation /which/ is the most likely route of human exposure. Inhalation exposure may cause severe symptoms of pulmonary edema with wheezing, difficulty in breathing, coughing up sputum and bluish discoloration of the skin. Coughing and chest pain may occur initially. However, severe symptoms of pulmonary edema may be delayed for several hours and then become rapidly worse. Over-exposure may cause death.

/CASE REPORTS/ /Investigators/ monitored 5 patients (2 men and 3 women) accidentally exposed to PFIB at work. Two were chemical plant operators and the other three were chemical engineer technologists involved in laboratory work. All but one [female] patient reported that the contact with PFIB lasted less than one minute during which time 2 to 5 breaths were taken. Immediately after exposure, all patients developed cough, difficulty breathing, and deep chest pains. Approximately 6 to 8 hours after exposure, these symptoms increased in severity. No ocular or upper respiratory irritation was noted. All patients ran fevers that lasted between 2 and 25 days, and all developed pulmonary edema. The duration of the in-patient stay of the three patients was 27 13, 17, and 23 days. They were discharged as healthy, and follow-up checkups over 2 years revealed no complications in these patients. One [male] patient remained hospitalized for over 2 months due to exudative pleuritis. Another [female] patient died two days after exposure; postmortem examination confirmed toxic fluid pneumonia and lung edema, hemorrhage into the left adrenal and full bloodiness of internal organs. One of the exposed workers in /this/ study was 15-16 weeks pregnant at the time of exposure. The pregnancy ended in a normal, term delivery, the child was reportedly healthy.

For more Human Toxicity Excerpts (Complete) data for PERFLUOROISOBUTYLENE (7 total), please visit the HSDB record page.

Perfluoroisobutylene's production and use as a synthetic intermediate for the production of polymeric materials(1) and use in the etching process for seimiconductors(2) may result in its release to the environment through various waste streams(SRC). Perfluoroisobutylene is generated during the thermal decomposition of polytetrafluoroethylene(4,5). Perfluoroisobutylene smoke is given off when Teflon burns at temperatures above 400 °C, such as in a vehicle fire(5). Perfluoroisobutylene is also produced by the thermal decomposition of the fluorinated primary fluid in the condensation reflow soldering process(6).

An estimated BCF of 46 was calculated in fish for perfluoroisobutylene(SRC), using an estimated log Kow of 3.03(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, perfluoroisobutylene decomposes rapidly in water via hydrolysis(3); therefore, bioconcentration is not expected to be an important fate process(SRC).

The Henry's Law constant for perfluoroisobutylene is estimated as 34 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that perfluoroisobutylene is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4.1 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5.6 days(SRC). The Henry's Law constant of perfluoroisobutylene indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from water surfaces and moist soil is expected to be attenuated by hydrolysis(SRC) because perfluoroisobutylene decomposes rapidly in water(3). Perfluoroisobutylene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1740 mm Hg at 25 °C(3).

/LABORATORY ANIMALS: Acute Exposure/ The aim of this study was to investigate in rats (1) the respiratory injury caused by nose-only exposure to perfluoroisobutene (PFIB), and (2) the therapeutic efficacy of a treatment at 4 and/or 8 h after exposure consisting of the natural surfactant Curosurf and/or the anti-inflammatory drug N-acetylcysteine (NAC). ...The following parameters were examined: respiratory frequency (RF), lung compliance (Cdyn), airway resistance (Raw), lung wet weight (LWW), airway histopathology; and in bronchoalveolar lavage (BAL) fluid, total protein, total phospholipid, cell count and differentiation, and changes in the surface tension of the BAL fluid. The mean (+/- SEM) surface tension of BAL fluid derived from PFIB-exposed (C . t = 1100-1200 mg/min/cu m, approximately 1LCt50; t = 20 min) animals at 24 hr following exposure (11 +/- 3 mN/m) was higher than that of unexposed rats (0.8 +/- 0.4 mN/m), reflecting damage to the surfactant system and justifying treatment with exogenous surfactant. Curosurf treatment (62.5 mg/kg it) decreased pulmonary edema caused by PFIB, reflected by a decreased LWW, and decreased the amount of protein in BAL fluid. NAC treatment (1000 mmol/kg ip) inhibited the interstitial pneumonia reflected by a decreased percentage of neutrophils in the alveolar space. It was concluded that a combined treatment of Curosurf + NAC improved respiration, that is, RF and Cdyn, whereby Curosurf predominantly decreased pulmonary edema and NAC predominantly reduced the inflammatory process. A combined treatment may therefore be considered a promising therapeutic approach in early-stage acute respiratory distress caused by PFIB, although the treatment regimes need further investigation.

/LABORATORY ANIMALS: Acute Exposure/ In an acute study, rats were exposed at 0.25 ppm PFIB for 4 hours. During exposure, some animals showed hyperpnea, while three of six animals had dyspnea for 3 hours postexposure. Hyperemia, sneezing, dyspnea, and mild responsiveness were also documented in some animals.

/LABORATORY ANIMALS: Acute Exposure/ Rats exposed by inhalation at either 0.24 or 0.49 ppm PFIB for 4 hours showed changes in conditioned reflexes, accompanied by an increase in the activity of glutamicoxaloacetic and glutamicpyruvic transaminases in the blood serum. Edema was seen in the lungs. Little or no changes were detected among rats exposed at 0.12 ppm for periods of 4 hours.

/LABORATORY ANIMALS: Acute Exposure/ The histopathology of rat lung has been studied after an acute exposure to perfluoroisobutylene (PFIB) at a concentration of 638 mg/cu m (78 ppm.) for 1.5 min giving a Ct = 957 mg min/cu m for the first 24 hr following exposure. Within 5 min of exposure changes to the bronchioles and peribronchial alveoli were observed which took the form of alterations to cilial structure, increased pinocytosis and electron lucency, with occasional vesicle formation of type I alveolar epithelial cells. Intercellular leakage with minimal fluid accumulation in the alveolar spaces was also seen. The very rapid action of PFIB strongly suggests a direct action by the compound. There then followed the gradual development of pulmonary edema which was visible histologically 2-3 hr post exposure with deaths occurring from 7 hr onwards. Animals sacrificed at 24 hr post exposure showed evidence of widespread pulmonary edema and alveolar interstitial infiltration by lympho-mononuclear cells and macrophages.

For more Non-Human Toxicity Excerpts (Complete) data for PERFLUOROISOBUTYLENE (15 total), please visit the HSDB record page.

Chemistry of PFIB /was studied/ by using electron paramagnetic resonance spin-trapping techniques and concluded that this highly electrophilic chemical likely undergoes electron transfer that leads to several highly reactive intermediates. PFIB is reactive towards nucleophilic reagents to yield substitution and addition radical byproducts. PFIB reacts with almost all known nucleophiles.

A decomposition product of Teflon (R) when heated to about 425 degrees C; [ICSC] Used for etching in semiconductor fabrication and to make polymeric materials; [HSDB]

Semiconductor Manufacturing [Category: Industry]

Etching for semiconductor fabrication.

Synthesis of polymeric materials

Potential chemical warfare agent

Synthesis: hydrogen fluoride and polytetrafluoroethylene (PTFE)

Fluoroolefins are produced by dehalogenation of chlorofluoro-, bromofluoro-, or iodofluoroalkanes with zinc and alcohol, by dehydrohalogenation of hydrogen-containing haloalkanes with alcoholic alkali, or by heating. Other common methods include addition of hydrogen halides to alkynes, decarboxylation of fluorocarboxylic acid salts, and pyrolysis of fluorohydrocarbons. /Fluoroolefins/