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Home > Encyclopedia > Perfluorotributylamine

Perfluorotributylamine

Perfluorotributylamine structure

Perfluorotributylamine 

structure
  • CAS No:

    311-89-7

  • Formula:

    C12F27N

  • Chemical Name:

    Perfluorotributylamine

  • Synonyms:

    1-Butanamine,1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-;Tributylamine,heptacosafluoro-;1-Butanamine,1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(nonafluorobutyl)-;1,1,2,2,3,3,4,4,4-Nonafluoro-N,N-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1-butanamine;FC 43;Tri(perfluorobutyl)amine;Heptacosafluorotributylamine;Fluorocarbon FC 43;Tris(nonafluorobutyl)amine;FC 47;Perfluorotri-n-butylamine;Fluorinert FC 43;Medifluor FC 47;Mediflor FC 43;Tris(perfluorobutyl)amine;Fluosol FC 43;Eftop EF-L 174;Oxyferol;PFTBA;Afluid E 18;Perfluorotributylamine;Fluorinert 43;NSC 3501;EFL 174S;Tri (n-butyl perfluoro);CT-solv 180;Flourinert FC 40;39289-23-1;69072-86-2;90803-72-8;93792-84-8;146175-90-8;178463-15-5;1201928-35-9

  • Categories:

    Organic Chemistry  >  Amides

Description

clear colourless liquid


Liquid


Perfluorotributylamine is an organofluorine compound that is tributylamine in which all the hydrogens have been replaced by fluorine atoms. It has a role as a member of greenhouse gas, a solvent and a blood substitute. It derives from a tributylamine.

Perfluorotributylamine Basic Attributes

671.09

671.09

1813883

206-223-1

3702Y1HQ6O

3501

DTXSID0027141

Liquid

29211990

Characteristics

3.2

19.45

Clear colorless liquid

1.884 g/cm3 @ Temp: 25 °C

-50 °C

178 °C

None

1.273

H2O: insoluble

2-8°C

1.3 mm Hg ( 25 °C)

23.3 (vs air)

6.00e-17 cm3/molecule*sec

Hygroscopic

60.4 kJ/mol

Safety Information

NONH for all modes of transport

2

36/37/38

26-36

YA1000000

Xi,T

Stable under normal temperatures and pressures.

P261-P305 + P351 + P338

H315-H319-H335

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.

Toxicity

LD50 Mouse iv 12 g/kg

Perfluorotributylamine's production and use as a heat-transfer fluid(1) and use as an oxygen carrying component in artificial blood(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+9(SRC), determined from a structure estimation method(2), indicates that perfluorotributylamine is expected to be immobile in soil(SRC). Volatilization of perfluorotributylamine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.5X10+4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, volatilization is expected to be attenuated by adsorption. Perfluorotributylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.552 mm Hg(4). Perfluorotributylamine is confirmed to be non-biodegradable according to the standard MITI test(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+9(SRC), determined from a structure estimation method(2), indicates that perfluorotributylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.5X10+4 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 2.6 hours and 10 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.1X10+4 years if adsorption is considered(5). As a class, fluorinated organic compounds are resistant to hydrolysis(6). According to a classification scheme(7), a BCF range of 3-34(8) suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Perfluorotributylamine is confirmed to be non-biodegradable according to the standard MITI test(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), perfluorotributylamine, which has a vapor pressure of 0.552 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. As a class, fluorinated organic compounds are resistant to photolysis(3).

As a class, fluorinated organic compounds are resistant to hydrolysis and photolysis(1).

BCF ranges of 3.3-3.8 and 19-34 were measured for perfluorotributylamine, using test chemical concns of 0.1 and 0.01 mg/l, respectively(1). According to a classification scheme(3), these BCF values suggest that bioconcentration in aquatic organisms is low to moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for perfluorotributylamine can be estimated to be 1.2X10+9(SRC). According to a classification scheme(2), this estimated Koc value suggests that perfluorotributylamine is expected to be immobile in soil.

The Henry's Law constant for perfluorotributylamine is estimated as 5.5X10+4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that perfluorotributylamine 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 2.6 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 10 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.1X10+4 years if adsorption is considered(3). Perfluorotributylamine's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC); however, this will be attenuated by adsorption. Perfluorotributylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.552 mm Hg(4).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 7 workers are potentially exposed to perfluorotributylamine in the US(1). Occupational exposure to perfluorotributylamine may occur through inhalation and dermal contact with this compound at workplaces where perfluorotributylamine is produced or used(SRC).

Drug Information

/EXPTL THER/ Perfluorotributylamine/Pluronic F68 Stem-Emulsion (FC43se), which is a blood substitute, has beneficial effects on endotoxin-induced disseminated imtramuscular coagulation ... /in the rat model/ as an anticoagulant and anti-inflammatory cytokine induced agent.|/EXPTL THER/ A perfluorocarbon emulsion, Fluosol-43, was used as a blood substitute for oxygen transport during isolation-perfusion of the dog liver at 37 and 43 degrees C. Preservation of hepatic functional integrity was assessed through analysis of perfusate constituents and animal survival after perfusion. Flow to the liver during perfusion was greater than 1 ml/min/g with one-third of total flow provided through the hepatic artery and two-thirds through the portal vein. Perfusion duration was 3 h. The pO2 gradient across the liver indicated that oxygen was consumed during perfusion at both temperatures. The expected rise in pCO2 and decrease in pH of the outflow perfusate is consistent with active aerobic metabolism. Perfusate chemistries lactate, pyruvate, glucose, urea, total alpha-amino acids, ketone bodies and SGPT demonstrated that hepatic functional integrity was maintained during perfusion. Significant differences (p less than 0.05) between temperatures occurred in the perfusate levels of lactate, pyruvate, L/P ratios, glucose and total alpha-amino acids. Animal survival after a 3-hour perfusion was 3/4 at 37 degrees C, and 2/5 at 43 degrees C. After perfusion, SGPT levels were significantly higher in dogs subjected to perfusion at 43 degrees C. The success of these experiments demonstrates that perfusion of the liver with Fluosol-43 was not in itself hepatotoxic, and that Fluosol-43 may allow perfusion of the liver at 43 degrees C with only mild toxicity. /oxypherol (FC-43)/|Perfluorochemicals have been shown to have a high affinity for oxygen and therefore, have potential use in circumstances in which conventional blood transfusions are not possible.|This study was undertaken to identify the combined effect of perfluorochemicals (Fluosol-43, 20 ml/kg) and chemotherapeutic agent (BCNU, LD10 dose; 13.3 mg/kg) in a rat brain-tumor model made by the intracerebral implantation of C6 rat glioma cells (1 X 10(5) cells/10 microliters). At 10 days after implantation, control animals had a macrotumor weighing about 100 mg with large part of central necrosis. The tumor-bearing rats for 10 days after implantation were randomly divided into 4 groups; a control group, a Fluosol-43 treatment group, a BCNU treatment group, and a Fluosol-43 plus BCNU treatment group. Control animals had mean survival time of 19.94 +/- 2.41 (S.D.) days, and mean survival time of Fluosol-43 treatment group was 19.47 +/- 1.36 days. BCNU treatment alone prolonged the mean survival time to 28.36 +/- 7.94 days (p less than 0.001). Fluosol-43 plus BCNU treatment group showed 36.00 +/- 10.15 days, which was significantly greater than that of BCNU treatment alone group (p less than 0.005). The long survivals lived over 50 days after implantation were 7 out of 27 rats in Fluosol-43 plus BCNU treatment group, in contrast to one out of 25 rats in BCNU treatment alone group. Perfluorochemicals (Fluosol-43) may have the synergistic effect on BCNU chemotherapy for brain tumors. /fluosol-43/|For more Therapeutic Uses (Complete) data for PERFLUOROTRIBUTYLAMINE (7 total), please visit the HSDB record page.

Since... /perfluoro chemical blood substitutes (PFC's) including oxypherol (perfluorotributylamine)/ have a profound influence on several important neutrophil functions, patients receiving PFC should be monitored closely for possible infectious complications.|Fluorocarbon emulsions that have recently been given to humans may produce a chronic stimulation of the reticuloendothelial system leading to alterations in production of immunoglobulins.|Treatment with perfluorochemicals induces morphologic alterations in monocytes and neutrophils and the phagocytic integrity of these cells is compromised.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

FC 43

Perfluorotributylamine Use and Manufacturing

Methods of Manufacturing

From tributylamine and hydrogen fluoride through electrolytic fluorination. The electrolysis product is washed with water, alkali washed, dried, and rectified to obtain a finished product.

Uses

1. Anti-corrosion isolation of instrumentation, transmission fluid. 2. Dielectric insulating liquid 3. Chemical reaction stabilizes thinner or special solvent, solvent. 4. Thermally conductive thermal coolant, which can be used in transformers, especially as small transformer oil for high-rise buildings. 5. Antioxidant lubricant. 6. Artificial blood of fluorocarbon emulsion. 7. Electronic components and devices


Functional fluids (closed systems)

FC-43, the Fluosol-43 (Oxypherol) fluorochemical emulsion of perfluorotributylamine in Pluronic F68.

Computer and electronic product manufacturing|1-Butanamine, 1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-: ACTIVE

PFAS (per- and polyfluoroalkyl substances) -> OECD Category

Computed Properties

Molecular Weight:671.09
XLogP3:9.9
Hydrogen Bond Acceptor Count:28
Rotatable Bond Count:9
Exact Mass:670.9599594
Monoisotopic Mass:670.9599594
Topological Polar Surface Area:3.2
Heavy Atom Count:40
Complexity:792
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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