Sulfuryl Fluoride

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Sulfuryl fluoride
	Template:Chembox image sbs cell
Names
	IUPAC name Sulfuryl fluoride
	Other names Sulfonyl fluoride; Sulfur dioxide difluoride; Sulphuryl fluoride; Sulfuryl difluoride
Identifiers
CAS Number	2699-79-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:39287 ;
ChemSpider	16647 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
PubChem CID	17607;
	InChI InChI=1S/F2O2S/c1-5(2,3)4 Key: OBTWBSRJZRCYQV-UHFFFAOYSA-N ; InChI=1/F2O2S/c1-5(2,3)4 Key: OBTWBSRJZRCYQV-UHFFFAOYAJ;
	SMILES FS(F)(=O)=O;
Properties
Chemical formula	SO2F2
Molar mass	102.06 g/mol
Hazards
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Template:Chembox E number Template:Chembox Appearance Template:Chembox Density Template:Chembox MeltingPt Template:Chembox BoilingPt Template:Chembox SolubilityInWater Template:Chembox Solubility Template:Chembox Structure Template:Chembox MainHazards Template:Chembox NFPA

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Sulfuryl fluoride (also spelled sulphuryl fluoride) is the inorganic compound with the formula SO₂F₂. This easily condensed gas has properties more similar to sulfur hexafluoride than sulfuryl chloride, being resistant to hydrolysis even up to 150 °C. So inert is this material that suspended molten "sodium metal retains its shiny metallic appearance."^[1]

Structure and preparation

The molecule is tetrahedral with C_2v symmetry. The S-O distance is 140.5 pm, S-F is 153.0 pm. As predicted by VSEPR, the O-S-O angle is more open than the F-S-F angle, 124° and 97°, respectively.^[1]

It is prepared by direct reaction of fluorine with sulfur dioxide:

SO₂ + F₂ → SO₂F₂

A laboratory-scale synthesis begins with the preparation of potassium fluorosulfite:^[2]

SO₂ + KF → KSO₂F

This salt is then chlorinated to give sulfuryl chloride fluoride:

KSO₂F + Cl₂ → SO₂ClF + KCl

Further heating (180 °C) of potassium fluorosulfite with the sulfuryl chloride fluoride gives the desired product:^[3]

SO₂ClF + KSO₂F → SO₂F₂ + KCl + SO₂

Heating metal fluorosulfonate salts also gives this molecule:^[1]

Ba(OSO₂F)₂ → BaSO₄ + SO₂F₂

Use as a fumigant

Use of SO
₂F
₂ as a fumigant has increased rapidly as it replaces methyl bromide, now being phased out because of harm to the ozone layer, and as an alternative to the risks of phosphine.^[4]

Originally developed by the Dow Chemical Company, sulfuryl fluoride is in widespread use as a structural fumigant insecticide to control drywood termites, particularly in warm-weather portions of the southwestern and southeastern United States and in Hawaii. Less commonly, it can also be used to control rodents, powderpost beetles, bark beetles, and bedbugs.

Sulfuryl fluoride is currently marketed by three distinct manufacturers, under four different brand names. Vikane (Dow) (EPA Reg. No. 62719- 4-ZA) has been commercially available since the early 1960s, with Zythor (marketed by competitor Ensystex of North Carolina) (EPA Reg. No. 81824- 1-AA) being more recently introduced gradually as its use is approved by individual states (in Florida circa 2004, but not in California until October 2006, for example). Dow recently has begun marketing sulfuryl fluoride as a post-harvest fumigant for dry fruits, nuts, and grains under the trade name ProFume (EPA Reg. No. 62719- 376-AA). [2] Most recently Drexel Chemical Company has registered Master Fume (EPA Reg. No. 19713-596-AA) for the structural market, competing against Vikane and Zythor.^[5]

During application, the building is enclosed in a tight tent and filled with the gas for a period of time, usually at least 16–18 hours, sometimes as long as 72 hours. The building must then be ventilated, generally for at least 6 hours, before occupants can return. Reentry to the home is allowed when the concentration level is at or below 5 ppm.^[6] Sulfuryl fluoride is colorless, odorless, and leaves no residue. During the fumigation process, a warning agent called Chloropicrin (similar to tear gas, but more toxic) is first released into the building to ensure that no occupants remain. Some pest control experts claim sulfuryl fluoride is the only effective treatment for drywood termites. (Heat is the only other approved method for whole structure treatment for termites in California.^[7]) Because it leaves no residue, sulfuryl fluoride provides no protection from future infestations, although heavy re-infestation can take several years since drywood termites have slower growing colonies than ground termites.

Safety considerations

Sulfuryl fluoride is toxic in humans and following inhalation may cause symptoms of fluoride poisoning. Symptoms may include weakness, nausea, vomiting, hypotension, metabolic acidosis, hypocalcemia, cardiac dysrhythmia, pulmonary edema, and death.^[8]^[9]^[10] Medical treatment may consist of giving calcium, correcting acidosis with sodium bicarbonate, and hemodialysis.^[8] They would have been advised to follow Nitschke^[11] as post treatment with phenobarbital was effective in rats, whereas post treatment to restore calcium was not effective.

Sulfuryl fluoride must be transported in a vehicle marked with "Inhalation Hazard 2" placards. Most U.S. states also require a license or certification for the individual applying the fumigant.

Environmental considerations

Based on the first high frequency, high precision, in situ atmospheric and archived air measurements of sulfuryl fluoride it was determined that sulfuryl fluoride has an atmospheric lifetime of 30–40 years,^[12] much longer than the 5 years earlier estimated.^[13]

Sulfuryl fluoride has been reported to be a greenhouse gas which is about 4000-5000 times more efficient in trapping infrared radiation (per kg) than carbon dioxide (per kg).^[12]^[14]^[15] It is important to note, however, that amounts of sulfuryl fluoride released into the atmosphere (about 2000 metric tons per yr^[12]) are far, far lower than the amounts of CO₂ released by hydrocarbon-burning vehicles, industry, and other processes (about 30 billion metric tons per year). The most important loss process of sulfuryl fluoride is dissolution of atmospheric sulfuryl fluoride in the ocean followed by hydrolysis.^[12]^[16]

References

↑ ^1.0 ^1.1 ^1.2 Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
↑ Seel, F. "Potassium Fluorosulfite" Inorganic Syntheses 1967, IX, pages 113-115. doi:10.1002/9780470132401.ch29.
↑ Seel, F. "Sulfuryl Chloride Fluoride and Sulfuryl Fluoride" Inorganic Syntheses 1967, IX, pages 111-113. doi:10.1002/9780470132401.ch28
↑ Bell, C. H. "Fumigation in the 21st century" "Crop Protection, 2000, 19, 563-569. ISSN 0261-2194. AN 2000:895590
↑ Output Reporting
↑ "SULFURYL FLUORIDE (Vikane®) RISK CHARACTERIZATION DOCUMENT" (PDF). State of California. Retrieved 16 July 2012.
↑ Termites Fact Sheet
↑ ^8.0 ^8.1 Schneir A, Clark RF, Kene M, Betten D (2008). "Systemic fluoride poisoning and death from inhalational exposure to sulfuryl fluoride". Clin Toxicol (Phila). 46 (9): 850–4. doi:10.1080/15563650801938662. PMID 18608259. Unknown parameter |month= ignored (help)
↑ Centers for Disease Control (CDC) (1987). "Fatalities resulting from sulfuryl fluoride exposure after home fumigation--Virginia". MMWR Morb Mortal Wkly Rep. 36 (36): 602–4, 609–11. PMID 3114607. Unknown parameter |month= ignored (help)
↑ Scheuerman EH (1986). "Suicide by exposure to sulfuryl fluoride". J Forensic Sci. 31 (3): 1154–8. PMID 3734735.
↑ Nitschke, K (1986). "Incapacitation and treatment of rats exposed to a lethal dose of sulfuryl fluoride". Fundamental and applied toxicology. 7 (4): 664–670. Unknown parameter |coauthors= ignored (help)
↑ ^12.0 ^12.1 ^12.2 ^12.3 Mühle, J., J. Huang, R.F. Weiss, R.G. Prinn, B.R. Miller, P.K. Salameh, C.M. Harth, P.J. Fraser, L.W. Porter, B.R. Greally, S. O'Doherty, and P.G. Simmonds, Sulfuryl Fluoride in the Global Atmosphere, Journal of Geophysical Research, 114, D05306, doi:10.1029/2008JD011162, 2009
↑ KEMI, SULFURYL FLUORIDE (PT8), Competent Authority Report, Document III-A7, Ecotoxicological Profile Including Environmental Fate and Behaviour, Swedish Chemicals Agency, Sweden, 2005.
↑ Papadimitriou, V.C., R.W. Portmann, D.W. Fahey, J. Mühle, R.F. Weiss, and J.B. Burkholder, Experimental and Theoretical Study of the Atmospheric Chemistry and Global Warming Potential of SO2F2, Journal of Physical Chemistry A, 112 (49), 12657-12666, doi:10.1021/jp806368u, 2008.
↑ Sulbaek Andersen, M.P., D.R. Blake, F.S. Rowland, M.D. Hurley, and T.J. Wallington, Atmospheric Chemistry of Sulfuryl Fluoride: Reaction with OH Radicals, Cl Atoms and O3, Atmospheric Lifetime, IR Spectrum, and Global Warming Potential, Environmental Science & Technology, doi:10.1021/es802439f, 2009.
↑ Cady, G.H., and S. Misra, Hydrolysis of Sulfuryl Fluoride, Inorganic Chemistry, 13 (4), 837-841, 1974. doi:10.1021/ic50134a016

External links

de:Sulfuryldifluorid fa:سولفوریل فلورید nl:Sulfurylfluoride fi:Sulfuryylifluoridi

[Holleman-1] 1.0 ^1.1 ^1.2 Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.

[2] Seel, F. "Potassium Fluorosulfite" Inorganic Syntheses 1967, IX, pages 113-115. doi:10.1002/9780470132401.ch29.

[3] Seel, F. "Sulfuryl Chloride Fluoride and Sulfuryl Fluoride" Inorganic Syntheses 1967, IX, pages 111-113. doi:10.1002/9780470132401.ch28

[4] Bell, C. H. "Fumigation in the 21st century" "Crop Protection, 2000, 19, 563-569. ISSN 0261-2194. AN 2000:895590

[5] Output Reporting

[6] "SULFURYL FLUORIDE (Vikane®) RISK CHARACTERIZATION DOCUMENT" (PDF). State of California. Retrieved 16 July 2012.

[7] Termites Fact Sheet

[Schneir-8] 8.0 ^8.1 Schneir A, Clark RF, Kene M, Betten D (2008). "Systemic fluoride poisoning and death from inhalational exposure to sulfuryl fluoride". Clin Toxicol (Phila). 46 (9): 850–4. doi:10.1080/15563650801938662. PMID 18608259. Unknown parameter |month= ignored (help)

[9] Centers for Disease Control (CDC) (1987). "Fatalities resulting from sulfuryl fluoride exposure after home fumigation--Virginia". MMWR Morb Mortal Wkly Rep. 36 (36): 602–4, 609–11. PMID 3114607. Unknown parameter |month= ignored (help)

[10] Scheuerman EH (1986). "Suicide by exposure to sulfuryl fluoride". J Forensic Sci. 31 (3): 1154–8. PMID 3734735.

[11] Nitschke, K (1986). "Incapacitation and treatment of rats exposed to a lethal dose of sulfuryl fluoride". Fundamental and applied toxicology. 7 (4): 664–670. Unknown parameter |coauthors= ignored (help)

[Muhleetal-12] 12.0 ^12.1 ^12.2 ^12.3 Mühle, J., J. Huang, R.F. Weiss, R.G. Prinn, B.R. Miller, P.K. Salameh, C.M. Harth, P.J. Fraser, L.W. Porter, B.R. Greally, S. O'Doherty, and P.G. Simmonds, Sulfuryl Fluoride in the Global Atmosphere, Journal of Geophysical Research, 114, D05306, doi:10.1029/2008JD011162, 2009

[13] KEMI, SULFURYL FLUORIDE (PT8), Competent Authority Report, Document III-A7, Ecotoxicological Profile Including Environmental Fate and Behaviour, Swedish Chemicals Agency, Sweden, 2005.

[14] Papadimitriou, V.C., R.W. Portmann, D.W. Fahey, J. Mühle, R.F. Weiss, and J.B. Burkholder, Experimental and Theoretical Study of the Atmospheric Chemistry and Global Warming Potential of SO2F2, Journal of Physical Chemistry A, 112 (49), 12657-12666, doi:10.1021/jp806368u, 2008.

[15] Sulbaek Andersen, M.P., D.R. Blake, F.S. Rowland, M.D. Hurley, and T.J. Wallington, Atmospheric Chemistry of Sulfuryl Fluoride: Reaction with OH Radicals, Cl Atoms and O3, Atmospheric Lifetime, IR Spectrum, and Global Warming Potential, Environmental Science & Technology, doi:10.1021/es802439f, 2009.

[16] Cady, G.H., and S. Misra, Hydrolysis of Sulfuryl Fluoride, Inorganic Chemistry, 13 (4), 837-841, 1974. doi:10.1021/ic50134a016

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