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{{Chembox |
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{{DISPLAYTITLE:''n''-Propyl bromide}} |
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| verifiedrevid = 302747260 |
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| verifiedrevid = 400503207 |
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| Name = ''n''-Propyl bromide |
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| Name = 1-Bromopropane |
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| ImageFile1 = N-propylBromide-2D-skeletal.png |
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| ImageFile = 1-broompropaan.png |
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| ImageSize1 = 150px |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageName1 = |
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| ImageSize = 150 |
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| ImageFile = N-propylBromide.png |
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| ImageName = Skeletal formula of n-propyl bromide |
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| ImageSize =200px |
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| ImageFile1 = N-propylBromide.png |
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| ImageName = |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| IUPACName = 1-bromopropane |
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| ImageSize1 = 120 |
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| OtherNames = bromomethylethane, 1-propyl bromide, 1-bromopropane, nPB |
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| ImageName1 = Spacefill model of 1-Bromopropane |
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| Section1 = {{Chembox Identifiers |
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| PIN = 1-Bromopropane<ref>{{Cite web|title=1-bromopropane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7840&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=15 June 2012|location=USA|date=27 March 2005|at=Identification}}</ref> |
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| SMILES = CCCBr |
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| OtherNames = {{Unbulleted list|Bromopropane, 1-propyl bromide, 1-bromopropane, ''n''-propyl bromide |
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| CASNo_Ref = {{cascite}} |
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|Section1={{Chembox Identifiers |
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| Abbreviations = ''n''-PB{{Citation needed| date = June 2012 |
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}} |
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| CASNo = 106-94-5 |
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| CASNo = 106-94-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = TX4110000 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = Y9746DNE68 |
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| PubChem = 7840 |
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| ChemSpiderID = 7552 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| EINECS = 203-445-0 |
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| UNNumber = 2344 |
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| MeSHName = 1-bromopropane |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 47105 |
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| ChEMBL = 1230095 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| RTECS = TX4110000 |
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| Beilstein = 505936 |
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| SMILES = CCCBr |
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| StdInChI = 1S/C3H7Br/c1-2-3-4/h2-3H2,1H3 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = CYNYIHKIEHGYOZ-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=3 | H=7 | Br=1 |
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| Formula = C<sub>3</sub>H<sub>7</sub>Br |
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| Appearance = Colorless liquid |
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| MolarMass = 122.99 |
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| Density = 1.354 g mL<sup>−1</sup> |
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| Appearance = Colorless liquid |
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| Density = 1.353 |
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| MeltingPtK = 162.7 |
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| BoilingPtK = 343.4 to 344.4 |
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| Solubility = 0.25 g/100 mL at 20 °C |
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| Solubility = 2.5 g L<sup>−1</sup> (at 20 °C) |
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| Solubility1 = fully ] |
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| Solvent1 = ethanol |
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| Solvent1 = ethanol |
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| Solubility1 = Miscible |
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| Solubility2 = fully ] |
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| Solvent2 = diethyl ether |
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| Solvent2 = diethyl ether |
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| Solubility2 = Miscible |
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| RefractIndex = 1.43414 |
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| MeltingPtC = -109.9 |
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| LogP = 2.319 |
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| VaporPressure = 19.5 kPa (at 20 °C) |
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| BoilingPtC = 71.0 |
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| HenryConstant = 1.4 μmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| pKa = |
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| RefractIndex = 1.43414 |
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| Viscosity = 6.509 c] at 0 °C<br/>5.241 c] at 20 °C |
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| Viscosity = 5.241 mPa s (at 20 °C) |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −125.8 to −123.0 kJ mol<sup>−1</sup> |
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| MainHazards = |
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| DeltaHc = −2.0580 to −2.0552 MJ mol<sup>−1</sup> |
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| FlashPt = None |
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| HeatCapacity = 134.6 J K<sup>−1</sup> mol<sup>−1</sup> |
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| NFPA-H = 2 |
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| NFPA-F = 0 |
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|Section4={{Chembox Hazards |
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| NFPA-R = 0 |
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| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS health hazard}} |
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| NFPA-O = |
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| GHSSignalWord = '''DANGER''' |
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| RPhrases = {{R11}} {{R60}} {{R63}} {{R36/37/38}} {{R48/20}} {{R67}} |
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| HPhrases = {{H-phrases|225|315|319|335|336|360|373}} |
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| SPhrases = {{S53}} {{S45}} |
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| PPhrases = {{P-phrases|201|210|261|305+351+338|308+313}} |
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| NFPA-H = 2 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| FlashPtC = 22 |
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| AutoignitionPtC = 490 |
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| ExploLimits = 4.6–?% |
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| LD50 = 2.950 mg kg<sup>−1</sup> <small>(intraperitoneal, rat)</small> |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = alkanes |
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| OtherFunction = {{Unbulleted list|]|]|]|]|]}} |
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| Section8 = {{Chembox Related |
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| Function = ]s |
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| OtherFunctn = ]<br>]<br>] }} |
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'''1-Bromopropane''' ('''''n''-propylbromide''' or '''nPB''') is a ] with the chemical formula CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br. It is a colorless liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century due to the phasing out of ] and ] such as ] under the ]. |
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'''''n''-Propyl bromide''' (also 1-bromopropane or 1-propyl bromide) is a ], ] ]. It has the chemical formula C<sub>3</sub>H<sub>7</sub>Br. It is an organic solvent used for the cleaning of metal surfaces, removal of soldering residues from electronic circuit boards, and as an adhesive solvent. It has a characteristic hydrocarbon odor. |
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== Preparation == |
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==Use as a degreasing agent== |
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Industrial routes to 1-bromopropane involve free-radical additions to the corresponding alkenes. In this way, the ] is obtained.<ref name=KO>David Ioffe, Arieh Kampf "Bromine, Organic Compounds" in Kirk-Othmer Encyclopedia of Chemical Technology 2002 by John Wiley & Sons. {{doi| 10.1002/0471238961.0218151325150606.a01}}.</ref> Alternatively, ] may be substitutively brominated.<ref>{{Ullmann|doi= 10.1002/14356007.a22_157.pub3|title=Propanal|year=2018|last1=Hensel|first1=A.|isbn=978-3527306732|p=5}}</ref> The latter reaction is also viable laboratory synthesis. |
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{{Inappropriate tone|section|date=December 2010}} |
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In the early 1990s, it was discovered that n-propyl bromide had been wrongly classified as a flammable solvent in reference books of the United Kingdom. In the USA, it has been proven to not be a flammable solvent as tested under the standard tests for flammability from the American Society for Testing and Materials (ASTM). Since that time, the use of n-propyl bromide (NPB) has flourished. In most of the modern world, NPB has seen increased use as a solvent for vapor degreasing of metals in industrial processes, defluxing of electronic circuit cards to remove flux, ionics, and particulates, also used as a diluent in the manufacturing of medicinal tablets, an extraction agent for the purification of herbs and natural plant extracts, and in some countries NPB is used in adhesive formulations and as a solvent in aerosol formulations. |
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One laboratory technique for substitutive bromination treats ] with a mixture of ] and ]s: |
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In practically all of the uses for NPB the solvent replaces the use of dangerous chlorinated solvents such as trichloroethylene (TCE), perchloroethylene (PCE), Dichloromethane (DCM or methylene chloride), and trans, dichloroethylene (Trans DCE). TCE, PCE, and DCM are rated as "Hazardous Air Pollutants" or HAPs in the United States and many other countries. HAPs have been identified by the US Government as Cancer-Causing products in most instances and therefore are under tighter environmental and personal exposure limits. '''N-propyl bromide is not a HAP''', so many companies are turning to NPB as the best alternative in order to achieve the final goal of cleaning parts or extracting herbs and so forth. |
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:CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH + HBr → CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br + H<sub>2</sub>O |
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Alternate synthetic routes include treating propanol with ]<ref>{{OrgSynth | title = Alkyl and alkylene bromides | author = Oliver Kamm and C. S. Marvel | collvol = 1 | collvolpages = 25 | year = 1941 | url=http://www.orgsyn.org/Content/pdfs/procedures/CV1P0025.pdf}}</ref> or via a ] with ].<ref>{{cite book|last1=Adams|first1=Rodger|title=Organic Reactions Volume IX|date=1957|publisher=John Wiley and Sons, Inc.|location=New York|isbn=9780471007265|page=356|url=https://books.google.com/books?id=8epyngEACAAJ&q=9780471007265|accessdate=3 September 2014}}</ref> |
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==Applications== |
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Competition to n-propyl bromide (NPB) is traced back to the manufacturers of chlorinated solvents as well as high-cost "fluorinated solvents" that tend to be promoted as alternatives to cleaning with chlorinated solvents. The fluorinated solvent options are generally safer to use in the manufacturing processes, however they are much less effective. So much so, that they are typically blended with a stronger solvent, such as the flammable trans, dichloroethylene, in order to increase the solubility of various contaminants in the solvent blend. |
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Like many other liquid halocarbons, 1-bromopropane finds use as a liquid or gaseous ]. It is a solvent for ]s in aerosol glues that glue foam cushions together.<ref name="NYT033013"/> It is a solvent in ] production, in the aviation industry for maintenance, and in synthetic fiber production.<ref name=Hazard>{{cite web |url = https://www.cdc.gov/niosh/docs/2013-150/pdfs/2013-150.pdf |title = Hazard Alert: 1-Bromopropane |publisher = National Institute for Occupational Safety and Health |accessdate = 17 January 2015 |date = July 2013 |work = DHHS (NIOSH) Publication Number 2013-150}}</ref> It is a solvent for ] plastics, optics and on metal surfaces, to remove soldering residues from electronic circuit boards.<ref name=Trout>{{cite web |url = http://blogs.cdc.gov/niosh-science-blog/2013/08/01/1bp-2/ |title = 1-Bromopropane |first1 = Doug |last1 = Trout |first2 = Naomi |last2 = Hudson |first3 = Scott |last3 = Dotson |first4 = Kevin |last4 = Hanley |date = 1 August 2013 |accessdate = 16 January 2015 |publisher = National Institute for Occupational Safety and Health}}</ref> It is an aggressive solvent with a ] of 129 which is similar to ].<ref>{{Cite book|last1=Kanegsberg|first1=Barbara|url=https://books.google.com/books?id=lPPLBQAAQBAJ&pg=PA72|title=Handbook for Critical Cleaning|last2=Kanegsberg|first2=Edward|date=2000-12-26|publisher=CRC Press|isbn=978-1-4200-3982-5|language=en}}</ref> |
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Its increasing use in the 21st century resulted from the need for a substitute for ]s and ] as a ],<ref name=CDC /> however its use in dry cleaning has been steadily declining and by 2020, its use for dry cleaning is nearly obsolete<ref>{{Cite journal|last1=Smith|first1=Carr J|last2=Perfetti|first2=Thomas A|last3=Morford|first3=Richard G|date=2020-01-01|title=Use of 1-bromopropane (N-propyl bromide) in dry cleaning is rare and rapidly declining toward obsolescence|journal=Toxicology Research and Application|language=en|volume=4|pages=2397847320966961|doi=10.1177/2397847320966961|issn=2397-8473|doi-access=|s2cid=228978817 }}</ref> while perchloroethylene remained the most common solvent in dry cleaning as of 2024. |
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The flammable characteristics of n-propyl bromide are contained to a narrow concentration in air between approximately 4% and 7% by volume. It is unusual for NPB to ever catch fire because the solvent is "self-extinguishing". Self-extinguishing refers to a chemical property where a solvent that has caught fire will overcome itself and consume or inhibit the available oxygen that is supporting the flame. This is the case with NPB. The vapor above the solvent can be lit to catch fire, however within a few moments the vapor loses the fuel and the fire will snuff itself out. This has been shown in several videos produced by Enviro Tech International Inc where the same test is conducted with other solvents and they all continue to burn, yet when a flame hovers over a solution of NPB, the bromine in the NPB apparently suffocates the oxygen from the vapor over the mixture and the flame disappears. |
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==Regulation== |
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The atmospheric properties of n-propyl bromide are short-lived and its a hydrocarbon, so by default NPB has been classified as a Volatile Organic Compound by the US Environmental Protection Agency. Recent studies by Whitten and Yarwood published in the ''Journal of the Air & Waste Management Association'' state that NPB is actually a VOC inhibitor, of sorts.<ref>Whitten and Yarwood, ''Journal of the Air & Waste Management Association'', Vol 58, July 2008, pp 891-901</ref> The details of this argument are left to the reader to pursue, but these peer-reviewed and published results are not the first case to show that NPB should be delisted as a VOC. ''The US EPA has not moved forward on the idea of delisting NPB as a VOC.'' |
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In the European Union, 1-bromopropane has been classified as reproductive toxicant per ], which makes it a "substance of very high concern".<ref name=EU>{{cite web|title=AGREEMENT OF THE MEMBER STATE COMMITTEE ON THE IDENTIFICATION OF 1-BROMOPROPANE AS A SUBSTANCE OF VERY HIGH CONCERN According to Articles 57 and 59 of Regulation (EC) 1907/20061|url=http://echa.europa.eu/documents/10162/7183371/agreement_1-bromopropane_en.pdf|publisher=European Union|accessdate=6 August 2014|date=29 November 2012}}</ref> |
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As of January 5, 2022, 1-bromopropane has been added to the United States Clean Air Act list of Hazardous Air Pollutants (HAP).<ref>87 FR 396, https://www.govinfo.gov/content/pkg/FR-2022-01-05/pdf/2021-28315.pdf</ref> |
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The application of NPB should probably be confined to industrial uses where the users will be properly outfitted with safety glasses, gloves, and in some cases, half-face respirators, at their leisure. All chemicals, and solvents, should be handled with the utmost care. The use of NPB is no different in that regard. |
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Since 2007, it has been approved for use under the U.S. EPA's Significant New Alternatives Policy (SNAP) as a suitable replacement for ozone depleting chemicals.<ref name=FR53007>{{cite web|title=Protection of Stratospheric Ozone: Listing of Substitutes for Ozone- Depleting Substances-n-Propyl Bromide in Solvent Cleaning|url=http://www.epa.gov/fedrgstr/EPA-AIR/2007/May/Day-30/a9707.pdf|work=Federal Register|publisher=U.S. Environmental Protection Agency|accessdate=March 31, 2013|date=May 30, 2007|quote=This final rule lists n-propyl bromide (nPB) as an acceptable substitute when used as a solvent in industrial equipment for metals cleaning, electronics cleaning, or precision cleaning. General metals, precision, and electronics cleaning includes cleaning with industrial cleaning equipment such as vapor degreasers, in-line cleaning systems, or automated equipment used for cleaning below the boiling point.}}</ref> In 2013, the U.S. EPA announced that, based on a work plan developed under the ], it would begin a full risk assessment of 1-Bromopropane.<ref>{{cite web|last=United States Environmental Protection Agency|title=List of Chemicals for Assessment|url=http://www.epa.gov/oppt/existingchemicals/pubs/assessment_chemicals_list.html|accessdate=23 April 2013|archive-url=https://web.archive.org/web/20131018010457/http://www.epa.gov/oppt/existingchemicals/pubs/assessment_chemicals_list.html|archive-date=2013-10-18|url-status=dead}}</ref> In December 2022, the U.S. EPA released a revised risk determination from the August 2020 risk evaluation, used to form a proposed risk management rule in July 2024.<ref>{{cite web|last=United States Environmental Protection Agency|title=Risk Evaluation for 1-Bromopropane (1-BP)|url=https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-evaluation-1-bromopropane-1-bp|accessdate=28 August 2024|archive-url=https://web.archive.org/web/20240709191050/https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-evaluation-1-bromopropane-1-bp|archive-date=2024-07-09|url-status=live}}</ref><ref>{{cite web|last=United States Environmental Protection Agency|title=Risk Management for 1-Bromopropane (1-BP)|url=https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-1-bromopropane-1-bp|accessdate=28 August 2024|archive-url=https://web.archive.org/web/20240815211415/https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-1-bromopropane-1-bp|archive-date=2024-08-15|url-status=live}}</ref> |
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==References== |
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{{Reflist}} |
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*EPA’s Proposed Regulation of n-Propyl Bromide |
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*USEPA SNAP Approval of n propyl bromide |
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The North Carolina Department of Labor's Occupational Safety and Health Division issued a Hazard Alert in 6/2014, as it "is not regulated to protect workers, consumers or the environment".<ref name=NC>{{cite web|author1=North Carolina Department of Labor|title=Hazard Alert|url=http://www.nclabor.com/osha/etta/hazard_alerts/1-Bromopropane.pdf|publisher=State of North Carolina|accessdate=6 August 2014|date=June 2014}}</ref> |
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{{DEFAULTSORT:Propyl Bromide, N-}} |
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==Safety== |
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In 2003, the ] (ACGIH) set the time-weighted average threshold limit value for an 8-hour exposure at 10 parts per million (ppm). In 2014, the ACGIH adopted a lower threshold limit value of 0.1 ppm as an 8-hour time-weighted average. The ] set the permissible exposure limit at 5 ppm in 2010. Though symptoms of overexposure can begin within 2 days of exposure, typically long-term exposure is more harmful.<ref name=Trout/> |
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In 2008, the U.S. CDC recommended that use of 1-bromopropane as a replacement for perchloroethylene may require adjustment and modification of equipment, improved ventilation, and use of ].<ref name=CDC /> |
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In 2013, a peer-review panel convened by the U.S. ] unanimously recommended that 1-bromopropane, be classified as reasonably anticipated ]s.<ref name=ntp>{{cite web|url=http://ntp.niehs.nih.gov/ntp/about_ntp/monopeerrvw/2013/march/draftroc1bpmonograph_508.pdf|publisher=National Toxicology Program|accessdate=6 August 2014|date=21 March 2013|title=Report on Carcinogens Monograph on 1-Bromopropane}}</ref> |
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Extended occupational exposure to 1-bromopropane in higher concentrations than recommended has resulted in significant injury to workers in the United States.<ref name=HSDB>{{cite web|title=1-BROMOPROPANE: Human Health Effects|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+106-94-5|publisher=Hazardous Substances Data Bank|accessdate=March 31, 2013}}</ref> Its use as a solvent in aerosol glues used to glue foam cushions has been especially controversial.<ref name="NYT033013"/> Reported symptoms of overexposure affect the nervous system and include confusion, ], dizziness, ]s, and ], unusual fatigue and headaches, development of ]s, visual disturbances (difficulty focusing), and muscle twitching. Symptoms may persist over one year.<ref name=CDC>{{cite web|title=Neurologic Illness Associated with Occupational Exposure to the Solvent 1-Bromopropane --- New Jersey and Pennsylvania, 2007--2008|url=https://www.cdc.gov/mmwr/preview/mmwrhtml/mm5748a2.htm|publisher=Centers for Disease Control|accessdate=March 31, 2013|date=December 5, 2008}}</ref> Other symptoms include irritation of ], ]s, upper respiratory tract, and skin, as well as transient loss of consciousness.<ref name=Trout/> Loss of feeling in the feet, an example of paresthesia, is colloquially called "dead foot" by workers who suffer from it.<ref name=NYT033013 /> Of nationwide "more than 140 cushion workers nationwide, mostly from plants in Utah, Mississippi and North Carolina, that had been exposed to dangerous levels of the chemical, many of them sickened and unable to walk".<ref name=NYT033013>{{cite news|title=As OSHA Emphasizes Safety, Long-Term Health Risks Fester|url=https://www.nytimes.com/2013/03/31/us/osha-emphasizes-safety-health-risks-fester.html|accessdate=March 31, 2013|newspaper=The New York Times|date=March 30, 2013|author=Ian Urbina}}</ref> One worker's long-term exposure resulting in neurological damage was covered in the NY Times.<ref name=NYT033013/> Air sampling for the level of 1-bromopropane and monitoring workers' urine for metabolites are both effective at measuring workers' exposure.<ref name=Trout/> |
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Occupational exposure to 1-bromopropane typically occurs through breathing or skin contact; it is easily absorbed into the blood via the skin. Replacing 1-bromopropane with water or acetone-based adhesives is the preferred NIOSH option for controlling occupational exposure, but other options include ]s like isolation and ventilation, ]s, and PPE that includes respiratory and skin protection.<ref name=Trout/> 1-Bromopropane can penetrate most gloves, but not those made of ] or laminates.<ref name=Hazard/> |
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===Animal studies=== |
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Animal studies of 1-bromopropane have showed that it is a carcinogen in those models.<ref name=Trout/> Rodents exposed to 1-bromopropane developed ], ], and ] at higher rates.<ref name=Hazard/> |
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==Environmental impact== |
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=== Stratospheric ozone layer damage === |
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Although 1-bromopropane is naturally produced,{{Citation needed|date=March 2021}} it is one of the ] that depletes ozone. Because 1-bromopropane is so short-lived, its ] (ODP) is dependent on the ] where it is released.<ref name=":0">{{Cite web|date=2007|title=Q and A 2007 Final and Proposed Regulations for n Propyl Bromide (nPB)|url=https://www.epa.gov/sites/production/files/2014-11/documents/qandacln5-1-07_0.pdf|publisher=US EPA}}</ref><ref>{{Cite journal|last1=Wuebbles|first1=Donald J.|last2=Patten|first2=Kenneth O.|last3=Johnson|first3=Matthew T.|last4=Kotamarthi|first4=Rao|date=2001-07-01|title=New methodology for Ozone Depletion Potentials of short-lived compounds: n-Propyl bromide as an example|journal=Journal of Geophysical Research|volume=106|issue=D13|pages=14|doi=10.1029/2001JD900008|bibcode=2001JGR...10614551W|issn=0148-0227|doi-access=free}}</ref> According to the ], the ODP is 0.013-0.018 in U.S. latitudes and 0.071-0.100 in tropical latitudes.<ref name=":0" /> |
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==References== |
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{{Reflist}} |
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==Further reading== |
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* |
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{{DEFAULTSORT:Bromopropane, 1-}} |
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] |
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] |
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] |
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] |
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] |
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] |