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ared in a variety of ways 15 industrially it can be made by the reaction of white phosphorus with sodium or potassium hydroxide producing potassium or sodium hypophosphite as a by product 3 koh p 4 3 h 2 o 3 kh 2 po 2 ph 3 3 naoh p 4 3 h 2 o 3 nah 2 po 2 ph 3 alternatively the acid catalyzed disproportionation of white phosphorus yields phosphoric acid and phosphine both routes have industrial significance the acid route is the preferred method if further reaction of the phosphine to substituted phosphines is needed the acid route requires purification and pressurizing laboratory routes edit it is prepared in the laboratory by disproportionation of phosphorous acid 16 4 h 3 po 3 ph 3 3 h 3 po 4 phosphine evolution occurs at around 200 c alternative methods include the hydrolysis of zinc phosphide 17 zn 3 p 2 6 h 2 o 3 zn oh 2 2 ph 3 some other metal phosphides could also be used including aluminium phosphide or calcium phosphide pure samples of phosphine free from p 2 h 4 may be prepared using the action of potassium hydroxide on phosphonium iodide ph 4 i koh ph 3 ki h 2 o occurrence edit phosphine is a worldwide constituent of the earth s atmosphere at very low and highly variable concentrations 18 it may contribute significantly to the global phosphorus biochemical cycle the most likely source is reduction of phosphate in decaying organic matter possibly via partial reductions and disproportionations since environmental systems do not have known reducing agents of sufficient strength to directly convert phosphate to phosphine 19 it is also found in jupiter s atmosphere 20 possible extraterrestrial biosignature edit main article life on venus phosphine in 2020 a spectroscopic analysis was reported to show signs of phosphine in the atmosphere of venus in quantities that could not be explained by known abiotic processes 21 22 23 later re analysis of this work showed interpolation errors had been made and re analysis of data with the fixed algorithm do not result in the detection of phosphine 24 25 the authors of the original study then claimed to detect it with a much lower concentration of 1 ppb 26 disputed discuss applications edit organophosphorus chemistry edit phosphine is a precursor to many organophosphorus compounds it reacts with formaldehyde in the presence of hydrogen chloride to give tetrakis hydroxymethyl phosphonium chloride which is used in textiles the hydrophosphination of alkenes is versatile route to a variety of phosphines for example in the presence of basic catalysts ph 3 adds of michael acceptors thus with acrylonitrile it reacts to give tris cyanoethyl phosphine 27 ph 3 3 ch 2 chz p ch 2 ch 2 z 3 z is no 2 cn or c o nh 2 acid catalysis is applicable to hydrophosphination with isobutylene and related analogues ph 3 r 2 c ch 2 r 2 ch 3 cph 2 where r is ch 3 alkyl etc microelectronics edit phosphine is used as a dopant in the semiconductor industry and a precursor for the deposition of compound semiconductors commercially significant products include gallium phosphide and indium phosphide 28 fumigant pest control edit see also fumigation phosphine is an attractive fumigant because it is lethal to insects and rodents but degrades to phosphoric acid which is non toxic as sources of phosphine for farm use pellets of aluminium phosphide alp calcium phosphide ca 3 p 2 or zinc phosphide zn 3 p 2 are used these phosphides release phosphine upon contact with atmospheric water or rodents stomach acid these pellets also contain reagents to reduce the potential for ignition or explosion of the released phosphine an alternative is the use of phosphine gas itself which requires dilution with either co 2 or n 2 or even air to bring it below the flammability point use of the gas avoids the issues related with the solid residues left by metal phosphide and results in faster more efficient control of the target pests one problem with phosphine fumigants is the increased resistance by insects 29 toxicity and safety edit further information aluminium phosphide poisoning see also white phosphorus munitions deaths have resulted from accidental exposure to fumigation materials containing aluminium phosphide or phosphine 30 31 32 33 it can be absorbed either by inhalation or transdermally 30 as a respiratory poison it affects the transport of oxygen or interferes with the utilization of oxygen by various cells in the body 32 exposure results in pulmonary edema the lungs fill with fluid 33 phosphine gas is heavier than air so it stays near the floor 34 phosphine appears to be mainly a redox toxin causing cell damage by inducing oxidative stress and mitochondrial dysfunction 35 resistance in insects is caused by a mutation in a mitochondrial metabolic gene 29 phosphine can be absorbed into the body by inhalation the main target organ of phosphine gas is the respiratory tract 36 according to the 2009 u s national institute for occupational safety and health niosh pocket guide and u s occupational safety and health administration osha regulation the 8 hour average respiratory exposure should not exceed 0 3 ppm niosh recommends that the short term respiratory exposure to phosphine gas should not exceed 1 ppm the immediately dangerous to life or health level is 50 ppm overexposure to phosphine gas causes nausea vomiting abdominal pain diarrhea thirst chest tightness dyspnea breathing difficulty muscle pain chills stupor or syncope and pulmonary edema 37 38 phosphine has been reported to have the odor of decaying fish or garlic at concentrations below 0 3 ppm the smell is normally restricted to laboratory areas or phosphine processing since the smell comes from the way the phosphine is extracted from the environment however it may occur elsewhere such as in industrial waste landfills exposure to higher concentrations may cause olfactory fatigue 39 fumigation hazards edit phosphine is used for pest control but its usage is strictly regulated due to high toxicity 40 41 gas from phosphine has high mortality rate 42 and has caused deaths in sweden and other countries 43 44 45 because the previously popular fumigant methyl bromide has been phased out in some countries under the montreal protocol phosphine is the only widely used cost effective rapidly acting fumigant that does not leave residues on the stored product pests with high levels of resistance toward phosphine have become common in asia australia and brazil high level resistance is also likely to occur in other regions but has not been as closely monitored genetic variants that contribute to high level resistance to phosphine have been identified in the dihydrolipoamide dehydrogenase gene 29 identification of this gene now allows rapid molecular identification of resistant insects explosiveness edit phosphine gas is denser than air and hence may collect in low lying areas it can form explosive mixtures with air and may also self ignite 12 in fiction edit anne mccaffrey s dragonriders of pern series features genetically engineered dragons that breathe fire by producing phosphine by extracting it from minerals of their native planet in the 2008 pilot of the crime drama television series breaking bad walter white poisons two rival gangsters by adding red phosphorus to boiling water to produce phosphine gas however this reaction in reality would require white phosphorus instead and for the water to contain sodium hydroxide 46 see also edit diphosphane h 2 p ph 2 simplified to p 2 h 4 diphosphene hp ph notes edit for further information about the early history of phosphine see the encyclopædia britannica 1911 edition vol 21 p 480 phosphorus phosphine archived 4 november 2015 at the wayback machine thomas thomson a system of chemistry 6th ed london england baldwin cradock and joy 1820 vol 1 p 272 archived 4 november 2015 at the wayback machine note on p 222 archived 24 april 2017 at the wayback machine of his traité élémentaire de chimie vol 1 paris france cuchet 1789 lavoisier calls the compound of phosphorus and hydrogen phosphure d hydrogène hydrogen phosphide however on p 216 archived 24 april 2017 at the wayback machine he calls the compound of hydrogen and phosphorus combinaison inconnue unknown combination yet in a footnote he says about the reactions of hydrogen with sulfur and with phosphorus ces combinaisons ont lieu dans l état de gaz il en résulte du gaz hydrogène sulfurisé phosphorisé these combinations occur in the gaseous state and there results from them sulfurized and phosphorized hydrogen gas in robert kerr s 1790 english translation of lavoisier s traité élémentaire de chimie namely lavoisier with robert kerr trans elements of chemistry edinburgh scotland william creech 1790 kerr translates lavoisier s phosphure d hydrogène as phosphuret of hydrogen p 204 and whereas lavoisier on p 216 of his traité élémentaire de chimie gave no name to the combination of hydrogen and phosphorus kerr calls it hydruret of phosphorus or phosphuret of hydrogen p 198 lavoisier s note about this compound combinaison inconnue is translated hitherto unknown lavoisier s footnote is translated as these combinations take place in the state of gas and form respectively sulphurated and phosphorated oxygen gas the word oxygen in the translation is an error because the original text clearly reads hydrogène hydrogen the error was corrected in subsequent editions in 1857 august wilhelm von hofmann announced the synthesis of organic compounds containing phosphorus which he named trimethylphosphine and triethylphosphine in analogy with amine organo nitrogen compounds arsine organo arsenic compounds and stibine organo antimony compounds references edit 1 2 3 4 5 6 niosh pocket guide to chemical hazards 0505 national institute for occupational safety and health niosh 1 2 zumdahl steven s 2009 chemical principles 6th ed houghton mifflin p a22 isbn 978 0 618 94690 7 1 2 phosphine immediately dangerous to life or health concentrations national institute for occupational safety and health iupac compendium of chemical terminology 5th ed the gold book 2025 online version 2006 phosphines doi 10 1351 goldbook p04553 iupac compendium of chemical terminology 5th ed the gold book 2025 online version 2006 phosphanes doi 10 1351 goldbook p04548 gengembre 1783 mémoire sur un nouveau gas obtenu par l action des substances alkalines sur le phosphore de kunckel memoir on a new gas obtained by the action of alkaline substances on kunckel s phosphorus mémoires de mathématique et de physique 10 651 658 paul thénard 1844 mémoire sur les combinaisons du phosphore avec l hydrogène archived 15 october 2015 at the wayback machine memoir on the compounds of phosphorus with hydrogen comptes rendus 18 652 655 a w hofmann auguste cahours 1857 researches on the phosphorus bases proceedings of the royal society of london 8 523 527 archived from the original on 10 february 2022 retrieved 19 november 2020 from page 524 the bases me 3 p and e 3 p the products of this reaction which we propose to call respectively trimethylphosphine and triethylphosphine william odling a course of practical chemistry arranged for the use of medical students 2nd ed london england longmans green and co 1865 pp 227 230 streitwieser andrew heathcock clayton h kosower edward m 2017 1st ed 1998 introduction to organic chemistry revised 4th ed new delhi medtech p 828 isbn 978 93 85998 89 8 sennikov p g 1994 weak h bonding by second row ph 3 h 2 s and third row ash 3 h 2 se hydrides journal of physical chemistry 98 19 4973 4981 doi 10 1021 j100070a006 1 2 3 material safety data sheet phosphine hydrogen gas mixture pdf report matheson tri gas 8 september 2008 archived from the original pdf on 5 july 2022 retrieved 4 july 2022 rabinowitz joseph woeller fritz flores jose krebsbach rita november 1969 electric discharge reactions in mixtures of phosphine methane ammonia and water nature 224 5221 796 798 bibcode 1969natur 224 796r doi 10 1038 224796a0 issn 1476 4687 pmid 5361652 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