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p305 p351 p338 p308 p313 p310 p311 p314 p332 p313 p337 p313 p362 p403 p233 p405 p501 nfpa 704 fire diamond 2 0 0 flash point nonflammable lethal dose or concentration ld lc ld 50 median dose 704 mg kg mouse dermal 6 lc 50 median concentration 47 702 mg m 3 rat 4 hr 7 lc lo lowest published 20 000 ppm guinea pig 2 hr 7 056 ppm cat 4 hr 25 000 ppm human 5 min 8 niosh us health exposure limits pel permissible 50 ppm 240 mg m 3 4 rel recommended ca st 2 ppm 9 78 mg m 3 60 minute 4 idlh immediate danger 500 ppm 4 safety data sheet sds related compounds related compounds deuterated chloroform cdcl 3 chloromethane ch 3 cl dichloromethane ch 2 cl 2 tetrachloromethane ccl 4 fluoroform chf 3 bromoform chbr 3 iodoform chi 3 chlorodifluoromethane chf 2 cl dichlorofluoromethane chfcl 2 bromodichloromethane chcl 2 br dibromochloromethane chclbr 2 bromodifluoromethane chf 2 br dibromofluoromethane chfbr 2 supplementary data page chloroform data page except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa y verify what is y n infobox references chemical compound chloroform 9 or trichloromethane often abbreviated as tcm is an organochloride with the formula c h cl 3 and a common solvent it is a volatile colorless sweet smelling dense liquid produced on a large scale as a precursor to refrigerants and polytetrafluoroethylene ptfe 10 chloroform was once used as an inhalational anesthetic between the 19th century and the first half of the 20th century 11 12 it is miscible with many solvents but it is only very slightly soluble in water only 8 g l at 20 c structure and name edit the molecule adopts a tetrahedral molecular geometry with c 3v symmetry 13 the chloroform molecule can be viewed as a methane molecule with three hydrogen atoms replaced with three chlorine atoms leaving a single hydrogen atom the name chloroform is a portmanteau of terchloride tertiary chloride a trichloride and formyle an obsolete name for the methylylidene radical ch derived from formic acid 14 natural occurrence edit many kinds of seaweed produce chloroform and fungi are believed to produce chloroform in soil 15 abiotic processes are also believed to contribute to natural chloroform productions in soils although the mechanism is still unclear 16 history edit chloroform was synthesized independently by several investigators c 1831 moldenhawer a german pharmacist from frankfurt an der oder appears to have produced chloroform in 1830 by mixing chlorinated lime with ethanol however he mistook it for chloräther chloric ether 1 2 dichloroethane 17 18 samuel guthrie a u s physician from sackets harbor new york also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol and noted its anaesthetic properties however he also believed that he had prepared chloric ether 19 20 21 justus von liebig carried out the alkaline cleavage of chloral liebig incorrectly states that the empirical formula of chloroform was c 2 cl 5 and named it chlorkohlenstoff carbon chloride 22 23 eugène soubeiran obtained the compound by the action of chlorine bleach on both ethanol and acetone 24 in 1834 french chemist jean baptiste dumas determined chloroform s empirical formula and named it 25 es scheint mir also erweisen dass die von mir analysirte substanz zur formel hat c 2 h 2 cl 6 thus it seems to me to show that the substance i analyzed has as its empirical formula c 2 h 2 cl 6 note the coefficients of his empirical formula should be halved diess hat mich veranlasst diese substanz mit dem namen chloroform zu belegen this had caused me to impose the name chloroform upon this substance i e formyl chloride or chloride of formic acid in 1835 dumas prepared the substance by alkaline cleavage of trichloroacetic acid in 1842 robert mortimer glover in london discovered the anaesthetic qualities of chloroform on laboratory animals 26 in 1847 scottish obstetrician james y simpson was the first to demonstrate the anaesthetic properties of chloroform provided by local pharmacist william flockhart of duncan flockhart and company 27 in humans and helped to popularize the drug for use in medicine 28 the application of chloroform remained dangerous and many deaths occurred through accidental overdose 29 30 in 1848 english physician john snow developed an inhaler that regulated the dosage 29 by the 1850s chloroform was being produced on a commercial basis 30 an apparatus that could apply it safely and controllably was invented by english physician joseph thomas clover in 1862 31 32 in britain about 750 000 doses a week were being produced by 1895 30 using the liebig procedure which retained its importance until the 1960s today chloroform along with dichloromethane is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane 10 production edit industrially chloroform is produced by heating a mixture of chlorine and either methyl chloride ch 3 cl or methane ch 4 10 at 400 500 c free radical halogenation occurs converting these precursors to progressively more chlorinated compounds ch 4 cl 2 ch 3 cl hcl ch 3 cl cl 2 ch 2 cl 2 hcl ch 2 cl 2 cl 2 chcl 3 hcl chloroform undergoes further chlorination to yield carbon tetrachloride ccl 4 chcl 3 cl 2 ccl 4 hcl the output of this process is a mixture of the four chloromethanes chloromethane methylene chloride dichloromethane trichloromethane chloroform and tetrachloromethane carbon tetrachloride these can then be separated by distillation 10 chloroform may also be produced on a small scale via the haloform reaction between acetone and sodium hypochlorite 3 naocl ch 3 2 co chcl 3 2 naoh ch 3 coona deuterochloroform edit main article deuterated chloroform deuterated chloroform is an isotopologue of chloroform with a single deuterium atom cdcl 3 is a common solvent used in nmr spectroscopy deuterochloroform is produced by the reaction of hexachloroacetone with heavy water 33 the haloform process is now obsolete for production of ordinary chloroform deuterochloroform can also be prepared by reacting sodium deuteroxide with chloral hydrate 34 35 inadvertent formation of chloroform edit the haloform reaction can also occur inadvertently in domestic settings sodium hypochlorite solution chlorine bleach mixed with common household liquids such as acetone methyl ethyl ketone ethanol or isopropyl alcohol can produce some chloroform in addition to other compounds such as chloroacetone or dichloroacetone 36 37 uses edit in terms of scale the most important reaction of chloroform is with hydrogen fluoride to give monochlorodifluoromethane hcfc 22 a precursor in the production of polytetrafluoroethylene teflon and other fluoropolymers 10 chcl 3 2 hf chclf 2 2 hcl the reaction is conducted in the presence of a catalytic amount of mixed antimony halides chlorodifluoromethane is then converted to tetrafluoroethylene the main precursor of teflon 38 solvent edit the hydrogen attached to carbon in chloroform participates in hydrogen bonding 39 40 making it a good solvent for many materials worldwide chloroform is also used in pesticide formulations as a solvent for lipids rubber alkaloids waxes gutta percha and resins as a cleaning agent as a grain fumigant and in fire extinguishers 41 42 cdcl 3 is a common solvent used in nmr spectroscopy 43 refrigerant edit chloroform is used as a precursor to make r 22 chlorodifluoromethane this is done by reacting it with hydrofluoric acid hf which fluorinates the chcl 3 molecule and releases hydrochloric acid as a byproduct 44 before the montreal protocol was enforced most of the chloroform produced in the united states was used in the production of chlorodifluoromethane however its production remains high as it is a key precursor of ptfe 45 although chloroform has properties such as a low boiling point and a low global warming potential of only 31 compared to the 1760 of r 22 which are appealing properties for a refrigerant there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products 46 lewis acid edit in solvents such as ccl 4 and alkanes chloroform hydrogen bonds to a variety of lewis bases hccl 3 is classified as a hard acid and the ecw model lists its acid parameters as e a 1 56 and c a 0 44 reagent edit as a reagent chloroform serves as a source of the dichlorocarbene intermediate ccl 2 47 it reacts with aqueous sodium hydroxide usually in the presence of a phase transfer catalyst to produce dichlorocarbene ccl 2 48 49 this reagent effects ortho formylation of activated aromatic rings such as phenols producing aryl aldehydes in a reaction known as the reimer tiemann reaction alternatively the carbene can be trapped by an alkene to form a cyclopropane derivative in the kharasch addition chloroform forms the chcl 2 free radical which adds to alkenes 50 anaesthetic edit antique bottles of chloroform chloroform is a powerful general anesthetic euphoriant anxiolytic and sedative when inhaled or ingested the anaesthetic qualities of chloroform were first described in 1842 in a thesis by robert mortimer glover which won the gold medal of the harveian society for that year 51 52 glover also undertook practical experiments on dogs to prove and refine his theories and subsequently presented them in his doctoral thesis at the university of edinburgh in the summer of 1847 identifying anaesthetizing halogenous compounds as a new order of poisonous substances 51 james young simpson a scottish obstetrician was one of those examiners required to read the thesis but later claimed to have never read it and to have come to his own conclusions independently 51 perkins mcvey among others have raised doubts about the credibility of simpson s claim noting that simpson s publications on the subject in 1847 explicitly echo glover s and being one of the thesis examiners simpson was likely aware of the content of glover s study even if he skirted his duties as an examiner 51 in 1847 and 1848 glover would pen a series of heated letters accusing simpson of stealing his discovery which had already earned simpson considerable notoriety 51 whatever the source of his inspiration on 4 november 1847 simpson argued that he had discovered the anaesthetic qualities of chloroform in humans he and two colleagues entertained themselves by trying the effects of various substances and thus revealed the potential for chloroform in medical procedures 27 an illustration depicting james young simpson and his friends found unconscious a few days later during the course of a dental procedure in edinburgh francis brodie imlach became the first person to use chloroform on a patient in a clinical context 53 in may 1848 robert halliday gunning made a presentation to the medico chirurgical society of edinburgh following a series of laboratory experiments on rabbits that confirmed glover s findings and also refuted simpson s claims of originality the laboratory experiments that proved the dangers of chloroform were largely ignored 54 the use of chloroform during surgery expanded rapidly in europe in the 1850s chloroform was used by the physician john snow during the births of queen victoria s last two children leopold and beatrice 55 in the united states chloroform began to replace ether as an anesthetic at the beginning of the 20th century 56 it was abandoned in favor of ether on discovery of its toxicity especially its tendency to cause fatal cardiac arrhythmias analogous to what is now termed sudden sniffer s death some people used chloroform as a recreational drug or to attempt suicide 57 one possible mechanism of action of chloroform is that it increases the movement of potassium ions through certain types of potassium channels in nerve cells 58 chloroform could also be mixed with other anesthetic agents such as ether to make c e mixture 59 or ether and alcohol to make a c e mixture 60 61 in 1848 hannah greener a 15 year old girl who was having an infected toenail removed died after being given the anaesthetic 62 her autopsy establishing the cause of death was undertaken by john fife assisted by robert mortimer glover 26 a number of physically fit patients died after inhaling it in 1848 however john snow developed an inhaler that regulated the dosage and so successfully reduced the number of deaths 29 joseph thomas clover improved on the design in 1862 further reducing the risk of accidental overdose 31 32 the opponents and supporters of chloroform disagreed on the question of whether the medical complications were due to respiratory disturbance or whether chloroform had a specific effect on the heart between 1864 and 1910 numerous commissions in britain studied chloroform but failed to come to any clear conclusions it was only in 1911 that levy proved in experiments with animals that chloroform can cause ventricular fibrillation 63 despite this between 1865 and 1920 chloroform was used in 80 to 95 of all narcoses performed in the uk and german speaking countries in germany comprehensive surveys of the fatality rate during anaesthesia were made by gurlt between 1890 and 1897 56 at the same time in the uk the medical journal the lancet carried out a questionnaire survey 64 and compiled a report detailing numerous adverse reactions to anesthetics including chloroform 65 in 1934 killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1 14 000 and 1 28 000 whereas with chloroform the chances were between 1 3 000 and 1 6 000 56 the rise of gas anaesthesia using nitrous oxide improved equipment for administering anesthetics and the discovery of hexobarbital in 1932 led to the gradual decline of chloroform narcosis 66 the latest reported anaesthetic use of chloroform in the western world dates to 1987 when the last doctor who used it retired about 140 years after its first use 67 recreational use edit in the 1910s in england a famous set of english aristocrats and intellectuals called the coterie were known to use chloroform recreationally often at extravagant parties margot asquith whose stepson raymond asquith was a member recorded lady diana cooper s usage at one such party stating that after dinner diana ejaculated i must be unconscious tonight and went away in a taxi to fetch chloroform from the chemist jolly old chlorers 68 criminal use edit chloroform has been used by criminals to knock out daze or murder victims joseph harris was charged in 1894 with using chloroform to rob people 69 serial killer h h holmes used chloroform overdoses to kill his female victims in september 1900 chloroform was implicated in the murder of the u s businessman william marsh rice the serial killer john wayne gacy chloroformed many of his victims chloroform was deemed a factor in the alleged murder of a woman in 1991 when she was asphyxiated while asleep 70 in 2002 13 year old kacie woody was sedated with chloroform when she was abducted by david fuller and duri...
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