1,1,1-Trichloroethane
Names
IUPAC name
1,1,1-trichloroethane
Other names
methyl chloroform, chlorothene, Solvent 111, Genklene, R-140a
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.000.688
KEGG
UNII
InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3
Y
Key: UOCLXMDMGBRAIB-UHFFFAOYSA-N
Y
InChI=1/C2H3Cl3/c1-2(3,4)5/h1H3
Key: UOCLXMDMGBRAIB-UHFFFAOYAP
Properties
C2 H3 Cl3 or CH3 CCl3
Molar mass
133.40 g/mol
Appearance
Colorless liquid
Odor
mild, chloroform-like[1]
Density
1.32 g/cm3
Melting point
−33 °C (−27 °F; 240 K)
Boiling point
74 °C (165 °F; 347 K)
0.4% (20°C)[1]
Vapor pressure
100 mmHg (20°C)[1]
Hazards
Main hazards
Irritant to the upper respiratory tract. Causes severe irritation and swelling to eyes.
R-phrases
R19 R20 R40 R59 R66
S-phrases
S9 S16 S24 S25 S46 S59 S61
NFPA 704
Explosive limits
7.5%-12.5%[1]
Lethal dose or concentration (LD , LC ):
9600 mg/kg (oral, rat)
6000 mg/kg (oral, mouse)
5660 mg/kg (oral, rabbit)[2]
3911 ppm (mouse, 2 hr)
18000 ppm (rat, 4 hr)[2]
US health exposure limits (NIOSH ):
TWA 350 ppm (1900 mg/m3 )[1]
C 350 ppm (1900 mg/m3 ) [15-minute][1]
700 ppm[1]
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
The organic compound 1,1,1-trichloroethane , also known as methyl chloroform , is a chloroalkane . This colourless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent .[3] It is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out.
Production [ edit ]
1,1,1-Trichloroethane was first reported by Henri Victor Regnault in 1840. Industrially, it is usually produced in a two-step process from vinyl chloride . In the first step, vinyl chloride reacts with hydrogen chloride at 20-50 °C to produce 1,1-dichloroethane :
CH2 =CHCl + HCl → CH3 CHCl2
This reaction is catalyzed by a variety of Lewis acids , mainly aluminium chloride , iron(III) chloride , or zinc chloride . The 1,1-dichloroethane is then converted to 1,1,1-trichloroethane by reaction with chlorine under ultraviolet irradiation:
CH3 CHCl2 + Cl2 → CH3 CCl3 + HCl
This reaction proceeds at 80-90% yield, and the hydrogen chloride byproduct can be recycled to the first step in the process. The major side-product is the related compound 1,1,2-trichloroethane , from which the 1,1,1-trichloroethane can be separated by distillation .
A somewhat smaller amount of 1,1,1-trichloroethane is produced from the reaction of vinylidene chloride and hydrogen chloride in the presence of an iron(III) chloride catalyst:
CH2 =CCl2 + HCl → CH3 CCl3
1,1,1-Trichloroethane is marketed with stabilizers since it is unstable with respect to dehydrochlorination and attacks some metals. Stabilizers comprise up to 8% of the formulation, including acid scavengers (epoxides, amines) and complexants . The Montreal Protocol targeted 1,1,1-trichloroethane as one of those compounds responsible for ozone depletion and banned its use beginning in 1996. Since then, its manufacture and use has been phased out throughout most of the world.
1,1,1-trichloroethane is generally considered a non-polar solvent. Owing to the good polarizability of the chlorine atoms, it is a superior solvent for organic compounds that do not dissolve well in hydrocarbons such as hexane . It is an excellent solvent for many organic materials and also one of the least toxic of the chlorinated hydrocarbons . Prior to the Montreal Protocol, it was widely used for cleaning metal parts and circuit boards , as a photoresist solvent in the electronics industry, as an aerosol propellant, as a cutting fluid additive, and as a solvent for inks, paints, adhesives and other coatings. 1,1,1-trichloroethane is also used as an insecticidal fumigant .[4]
It was also the standard cleaner for photographic film (movie/slide/negatives, etc.). Other commonly available solvents damage emulsion, and thus are not suitable for this application. The standard replacement, Forane 141 is much less effective, and tends to leave a residue. 1,1,1-trichloroethane was used as a thinner in correction fluid products such as liquid paper . Many of its applications previously used carbon tetrachloride (which was banned in US consumer products in 1970). In turn, 1,1,1-trichloroethane itself is now being replaced by other solvents in the laboratory.[5]
Although not as toxic as many similar compounds, inhaled or ingested 1,1,1-trichloroethane does act as a central nervous system depressant and can cause effects similar to those of ethanol intoxication , including dizziness , confusion, and in sufficiently high concentrations, unconsciousness and death.[6] Fatal poisonings and illnesses linked to intentional inhalation of trichloroethane have been reported.[7] [8] [9] [10] The removal of the chemical from correction fluid commenced due to Proposition 65 declaring it hazardous and toxic[11] [12]
Prolonged skin contact with the liquid can result in the removal of fats from the skin, resulting in chronic skin irritation. Studies on laboratory animals have shown that 1,1,1-trichloroethane is not retained in the body for long periods of time. However, chronic exposure has been linked to abnormalities in the liver, kidneys, and heart. Pregnant women should avoid exposure, as the compound has been linked to birth defects in laboratory animals (see teratogenesis ).
References [ edit ]
^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0404" . National Institute for Occupational Safety and Health (NIOSH).
^ a b "Methyl chloroform" . Immediately Dangerous to Life and Health . National Institute for Occupational Safety and Health (NIOSH).
^ Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, Trevor Mann "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi :10.1002/14356007.a06_233.pub2 .
^ Methylchloroform data sheet , alanwood.net
^ Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003
^ Toxicological Profile for 1,1,1-Trichloroethane , Agency for Toxic Substances and Disease Registry (ATSDR). 2006
^ King, Gregory S.; Smialek, John E.; Troutman, William G. (15 March 1985). "Sudden Death in Adolescents Resulting From the Inhalation of Typewriter Correction Fluid" . JAMA: the Journal of the American Medical Association . 253 (11): 1604–1606. doi :10.1001/jama.253.11.1604 . PMID 3974043 . Archived from the original on 2009-07-25. Retrieved 2010-01-05 . We describe four cases of sudden death in adolescents associated with recreational sniffing of typewriter correction fluid occurring during the period 1979 through mid-1984.
^ D'costa, DF; Gunasekera, NP (August 1990). "Fatal cerebral oedema following trichloroethane abuse" . Journal of the Royal Society of Medicine . 83 (8): 533–534. PMC 1292788 . PMID 2231588 .
^ Winekab, Charles L.; Wahba, Wagdy W.; Huston, Robert; Rozin, Leon (6 June 1997). "Fatal inhalation of 1,1,1-trichloroethane" . Forensic Science International . 87 (2): 161–165. doi :10.1016/S0379-0738(97)00040-6 . PMID 9237378 . Archived from the original on 2009-07-25. Retrieved 2010-01-05 . A 13-year-old male was found dead in the woods subsequent to 1,1,1-trichloroethane (TCE) inhalation.
^ Wodka, Richard M.; Jeong, Erwin W. S. (1 January 1989). "Cardiac Effects of Inhaled Typewriter Correction Fluid" . Annals of Internal Medicine . 110 (1): 91–92. doi :10.7326/0003-4819-110-1-91_2 . PMID 2908837 . Archived from the original on 2009-07-25. Retrieved 2010-01-05 .
^ Paddock, Richard C. (29 September 1989). "Gillette Agrees to Remove Toxics From Its Paper Correction Fluid" . Los Angeles Times . Sacramento. Archived from the original on 23 July 2009. Retrieved 5 January 2010 .
^ Estrin, Norman F.; Akerson, James M. (2000). "Proposition 65". Cosmetic regulation in a competitive environment . New York, New York: Marcel Dekker . p. 138. ISBN 0-8247-7516-3 . Retrieved 5 January 2010 . Gillette agreed to reformulate the product so that it would not pose a risk requiring a Proposition 65 warning
Further reading [ edit ]
Alcohols
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Unsorted benzodiazepine site PAMs: MRK-409 (MK-0343)
TCS-1105
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(ligands )
PAMs: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol , tert -butanol (2M2P) , tribromoethanol , trichloroethanol , trifluoroethanol )
Alkylbenzene sulfonate
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Xenon
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Antagonists: 2-Aminostrychnine
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4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline
Brucine
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RU-5135
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Picrotoxin (i.e., picrotin and picrotoxinin )
PMBA
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Verapamil
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Transporter
(blockers )
Others
5-HT1A
Agonists: 8-OH-DPAT
Adatanserin
Amphetamine
Antidepressants (e.g., etoperidone , nefazodone , trazodone , vilazodone , vortioxetine )
Atypical antipsychotics (e.g., aripiprazole , asenapine , clozapine , lurasidone , quetiapine , ziprasidone )
Azapirones (e.g., buspirone , eptapirone , gepirone , perospirone , tandospirone )
Bay R 1531
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BMY-14802
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F-11461
F-12826
F-13714
F-14679
F-15063
F-15599
Flesinoxan
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Flumexadol
Lesopitron
LY-293284
LY-301317
mCPP
MKC-242
Naluzotan
NBUMP
Osemozotan
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Pardoprunox
Piclozotan
Rauwolscine
Repinotan
Roxindole
RU-24969
S-14506
S-14671
S-15535
Sarizotan
Serotonin (5-HT)
SSR-181507
Sunepitron
Tryptamines (e.g., 5-CT , 5-MeO-DMT , 5-MT , bufotenin , DMT , indorenate , N-Me-5-HT , psilocin , psilocybin )
TGBA01AD
U-92016A
Urapidil
Vilazodone
Xaliproden
Yohimbine
Antagonists: Atypical antipsychotics (e.g., iloperidone , risperidone , sertindole )
AV965
Beta blockers (e.g., alprenolol , cyanopindolol , iodocyanopindolol , oxprenolol , pindobind , pindolol , propranolol , tertatolol )
BMY-7378
CSP-2503
Dotarizine
Ergolines (e.g., metergoline )
Flopropione
GR-46611
Isamoltane
Lecozotan
Mefway
Metitepine (methiothepin)
MIN-117 (WF-516)
MPPF
NAN-190
Robalzotan
S-15535
SB-649915
SDZ 216-525
Spiperone
Spiramide
Spiroxatrine
UH-301
WAY-100135
WAY-100635
Xylamidine
5-HT1B
Agonists: CGS-12066A
CP-93129
CP-94253
CP-122,288
CP-135807
Eltoprazine
Ergolines (e.g., bromocriptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
mCPP
RU-24969
Serotonin (5-HT)
Triptans (e.g., avitriptan , donitriptan , eletriptan , sumatriptan , zolmitriptan )
TFMPP
Tryptamines (e.g., 5-BT , 5-CT , 5-MT , DMT )
Vortioxetine
5-HT1D
Agonists: CP-122,288
CP-135807
CP-286601
Ergolines (e.g., bromocriptine , cabergoline , dihydroergotamine , ergotamine , LSD , methysergide )
GR-46611
L-694247
L-772405
mCPP
PNU-109291
PNU-142633
Serotonin (5-HT)
TGBA01AD
Triptans (e.g., almotriptan , avitriptan , donitriptan , eletriptan , frovatriptan , naratriptan , rizatriptan , sumatriptan , zolmitriptan )
Tryptamines (e.g., 5-BT , 5-CT , 5-Et-DMT , 5-MT , 5-(nonyloxy)tryptamine , DMT )
5-HT1E
5-HT1F
5-HT2A
Agonists: 25H/NB series (e.g., 25I-NBF , 25I-NBMD , 25I-NBOH , 25I-NBOMe , 25B-NBOMe , 25C-NBOMe , 25TFM-NBOMe , 2CBCB-NBOMe , 25CN-NBOH , 2CBFly-NBOMe )
2Cs (e.g., 2C-B , 2C-E , 2C-I , 2C-T-2 , 2C-T-7 , 2C-T-21 )
2C-B-FLY
2CB-Ind
5-Methoxytryptamines (5-MeO-DET , 5-MeO-DiPT , 5-MeO-DMT , 5-MeO-DPT , 5-MT )
α-Alkyltryptamines (e.g., 5-Cl-αMT , 5-Fl-αMT , 5-MeO-αET , 5-MeO-αMT , α-Me-5-HT , αET , αMT )
AL-34662
AL-37350A
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Dimemebfe
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DOx (e.g., DOB , DOC , DOI , DOM )
Efavirenz
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O-4310
Oxaflozane
PHA-57378
PNU-22394
PNU-181731
RH-34
Phenethylamines (e.g., lophophine , mescaline )
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Serotonin (5-HT)
TCB-2
TFMFly
Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
Antagonists: 5-I-R91150
5-MeO-NBpBrT
AC-90179
Adatanserin
Altanserin
AMDA
APD-215
Atypical antipsychotics (e.g., amperozide , aripiprazole , asenapine , blonanserin , carpipramine , clocapramine , clorotepine , clozapine , fluperlapine , gevotroline , iloperidone , melperone , mosapramine , ocaperidone , olanzapine , paliperidone , quetiapine , risperidone , sertindole , zicronapine , ziprasidone , zotepine )
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S-14671
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SR-46349B
TGBA01AD
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Trazodone
Tricyclic antidepressants (e.g., amitriptyline )
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Volinanserin
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5-HT2B
Agonists: 4-Methylaminorex
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Amphetamines (eg., chlorphentermine , cloforex , dexfenfluramine , fenfluramine , levofenfluramine , norfenfluramine )
BW-723C86
DOx (e.g., DOB , DOC , DOI , DOM )
Ergolines (e.g., cabergoline , dihydroergocryptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
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PNU-22394
Ro60-0175
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , 5-MT , α-Me-5-HT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
5-HT2C
Agonists: 2Cs (e.g., 2C-B , 2C-E , 2C-I , 2C-T-2 , 2C-T-7 , 2C-T-21 )
5-Methoxytryptamines (5-MeO-DET , 5-MeO-DiPT , 5-MeO-DMT , 5-MeO-DPT , 5-MT )
α-Alkyltryptamines (e.g., 5-Cl-αMT , 5-Fl-αMT , 5-MeO-αET , 5-MeO-αMT , α-Me-5-HT , αET , αMT )
A-372159
AL-38022A
Alstonine
CP-809101
Dimemebfe
DOx (e.g., DOB , DOC , DOI , DOM )
Ergolines (e.g., ALD-52 , cabergoline , dihydroergotamine , ergine (LSA) , ergotamine , lisuride , LA-SS-Az , LSB , LSD , LSD-Pip , LSH , LSP , pergolide )
Flumexadol
Lorcaserin
MDxx (e.g., MDA , MDMA , MDOH , MMDA )
MK-212
Org 12962
Org 37684
Oxaflozane
PHA-57378
Phenethylamines (e.g., lophophine , mescaline )
Piperazines (e.g., aripiprazole , BZP , mCPP , quipazine , TFMPP )
PNU-22394
PNU-181731
Ro60-0175
Ro60-0213
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
Vabicaserin
WAY-629
WAY-161503
YM-348
Antagonists: Adatanserin
Agomelatine
Atypical antipsychotics (e.g., asenapine , clorotepine , clozapine , fluperlapine , iloperidone , melperone , olanzapine , paliperidone , quetiapine , risperidone , sertindole , ziprasidone , zotepine )
Captodiame
CEPC
Cinanserin
Cyproheptadine
Deramciclane
Dotarizine
Eltoprazine
Ergolines (e.g., amesergide , bromocriptine , LY-53857 , LY-215840 , mesulergine , metergoline , methysergide , sergolexole )
Etoperidone
Fluoxetine
FR-260010
Irindalone
Ketanserin
Ketotifen
Latrepirdine (dimebolin)
Medifoxamine
Metitepine (methiothepin)
Nefazodone
Pirenperone
Pizotifen
Propranolol
Ritanserin
RS-102221
S-14671
SB-200646
SB-206553
SB-221284
SB-228357
SB-242084
SB-243213
SDZ SER-082
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
TIK-301
Trazodone
Tricyclic antidepressants (e.g., amitriptyline , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine , pimozide , pipamperone , thioridazine )
Xylamidine
5-HT3
Agonists: Alcohols (e.g., butanol , ethanol , trichloroethanol )
m-CPBG
Phenylbiguanide
Piperazines (e.g., BZP , mCPP , quipazine )
RS-56812
Serotonin (5-HT)
SR-57227
SR-57227A
Tryptamines (e.g., 2-Me-5-HT , 5-CT , bufotenidine (5-HTQ) )
Volatiles/gases (e.g., halothane , isoflurane , toluene , trichloroethane )
YM-31636
Antagonists: Alosetron
AS-8112
Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine )
Azasetron
Batanopride
Bemesetron (MDL-72222)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
ICS-205930
Lerisetron
Memantine
Ondansetron
Palonosetron
Ramosetron
Renzapride
Ricasetron
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , mianserin , mirtazapine )
Thujone
Tropanserin
Tropisetron
Typical antipsychotics (e.g., loxapine )
Volatiles/gases (e.g., nitrous oxide , sevoflurane , xenon )
Vortioxetine
Zacopride
Zatosetron
5-HT4
5-HT5A
5-HT6
Agonists: Ergolines (e.g., dihydroergocryptine , dihydroergotamine , ergotamine , lisuride , LSD , mesulergine , metergoline , methysergide )
Serotonin (5-HT)
Tryptamines (e.g., 2-Me-5-HT , 5-BT , 5-CT , 5-MT , Bufotenin , E-6801 , E-6837 , EMD-386088 , EMDT , LY-586713 , N-Me-5-HT , tryptamine )
WAY-181187
WAY-208466
Antagonists: ABT-354
Atypical antipsychotics (e.g., aripiprazole , asenapine , clorotepine , clozapine , fluperlapine , iloperidone , olanzapine , tiospirone )
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12233
GW-742457
Idalopirdine
Ketanserin
Latrepirdine (dimebolin)
Metitepine (methiothepin)
MS-245
PRX-07034
Ritanserin
Ro04-6790
Ro 63-0563
SB-258585
SB-271046
SB-357134
SB-399885
SB-742457
Tetracyclic antidepressants (e.g., amoxapine , mianserin )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g., amisulpride , aripiprazole , asenapine , clorotepine , clozapine , fluperlapine , olanzapine , risperidone , sertindole , tiospirone , ziprasidone , zotepine )
Butaclamol
DR-4485
EGIS-12233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , imipramine )
Typical antipsychotics (e.g., acetophenazine , chlorpromazine , chlorprothixene , fluphenazine , loxapine , pimozide )
Vortioxetine