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tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

tert-Butyl alcohol
Names
Preferred IUPAC name
2-Methylpropan-2-ol
Other names
  • t-Butyl alcohol
  • tert-Butanol
  • t-Butanol
  • t-BuOH
  • Trimethyl carbinol
  • 2-Methyl-2-propanol
  • 2M2P
Identifiers
3D model (JSmol)
906698
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.809
EC Number
  • 200-889-7
1833
MeSH tert-Butyl+Alcohol
RTECS number
  • EO1925000
UNII
UN number 1120
  • InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3 Y
    Key: DKGAVHZHDRPRBM-UHFFFAOYSA-N Y
  • CC(C)(C)O
Properties
C4H10O
Molar mass 74.123 g·mol−1
Appearance Colorless solid
Odor Camphorous
Density 0.775 g/mL
Melting point 25 to 26 °C; 77 to 79 °F; 298 to 299 K
Boiling point 82 to 83 °C; 179 to 181 °F; 355 to 356 K
miscible
log P 0.584
Vapor pressure 4.1 kPa (at 20 °C)
Acidity (pKa) 16.54
5.742×10−5 cm3/mol
1.387
1.31 D
Thermochemistry
215.37 J K−1 mol−1
189.5 J K−1 mol−1
−360.04 to −358.36 kJ mol−1
−2.64479 to −2.64321 MJ mol−1
Hazards
GHS labelling:
Danger
H225, H319, H332, H335
P210, P261, P305+P351+P338
NFPA 704 (fire diamond)
2
3
0
Flash point 11 °C (52 °F; 284 K)
480 °C (896 °F; 753 K)
Explosive limits 2.4–8.0%
Lethal dose or concentration (LD, LC):
3559 mg/kg (rabbit, oral)
3500 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm (300 mg/m3)
REL (Recommended)
TWA 100 ppm (300 mg/m3) ST 150 ppm (450 mg/m3)
IDLH (Immediate danger)
1600 ppm
Safety data sheet (SDS) inchem.org
Related compounds
Related butanols
2-Butanol

n-Butanol
Isobutanol

Related compounds
2-Methyl-2-butanol
Trimethylsilanol

Nonafluoro-tert-butyl alcohol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yverify (what is YN ?)

Contents

tert-Butyl alcohol has been identified in beer and chickpeas. It is also found in cassava, which is used as a fermentation ingredient in certain alcoholic beverages.

tert-Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production. It can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride.

Purification cannot be performed by simple distillation due to formation of an azeotrope with water, although initial drying of the solvent containing large amounts of water is performed by adding benzene to form a tertiary azeotrope and distilling off the water. Smaller amounts of water are removed by drying with calcium oxide (CaO), potassium carbonate (K2CO3), calcium sulfate (CaSO4), or magnesium sulfate (MgSO4), followed by fractional distillation. Anhydrous tert-butyl alcohol is obtained by further refluxing and distilling from magnesium activated with iodine, or alkali metals such as sodium or potassium. Other methods include the use of 4 Å molecular sieves, aluminium tert-butylate, calcium hydride (CaH2), or fractional crystallization under inert atmosphere.

tert-Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate. It is a chemical intermediate used to produce methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE) by reaction with methanol and ethanol, respectively, and tert-butyl hydroperoxide (TBHP) by reaction with hydrogen peroxide.

As a tertiary alcohol, tert-butyl alcohol is more resistant to oxidation than the other isomers of butanol.

tert-Butyl alcohol is deprotonated with a strong base to give the alkoxide. Particularly common is potassium tert-butoxide, which is prepared by treating tert-butanol with potassium metal.

K + t-BuOH → t-BuOK+ +1/2 H2

The tert-butoxide is a strong, non-nucleophilic base in organic chemistry. It readily abstracts acidic protons from substrates, but its steric bulk inhibits the group from participating in nucleophilic substitution, such as in a Williamson ether synthesis or an SN2 reaction.

tert-Butyl alcohol reacts with hydrogen chloride to form tert-butyl chloride.

O-Chlorination of tert-butyl alcohol with hypochlorous acid to give tert-butyl hypochlorite:

(CH3)3COH + HOCl → (CH3)3COCl + H2O

There is limited data on the pharmacology and toxicology of tert-butanol in humans and other animals. Human exposure may occur due to fuel oxygenate metabolism. Tert-butanol is poorly absorbed through skin but rapidly absorbed if inhaled or ingested. Tert-butanol is irritating to skin or eyes. Toxicity of single doses is usually low but high doses can produce a sedative or anesthetic effect.

  1. NIOSH Pocket Guide to Chemical Hazards. "#0078". National Institute for Occupational Safety and Health (NIOSH).
  2. "ICSC 0114 – tert-Butanol". Inchem.org. Retrieved29 March 2018.
  3. Reeve, W.; Erikson, C. M.; Aluotto, P. F. (1979). "tert-Butyl alcohol". Can. J. Chem. 57: 2747. doi:10.1139/v79-444.
  4. "tert-Butyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. "t-Butyl Alcohol". National Library of Medicine HSDB Database. National Institute for Health. Retrieved29 March 2018.
  6. "Archived copy"(PDF). Archived from the original(PDF) on 2016-03-04. Retrieved2013-03-05.{{cite web}}: CS1 maint: archived copy as title (link)
  7. Perrin, D. D.; Armarego, W. L. F. (1988).Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. ISBN 9780080347141.
  8. Johnson, W. S.; Schneider, W. P. (1950). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid". Organic Syntheses. 30: 18. doi:10.15227/orgsyn.030.0018.
  9. Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth. 49: 9. doi:10.15227/orgsyn.049.0009.
  10. Douglas McGregor (2010). "Tertiary-Butanol: a toxicological review". Critical Reviews in Toxicology. 40 (8): 697–727. doi:10.3109/10408444.2010.494249. PMID 20722584. S2CID 26041562.

tert Butyl alcohol Article Talk Language Watch Edit 160 160 Redirected from Tert butanol tert Butyl alcohol is the simplest tertiary alcohol with a formula of CH3 3COH sometimes represented as t BuOH Its isomers are 1 butanol isobutanol and butan 2 ol tert Butyl alcohol is a colorless solid which melts near room temperature and has a camphor like odor It is miscible with water ethanol and diethyl ether tert Butyl alcohol NamesPreferred IUPAC name 2 Methylpropan 2 olOther names t Butyl alcoholtert Butanolt Butanolt BuOHTrimethyl carbinol 1 2 Methyl 2 propanol2M2PIdentifiersCAS Number 75 65 0 Y3D model JSmol Interactive imageBeilstein Reference 906698ChEBI CHEBI 45895 YChEMBL ChEMBL16502 YChemSpider 6146 YDrugBank DB03900 YECHA InfoCard 100 000 809EC Number 200 889 7Gmelin Reference 1833MeSH tert Butyl AlcoholPubChem CID 6386RTECS number EO1925000UNII MD83SFE959 YUN number 1120CompTox Dashboard EPA DTXSID8020204InChI InChI 1S C4H10O c1 4 2 3 5 h5H 1 3H3 YKey DKGAVHZHDRPRBM UHFFFAOYSA N YSMILES CC C C OPropertiesChemical formula C 4H 10OMolar mass 74 123 g mol 1Appearance Colorless solidOdor CamphorousDensity 0 775 g mLMelting point 25 to 26 C 77 to 79 F 298 to 299 KBoiling point 82 to 83 C 179 to 181 F 355 to 356 KSolubility in water miscible 2 log P 0 584Vapor pressure 4 1 kPa at 20 C Acidity pKa 16 54 3 Magnetic susceptibility x 5 742 10 5 cm3 molRefractive index nD 1 387Dipole moment 1 31 DThermochemistryHeat capacity C 215 37 J K 1 mol 1Std molar entropy So298 189 5 J K 1 mol 1Std enthalpy of formation DfH 298 360 04 to 358 36 kJ mol 1Std enthalpy of combustion DcH 298 2 64479 to 2 64321 MJ mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H319 H332 H335Precautionary statements P210 P261 P305 P351 P338NFPA 704 fire diamond 230Flash point 11 C 52 F 284 K Autoignition temperature 480 C 896 F 753 K Explosive limits 2 4 8 0 Lethal dose or concentration LD LC LD50 median dose 3559 mg kg rabbit oral 3500 mg kg rat oral 4 NIOSH US health exposure limits PEL Permissible TWA 100 ppm 300 mg m3 1 REL Recommended TWA 100 ppm 300 mg m3 ST 150 ppm 450 mg m3 1 IDLH Immediate danger 1600 ppm 1 Safety data sheet SDS inchem orgRelated compoundsRelated butanols 2 Butanol n Butanol IsobutanolRelated compounds 2 Methyl 2 butanol Trimethylsilanol Nonafluoro tert butyl alcoholExcept 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 Contents 1 Natural occurrence 2 Preparation 3 Applications 4 Reactions 5 Pharmacology and toxicology 6 References 7 External linksNatural occurrence Edittert Butyl alcohol has been identified in beer and chickpeas 5 It is also found in cassava 6 which is used as a fermentation ingredient in certain alcoholic beverages Preparation Edittert Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production It can also be produced by the catalytic hydration of isobutylene or by a Grignard reaction between acetone and methylmagnesium chloride Purification cannot be performed by simple distillation due to formation of an azeotrope with water although initial drying of the solvent containing large amounts of water is performed by adding benzene to form a tertiary azeotrope and distilling off the water Smaller amounts of water are removed by drying with calcium oxide CaO potassium carbonate K2CO3 calcium sulfate CaSO4 or magnesium sulfate MgSO4 followed by fractional distillation Anhydrous tert butyl alcohol is obtained by further refluxing and distilling from magnesium activated with iodine or alkali metals such as sodium or potassium Other methods include the use of 4 A molecular sieves aluminium tert butylate calcium hydride CaH2 or fractional crystallization under inert atmosphere 7 Applications Edittert Butyl alcohol is used as a solvent ethanol denaturant paint remover ingredient and gasoline octane booster and oxygenate It is a chemical intermediate used to produce methyl tert butyl ether MTBE and ethyl tert butyl ether ETBE by reaction with methanol and ethanol respectively and tert butyl hydroperoxide TBHP by reaction with hydrogen peroxide Reactions EditAs a tertiary alcohol tert butyl alcohol is more resistant to oxidation than the other isomers of butanol tert Butyl alcohol is deprotonated with a strong base to give the alkoxide Particularly common is potassium tert butoxide which is prepared by treating tert butanol with potassium metal 8 K t BuOH t BuO K 1 2 H2 The tert butoxide is a strong non nucleophilic base in organic chemistry It readily abstracts acidic protons from substrates but its steric bulk inhibits the group from participating in nucleophilic substitution such as in a Williamson ether synthesis or an SN2 reaction tert Butyl alcohol reacts with hydrogen chloride to form tert butyl chloride O Chlorination of tert butyl alcohol with hypochlorous acid to give tert butyl hypochlorite 9 CH3 3COH HOCl CH3 3COCl H2OPharmacology and toxicology EditThere is limited data on the pharmacology and toxicology of tert butanol in humans and other animals 10 Human exposure may occur due to fuel oxygenate metabolism Tert butanol is poorly absorbed through skin but rapidly absorbed if inhaled or ingested Tert butanol is irritating to skin or eyes Toxicity of single doses is usually low but high doses can produce a sedative or anesthetic effect References Edit a b c d NIOSH Pocket Guide to Chemical Hazards 0078 National Institute for Occupational Safety and Health NIOSH ICSC 0114 tert Butanol Inchem org Retrieved 29 March 2018 Reeve W Erikson C M Aluotto P F 1979 tert Butyl alcohol Can J Chem 57 2747 doi 10 1139 v79 444 tert Butyl alcohol Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH t Butyl Alcohol National Library of Medicine HSDB Database National Institute for Health Retrieved 29 March 2018 Archived copy PDF Archived from the original PDF on 2016 03 04 Retrieved 2013 03 05 a href wiki Template Cite web title Template Cite web cite web a CS1 maint archived copy as title link Perrin D D Armarego W L F 1988 Purification of Laboratory Chemicals 3rd ed Pergamon Press ISBN 9780080347141 Johnson W S Schneider W P 1950 b Carbethoxy g g diphenylvinylacetic acid Organic Syntheses 30 18 doi 10 15227 orgsyn 030 0018 Mintz H M Walling C 1969 t Butyl Hypochlorite Org Synth 49 9 doi 10 15227 orgsyn 049 0009 Douglas McGregor 2010 Tertiary Butanol a toxicological review Critical Reviews in Toxicology 40 8 697 727 doi 10 3109 10408444 2010 494249 PMID 20722584 S2CID 26041562 External links EditInternational Chemical Safety Card 0114 NIOSH Pocket Guide to Chemical Hazards 0078 National Institute for Occupational Safety and Health NIOSH IPCS Environmental Health Criteria 65 Butanols four isomers IPCS Health and Safety Guide 7 tert Butanol Retrieved from https en wikipedia org w index php title Tert Butyl alcohol amp oldid 1084312073, wikipedia, wiki, 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