1-Propanol

1-Propanol
Names
Pronunciation	ˈprəʊpən.wən.ɒl
	Preferred IUPAC name Propan-1-ol
	Other names n-Propyl alcohol; n-Propanol; n-PrOH; Ethyl carbinol; 1-Hydroxypropane; Propionic alcohol; Propionyl alcohol; Propionylol; Propyl alcohol; Propylic alcohol; Propylol;
Identifiers
CAS Number	71-23-8;
3D model (JSmol)	Interactive image;
3DMet	B00883;
Beilstein Reference	1098242
ChEBI	CHEBI:28831;
ChEMBL	ChEMBL14687;
ChemSpider	1004;
DrugBank	DB03175;
ECHA InfoCard	100.000.679
EC Number	200-746-9;
Gmelin Reference	25616
KEGG	C05979;
MeSH	1-Propanol
PubChemCID	1031;
RTECS number	UH8225000;
UNII	96F264O9SV;
UN number	1274
CompTox Dashboard(EPA)	DTXSID2021739;
	InChI InChI=1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 Key: BDERNNFJNOPAEC-UHFFFAOYSA-N;
	SMILES CCCO;
Properties
Chemical formula	C3H8O
Molar mass	60.096g·mol−1
Appearance	Colorless liquid
Odor	mild, alcohol-like
Density	0.803 g/mL
Melting point	−126 °C; −195 °F; 147 K
Boiling point	97 to 98 °C; 206 to 208 °F; 370 to 371 K
Solubility in water	miscible
logP	0.329
Vapor pressure	1.99 kPa (at 20 °C)
Acidity(pKa)	16
Basicity(pKb)	−2
Magnetic susceptibility(χ)	−45.176·10−6cm3/mol
Refractive index(nD)	1.387
Viscosity	1.959 mPa·s (at 25 °C)
Dipole moment	1.68 D
Thermochemistry
Heat capacity(C)	143.96 J/(K·mol)
Std molar; entropy(S⦵298)	192.8 J/(K·mol)
Std enthalpy of; formation(ΔfH⦵298)	−302.79…−302.29 kJ/mol
Std enthalpy of; combustion(ΔcH⦵298)	−2.02156…−2.02106 MJ/mol
Pharmacology
ATC code	D08AX03(WHO)
Hazards
	Occupational safety and health(OHS/OSH):
Main hazards	Flammable liquid
	GHSlabelling:
Pictograms
Signal word	Danger
Hazard statements	H225,H302,H318,H336
Precautionary statements	P210,P261,P280,P305+P351+P338
NFPA 704(fire diamond)	1 3 0
Flash point	22 °C (72 °F; 295 K)
Autoignition; temperature	371 °C (700 °F; 644 K)
Explosive limits	2.2–13.7%
	Lethal doseor concentration (LD, LC):
LD50(median dose)	2800 mg/kg (rabbit, oral); 1699 mg/kg (mouse, oral); 1870 mg/kg (rat, oral)
	NIOSH(US health exposure limits):
PEL(Permissible)	TWA 200 ppm (500 mg/m3)
REL(Recommended)	TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin]
IDLH(Immediate danger)	800 ppm
Related compounds
Related compounds	Propane; Isopropyl alcohol; Propanamine; Ethanol; Butanol
Supplementary data page
	1-Propanol (data page)
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). verify(what is?) Infobox references

1-Propanol(alsopropan-1-ol,propanol,n-propyl alcohol) is aprimary alcoholwith the formulaCH₃CH₂CH₂OHand sometimesrepresentedasPrOHorn-PrOH.It is a colourless liquid and anisomerof2-propanol.1-Propanol is used as asolventin the pharmaceutical industry, mainly forresinsandcelluloseesters, and, sometimes, as adisinfectingagent.

Occurrence

Fusel alcoholslike 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present inmany alcoholic beverages.

Chemical properties

Some example reactions of 1-propanol

1-Propanol shows the normal reactions of aprimary alcohol.Thus it can be converted toalkyl halides;for example redphosphorusandiodineproducen-propyl iodidein 80% yield, whilePCl₃with catalyticZnCl₂givesn-propyl chloride.Reaction withacetic acidin the presence of anH₂SO₄catalyst underFischer esterificationconditions givespropyl acetate,while reflu xing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol withNa₂Cr₂O₇andH₂SO₄gives a 36% yield ofpropionaldehyde,and therefore for this type of reaction higher yielding methods usingPCCor theSwern oxidationare recommended. Oxidation withchromic acidyieldspropionic acid.

Preparation

1-Propanol is manufactured by catalytichydrogenationofpropionaldehyde.Propionaldehyde is produced via theoxo processbyhydroformylationofethyleneusingcarbon monoxideandhydrogenin the presence of a catalyst such ascobalt octacarbonylor arhodiumcomplex.^[5]

H₂C=CH₂+ CO + H₂→ CH₃CH₂CH=O

CH₃CH₂CH=O + H₂→ CH₃CH₂CH₂OH

A traditional laboratory preparation of 1-propanol involves treatingn-propyl iodidewith moistAg₂O.

Safety

1-Propanol is thought to be similar toethanolin its effects on the human body, but 2–4 times more potent according to a study conducted on rabbits. Many toxicology studies find oral acute LD₅₀ranging from 1.9 g/kg to 6.5 g/kg (compared to 7.06 g/kg for ethanol). It is metabolized intopropionic acid.Effects includealcoholic intoxicationandhigh anion gap metabolic acidosis.As of 2011, one case of lethal poisoning was reported following oral ingestion of 500mL of 1-propanol.^[6]Due to lack of long term data, the carcinogenicity of 1-propanol in human beings is unknown.

1-Propanol as fuel

1-Propanol has highoctane numberand is suitable forenginefuel usage. However, propanol is too expensive to use as a motor fuel. Theresearch octane number(RON) of propanol is 118, andanti-knock index(AKI) is 108.^[7]

References

^Favre HA, Powell WH (2014).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book).Cambridge:The Royal Society of Chemistry.p. 61.doi:10.1039/9781849733069.ISBN 9780854041824.
^^a ^b ^c ^d ^eNIOSH Pocket Guide to Chemical Hazards."#0533".National Institute for Occupational Safety and Health(NIOSH).
^Pal A, Gaba R (2008). "Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K".J. Chem. Thermodyn.40(5): 818–828.doi:10.1016/j.jct.2008.01.008.
^"n-Propyl alcohol".Immediately Dangerous to Life or Health Concentrations (IDLH).National Institute for Occupational Safety and Health(NIOSH).
^ Papa AJ (2011). "Propanols".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a22_173.pub2.ISBN 9783527303854.
^Unmack JL (2011)."N-PROPANOL Health-Base Assessment and Recommendation for HEAC"(PDF).
^"Bioalcohols".Biofuel.org.uk.2010.Retrieved16 Apr2014.

External links

[1] Favre HA, Powell WH (2014).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book).Cambridge:The Royal Society of Chemistry.p. 61.doi:10.1039/9781849733069.ISBN 9780854041824.

[PGCH-2] NIOSH Pocket Guide to Chemical Hazards."#0533".National Institute for Occupational Safety and Health(NIOSH).

[3] Pal A, Gaba R (2008). "Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K".J. Chem. Thermodyn.40(5): 818–828.doi:10.1016/j.jct.2008.01.008.

[4] "n-Propyl alcohol".Immediately Dangerous to Life or Health Concentrations (IDLH).National Institute for Occupational Safety and Health(NIOSH).

[5] Papa AJ (2011). "Propanols".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a22_173.pub2.ISBN 9783527303854.

[6] Unmack JL (2011)."N-PROPANOL Health-Base Assessment and Recommendation for HEAC"(PDF).

[7] "Bioalcohols".Biofuel.org.uk.2010.Retrieved16 Apr2014.

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