n-pentadecanol

n-pentadecanol
Compound Structure:
Synonyms: Pentadecan-1-ol; 1-PENTADECANOL; Pentadecyl alcohol; Pentadecanol; n-Pentadecanol; Neodol 5; n-pentadecyl alcohol; n-pPentadecanol; Pentadecanol-(1); 1-Pentadecanol
Compound ID: NMPC-1331
PubChem ID:

12397

Molecular Formula: C15H32O
Canonical SMILES: CCCCCCCCCCCCCCCO
InChIKey: REIUXOLGHVXAEO-UHFFFAOYSA-N
About the compound:

Pentadecan-1-ol, also known as 1-pentadecanol, is a long-chain fatty alcohol. It is essentially pentadecane with one of the terminal methyl hydrogens replaced by a hydroxy group. This compound is a saturated long-chain fatty alcohol, consisting of a pentadecane chain with a hydroxy group substituent at one end. It is an achiral molecule, meaning it lacks mirror-image isomers. At room temperature, 1-pentadecanol appears as a white, flaky solid. It finds various applications in industrial chemicals, lubricating oils, and consumer products like lotions and creams. 1-Pentadecanol is also used as a feedstock in processes involving ethoxylation and sulfation to produce surfactants, which are primarily used in detergents. In terms of safety and handling, 1-pentadecanol is generally a stable compound and exhibits low oral, skin, and respiratory toxicity. However, it can be irritating to the eyes and skin, especially with prolonged contact, leading to defatting of the skin. Consequently, when handling large amounts, protective measures such as eye protection, chemical-resistant gloves, and other protective clothing are recommended. The substance is also flammable under certain conditions, and in the event of a fire, specific types of fire extinguishers are recommended. According to product literature from Shell, high-chain primary alcohols like 1-pentadecanol are readily biodegradable and unlikely to bioaccumulate. They are not corrosive to carbon steel and are compatible with various polymers. However, ethylene propene-diene monomer (EPDM) rubber is not recommended for use with these alcohols. Compared to other 1-alkanols, 1-pentadecanol has lower solubility in supercritical carbon dioxide, a trend consistent with longer chain alcohols. When cooled from a liquid state, 1-pentadecanol assumes a crystalline structure known as the α-form. Upon further cooling, it exclusively transitions to a β-form, which is characterized by its vertical chains. This behavior has been studied through differential thermal analysis and dielectric measurements, confirming the compound's phase transitions and orientational disorder. Interestingly, no triple point is observed for 1-pentadecanol.

GHS Hazard Statements

H315 (61.29%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (76.34%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H400 (38.71%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (29.03%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

H411 (15.05%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

First Aid

INHALATION: if necessary, support respiration.

INGESTION: induce vomiting and call a doctor.

SKIN OR EYES: wash with copious amounts of water. (USCG, 1999)

U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

228.41 g/mol

XLogP3

6.8

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

13

Exact Mass

228.245315640 g/mol

Monoisotopic Mass

228.245315640 g/mol

Topological Polar Surface Area

20.2Ų

Heavy Atom Count

16

Formal Charge

0

Complexity

112

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Pentadecanol is a colorless liquid with a faint odor of alcohol. Floats on water. (USCG, 1999)

Boiling Point

298.00 to 299.00 °C. @ 760.00 mm Hg

Melting Point

45 - 46 °C

Density

0.829 at 122 °F (USCG, 1999) - Less dense than water; will float

Vapor Pressure

0.000038 [mmHg]

Source: PubChem

Source Species: Jatropha curcas
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