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Stearoyl chloride

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Identification
Molecular formula
C18H35ClO
CAS number
112-76-5
IUPAC name
octadecanoyl chloride
State
State

Stearoyl chloride is typically a liquid at room temperature but can be waxy or solid if the temperature is cooler, approaching its melting point of 25°C.

Melting point (Celsius)
25.00
Melting point (Kelvin)
298.15
Boiling point (Celsius)
361.00
Boiling point (Kelvin)
634.15
General information
Molecular weight
318.94g/mol
Molar mass
318.9290g/mol
Density
0.8850g/cm3
Appearence

Stearoyl chloride is a colorless to pale yellow liquid. It may appear as a waxy solid at lower temperatures due to its relatively high melting point. Exposure to air may cause it to fume slightly due to moisture absorption and hydrochloric acid formation.

Comment on solubility

Solubility of Octadecanoyl Chloride

Octadecanoyl chloride, also known as stearoyl chloride, is a fatty acid chloride with the chemical formula C18H35ClO. When it comes to its solubility, there are several key points to consider:

  • Non-polar Nature: As a long-chain fatty acid derivative, octadecanoyl chloride is largely non-polar due to its long hydrocarbon chain.
  • Solubility in Organic Solvents: It is soluble in non-polar organic solvents such as hexane, chloroform, and benzene, making it suitable for various organic synthesis applications.
  • Poor Water Solubility: Due to its large hydrophobic carbon chain, octadecanoyl chloride exhibits very low solubility in water, which can limit its use in aqueous environments.

In summary, octadecanoyl chloride presents a fascinating case of solubility behavior. Its solubility in organic solvents vs its poor solubility in water showcases the impact of molecular structure on solubility in different solvents:

  1. Highly soluble in non-polar solvents.
  2. Poorly soluble in polar solvents (e.g., water).

Understanding these solubility properties is essential for the application of octadecanoyl chloride in chemical processes.

Interesting facts

Interesting Facts about Octadecanoyl Chloride

Octadecanoyl chloride, commonly known in the scientific community for its use in various chemical syntheses, is an acyl chloride that plays a crucial role in organic chemistry. Here are some intriguing aspects of this compound:

  • Reactivity: Octadecanoyl chloride is highly reactive due to the presence of the carbonyl group and the chlorine atom. This makes it a valuable reagent for the synthesis of esters, amides, and other derivatives.
  • Applications: It is widely used in the production of fatty acid derivatives, in the synthesis of surfactants, and in the modification of polymers.
  • Safety Considerations: Being a reactive halide, it can be hazardous. It is known to release hydrogen chloride gas upon contact with water, making proper handling and personal protective equipment essential during laboratory work.
  • Chemical History: The interest in acyl chlorides like octadecanoyl chloride stems from their ability to simplify the process of acylation, which is a fundamental reaction in organic synthesis.
  • Structural Characteristics: The long hydrocarbon chain (18 carbon atoms) of octadecanoyl chloride contributes to its unique properties, making it a subject of study for those interested in lipid chemistry and fatty acid interactions.

As a noteworthy compound, octadecanoyl chloride illustrates the importance of acyl chlorides in organic synthesis and serves as a reminder of the delicate balance between utility and hazard in the world of chemistry. As the saying goes, "With great power comes great responsibility." Thus, understanding its properties and safety measures is essential for any chemist utilizing this compound.

Synonyms
STEAROYL CHLORIDE
Octadecanoyl chloride
112-76-5
Stearic acid chloride
Stearic chloride
n-Octadecanoyl chloride
octadecanoic acid chloride
Octadecanoic acid, chloride
HSDB 5576
UNII-MYP8E32GM2
EINECS 204-004-5
MYP8E32GM2
BRN 0639784
Octadecanoyl-chloride-
DTXSID9051583
STEAROYL CHLORIDE [HSDB]
EC 204-004-5
4-02-00-01240 (Beilstein Handbook Reference)
MFCD00000744
octadecanoylchloride
stearoylchloride
nOctadecanoyl chloride
1-octadecanoyl chloride
Stearoyl chloride, 97%
SCHEMBL177408
DTXCID3030135
AKOS015907690
FS36862
HY-W539878
AS-39887
BP-30115
NS00009008
S0404
Stearic acetyl chlorine(18 acetyl chlorine)
EN300-90229
A802648
Q27284300
Stearoyl chloride, technical, >=90% (GC), strongly brown
204-004-5