Octanohydroxamic acid
[CAS# 7377-03-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Hydroxylamine
• Name: Octanohydroxamic acid
• Synonyms: Caprylohydroxamic acid; N-Hydroxyoctanamide; Octanoylhydroxamic acid; Taselin
• Molecular Formula: C₈H₁₇NO₂
• Molecular Weight: 159.23
• CAS Registry Number: 7377-03-9
• EC Number: 230-936-7
• SMILES: CCCCCCCC(=O)NO

Properties

• Density: 0.97±0.1 g/cm³, Calc.^*
• Melting point: 78 °C (Expl.)
• Index of Refraction: 1.452, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H350-H411
• Safety Statements: P201-P202-P264-P270-P280-P301+P312-P308+P313-P330-P403-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Octanohydroxamic acid is a chemical compound characterized by the functional group hydroxamic acid attached to an octyl chain. It is part of a broader class of hydroxamic acids, which are known for their ability to form stable complexes with metal ions. The molecular structure of octanohydroxamic acid includes a long hydrocarbon chain, which contributes to its unique properties and wide range of applications in various industries.

The discovery of octanohydroxamic acid can be traced back to the study of hydroxamic acids, which have long been recognized for their metal-binding properties. Hydroxamic acids are typically derived from the reaction of hydroxylamine with carboxylic acids, resulting in the formation of an amide group that contains a hydroxyl group (-OH) attached to the nitrogen atom. The addition of an octyl group to the hydroxamic acid structure provides octanohydroxamic acid with hydrophobic properties, making it useful in various industrial processes, including metal extraction, surface treatments, and catalysis.

One of the primary applications of octanohydroxamic acid is in the field of hydrometallurgy, where it is used as a reagent for the selective extraction of metal ions from ores and solutions. The hydroxamic acid group binds to metal ions, forming a stable complex that can be separated from the solution. Octanohydroxamic acid, with its long hydrophobic chain, enhances the solubility and stability of metal complexes in organic solvents, making it an effective agent in the extraction of metals like copper, nickel, and cobalt. This property has made it an important tool in the mining industry for the efficient recovery of valuable metals.

Octanohydroxamic acid also finds use in the field of corrosion inhibition. The compound can interact with metal surfaces, forming a protective layer that prevents the oxidation and degradation of the metal. This application is particularly useful in industries where metals are exposed to harsh environmental conditions, such as in marine, automotive, and construction applications. By preventing corrosion, octanohydroxamic acid helps extend the lifespan of metal structures and reduces maintenance costs.

In addition, octanohydroxamic acid has potential applications in polymer chemistry. The ability of the hydroxamic acid group to coordinate with metal ions makes it a useful component in the synthesis of metal-containing polymers. These polymers can exhibit unique properties such as enhanced conductivity, magnetic properties, or improved thermal stability. Octanohydroxamic acid is therefore a valuable building block for the development of advanced materials with specialized characteristics, particularly in the fields of electronics and materials science.

The compound is also being explored for its potential role in environmental remediation. Its ability to form complexes with metal ions can be leveraged for the removal of toxic metals from contaminated water sources. By selectively binding to harmful metals, octanohydroxamic acid can be used in water treatment processes to reduce pollution and improve water quality. This application holds promise for addressing the growing issue of heavy metal contamination in aquatic environments.

Moreover, octanohydroxamic acid is studied for its potential as an inhibitor in catalytic processes. In particular, it has been shown to affect the activity of certain enzymes and metal catalysts, making it useful in the fine-tuning of catalytic reactions in organic synthesis. By controlling the coordination of metal centers, octanohydroxamic acid can influence reaction rates and selectivity, offering an efficient tool for chemists in various synthetic applications.

In conclusion, octanohydroxamic acid is a versatile compound with a wide array of applications across several industries. From metal extraction and corrosion inhibition to polymer chemistry and environmental remediation, its ability to form stable metal complexes makes it an invaluable tool. Ongoing research into its properties and potential applications will likely continue to expand its role in industrial and scientific advancements.

References

2010. Spectroscopic characterisation of n-octanohydroxamic acid and potassium hydrogen n-octanohydroxamate. Inorganica Chimica Acta.
DOI: 10.1016/j.ica.2009.12.034

2016. Surface Chemistry and Microflotation of Xenotime and Selected Gangue Minerals Using Octanohydroxamic Acid as the Collector. Journal of Sustainable Metallurgy, 2(4).
DOI: 10.1007/s40831-016-0081-5

2017. Surface Chemistry and Flotation Behaviors of Monazite-Apatite-Ilmenite-Quartz-Rutile-Zircon with Octanohydroxamic Acid. Journal of Sustainable Metallurgy, 3(1).
DOI: 10.1007/s40831-016-0114-0