2-ethylhexanoic acid, iron salt

• CAS: 19583-54-1
• Catalog Number: ACM19583541
• Category: Main Products
• Molecular Weight: 485.45
• Molecular Formula: C24H45FeO6
• Synonyms: Iron 2-ethylhexanoate
• Appearance: Brown red uniform oily liquid

Case Study

Iron 2-Ethylhexanoate as a Tunable Co-Catalyst for Efficient Oxidation and Oligomerization of Ethyl Linoleate

Miccichè, Fabrizio, et al. Applied Catalysis A: General 297.2 (2006): 174-181.

In the development of drying oils and alkyd resin coatings, efficient catalysts are required to accelerate the oxidation and oligomerization of unsaturated fatty esters, a process essential for film formation. This study investigated iron 2-ethylhexanoate (Fe-eh) as a metal catalyst, focusing on its synergistic potential when combined with ascorbic acid 6-palmitate (AsA6p) to overcome the typical efficiency limitations of iron-based driers.
A specific AsA6p/Fe-eh molar ratio of 2:1 delivered the best overall performance. At this ratio, the system catalyzed the fastest rates of both EL oxidation and oligomerization. While Fe-eh alone exhibited a significant induction period (approximately 100 hours) before catalyzing oxidation, the optimal 2:1 combination with AsA6p completely eliminated this delay, initiating catalytic activity immediately. The catalytic activity of the optimized AsA6p/Fe-eh (2:1) system was found to be comparable to that of a commercial cobalt-based drier, a benchmark in the industry.
Molar ratios below or above the optimal 2:1 point resulted in decreased reaction rates. The performance is attributed to the dual pro-oxidant/antioxidant role of AsA6p and its interaction with the iron complex.
Mechanistic Behavior: AsA6p can act either as a pro-oxidant (promoting Fe-mediated radical cycles) or an antioxidant (scavenging radicals), depending on its ratio to Fe-eh. Data are consistent with AsA6p interacting with Fe-eh to form mixed-valence iron complexes that alter redox cycling and hydroperoxide decomposition rates.

Iron 2-Ethylhexanoate as the Active Component in a Ziegler-Natta Type Catalyst for Living 1,3-Butadiene Polymerization

Gong, Dirong, et al. Polymer 50.13 (2009): 2826-2829.

In synthetic polymer chemistry, achieving precise control over molecular weight and architecture in diene polymerization is a significant challenge. Living polymerization systems offer this control but often rely on complex or sensitive catalysts. Iron(III) 2-ethylhexanoate was employed as the pre-catalyst in combination with triisobutylaluminum (Al(i-Bu)3) and diethyl phosphite (DEP) as co-catalysts. The catalyst was prepared in situ by consecutively injecting the components into a solution of 1,3-butadiene in hexane at 40°C. This facile system was evaluated for its ability to conduct living polymerization, as evidenced by kinetic behavior, molecular weight control, and the feasibility of block copolymerization.
The system was highly active, achieving over 80% polymer yield within 35 minutes. The polymerization exhibited first-order kinetics with respect to monomer consumption. The resulting polybutadiene possessed a consistently narrow molecular weight distribution (Mw/Mn ≈ 1.5) across the entire conversion range, a hallmark of controlled polymerization. A direct linear relationship was observed between the number-average molecular weight (Mn) and the polymer yield, confirming the living nature of the propagating chains.
The living character was further verified by the successful execution of post-polymerization and block copolymerization with isoprene. The obtained polybutadiene exhibited a microstructure comprising approximately 44.0% cis-1,4 units, 51.0% 1,2-units, and 5.0% trans-1,4 units.

Custom Q&A

What is the molecular formula of 2-ethylhexanoic acid, iron salt?

The molecular formula is C16H30FeO4.

What are the synonyms for 2-ethylhexanoic acid, iron salt?

The synonyms are Iron 2-ethylhexanoate and Iron bis(2-ethylhexanoate).

What is the CAS number of 2-ethylhexanoic acid, iron salt?

The CAS number is 19583-54-1.

What is the molecular weight of 2-ethylhexanoic acid, iron salt?

The molecular weight is 342.25 g/mol.

What is the IUPAC name of 2-ethylhexanoic acid, iron salt?

The IUPAC name is 2-ethylhexanoate;iron(2+).

What is the InChI of 2-ethylhexanoic acid, iron salt?

The InChI is InChI=1S/2C8H16O2.Fe/c2*1-3-5-6-7(4-2)8(9)10;/h2*7H,3-6H2,1-2H3,(H,9,10);/q;;+2/p-2.

What is the InChIKey of 2-ethylhexanoic acid, iron salt?

The InChIKey is SMSVUYQRWYTTLI-UHFFFAOYSA-L.

What is the Canonical SMILES of 2-ethylhexanoic acid, iron salt?

The Canonical SMILES is CCCCC(CC)C(=O)[O-].CCCCC(CC)C(=O)[O-].[Fe+2].

What is the EC number of 2-ethylhexanoic acid, iron salt?

The EC number is 243-169-8.

What are the chemical and physical properties of 2-ethylhexanoic acid, iron salt?

The properties include a molecular weight of 342.25 g/mol, a hydrogen bond acceptor count of 4, a rotatable bond count of 8, an exact mass of 342.149345 g/mol, a topological polar surface area of 80.3Ų, a heavy atom count of 21, a complexity of 93.9, and a covalently-bonded unit count of 3.