Industrial grade98% 2-Ethylhexanoyl chloride 760-67-8

What is 2-Ethylhexanoyl chloride? How does it work?

2-Ethylhexanoyl chloride, also known as isooctanoyl chloride, is an acyl chloride derivative of 2-ethylhexanoic acid, with the chemical formula C8H15ClO and CAS number 760-67-8. It is a colorless to pale yellow liquid with a strong, pungent odor. The acyl chloride group (-COCl) in its molecule endows it with extremely high reactivity—it can undergo acylation reactions with alcohols, amines, hydrogen peroxide, etc., to produce esters, amides, and peroxides. It is an important acylating agent and intermediate in fine chemicals. Industrial-grade 2-ethylhexanoyl chloride is widely used in the preparation of 2-ethylhexanoyl peroxide polymerization initiators, pesticide intermediates, and raw materials for materials and daily chemicals.

Basic information: Chinese name: 2-ethylhexanoyl chloride (also known as isooctanoyl chloride, 2-ethylhexanoic acid chloride); English name: 2-Ethylhexanoyl chloride; CAS number: 760-67-8; Molecular formula: C8H15ClO; Molecular weight: 162.66; Boiling point: approximately 170℃; Density: approximately 0.95 g/cm³; At room temperature, it is a colorless to pale yellow liquid, and reacts violently with water; Synonyms: isooctanoyl chloride, 2-ethylhexanoic acid chloride, etc.

Structurally, 2-ethylhexanoyl chloride is an acyl chloride derivative of 2-ethylhexanoic acid (isooctanoic acid): the hydroxyl group in the carboxyl group is replaced by a chlorine atom to form an acyl chloride group -COCl; the alkyl part is 2-ethylhexyl, that is, an ethyl branch attached to the 2 position of the butyl chain, with the structural formula CH3(CH2)3CH(C2H5)COCl. The carbonyl carbon is simultaneously connected to a chlorine atom and a branched alkyl group. Chlorine is an excellent leaving group, making the carbonyl carbon a strongly electrophilic center—this is the structural root of the entire molecule's reactivity.

Physically, 2-ethylhexanoyl chloride is a colorless to pale yellow transparent liquid with a strong, pungent (tear-inducing) odor; it is almost insoluble in water (it hydrolyzes rapidly upon contact with water), but soluble in organic solvents such as ether, hydrocarbons, and chlorinated hydrocarbons; its boiling point is about 170℃, and its density is about 0.95 g/cm³; when exposed to humid air, it emits white fumes, which are hydrochloric acid mists produced by hydrolysis.

Chemically, acyl chlorides are among the most reactive of carboxylic acid derivatives: 2-ethylhexanoyl chloride undergoes violent hydrolysis in water to produce 2-ethylhexanoic acid and hydrogen chloride; it reacts with alcohols to form esters, with amines to form amides, and with hydrogen peroxide to form peroxy esters; the reactions are usually exothermic and accompanied by the release of hydrogen chloride; it is highly corrosive and irritating, and must be stored under anhydrous and sealed conditions.

Why does 2-Ethylhexanoyl chloride play these roles in industrial fields such as polymerization initiation, pesticide synthesis, and materials processing? Its mechanism of action mainly includes the following:

The high reactivity mechanism of acyl chlorides: the chlorine atom is an excellent leaving group, making the carbonyl carbon a strong electrophilic center, which is easily attacked by nucleophiles. The acylation reaction conditions are mild and the conversion rate is high - this is the core of its use as a general acylation agent.

Nucleophilic acylation reaction mechanism: Nucleophiles such as alcohols, amines, and hydrogen peroxide attack the carbonyl carbon and replace the chlorine atom, respectively generating esters, amides, and peroxy esters. The byproduct hydrogen chloride is removed by neutralization. The reaction pathway is clear and the products are controllable.

Branched alkyl properties mechanism: The branched structure of 2-ethylhexyl makes downstream products less prone to crystallization, has good solubility and flexibility, and the generated esters and peroxides are easier to process and use in materials and oils.

Peroxide initiation mechanism: 2-Ethylhexanoyl peroxide generates free radicals upon heating and homolytic cracking, which can initiate the free radical polymerization of monomers such as vinyl chloride and acrylates, and is the source of initiation activity in PVC production.

Anhydrous stable storage mechanism: Acyl chlorides are chemically stable in anhydrous and moisture-free environments and can be stored for a long time, making their industrial-scale use feasible.

All uses of industrial grade 2-Ethylhexanoyl chloride

1. Polymerization initiator field

Peroxide, 2-Ethylhexanoyl

It reacts with hydrogen peroxide to afford 2-ethylhexanoyl peroxide, a highly efficient initiator for the polymerization of monomers like vinyl chloride and acrylates.

Matching products: 2-ethylhexanoyl peroxide, polymerization initiators, etc.

PVC resin and product

It starts suspension polymerization of vinyl chloride to PVC resin which can be further processed into products such as pipes, profiles and cable materials.

Similar products: PVC resin, tubes, profiles, cable materials, etc.

2. Pesticides and agrochemicals

pesticide synthesis intermediates

Acylation synthesis of key intermediates for pesticides such as herbicides and fungicides.

Corresponding products: agrochemical intermediates, pesticide technicals, etc.

3. Surfactants and daily chemical raw materials

Amino acid surfactants

It undergoes an acylation reaction with amino acids to generate mild acyl amino acid surfactants with low irritation.

Corresponding products: Acyl amino acid surfactants, mild facial cleansing and care ingredients, etc.

4. Materials and Fine Chemicals

Ester plasticizers and synthetic lubricants

It can be esterified with alcohols to form 2-ethylhexanoates, which are used as plasticizers and synthetic ester lubricants.

Corresponding products: synthetic ester lubricants, plasticizers, etc.

Coatings, Inks and Modified Materials

It is used as an acylated modified resin as a material intermediate in coatings, inks and functional materials.

Corresponding products: coating additives, modified resins, material intermediates, etc.

Summary

2-Ethylhexanoyl chloride (CAS 760-67-8) is an acyl chloride derivative of 2-ethylhexanoic acid. The strong electrophilicity of the acyl chloride group makes it a common reagent in industrial acylation reactions, while the branched structure of the 2-ethylhexyl group gives downstream products good solubility and flexibility—a combination of "activity" and "compliance" that makes it play a low-key yet crucial intermediate role, from polymerization initiators and pesticide intermediates to surfactants and material modifiers. Although it exists only on chemical production lines, PVC pipes, wires and cables, and daily chemical products synthesized from it are ubiquitous in daily life. Understanding its strongly electrophilic -COCl center and branched alkyl structure explains its enduring popularity in fine chemicals.