Industrial-grade 98% 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, irritating liquid. The acyl chloride group (-COCl) in its molecule is one of the most reactive functional groups among carboxylic acid derivatives, capable of undergoing acylation reactions with alcohols, amines, hydrogen peroxide, etc., "grafting" the 2-ethylhexanoyl group onto various molecules. It is this "active acyl group" ability that allows it to span multiple fields, from polymerization initiators and pesticide intermediates to surfactants, material additives, and research reagents.

3-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, the molecule of 2-ethylhexanoyl chloride consists of two parts: one end is a 2-ethylhexyl branched alkyl group (with an ethyl group attached to the 2-position of the butyl chain), and the other end is an acyl chloride group -COCl; the structural formula is CH3(CH2)3CH(C2H5)COCl. The carbonyl carbon is directly connected to the chlorine atom and the alkyl group. The strong electron-withdrawing effect of chlorine makes the carbonyl carbon significantly positively charged, becoming a target for nucleophilic attack—this is the structural root of the entire molecule's chemical activity, while the branched alkyl group provides the basis for solubility and flexibility.

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; it emits white fumes in humid air, which are the hydrochloric acid mist produced by hydrolysis.

Chemically, acyl chlorides are the most reactive carboxylic acid derivatives: 2-ethylhexanoyl chloride hydrolyzes in water to produce 2-ethylhexanoic acid and hydrogen chloride; it forms esters with alcohols, amides with amines, and peroxy esters with hydrogen peroxide; the reaction is often exothermic and releases hydrogen chloride; it is highly corrosive and irritating, and must be stored under anhydrous and sealed conditions, and protective measures must be taken during operation.

Why does 2-Ethylhexanoyl chloride play these roles in polymerization initiation, daily chemical raw materials, and materials chemistry? Its mechanism of action mainly includes the following:

The activation mechanism of strongly electrophilic carbonyl groups: The strong electron-withdrawing effect of chlorine atoms gives the carbonyl carbon a significant positive charge, making it easy for nucleophiles such as alcohols, amines, and peroxide anions to add to it. Subsequently, hydrogen chloride is eliminated to complete the acyl transfer—this is the chemical basis for the role of acyl chlorides as acylation reagents.

Leaving group driven mechanism: Chloride ions are excellent leaving groups. The addition-elimination process is thermodynamically favorable, with few side reactions, high acylation yield, and easy product purification, making acyl chlorides one of the preferred reagents for industrial acylation reactions.

The mechanism of functional group transformation diversity: the same acyl chloride group can be transformed into a variety of functional groups such as esters, amides, peroxy esters, and acid anhydrides. One intermediate can bring out a family of downstream products, which is why it is used in many fields.

Molecular structure customization mechanism: The branched carbon skeleton of 2-ethylhexyl is "inherited" to downstream molecules, giving esters, peroxides and surfactants customized properties such as low melting point, high solubility and low irritation.

Polymerization chain initiation mechanism: The 2-ethylhexanoyl peroxide prepared from it generates free radicals by homolytic cleavage of its peroxy bonds upon heating, which can initiate the chain polymerization of monomers such as vinyl chloride, extending the activity of acyl chloride to the field of polymer materials.

All uses of 2-Ethylhexanoyl chloride

1. Polymerization Initiation and the Polymer 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.

3. Pesticides and agrochemicals

Herbicide and fungicide intermediates

Acylation synthesis of key intermediates for various pesticide technicals.

Corresponding products: agrochemical intermediates, etc.

4. Surfactants and daily chemical raw materials

Amino acid surfactants

Acylation with amino acids produces mild, low-irritation acyl amino acid surfactants.

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

Ester-based skin moisturizing and care ingredients

It can be esterified with polyols to form moisturizing esters, which are used in skin care and personal care products.

Corresponding products: emollient esters, raw materials for skin care products, etc.

5. Materials and Fine Chemicals

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 Functional 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.

6. Scientific Research and Reagents

Laboratory acylation reagents

As a laboratory acylation and derivatization reagent, it is used in the development of organic synthesis and analytical methods.

Corresponding products: laboratory acylation reagents, derivatization reagents, etc.

Standards and Fine Synthesis

Used for the synthesis of standard products and the small-batch customization of fine chemicals.

Corresponding products: standard products, fine chemicals, etc.

Summary

2-Ethylhexanoyl chloride (CAS 760-67-8) is an acyl chloride derivative of 2-ethylhexanoic acid. The branched alkyl group imparts solubility, flexibility and low irritation to downstream products, while the strongly electrophilic acyl chloride group readily transfers the acyl group to alcohols, amines and peroxides. The combination of a “active acyl group” and a “customized skeleton” makes it applicable in a wide range of applications, from PVC polymerization initiators and pesticide intermediates, to surfactants, material additives and research reagents. It is mainly used for chemical production and laboratories. PVC pipes, wires and cables, pharmaceuticals and daily chemical products synthesized from PVC are already ubiquitous in daily life. With its known -COCl structure and branched alkyl group, it is no surprise that it has become a low-key but important intermediate in fine chemicals.