822-23-1

Usage

Uses

Used in Insect Pheromone Research:
Stearyl Acetate is used as a chemical signal for attracting female castniid palm borers during the mating process. This pheromone helps in the identification and study of insect mating behaviors and communication.
Used in Pest Management:
Stearyl Acetate can be utilized in pest management strategies targeting the castniid palm borer. By mimicking the natural pheromone, it can be employed to trap and control the population of these insects, reducing their impact on palm trees and agriculture.

Purification Methods

Distil the ester under high vacuum, then crystallise it from Et2O/MeOH, EtOH (m 32.8o) or Me2CO (m 32.4o). Also recorded are m 30.2o; and 35.3o for an form as well as 38-39o for a  form. [Phillips & Mumford J Chem Soc 1663 1934, Beilstein 2 H 136, 2 II 147, 2 III 266, 2 IV 171.]

InChI:InChI=1/C20H40O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-20(2)21/h3-19H2,1-2H3

Upstream product

• 3386-32-1 n-octadecyl p-toluenesulfonate 
• 127-08-2 potassium acetate 
• 4889-45-6 phosphoric acid trioctadecyl ester 
• 108-24-7 acetic anhydride 
• 112-92-5 1-octadecanol 
• 75-36-5 acetyl chloride 
• 141-78-6 ethyl acetate 
• 64-19-7 acetic acid 
• 69820-27-5 (Z)-octadec-13-en-1-ol 
• 930-02-9 octadecyl-vinyl ether 

Downstream Products

• 112-92-5 1-octadecanol 
• 593-45-3 octadecane 
• 112-88-9 octadec-1-ene 

Relevant academic research and scientific papers

Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy

We report the dehydrogenative synthesis of esters from enol ethers using water as the formal oxidant, catalyzed by a newly developed ruthenium acridine-based PNP(Ph)-type complex. Mechanistic experiments and density functional theory (DFT) studies suggest that an inner-sphere stepwise coupled reaction pathway is operational instead of a more intuitive outer-sphere tandem hydration-dehydrogenation pathway.

Preparation method of rice borer pheromone component

The invention provides a preparation method of a rice borer pheromone component, and belongs to the technical field of organic synthesis. The preparation method uses Sodium Hexamethyldisilazane, namely sodium bis(trimethylsilyl)amide as an alkali to obtain relatively high yield, the cis-isomer content is improved, by controlling first wittig reaction at the temperature of -70 DEG C or less and limiting dropwise addition of acetate 12-oxo-dodecyl ester into the reaction system, the problem of increase of trans-type products caused by local overheating of the reaction system can be avoided, andthe reaction yield is improved. The data shows that the yield of the first wittig reaction is 72%, wherein the cis-isomer content is over 97%.

Ethyl acetate as an acetyl surrogate for the iodine catalyzed acetylation of alcohols

The use of readily available ethyl acetate in the presence of iodine as an alternative acetylating agent is reported. Amines and phenols were unreactive under the examined reaction conditions, indicating that the method is highly chemoselective.

Sulfonic acid-functionalized periodic mesoporous organosilicas in esterification and selective acylation reactions

The application of sulfonic acid-functionalized periodic mesoporous organosilicas (PMOs) having either phenyl (1a) or ethyl (1b) bridging groups was investigated in the esterification of a variety of alcohols and fatty acids. It was found that 1b consistently exhibited higher catalytic performance than 1a in the described reaction. In particular, it was proposed that the superior catalytic activity of 1b in esterification of fatty acids with methanol is a result of adequate hydrophobic-hydrophilic surface balance in the ethyl PMO catalyst. In addition, the study of chemoselective acylation of 1,3-butanediol with dodecanoic acid with varied mesoporous silica-supported solid sulfonic acids including both 1a and 1b implies that there is a compromise between the reaction selectivity and the surface physicochemical properties of the employed catalyst. Our results clearly show that the catalyst having high surface hydrophilic nature gives high selectivity toward the formation of mono-acylated products whereas those with relatively high hydrophobic characteristics showed enhanced selectivity toward the formation of di-acylated products.

Synthesis of sulfonic acid containing ionic-liquid-based periodic mesoporous organosilica and study of its catalytic performance in the esterification of carboxylic acids

A new sulfonic acid containing ionic-liquid-based periodic mesoporous organosilica (PMO-IL-SO3H) material was prepared and its catalytic application was investigated in the esterification of carboxylic acids with alcohols. The PMO-IL-SO3H nanocatalyst was first characterized with diffuse reflectance infrared Fourier transform (DRIFT) spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), and nitrogen sorption analysis. Then, the catalytic performance of this material was studied in the esterification of carboxylic acids with short- and long-chain aliphatic alcohols, cyclic alcohols, and benzylic alcohols under solvent-free conditions. The results showed that the catalyst has superior activity for the conversion of several alcohols to afford the corresponding ester products in excellent yields and high purity. Moreover, the catalyst could be recovered and reused several times without a significant decrease in activity and product selectivity. Copyright

A simple, general, and highly chemoselective acetylation of alcohols using ethyl acetate as the acetyl donor catalyzed by a tetranuclear zinc cluster

In the presence of a Zn-cluster catalyst, alcohols are efficiently converted to the corresponding acetate just by refluxing in EtOAc. The mild reaction conditions enabled the reactions of various functionalized alcohols to proceed in good to excellent yield. Moreover, even when a large excess of the acetyl donor is used, the hydroxyl groups are selectively acetylated in the presence of highly nucleophilic aliphatic amino groups, approaching chemoselectivity to that of enzymatic system. Georg Thieme Verlag Stuttgart.

Rapid and efficient method for acetylation of alcohols and phenols with acetic anhydride catalyzed by silica sulfate

A rapid and efficient method is described for acetylation of a series of alcohols and phenols with acetic anhydride catalyzed by silica sulfate solid acid at room temperature or at refluxing temperature in excellent yield. Copyright Taylor & Francis Group, LLC.

Silica gel-supported phosphotungstic acid (PTA) catalysed acylation of alcohols and phenols with acetic anhydride under mild reaction conditionst

Phosphotungstic acid, which is commercially available, practically and efficiently catalyses the acylation of a series of alcohols and phenols with acetic anhydride at room temperature of at refluxing temperature.

Reptilian chemistry: volatile compounds from paracloacal glands of the American crocodile (Crocodylus acutus).

The secretion of the paracloacal glands of the American crocodile (Crocodylus acutus) contains over 80 lipophilic compounds, including saturated and unsaturated long-chain alcohols along with their formic, acetic, and butyric acid esters, and several isoprenoids. Most of these compounds were identified on the basis of mass spectra, obtained by GC-MS. In addition, identification of the major components was supported by infrared spectra obtained by GC-FTIR. Major differences are indicated in the composition of the paracloacal gland secretion of C. acutus and that of another crocodylid, the African dwarf crocodile (Osteolaemus tetraspis).

Chemoselective acetylation of alcohols, amines, and thiols without catalyst and solvent

Microwave induced rapid and selective acetylation of alcohols, amines and thiols with acetic anhydride was carried out under non-catalytic and solvent free conditions.