Allyl hexanoate

Base Information

• Chemical Name: Allyl hexanoate
• CAS No.: 123-68-2
• Molecular Formula: C9H16O2
• Molecular Weight: 156.225
• Hs Code.: 29159080
• European Community (EC) Number: 204-642-4
• NSC Number: 20962
• UNII: 3VH84A363D
• DSSTox Substance ID: DTXSID1047653
• Nikkaji Number: J36.964K
• Wikipedia: Allyl_hexanoate
• Wikidata: Q3270746
• RXCUI: 1807113
• Metabolomics Workbench ID: 48907
• ChEMBL ID: CHEMBL2229585
• Mol file: 123-68-2.mol

Synonyms:allyl caproate

Chemical Property of Allyl hexanoate

Chemical Property:

• Appearance/Colour: clear, colorless liquid.
• Vapor Pressure: 0.678mmHg at 25°C
• Melting Point: -57.45°C (estimate)
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 186 °C at 760 mmHg
• Flash Point: 66.1 °C
• PSA: 26.30000
• Density: 0.889 g/cm³
• LogP: 2.29590
• Storage Temp.: Store below +30°C.
• Solubility.: 0.06g/l
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 156.115029749
• Heavy Atom Count: 11
• Complexity: 119

Purity/Quality:

99% ^*data from raw suppliers

Allyl hexanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 22-24-51/53-R51/53-R24-R22
• Safety Statements: 36/37-45-61-S61-S45-S36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)OCC=C
• Uses: 1. Allyl hexanoate is Used for the preparation of pineapple and other fruit flavors.2. China provides that allyl hexanoate is the spices temporally allowed to use, which is commonly used in the modulation of food spices and tobacco spices with the flavor of strawberry, apricot, peach, sweet orange, pineapple, apple and other fruit. The use amount of allyl hexanoate is according to the normal production needs, such as 210 mg/kg in chewing gum, 32mg/kg in confectionery, 25 mg/kg in baked goods and 11 mg/kg in cold drinks.3. Allyl caproate finds use in perfumes as a part of fruity top notes in combination with green mossy notes. it may form a characteristic part of the fragrance. It also tends to round off the Aldehyde notes in combination with styrallyl esters. it has found extensive use in apple, apricot, orange, peach, pineapple, rum, strawberry, tutti-frutti, etc.4. Widely used in the preparation of food flavors, spices, tobacco flavors and pineapple and other fruit flavors, and also used as an organic synthesis of intermediates. Allyl Hexanoate is a liquid flavoring agent with a strong pineapple odor and pale yellow color. it is practically insoluble in propylene glycol and miscible with alcohol, most fixed oils, and mineral oil. it is obtained by chemical synthesis. it can be used alone or in com- bination with other flavoring substances or adjuvants. it is also termed allyl caproate.
• Production method: synthesis of allyl hexanoate(1) solid acid catalytic method: Add 23.2 g (0.4 mol) of propenol, 23.2 g (0.2 mol) of hexanoic acid, 0.1 g of hydroquinone, 3.0 g of solid super TiO2/SO4-2 and 30 mL of toluene into a 150 mL flask. Heat for reflux for 1.5h and the generated water were taken out by the azeotropic agent toluene. The reaction solution was cooled and filtered, and the solid acid could be repeatedly used after being dried. Add 0.1g of cuprous chloride in the filtrate, and then distillate them to collect the fraction of 186-188 ° C. The obtained finished products was 27.1g with a yield of 86.9%, and the refractive index n20d was 1.4241.(2) sulfuric acid catalytic method: Firstly, hexanoic acid and allyl alcohol performed esterification in catalysis of sulfuric acid. After the end of the reaction, the above esters were washed with water and then were neutralized with 15% Na2CO3 solution and washed with water to neutral. Add anhydrous sodium carbonate or anhydrous calcium chloride for dehydration. Finally, Allyl hexanoate were obtained by further filtration and vacuum distillation.

Technology Process of Allyl hexanoate

There total 11 articles about Allyl hexanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

allyl bromide (106-95-6) + hexanoic acid (142-62-1) → allyl hexanoate (123-68-2)

Guidance literature:

With cesium fluoride; In acetonitrile; for 2h; Heating;

DOI:10.1080/00397919808007177

Reference yield: 92.0%

allyl alcohol (107-18-6) + hexanoic acid (142-62-1) → allyl hexanoate (123-68-2)

Guidance literature:

With silica gel-immobilized perchloric acid; at 80 ℃; for 8h; Inert atmosphere; Neat (no solvent);

DOI:10.1021/jo900614s

Reference yield: 88.0%

sodium caproate (10051-44-2) + allyl bromide (106-95-6) → allyl hexanoate (123-68-2)

Guidance literature:

With polyethylene glycol 400; at 65 - 70 ℃; for 4h;

DOI:10.1080/00397910600941380

upstream raw materials:

allyl alcohol

hexanoic acid

diallyl butylmalonate

allyl bromide

Downstream raw materials:

hexanoic acid-(2,3-dibromo-propyl ester)

hexanoic acid

(E)-3-(2,5-dimethoxyphenyl)allyl hexanoate

(Z)-3-(2,5-dimethoxyphenyl)allyl hexanoate

Refernces

• 1、 Deulofeu. "". . p. 528. Retrieved 1928.
• 2、 Chakraborti, Asit K.,Singh, Bavneet,Chankeshwara, Sunay V.,Patel, Alpesh R.. "Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols". supporting information; experimental part. p. 5967 - 5974. Retrieved 2009/12/24.