Diethyl sebacate

Base Information

• Chemical Name: Diethyl sebacate
• CAS No.: 110-40-7
• Molecular Formula: C14H26O4
• Molecular Weight: 258.358
• Hs Code.: 29171390
• European Community (EC) Number: 203-764-5
• NSC Number: 8911
• UNII: I41B9FJK6V
• DSSTox Substance ID: DTXSID0021915
• Nikkaji Number: J5.519K
• Wikidata: Q27280379
• NCI Thesaurus Code: C77461
• RXCUI: 1426475
• Metabolomics Workbench ID: 49038
• ChEMBL ID: CHEMBL1884461
• Mol file: 110-40-7.mol

Synonyms:diethyl decanedioate;diethyl sebacate;ethyl sebacate;sebacic acid diethyl ester

Chemical Property of Diethyl sebacate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 0.000544mmHg at 25°C
• Melting Point: 1-2 °C(lit.)
• Refractive Index: n20/D 1.436(lit.)
• Boiling Point: 312 °C at 760 mmHg
• Flash Point: 135 °C
• PSA: 52.60000
• Density: 0.969 g/cm³
• LogP: 3.23340
• Storage Temp.: Store below +30°C.
• Solubility.: <0.1g/l
• Water Solubility.: slightly soluble
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 258.18310931
• Heavy Atom Count: 18
• Complexity: 202

Purity/Quality:

99.9% ^*data from raw suppliers

Diethyl Sebacate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)CCCCCCCCC(=O)OCC
• Description: Dibutyl sebacate (DBS) is an organic colorless liquid chemical, a dibutyl ester of sebacic acid.Its main use is as a plasticizer in production of plastics, namely cellulose acetate butyrate, cellulose acetate propionate, ethyl cellulose, polyvinyl butyral, polyvinyl chloride, polystyrene, and many synthetic rubbers (especially nitrile rubber and neoprene) and other plastics. It can be used for plastics in use in the food packaging industry, in plastics used for medical devices, and for pharmaceutical applications, e.g. as a plasticizer for film coating of tablets, beads, and granules.[2] It is also used as a lubricant in shaving lotions, and a flavoring additive in non-alcoholic beverages, ice cream, ices, candy, and baked goods. It provides excellent compatibility with a range of plastic materials, superior properties at low temperatures, and good oil resistivity. Its other names include Morflex, Kodaflex, polycizer, Proviplast 1944 and PX 404. Dibutyl sebacate is also used as a desensitizer in Otto fuel II, a torpedo monopropellant.
• Uses: A permitted flavoring listed in GB 2760-96. Mainly used in the preparation of grapes, pears and other flavors and fruit flavor solvent. In addition, it is often used as plasticizer for resin and vinyl resin as its better compatibility with nitrocellulose and butyl acetate cellulose. It can also be used as synthesis solvent for organic synthesis, solvents and pigments, pharmaceutical intermediates and polymers compound. Diethyl Sebacate is a flavoring agent that is a liquid, colorless to pale yellow in appearance with a slight odor. it is insoluble in water and miscible in alcohol, ether, and other organic solvents. it is obtained by chemical synthesis. it is also termed ethyl sebacate.
• Production method: It is derived by esterification of succinic anhydride and ethanol; It can also be obtained through heating esterification of sebacic acid and ethanol in the presence of concentrated sulfuric acid.

Technology Process of Diethyl sebacate

There total 7 articles about Diethyl sebacate 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: 98.0%

1,10-decanedioic acid (111-20-6,26776-29-4) + ethanol (64-17-5) → diethyl sebacate (110-40-7)

Guidance literature:

for 2h; Reflux; Acidic conditions;

DOI:10.1039/c0ob00683a

Reference yield: 37.0%

1,10-decanedioic acid (111-20-6,26776-29-4) + ethanol (64-17-5) → monoethyl sebacate (693-55-0) + diethyl sebacate (110-40-7)

Guidance literature:

With sulfuric acid; In cyclohexane; water; for 24h;

DOI:10.1021/la204412t

Reference yield:

bis-(5-ethoxycarbonyl-valeryl)-peroxide (42367-85-1) → ethyl n-valerate (539-82-2) + ethyl 4-pentenoate (1968-40-7) + diethyl adipate (141-28-6) + diethyl sebacate (110-40-7)

Guidance literature:

bei der explosiven Zersetzung;

upstream raw materials:

1,10-decanedioic acid

ethanol

adipinic acid monoethyl ester

monoethyl sebacate

Downstream raw materials:

cyclononanone

cyclooctadecane-1,10-dione

monoethyl sebacate

4-diethylamino-o-toluidine

Refernces

• 1、 Zhang, Yong,Fu, Qi,Shi, Wenfang. "Synthesis and intrinsic blue fluorescence study of hyperbranched poly(ester-amide-ether)". . p. 2452 - 2460. Retrieved 2010.
• 2、 Chen, Zhe,Han, Sheng,Lu, Deli,Xu, Yumeng. "Biomass-derived dibasic acids to diesters with inorganic ligand-supported catalyst: synthesis, optimization, characterization". . . Retrieved 2021/08/23.
• 3、 -. "METHOD FOR CONTINUOUSLY PREPARING CARBOXYLIC ACID ESTER". Paragraph 0030; 0034. . Retrieved 2013/11/19.