Dibutyl sebacate

Base Information

• Chemical Name: Dibutyl sebacate
• CAS No.: 109-43-3
• Deprecated CAS: 39393-66-3,98781-27-2
• Molecular Formula: C18H34O4
• Molecular Weight: 314.466
• Hs Code.: 29171390
• European Community (EC) Number: 203-672-5
• ICSC Number: 1349
• NSC Number: 3893
• UNII: 4W5IH7FLNY
• DSSTox Substance ID: DTXSID1041847
• Nikkaji Number: J1.968B
• Wikipedia: Dibutyl_sebacate
• Wikidata: Q411272
• NCI Thesaurus Code: C76705
• RXCUI: 1363700
• Metabolomics Workbench ID: 49288
• ChEMBL ID: CHEMBL2106225
• Mol file: 109-43-3.mol

Synonyms:dibutyl sebacate;dibutylsebacate

Chemical Property of Dibutyl sebacate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 4.14E-05mmHg at 25°C
• Melting Point: -10 ºC
• Refractive Index: n20/D 1.441(lit.)
• Boiling Point: 351.3 ºC at 760 mmHg
• Flash Point: 157.5 ºC
• PSA: 52.60000
• Density: 0.945 g/cm³
• LogP: 4.79380
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: hexane, toluene, ethanol and acetone: soluble
• Water Solubility.: 50mg/L(temperature not stated)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 17
• Exact Mass: 314.24570956
• Heavy Atom Count: 22
• Complexity: 248

Purity/Quality:

99% min ^*data from raw suppliers

Aniline red ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 40-36/37/38
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCCCOC(=O)CCCCCCCCC(=O)OCCCC
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: Dibutyl sebacate (DBS) is a dibutyl ester of sebacic acid. Dibutyl sebacate can be used for plastics in use in the food packaging industry, in plastics used for medical devices, and for pharmaceutical applications. Dibutyl sebacate is also used as a desensitizer in Otto fuel II, a torpedo monopropellant. Dibutyl sebacate has been used as a plasticizer to prepare free ethylcellulose films. It can be utilized as a core in liquid-core capsules with cross-linked alginate/polyacrylamide membrane prepared via co-extrusion jet-break-up method for the extraction of the pesticide, atrazine.

Technology Process of Dibutyl sebacate

There total 8 articles about Dibutyl 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: 96.0%

1,10-decanedioic acid (111-20-6,26776-29-4) + butan-1-ol (71-36-3) → dibutyl sebacate (109-43-3)

Guidance literature:

With triflic acid on silica-encapsulated superparamagnetic iron oxide nanoparticles; In neat (no solvent); at 90 ℃; for 0.25h; Time; Reagent/catalyst; Catalytic behavior; Flow reactor; Green chemistry;

DOI:10.1039/C8RA07838F

Reference yield: 93.0%

1,10-decanedioic acid (111-20-6,26776-29-4) + n-butyl formate (592-84-7) → Decanedioic acid monobutyl ester (5278-98-8) + dibutyl sebacate (109-43-3)

Guidance literature:

With Dowex 50W-X₂ (50-100 mesh); In octane; at 100 ℃; for 4.33333h;

DOI:10.1016/S0040-4039(96)01454-2

Reference yield:

octa-1,3-diene (1002-33-1) + carbon monoxide (201230-82-2) + butan-1-ol (71-36-3) → dibutyl sebacate (109-43-3)

Guidance literature:

With palladium(II) trifluoroacetate; HeMaRaphos; toluene-4-sulfonic acid; In toluene; at 120 ℃; for 24h; under 30003 Torr; regioselective reaction;

DOI:10.1126/science.aaz1293

upstream raw materials:

1,10-decanedioic acid

butan-1-ol

sebacoyl chloride

1-bromo-butane

Downstream raw materials:

1,10-Decanediol

decanedioic acid benzyl ester-butyl ester

1,8-Bis<4,6-diamino(1,3,5)triazin-2-yl>octan

1,10-decanedioic acid

Refernces

• 1、 Szelwicka, Anna,Boncel, S?awomir,Jurczyk, Sebastian,Chrobok, Anna. "Exceptionally active and reusable nanobiocatalyst comprising lipase non-covalently immobilized on multi-wall carbon nanotubes for the synthesis of diester plasticizers". . p. 41 - 47. Retrieved 2019/02/07.
• 2、 Tashi, Maryam,Shafiee, Behnaz,Sakamaki, Yoshie,Hu, Ji-Yun,Heidrick, Zachary,Khosropour, Ahmad R.,Beyzavi, M. Hassan. "Micro-flow nanocatalysis: synergic effect of TfOH@SPIONs and micro-flow technology as an efficient and robust catalytic system for the synthesis of plasticizers". . p. 37835 - 37840. Retrieved 2018/11/26.