Dibutyl itaconate

Base Information

• Chemical Name: Dibutyl itaconate
• CAS No.: 2155-60-4
• Molecular Formula: C13H22O4
• Molecular Weight: 242.315
• Hs Code.: 29171900
• European Community (EC) Number: 218-451-9
• NSC Number: 8487,5251
• DSSTox Substance ID: DTXSID5062213
• Nikkaji Number: J120.053D
• Wikidata: Q81989908
• Mol file: 2155-60-4.mol

Synonyms:Dibutyl itaconate;2155-60-4;Dibutyl 2-methylenesuccinate;Di(n-butyl) itaconate;dibutyl 2-methylidenebutanedioate;Butanedioic acid, methylene-, dibutyl ester;Itaconic acid, dibutyl ester;Itaconic acid di-n-butyl ester;NSC8487;Succinic acid, methylene-, dibutyl ester;Itaconic Acid Dibutyl Ester;dibutylitaconate;Butanedioic acid,2-methylene-, 1,4-dibutyl ester;bis(butyl) itaconate;1,4-dibutyl 2-methylidenebutanedioate;Dibutyl itaconate, 96%;SCHEMBL194857;Dibutyl 2-methylenesuccinate #;DTXSID5062213;NSC5251;NSC 5251;NSC 8487;NSC-5251;NSC-8487;EINECS 218-451-9;MFCD00027211;Dibutyl itaconate(stabilized with HQ);AKOS015916161;AS-59412;AI3-15511;Butanedioic acid, 2-methylene, dibutyl ester;CS-0187350;FT-0624679;I0201;A879029;Butanedioic acid, 2-methylene-, 1,4-dibutyl ester

Chemical Property of Dibutyl itaconate

Chemical Property:

• Vapor Pressure: 0.000728mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Boiling Point: 307.4 °C at 760 mmHg
• Flash Point: 142.2 °C
• PSA: 52.60000
• Density: 0.989 g/cm³
• LogP: 2.61930
• Storage Temp.: 2-8°C
• Water Solubility.: 74.8mg/L at 20℃
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 242.15180918
• Heavy Atom Count: 17
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

Dibutyl Itaconate (stabilized with HQ) >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCOC(=O)CC(=C)C(=O)OCCCC
• Uses: DBI is a monomer that can be copolymerized with pyridine groups to form nanocomposites for the development of bio-based elastomers. Copolymerization of DBI with acrylated epoxidized soya oil (AESO) can produce a thermoset material which finds potential applications in the modification of fatty acids.

Technology Process of Dibutyl itaconate

There total 7 articles about Dibutyl itaconate 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: 97.8%

2-methylenesuccinic acid (97-65-4,25119-64-6) + butan-1-ol (71-36-3) → di-n-butyl itaconate (2155-60-4)

Guidance literature:

With hydrogenated D₀₀₁ type strong acid cation exchange resin; at 115 ℃; for 4h; Temperature;

Reference yield: 58.0%

2-Ethylsulfanylmethyl-succinic acid dibutyl ester (108671-29-0) → di-n-butyl itaconate (2155-60-4)

Guidance literature:

With tetrabutylammomium bromide; ammonium chloride; In ethanol; electrolysis;

DOI:10.1016/S0040-4039(00)84941-2

Reference yield: 50.0%

dibutyl fumarate (105-75-9,29014-71-9) + N-(trimethylsilylmethyl)pyridinium triflate (89680-36-4) → di-n-butyl itaconate (2155-60-4)

Guidance literature:

With cesium fluoride; In 1,2-dimethoxyethane; for 24h; Heating;

DOI:10.1246/cl.1984.281

upstream raw materials:

2-methylenesuccinic acid

butan-1-ol

dibutyl fumarate

N-(trimethylsilylmethyl)pyridinium triflate

Downstream raw materials:

(S)-dimethyl 2-methylsuccinate

dibutyl 2-(acetoxy(phenyl)methyl)succinate

5-oxo-1-phenyl-pyrrolidine-3-carboxylic acid butyl ester

Refernces

• 1、 Lei, Weiwei,Wang, Runguo,Yang, Dan,Hou, Guanyi,Zhou, Xinxin,Qiao, He,Wang, Wencai,Tian, Ming,Zhang, Liqun. "Design and preparation of bio-based dielectric elastomer with polar and plasticized side chains". . p. 47429 - 47438. Retrieved 2015.
• 2、 Okuda, Tomoya,Ishimoto, Kiyoaki,Ohara, Hitomi,Kobayashi, Shiro. "Renewable biobased polymeric materials: Facile synthesis of itaconic anhydride-based copolymers with poly(l -lactic acid) grafts". . p. 4166 - 4174. Retrieved 2012.
• 3、 Boschert, David,Schneider-Chaabane, Alexandra,Himmelsbach, Andreas,Eickenscheidt, Alice,Lienkamp, Karen. "Synthesis and Bioactivity of Polymer-Based Synthetic Mimics of Antimicrobial Peptides (SMAMPs) Made from Asymmetrically Disubstituted Itaconates". . p. 8217 - 8227. Retrieved 2018/05/30.