Methyl linolelaidate

Base Information

• Chemical Name: Methyl linolelaidate
• CAS No.: 2566-97-4
• Molecular Formula: C19H34O2
• Molecular Weight: 294.478
• European Community (EC) Number: 219-560-4,219-901-7
• UNII: JRB7ACQ5NW
• DSSTox Substance ID: DTXSID90880893
• Nikkaji Number: J280.486G,J45.228I,J47.156I
• Wikidata: Q27281652
• Mol file: 2566-97-4.mol

Synonyms:9,11-octadecadienoic acid, 13-hydroperoxy-, methyl ester, (9Z,11E);9,12-octadecadienoic acid (9Z,12Z)-, methyl ester, hydroperoxide;methyl (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate;methyl 13-hydroperoxy-cis,trans-9,11-octadecadienoate;methyl linoleate 13-hydroperoxide, (9Z,11E)-;methyl linoleate hydroperoxide

Chemical Property of Methyl linolelaidate

Chemical Property:

• Appearance/Colour: CLEAR COLORLESS LIQUID
• Refractive Index: 1.4580-1.4620
• Boiling Point: 373.3 °C at 760 mmHg
• Flash Point: 97 °C
• PSA: 26.30000
• Density: 0.884 g/cm³
• LogP: 5.97290
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 294.255880323
• Heavy Atom Count: 21
• Complexity: 279

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl trans,trans-9,12-Octadecadienoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F; Xn; N
• Hazard Codes: F,Xn,N
• Statements: 11-38-50/53-65-67
• Safety Statements: 9-16-29-33-60-61-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OC
• Isomeric SMILES: CCCCC/C=C/C/C=C/CCCCCCCC(=O)OC
• Uses: Methyl trans,trans-9,12-Octadecadienoate is a useful synthetic intermediate. It is an intermediate used to prepare (±)-trans-9,10-Epoxy-12(E)-octadecenoic acid methyl ester and (±)-trans-12,13-Epoxy-12(E)-octadecenoic acid methyl ester. It is also a biodiesel component that provides lubricity enhancement.

Technology Process of Methyl linolelaidate

There total 16 articles about Methyl linolelaidate 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: 93.8%

methanol (67-56-1) + 9,12-octadecadienoic acid (60-33-3,506-21-8,2197-37-7,2420-42-0,2420-55-5,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → linoleic acid methyl ester (2462-85-3,2566-97-4,20221-26-5,20221-27-6,112-63-0)

Guidance literature:

With toluene-4-sulfonic acid; at 60 ℃; for 6h; Inert atmosphere;

Reference yield:

methanol (67-56-1) → methyl α-eleostearate (4175-47-7) + linoleic acid methyl ester (2462-85-3,2566-97-4,20221-26-5,20221-27-6,112-63-0) + hexadecanoic acid methyl ester (112-39-0)

Guidance literature:

With sodium; at 55 ℃; for 1.5h; Overall yield = 48 g; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.jorganchem.2017.04.018

Reference yield:

methanol (67-56-1) + olive oil (8001-25-0) → octadec-9-enoic acid methyl ester (112-62-9) + linoleic acid methyl ester (2462-85-3,2566-97-4,20221-26-5,20221-27-6,112-63-0) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0)

Guidance literature:

With sodium hydroxide; at 40 - 45 ℃; for 6h; Product distribution / selectivity;

upstream raw materials:

methanol

Methyl linoleate

chlorine

toluene-4-sulfonic acid

Downstream raw materials:

azelaic acid

hexanoic acid

malonic acid

oxalic acid

Refernces

• 1、 Kovács, Ervin,Sághy, Péter,Turczel, Gábor,Tóth, Imre,Lendvay, Gy?rgy,Domján, Attila,Anastas, Paul T.,Tuba, Róbert. "Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species". supporting information. p. 213 - 217. Retrieved 2017/09/12.
• 2、 Dos Santos, Daiane S.,Piovesan, Luciana A.,D'Oca, Caroline R. Montes,Hack, Carolina R. Lopes,Treptow, Tamara G.M.,Rodrigues, Marieli O.,Vendramini-Costa, Débora B.,Ruiz, Ana Lucia T.G.,De Carvalho, Jo?o Ernesto,D'Oca, Marcelo G. Montes. "Antiproliferative activity of synthetic fatty acid amides from renewable resources". . p. 340 - 347. Retrieved 2015/02/02.