9-Octadecenedioic acid, 1,18-dimethyl ester

Base Information

• Chemical Name: 9-Octadecenedioic acid, 1,18-dimethyl ester
• CAS No.: 13481-97-5
• Molecular Formula: C20H36O4
• Molecular Weight: 340.503
• European Community (EC) Number: 603-876-8
• DSSTox Substance ID: DTXSID10884616
• Mol file: 13481-97-5.mol

Synonyms:9-Octadecenedioic acid, 1,18-dimethyl ester;13481-97-5;dimethyl 9-octadecene-1,18-dioate;dimethyl-9-octadecenedioate;DTXSID10884616;HGGLIXDRUINGBB-UHFFFAOYSA-N

Chemical Property of 9-Octadecenedioic acid, 1,18-dimethyl ester

Chemical Property:

• Vapor Pressure: 3.43E-07mmHg at 25°C
• Boiling Point: 417.8oC at 760 mmHg
• Flash Point: 195.5oC
• PSA: 52.60000
• Density: 0.947g/cm3
• LogP: 5.35000
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 18
• Exact Mass: 340.26135963
• Heavy Atom Count: 24
• Complexity: 305

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC

Technology Process of 9-Octadecenedioic acid, 1,18-dimethyl ester

There total 113 articles about 9-Octadecenedioic acid, 1,18-dimethyl ester 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: 23.0%

Methyl oleate (112-62-9) → octadeca-9Z-ene (1779-13-1) + dimethyl (Z)-octadec-9-ene-1,18-dioate (13481-97-5,24753-49-9,40393-46-2) + Dimethyl (E)-octadec-9-enedioate (24753-49-9)

Guidance literature:

With tetradecane; C₄₅H₄₆N₂ORuS₂; In tetrahydrofuran; for 2h; Reagent/catalyst; Overall yield = 23 %; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/acs.organomet.7b00555

Reference yield: 22.0%

methyl (9E)-octadec-9-enoate (2462-84-2) → trans-9-octadecene (7206-25-9) + dimethyl (Z)-octadec-9-ene-1,18-dioate (13481-97-5,24753-49-9,40393-46-2) + Dimethyl (E)-octadec-9-enedioate (24753-49-9)

Guidance literature:

With tetradecane; C₄₁H₄₄N₂ORuS₂; In tetrahydrofuran; for 24h; Overall yield = 22 %; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/acs.organomet.7b00555

Reference yield:

methyl 9-decenoate (25601-41-6) → dimethyl (Z)-octadec-9-ene-1,18-dioate (13481-97-5,24753-49-9,40393-46-2) + Dimethyl (E)-octadec-9-enedioate (24753-49-9)

Guidance literature:

methyl 9-decenoate; at 35 ℃; for 16h;

tris(hydroxymethyl)phosphine; at 90 ℃; for 4h; Product distribution / selectivity;

upstream raw materials:

cis-16-bromo-9-hexadecenoic acid methyl ester

sodium diethylmalonate

Methyl oleate

9-octadecyne-1,18-dioic acid dimethyl ester

Downstream raw materials:

methyl 9-decenoate

methyl 10-cyano-dec-9-enoate

methyl (Z)-10-cyano-9-decenoate

methyl (E)-10-cyano-9-decenoate

Refernces

• 1、 Xiaoding, Xu,Mol, J. C.. "Re2O7/SiO2*Al2O3-SnR4 or -PbR4, a Highly Active Catalyst for the Metathesis of Functionalized Alkenes". . p. 631 - 633. Retrieved 1985.
• 2、 Brunow, Goesta,Stick, Robert V.,Syrjaenen, Kaisa,Tilbrook, D. Matthew G.,Williams, Spencer J.. "A Synthesis of (Z)-Octadec-9-enedioic Acid". . p. 1893 - 1898. Retrieved 1995.
• 3、 Grubbs, Robert H.,Samkian, Adrian E.,Virgil, Scott C.,Xu, Yan,Yoon, Ki-Young. "Synthesis and Activity of Six-Membered Cyclic Alkyl Amino Carbene-Ruthenium Olefin Metathesis Catalysts". . . Retrieved 2020.
• 4、 Johns, Adam M.,Fiamengo, Bryan A.,Herron, Jessica R.,Bourg, Jean-Baptiste,Doppiu, Angelino,Karch, Ralf,Pederson, Richard L.. "Cis-Dichloro Sulfoxide Ligated Ruthenium Metathesis Precatalysts". . p. 218 - 222. Retrieved 2019.
• 5、 Zelin, Juan,Trasarti, Andrés F.,Apesteguía, Carlos R.. "Self-metathesis of methyl oleate on silica-supported Hoveyda-Grubbs catalysts". . p. 84 - 88. Retrieved 2013.
• 6、 Zelin,Nieres,Trasarti,Apesteguía. "Valorisation of vegetable oils via metathesis reactions on solid catalysts: Cross-metathesis of methyl oleate with 1-hexene". . p. 410 - 417. Retrieved 2015.
• 7、 Xiaoding, Xu,Boelhouwer, Cornelis,Benecke, Jeanet I.,Vonk, Douwe,Mol, Johannes C.. "Re2O7/Al2O3*B2O3 Metathesis Catalysts". . p. 1945 - 1954. Retrieved 1986.
• 8、 Johns, Adam M.,Ahmed, Tonia S.,Jackson, Bradford W.,Grubbs, Robert H.,Pederson, Richard L.. "High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention". . p. 772 - 775. Retrieved 2016.
• 9、 Byun, Seunghwan,Seo, Huiyeong,Choi, Jun-Ho,Ryu, Ji Yeon,Lee, Junseong,Chung, Won-Jin,Hong, Sukwon. "Fluoro-imidazopyridinylidene Ruthenium Catalysts for Cross Metathesis with Ethylene". . p. 4121 - 4132. Retrieved 2019.
• 10、 Aydos, Guilherme L.P.,Leal, Bárbara C.,Perez-Lopez, Oscar W.,Dupont, Jairton. "Ionic-tagged catalytic systems applied to the ethenolysis of methyl oleate". . p. 57 - 61. Retrieved 2014.