Sebacic acid

Base Information

• Chemical Name: Sebacic acid
• CAS No.: 111-20-6
• Molecular Formula: C10H18O4
• Molecular Weight: 202.251
• Hs Code.: 2917131000
• European Community (EC) Number: 203-845-5
• ICSC Number: 1685
• NSC Number: 19492
• UNII: 97AN39ICTC
• DSSTox Substance ID: DTXSID7026867
• Nikkaji Number: J10.109E
• Wikipedia: Sebacic_acid
• Wikidata: Q413454
• NCI Thesaurus Code: C84144
• RXCUI: 1427068
• Metabolomics Workbench ID: 1930
• ChEMBL ID: CHEMBL1232164
• Mol file: 111-20-6.mol

Synonyms:Sebacic acids;1, 10-Decanedioic acid;Sebacicacid;1,10-decanedioic acid;Sebacinsaeure;Decanedioic acid;Usaf hc-1;Decanedicarboxylic acid;1,8-Octanedicarboxylic acid;

Chemical Property of Sebacic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Melting Point: 131–134.5 °C
• Refractive Index: 1.422
• Boiling Point: 374.3 °C at 760 mmHg
• Flash Point: 198.3 °C
• PSA: 74.60000
• Density: 1.106 g/cm³
• LogP: 2.27640
• Water Solubility.: 1 g/L (20℃)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 202.12050905
• Heavy Atom Count: 14
• Complexity: 157

Purity/Quality:

99% min ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S36:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(CCCCC(=O)O)CCCC(=O)O
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Chemical Composition and Structure: Sebacic acid is a ten-carbon aliphatic dicarboxylic acid with the chemical formula C10H18O4. It has a linear structure with two carboxylic acid functional groups.
• Chemistry Applications: Sebacic acid is used in the synthesis of polymers such as liquid crystal copolyesters and hydroxyapatite crystals.^[2]
• Medical Applications: Sebacic acid plays a role in bone tissue engineering as an additive in the synthesis of hydroxyapatite crystals.
• Production Methods: Sebacic acid can be synthesized from castor oil through a series of chemical transformations involving oxidation, isomerization, dihydroxylation, and hydrolysis.^[3]
• Analysis Method: Sebacic acid and its intermediates can be characterized using chromatographic and spectral analysis techniques such as 1H and 13C-NMR, high-resolution mass spectrometry, Fourier-transform infrared spectroscopy, Raman spectroscopy, XRD, and transmission electron microscopy.
• References: [1] Mechanism and Kinetics of Lipase-Catalyzed Polycondensation of Glycerol and Sebacic Acid: Influence of Solvent and Temperature; DOI 10.1021/acs.biomac.2c00458; [2] On the Crystallization of Hydroxyapatite under Hydrothermal Conditions: Role of Sebacic Acid as an Additive; DOI 10.1021/acsomega.0c03297; [3] Design and Synthesis of Sebacic Acid from Castor Oil by New Alternate Route; DOI 10.1002/ejlt.202100244

Technology Process of Sebacic acid

There total 218 articles about Sebacic acid 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: 51.0%

10-undecenoic acid (112-38-9) → 1,10-decanedioic acid (111-20-6,26776-29-4) + ω-oxydecanocarboxylic acid (5578-80-3)

Guidance literature:

10-undecenoic acid; With ozone; In dichloromethane; Inert atmosphere;

With semicarbazide hydrochloride; at 0 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1007/s10600-014-1031-8

Reference yield: 12.0%

→ 1,10-decanedioic acid (111-20-6,26776-29-4) + rac-octan-2-ol (4128-31-8,113301-48-7,4128-32-9) + hexyl-methyl-ketone (111-13-7)

Guidance literature:

at 240 ℃; for 7h;

DOI:10.1016/S0040-4020(01)99322-6

Reference yield:

2-methyldecanal (19009-56-4) + Castor oil (8001-79-4) → 1,10-decanedioic acid (111-20-6,26776-29-4) + rac-octan-2-ol (4128-31-8,113301-48-7,4128-32-9) + 2-methyl decanoic acid (24323-23-7) + hexyl-methyl-ketone (111-13-7)

Guidance literature:

2-methyldecanal; Castor oil; With sodium hydroxide; In water; at 200 - 300 ℃;

With sulfuric acid; In water; Product distribution / selectivity;

upstream raw materials:

1,4-dibromo-butane

peracetic acid

undec-10-ynoic acid

1 ,6-dibromohexane

Downstream raw materials:

1,10-di(piperidin-1-yl)decane-1,10-dione

decanedioic acid bis-tetrahydrofurfuryl ester

1,7-dioxa-cycloheptadecane-8,17-dione

1,6-dioxa-cyclohexadecane-7,16-dione

Refernces

• 1、 Taylor. "". . p. 4562,4564. Retrieved 1960.
• 2、 Schneider, Carolin,Franke, Robert,Jackstell, Ralf,Beller, Matthias. "A direct synthesis of carboxylic acidsviaplatinum-catalysed hydroxycarbonylation of olefins". . p. 2703 - 2707. Retrieved 2021.
• 3、 Hawkins. "-". . p. 3463,3466. Retrieved 1955.
• 4、 Gabriel, Adeyemi Francis,Li, Zhen,Kusuda, Ryouhei,Tanaka, Chiaki,Miyamoto, Tomofumi. "Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp.". . p. 469 - 475. Retrieved 2015.
• 5、 Saito,Nagata,Yuba,Matsuura. "Synthesis of α,ω-dicarboxylic acids and unsaturated carboxylic acids from silyl enol ethers". . p. 4439 - 4442. Retrieved 1983.
• 6、 Wynberg,H.,Bantjes,A.. "-". . p. 1447 - 1450. Retrieved 1960.
• 7、 Narula,Dev. "". . p. 1733. Retrieved 1969.
• 8、 Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji. "Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols". supporting information. p. 20394 - 20398. Retrieved 2020/09/21.