1732-10-1

Basic information

• Product Name: Dimethyl azelate
• Synonyms: DIMETHYL AZELATE, TECH., 80%;AZELAIC ACID DIMETHYL ESTER 98+%;Dimethylazelat;Dimethyl nonanedioate, Methyl azelate;Nonanedioic acid dimethyl;Dimethyl azelate,Dimethyl nonanedioate, Methyl azelate;Azelaic Acid Dimethyl Ester Dimethyl Nonanedioate Nonanedioic Acid Dimethyl Ester;NONANEDIOIC ACID DIMETHYL ESTER
• CAS NO: 1732-10-1
• Molecular Formula: C₁₁H₂₀O₄
• Molecular Weight: 216.27
• EINECS: 217-060-0
• Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer
• Mol File: 1732-10-1.mol
• Article Data: 41

Chemical Properties

• Melting Point: 18 °C
• Boiling Point: 156 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.007 g/mL at 25 °C(lit.)
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.435(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: 863mg/L at 25℃
• Merck: 905
• BRN: 1710125
• CAS DataBase Reference: Dimethyl azelate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl azelate(1732-10-1)
• EPA Substance Registry System: Dimethyl azelate(1732-10-1)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 1732-10-1(Hazardous Substances Data)

Usage

Description

Dimethyl azelate, also known as dimethyl nonanedioate, is an organic compound belonging to the family of dicarboxylic esters. It is a colorless transparent liquid with a slight odor and is derived from azelaic acid, which is found in various plant sources. Dimethyl azelate is known for its versatile applications across different industries due to its unique chemical properties.

Uses

Used in Lubricant Industry:
Dimethyl azelate is used as a complexing agent in the production of lithium soap and lithium complex greases, which are the most widely used multipurpose greases. The fatty acid portion in these greases is often 12-hydroxystearic acid, made from hydrogenated castor oil. The use of dimethyl azelate enhances the performance and stability of these greases, making them suitable for various applications.
Used in Analytical Chemistry:
Dimethyl azelate is employed in analytical studies for determining particulate matter in air. Its chemical properties make it a valuable reagent in the process of identifying and quantifying airborne particles, which is crucial for understanding air quality and its impact on human health and the environment.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H20O4/c1-14-10(12)8-6-4-3-5-7-9-11(13)15-2/h3-9H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 123-99-9 azelaic acid 
• 32853-28-4 non-4-enedioic acid dimethyl ester 
• 186581-53-3 diazomethane 
• 112-63-0 Methyl linoleate 
• 301-00-8 methyl linolenate 
• 112-62-9 Methyl oleate 
• 56555-02-3 methyl 9-chloro-9-oxononanoate 
• 101-34-8 castor oil acetate 
• 112-80-1 cis-Octadecenoic acid 
• 1123248-65-6 1,22-cis-9-docosenedioic acid 
• 20701-68-2 (9Z)-octadec-9-enedioic acid 
• 120-87-6 Dihydroxystearic Acid 
• 1115-01-1 methyl 9,10-dihydroxy stearate 

Downstream Products

• 2104-19-0 azelaic monomethyl ester 
• 22092-58-6 2,10-dimethyl-2,10-undecanediol 
• 3937-56-2 1,9-Nonanediol 
• 3788-56-5 9-hydroxynonanoic acid 
• 496-83-3 2-Hydroxy-1-cyclononanon 
• 5452-73-3 methyl 2-oxocyclooctanecarboxylate 
• 13688-67-0 1,10-undecadiene 
• 65850-96-6 1,11-Bis-(toluene-4-sulfonyl)-undecane-2,10-diol 
• 4549-33-1 1,9-Dibromononane 
• 4900-30-5 nona-1,8-diene 
• 3669-80-5 11-hydroxyundecanoic acid 
• 51308-99-7 9-chloro-1-nonanol 
• 55362-80-6 9-bromononan-1-ol 
• 2834-05-1 11-bromoundecanoic acid 

Relevant articles and documents

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FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

Synthesis of Branched Biolubricant Base Oil from Oleic Acid

The mature manufacturing of synthetic lubricants (poly-α-olefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C45 biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C9 chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C45 biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C9 bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of value-added biolubricant base oils.

Conversion of oleic acid into azelaic and pelargonic acid by a chemo-enzymatic route

A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H2O2 is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO3)3·9·H2O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H2O2 in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid.