3012-69-9

Basic information

• Product Name: methyl 9,10-12,3-diepoxystearate
• Synonyms: methyl 9,10-12,3-diepoxystearate;9,10:12,13-DIEPOXYSTEARICACID;3-[(3-Pentyloxiran-2-yl)methyl]-2-oxiraneoctanoic acid;9,10:12,13-Diepoxyoctadecanoic acid
• CAS NO: 3012-69-9
• Molecular Formula: C18H32 O4
• Molecular Weight: 312.50
• Mol File: 3012-69-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 77.8-78.2 °C
• Boiling Point: 372.36°C (rough estimate)
• Flash Point: 153.1°C
• Appearance: /
• Density: 0.9998 (rough estimate)
• Vapor Pressure: 2.86E-09mmHg at 25°C
• Refractive Index: 1.4397 (estimate)
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: methyl 9,10-12,3-diepoxystearate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 9,10-12,3-diepoxystearate(3012-69-9)
• EPA Substance Registry System: methyl 9,10-12,3-diepoxystearate(3012-69-9)

Safety Data

• Hazardous Substances Data: 3012-69-9(Hazardous Substances Data)

Usage

Uses

9,10-12,13-Diepoxyoctadecanoic Acid is a fatty acid with epoxy groups that exists naturally in Sunflower Oil.

InChI:InChI=1/C18H32O4/c1-2-3-7-10-14-16(21-14)13-17-15(22-17)11-8-5-4-6-9-12-18(19)20/h14-17H,2-13H2,1H3,(H,19,20)

Upstream product

• 79-21-0 peracetic acid 
• 60-33-3 linoleic acid 
• 112-63-0 Methyl linoleate 
• 93-59-4 Perbenzoic acid 
• 64-19-7 acetic acid 
• 60-33-3 9,12-octadecadienoic acid 

Relevant articles and documents

Chemical modification of camelina oil based unsaturated fatty acid for renewable biolubricant base stock

A green and eco-friendly method for preparation of oleochemicals from Camelina oil was developed for possible application for bio-lubricant basestocks, The steps involved are consisting of epoxidation of Camelina oil based fatty acid followed by further branching with wide range of alcohol such as 2-propanol, n-butanol, isoamyl alcohol and 2-ethylhexanol. These products were evaluated with physico-chemical properties such as acid value, oxirane oxygen content (OOC), hydroxyl value, low temperature properties, viscosity at 40 and 100 °C, viscosity index and characterized by FTIR, 1H NMR. The appearance of peak at 824 cm-1 in the FTIR spectra was due to the formation of epoxy group and broad peak appeared at 3500-3300 cm-1 is for hydrogen bonded O-H stretching vibration of hydroxy group. The 1H NMR spectra showed a signal at 2.9-3.2 ppm region indicated CH-proton attached to the oxygen atom of the both epoxy group for epoxidized product, peaks for newly formed secondary alcohols emerged at 4.25-3.35 in alkoxy derivatives. The Camelina based synthetic product may find application in biolubricants base stock.

Highly efficient epoxidation of vegetable oils catalyzed by a manganese complex with hydrogen peroxide and acetic acid

Epoxidized vegetable oils (EVOs) are versatile building blocks for lubricants, plasticizers, polyvinyl chloride (PVC) stabilizers, and surface coating formulations. In this paper, a catalytic protocol for the efficient epoxidation of vegetable oils is presented that is based on a combination of a manganese catalyst, H2O2 as an oxidant, and acetic acid as an additive. This protocol relies on the use of a homogeneous catalyst based on the non-noble metal manganese in combination with a racemic mixture of the N,N′-bis(2-picolyl)-2,2′-bispyrrolidine ligand (rac-BPBP). The optimized reaction conditions entail only 0.03 mol% of the manganese catalyst with respect to the number of double bonds (ca. 0.1 wt% with respect to the oil) and ambient temperature. This epoxidation protocol is highly efficient, since it allows most of the investigated vegetable oils, including cheap waste cooking oil, to be fully epoxidized to EVOs in more than 90% yield with excellent epoxide selectivities (>90%) within 2 h of reaction time. In addition, the protocol takes place in a biphasic reaction medium constituted by the vegetable oil itself and an aqueous acetic acid phase, from which the epoxidized product can be easily separated via simple extraction. In terms of efficiency and reaction conditions, the current epoxidation protocol outperforms previously reported catalytic protocols for plant oil epoxidation, representing a promising alternative method for EVO production.

Selective Epoxidation of Fatty Acids and Fatty Acid Methyl Esters by Fungal Peroxygenases

Recently discovered fungal unspecific peroxygenases from Marasmius rotula and Chaetomium globosum catalyze the epoxidation of unsaturated fatty acids (FA) and FA methyl esters (FAME), unlike the well-known peroxygenases from Agrocybe aegerita and Coprinopsis cinerea. Reactions of a series of unsaturated FA and FAME with cis-configuration revealed high (up to 100 %) substrate conversion and selectivity towards epoxidation, although some significant differences were observed between enzymes and substrates with the best results being obtained with the C. globosum enzyme. This and the M. rotula peroxygenase appear as promising biocatalysts for the environmentally-friendly production of reactive FA epoxides given their self-sufficient monooxygenase activity and the high conversion rate and epoxidation selectivity.