22348-93-2

Basic information

• Product Name: methyl 9-chloro-10-hydroxyoctadecanoate
• CAS NO: 22348-93-2
• Molecular Formula: C₁₉H₃₇ClO₃
• Molecular Weight: 348.9483
• Mol File: 22348-93-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 426.7°C at 760 mmHg
• Flash Point: 211.8°C
• Density: 0.982g/cm³
• Vapor Pressure: 4.55E-09mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: methyl 9-chloro-10-hydroxyoctadecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 9-chloro-10-hydroxyoctadecanoate(22348-93-2)
• EPA Substance Registry System: methyl 9-chloro-10-hydroxyoctadecanoate(22348-93-2)

Safety Data

• Hazardous Substances Data: 22348-93-2(Hazardous Substances Data)

Upstream product

• 2500-59-6 (Z)-9,10-epoxyoctadecanoic acid methyl ester 
• 104-76-7 2-Ethylhexyl alcohol 
• 112-62-9 Methyl oleate 
• 75-65-0 tert-butyl alcohol 
• 78-83-1 2-methyl-propan-1-ol 
• 67-63-0 isopropyl alcohol 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 2566-91-8 epoxidized methyl oleate 
• 24560-98-3 cis-9,10-epoxystearic acid 
• 186581-53-3 diazomethane 
• 2632-61-3 (+/-)-threo-9-chloro-10-hydroxy-octadecanoic acid 

Relevant articles and documents

Synthesis of chloro alkoxy and alkoxy derivatives of methyl oleate

Vegetable oil based lubricants typically have improved lubricity and biodegradability over their mineral oil based counterparts. However, vegetable oil lubricants often fail to meet the performance standards of mineral based oils with respect to cold temperature and resistance to oxidation. Olefins are an oxidatively weak point for vegetable based compounds. Removal of the olefin in a vegetable based lubricant through functionalization may increase resistance to oxidation. If the added functionality also causes branching of the alkyl chain, cold temperature properties may be improved. Any chemical modifications considered must be scalable and cost-effective to be useful in a commercial application. In this study, methyl oleate was functionalized into a chloro alkoxy derivative. Sodium hypochlorite (household bleach) and calcium hypochlorite were both used to generate hypochlorous acid in situ. Hypochlorous acid and a series of alcohols (methanol, ethanol, and butanol) were reacted with methyl oleate to make chloro alkoxy compounds in 29.8-77.9 % yields. In an effort to make a branched saturated ether we removed the chlorine moiety of the chloro alkoxy compounds. Dehalogenation was achieved under basic conditions over a Pd/C catalyst in 2-propanol. Reaction times increased substantially as the size of the adjacent alkoxy group increased. The reaction rate could be improved by heating the reactions above 100 C in a pressure reactor. Increased reaction temperature also resulted in an increase in ketone side products from the competing elimination reactions. Saturated ether yields were 4.1-43.2 %.

Studies on Nitrosochlorination: Part II - Reaction of Epoxy Fatty Acids, a Route to the Synthesis of Alkyl Nitrites

Nitrosochlorination of methyl 10,11-epoxyundecanoate (I) and methyl 9,10-epoxyoctadecanoate (IV) yields the respective chloronitrites (II and V) and chlorohydrins (III and VI).However, methyl 12,13-epoxyoctadec-cis-9-enoate (VII; methyl vernolate) on similar treatment for 30 min yields only the double bond addition products (VIII) and (IX) while treatment for a longer period (1h) involves addition as well as cleavage reactions to give three products (X, XI and XII).Structures of all the reaction products have been established on the basis of chemical and spectral evidences.