140-03-4

Basic information

• Product Name: O-ACETYLRICINOLEIC ACID METHYL ESTER
• Synonyms: O-ACETYLRICINOLEIC ACID METHYL ESTER;METHYL (Z)-12-ACETOXY-9-OCTADECENOATE;METHYL O-ACETYLRICINOLEATE;METHYL ACETYL RICINOLEATE;12-(acetyloxy)-,methylester,[R-(Z)]-9-Octadecenoicacid;12-(acetyloxy)-,methylester,[theta-(z)]-9-octadecenoicaci;9-Octadecenoic acid, 12-(acetyloxy)-, methyl ester, [R-(Z)]-;Flexricin P-4
• CAS NO: 140-03-4
• Molecular Formula: C₂₁H₃₈O₄
• Molecular Weight: 354.52
• EINECS: 205-392-9
• Product Categories: Functional Materials;Hydroxycarboxylic Acid Esters (Plasticizer);Plasticizer
• Mol File: 140-03-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: -26°C
• Boiling Point: 185°C 2mm
• Flash Point: 198°C
• Appearance: /
• Density: 0,94 g/cm3
• Vapor Pressure: 1.51E-07mmHg at 25°C
• Refractive Index: 1.4540-1.4580
• CAS DataBase Reference: O-ACETYLRICINOLEIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: O-ACETYLRICINOLEIC ACID METHYL ESTER(140-03-4)
• EPA Substance Registry System: O-ACETYLRICINOLEIC ACID METHYL ESTER(140-03-4)

Safety Data

• RTECS: VJ3410000
• Hazardous Substances Data: 140-03-4(Hazardous Substances Data)

Usage

Chemical Properties

Pale-yellow, low viscosity, oily liquid. Mild odor, Soluble in most organic liquids; insoluble in water. Combustible.

Uses

Different sources of media describe the Uses of 140-03-4 differently. You can refer to the following data:
1. Methyl Acetylricinoleate is a plasticizer; used in method for preparing agricultural mulching film using PVA/bio-based composite material.
2. Plasticizer, lubricant, protective coatings, synthetic rubbers, vinyl compounds.

InChI:InChI=1/C21H38O4/c1-4-5-6-13-16-20(25-19(2)22)17-14-11-9-7-8-10-12-15-18-21(23)24-3/h11,14,20H,4-10,12-13,15-18H2,1-3H3/b14-11-/t20-/m1/s1

Synthetic route

methyl ricinoleate (141-24-2) + acetyl chloride (75-36-5) → [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4)

Conditions	Yield
With pyridine In benzene for 2h; Heating;	98%
With pyridine In benzene

methyl ricinoleate (141-24-2) + acetic anhydride (108-24-7) → [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4)

Conditions	Yield
With [Hmim][HSO4] at 80℃; for 4h; Concentration; Temperature;	94.47%
With pyridine at 20℃;

methanol (67-56-1) + 12-O-acetylricinoleic acid (14936-79-9) → [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4)

Conditions	Yield
With toluene-4-sulfonic acid at 100℃; for 4h;	73%

Isopropenyl acetate (108-22-5) + methyl ricinoleate (41989-07-5) → [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) + (Z)-(S)-12-hydroxyoctadec-9-enoic acid methyl ester (84799-82-6)

Conditions	Yield
With Candida cylindrica lipase In hexane for 12h; Ambient temperature;	A 30% B 50%

methyl ricinoleate (41989-07-5) + acetic anhydride (108-24-7) → [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4)

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → Ricinoleic acid (141-22-0)

Conditions	Yield
With lithium hydroxide; water In tetrahydrofuran for 6h; Ambient temperature;	83%

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → methyl (12R)-acetoxy-9,10-dihydroxyoctadecanoate (1269416-82-1)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; acetic acid at 40℃; for 4h;	65%
Multi-step reaction with 2 steps 1: formic acid; dihydrogen peroxide / water / 6 h / 50 °C 2: phosphonic Acid / water / 3 h / 90 °C View Scheme

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → methyl 8-(3-((R)-2-acetoxyoctyl)oxiran-2-yl)octanoate

Conditions	Yield
With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide In water; acetonitrile at 25℃; for 24h;	35%
With formic acid; dihydrogen peroxide In water at 50℃; for 6h;

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → 12-acetoxy-octadecanoic acid methyl ester (2380-06-5)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → (9R,10S,12R)-12-acetoxy-9,10-epoxy-octadecanoic acid methyl ester (94904-75-3, 94943-30-3, 102518-16-1)

Conditions	Yield
With peracetic acid; diethyl ether

diazomethane (186581-53-3, 908094-01-9) + [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → methyl cis-(9S,10S,12R)-12-acetoxy-9,10-methyleneoctadecenoate + methyl cis-(9R,10R,12R)-12-acetoxy-9,10-methyleneoctadecenoate

Conditions	Yield
With palladium(II) acetylacetonate In diethyl ether at 0℃; for 2h;

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → (9R,10S,12R)-12-acetoxy-9,10-epoxy-octadecanoic acid methyl ester (94904-75-3, 94943-30-3, 102518-16-1) + 8-[(2S,3R)-3-((R)-2-Acetoxy-octyl)-oxiranyl]-octanoic acid methyl ester

Conditions	Yield
With monoperoxyphthalic acid In diethyl ether

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → C23H42O5

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / LiOH, H2O / tetrahydrofuran / 6 h / Ambient temperature 2: (i-Pr)2NEt/4-pyrrolidinopyridine / toluene / 2 h / Ambient temperature View Scheme

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → methyl 8-(5-((2R)-acetoxyoctyl)-2-oxo-1,3-dioxolan-4-yl)-octanoate + C22H38O7

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide; tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid / acetonitrile; water / 24 h / 25 °C 2: molybdenum(VI) oxide; tetrabutyl phosphonium bromide / neat (no solvent) / 20 h / 100 °C / 37503.8 Torr / Autoclave View Scheme

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → methyl 8-(3-acetoxy-5-hexyltetrahydrofuran-2-yl)octanoate + methyl 8-(3-acetoxy-5-hexyltetrahydrofuran-2-yl)octanoate

Conditions	Yield
Multi-step reaction with 3 steps 1: formic acid; dihydrogen peroxide / water / 6 h / 50 °C 2: phosphonic Acid / water / 3 h / 90 °C 3: 5 wt% ruthenium/carbon / neat (no solvent) / 3 h / 175 °C / 75.01 Torr / Inert atmosphere; Green chemistry View Scheme

Upstream product

• 108-22-5 Isopropenyl acetate 
• 41989-07-5 methyl ricinoleate 
• 67-56-1 methanol 
• 14936-79-9 12-O-acetylricinoleic acid 
• 141-24-2 methyl ricinoleate 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 

Downstream Products

• 141-22-0 Ricinoleic acid 

Relevant articles and documents

Boc2O mediated macrolactonisation: Syntheses of R-(+)-ricinoleic acid lactone and (±)-12-OH-stearic acid lactone

An efficient chemoenzymatic synthesis of R-(+)-ricinoleic acid lactone and (±)-12-OH-stearic acid lactone using Boc2O mediated macrolactonisation is reported.

Catalytic cyclopropanation of ricinolic acid derivatives with diazomethane

The reaction of ricinolic acid methyl ester with diazomethane in the presence of Co(BF4)2·6H2O results in selective methylation of the hydroxy group. Methyl (2Z, 12R)-12-acetoxy-9-octadecenoate reacts with diazomethane in the presence of Pd(acac)2, leading to formation of a mixture of cis-cyclopropanated (9S, 10S, 12/R)- and (9R, 10R, 12R)-diastereoisomers at a ratio of 3:2 (overall yield 73%). Under similar conditions methyl (9Z)-12-oxo-9-octadecenoate gives rise to optically inactive methyl cis-8-[2-(2-oxooctyl)-cyclopropyl]octanoate.

A process for the preparation of acetyl-ricinoleic acid methyl ester

The invention provides a preparation method of methyl acetylricinolate, the preparation method comprises the following steps: step a, using ionic liquid catalyst (Hmim) HSO4 for methyl esterification of castor oil to obtain methyl ricinoleate; and step b: using the ionic liquid catalyst (Hmim) HSO4 for acetylization of the methyl ricinoleate to obtain the methyl acetylricinolate. According to the preparation method, the (Hmim) HSO4 ionic liquid catalyst is used for methyl esterification and acetylation of the castor oil to obtain the methyl acetylricinolate, and the method has the advantages of simple production process, low cost and high product yield, and is conducive to the realization of the industrialized mass production of the methyl acetylricinolate.