870-10-0

Basic information

• Product Name: 10-Oxostearic acid methyl ester
• Synonyms: 10-Oxooctadecanoic acid methyl ester;10-Oxostearic acid methyl ester;Methyl 10-ketostearate;Octadecanoic acid,10-oxo-,methyl ester
• CAS NO: 870-10-0
• Molecular Formula: C₁₉H₃₆O₃
• Molecular Weight: 312.49
• Mol File: 870-10-0.mol

Chemical Properties

• Melting Point: 46-47 °C
• Boiling Point: 407.8±28.0 °C(Predicted)
• Appearance: /
• Density: 0.911±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 10-Oxostearic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Oxostearic acid methyl ester(870-10-0)
• EPA Substance Registry System: 10-Oxostearic acid methyl ester(870-10-0)

Safety Data

• Hazardous Substances Data: 870-10-0(Hazardous Substances Data)

Usage

Chemical origin

Derived from stearic acid

Chemical structure

A 10-carbon chain with a ketone functional group at the 10th carbon and a methyl ester at the end of the chain

Industrial applications

Used as an intermediate in the production of various industrial and consumer products

Lubricant

Utilized as a lubricant in the manufacturing process

Emollient

Serves as an emollient in the production of cosmetics and personal care products

Surfactant

Acts as a surfactant in the creation of emulsions

Precursor

Serves as a precursor for the synthesis of other organic compounds, such as flavors, fragrances, and plasticizers

Regulatory approval

Included in the list of ingredients approved by the Cosmetic Ingredient Review Expert Panel for use in personal care products at certain concentrations

Usage in cosmetics

Commonly used in the manufacturing of cosmetics, pharmaceuticals, and emulsions

Upstream product

• 67-56-1 methanol 
• 112-80-1 cis-Octadecenoic acid 
• 112-62-9 Methyl oleate 
• 1115-01-1 erythro-9,10-dihydroxyoctadecanoic acid methyl ester 
• 7664-93-9 sulfuric acid 
• 104-15-4 toluene-4-sulfonic acid 
• 2566-91-8 epoxidized methyl oleate 
• 120-87-6 Dihydroxystearic Acid 
• 1115-01-1 methyl 9,10-dihydroxy stearate 
• 2500-59-6 (E)-9,10-epoxyoctadecanoic acid methyl ester 
• 2500-59-6 (Z)-9,10-epoxyoctadecanoic acid methyl ester 
• 507-40-4 tert-butylhypochlorite 

Downstream Products

• 638-26-6 10-hydroxystearic acid 
• 146064-84-8 C₂₉H₄₆O₆ 
• 104855-14-3 10-iodostearic acid 
• 111-20-6 1,10-decanedioic acid 
• 1357001-12-7 C₂₆H₄₃⁽²⁾HO₅S 
• 1357001-13-8 [10,10-²H₂]-4-nitrophenyl octadecanoate 
• 50613-98-4 10-doxylstearic acid 
• 35203-84-0 methyl 9-(2-octyl-3-oxyl-4,4-dimethyl-1,3-oxazolidine-2-yl)nonanoate 

Relevant articles and documents

Synthesis of fatty ketoesters by tandem epoxidation-rearrangement with heterogeneous catalysis

Unsaturated fatty esters can be easily transformed into ketoesters through a two-step process. The highly efficient epoxidation is carried out with tert-butyl hydroperoxide (TBHP) in α,α,α-trifluorotoluene (TFT) using a Ti-silica heterogeneous catalyst. The formed epoxide is easily rearranged by a heterogeneous Br?nsted acid, with Nafion-silica SAC13 as the most efficient one. Both reactions can be combined in a tandem process, with separation of the Ti-silica catalyst by filtration from the reaction medium and addition of the second acid catalyst to perform the second reaction. Each catalyst is separated individually and can be reused, with or without re-activation, under the same conditions to maximize the productivity.

Transformation of Unsaturated Fatty Acids/Esters to Corresponding Keto Fatty Acids/Esters by Aerobic Oxidation with Pd(II)/Lewis Acid Catalyst

Utilization of renewable biomass to partly replace the fossil resources in industrial applications has attracted attention due to the limited fossil feedstock with the increased environmental concerns. This work introduced a modified Wacker-type oxidation for transformation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, in which Cu2+ cation was replaced with common nonredox metal ions, that is, a novel Pd(II)/Lewis acid (LA) catalyst. It was found that adding nonredox metal ions can effectively promote Pd(II)-catalyzed oxidation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, even much better than Cu2+, and the promotional effect is highly dependent on the Lewis acidity of added nonredox metal ions. The improved catalytic efficiency is attributed to the formation of heterobimetallic Pd(II)/LA species, and the oxidation mechanism of this Pd(II)/LA catalyst is also briefly discussed.

Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones

Herein, the preparation of methyl oleate α-hydroxyketone from the corresponding 1,2-diol was investigated using both homogeneous and heterogeneous systems. Homogeneous conditions using a Pd(OAc)2/neocuproine complex were first developed using oxygen as a sole oxidant under mild conditions (MeOH, 50 °C). Under these conditions, the conversion of diol reached 95%, and α-hydroxyketone was obtained with 97% selectivity. The access to α-hydroxyketone has also been studied by dehydrogenation using a range of heterogeneous catalysts under solvent-free conditions at high temperatures (160-180 °C). Dehydrogenation using activated Ru/C under vacuum provided α-hydroxyketone with 93% conversion and 82% GC yield. The optimized conditions were applied to a range of oleochemical diols, including a vegetable oil derivative, to obtain the corresponding α-hydroxyketones with up to 74% isolated yields.

Dual functionality of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids: Surfactants with catalytic function

A series of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids were synthesized. Acidic hydrogen sulfate ionic liquids with the alkyl chains C6-C14 are characterized by good surface properties. Their surface properties (adsorption and micellization parameters, degree of ionization of micelles, Krafft temperatures and thermodynamic parameters) were determined. Synthesized ionic liquids were applied as a co-catalyst in an oxirane ring opening reaction in epoxidized fatty acid methyl esters (FAME). Their co-catalytic activities were determined and discussed as a function of their structure and surface properties. It was found that the co-catalytic properties, both conversion and selectivity, of alkylimidazolium hydrogen sulfate ionic liquids noticeably depended on the alkyl chain lengths, and in consequence their properties.

Process For Preparing A Carboxylic Acid

A process for preparing a carboxylic acid, including a step of bringing at least one vicinal diol or at least one vicinal polyol into contact with an atmosphere including oxygen, and a catalyst, and in the absence of additional solvent.

Influence of alkenyl structures on the epoxidation of unsaturated fatty acid methyl esters and vegetable oils

Epoxidation of vegetable oils or fatty acid methyl esters (FAMEs) produce important monomers which are widely used as plasticizers or stabilizers in the polymer industry. However, little attention has been focused on the influence of the alkenyl structure of the fatty acid on the efficiency and selectivity of their epoxidation. In this work, the influence of the alkenyl structure (the number of double bonds) of the FAMEs on the epoxidation reaction has been investigated. Three model FAMEs with 1 to 3 double bonds were epoxidized using both a weak (formic acid) and a strong (sulfuric acid/acetic acid) acid system. It was found that FAMEs with more double bonds have higher reactivities toward the epoxidation reaction. In addition, the electron-donating effect of the double bonds on the fatty acid chain tends to stabilize the resulting epoxide adjacent to it with the weak acid system. Furthermore, FAMEs with more double bonds easily undergo side reactions with the strong acid system (H2SO4). Epoxidation of two vegetable oils with different fatty acid compositions were carried out with the same two acid catalyst systems. And the results were in agreement with those from the FAMEs. The current findings could provide useful guidance for the epoxidation of different vegetable oils with different alkenyl structure compositions.

Highly efficient nano-sized TS-1 with micro-/mesoporosity from desilication and recrystallization for the epoxidation of biodiesel with H2O2

The epoxidation of the unsaturated fatty acid methyl esters (FAME) in biodiesel with H2O2 was investigated at 323 K in the liquid phase over microporous nano-sized TS-1 as well as micro-/mesoporous nano-sized TS-1. Nano-sized TS-1 with stacked morphology exhibits a catalytic activity per number of Ti sites up to 30% higher than a conventional, industrial TS-1 catalyst. Mesoporosity was successfully introduced by a desilication-recrystallization approach. Desilication by alkaline treatment in the presence of the structure-directing agent tetrapropylammonium cation (TPA+) or NaOH leads to the generation of undefined mesopores (10-40 nm), probably accompanied by an increase of the surface hydrophilicity. Consequently, the alkaline-treated materials show a two times lower catalytic activity in the epoxidation of biodiesel than the purely microporous parent material. The surfactant-assisted recrystallization of the alkaline-treated materials results in more uniform and smaller mesopores (3-10 nm). In the epoxidation, the recrystallized materials are remarkably more active with respect to both the purely microporous parent and alkaline-treated materials reaching a FAME conversion of 65% with an epoxide selectivity of 82%.

Highly efficient oxyfunctionalization of unsaturated fatty acid esters: An attractive route for the synthesis of polyamides from renewable resources

An efficient and environmentally benign strategy for the oxyfunctionalization of fatty acid methyl esters (FAMEs) employing molecular oxygen as an oxidizing agent is described. Keto-fatty acid esters were directly synthesized by co-catalyst-free Wacker oxidations employing oxygen as a sole re-oxidant. Amine functionalization of the thus obtained keto-fatty acid esters was achieved by reductive amination. The prepared renewable AB-type monomers were studied in homopolymerizations as well as in copolymerization reactions with hexamethylendimethylamine and dimethyl adipate to modify the properties of conventional Nylon 6,6. The obtained (co)-polymers were characterized by SEC, NMR and DSC analysis as well as water uptake tests. the Partner Organisations 2014.

PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES

The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

Practical and general palladium-catalyzed synthesis of ketones from internal olefins

Make it simple! A convenient and general palladium-catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed-oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features. Copyright