1842-70-2

Usage

Uses

Used in Chemical Industry:
METHYL 10-OXOOCTADECANOATE is used as a chemical intermediate for the synthesis of various compounds and materials, such as lubricants, plasticizers, and additives, due to its long-chain aliphatic structure and ester functionality.
Used in Pharmaceutical Industry:
METHYL 10-OXOOCTADECANOATE is used as an active pharmaceutical ingredient or a precursor in the development of drugs targeting specific medical conditions, leveraging its unique chemical properties and reactivity.
Used in Cosmetics Industry:
METHYL 10-OXOOCTADECANOATE is used as an ingredient in the formulation of cosmetics and personal care products, such as creams, lotions, and shampoos, for its emollient, moisturizing, and conditioning effects on the skin and hair.
Used in Flavor and Fragrance Industry:
METHYL 10-OXOOCTADECANOATE is used as a component in the creation of flavors and fragrances, taking advantage of its unique scent profile and ability to enhance or modify the aroma of various products.
Used in Research and Development:
METHYL 10-OXOOCTADECANOATE is utilized as a research compound for studying its properties, reactivity, and potential applications in various fields, including material science, biotechnology, and nanotechnology.

InChI:InChI=1/C19H36O3/c1-3-4-5-6-7-9-12-15-18(20)16-13-10-8-11-14-17-19(21)22-2/h3-17H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 507-40-4 tert-butylhypochlorite 
• 112-62-9 Methyl oleate 
• 4114-74-3 9-oxo-octadecanoic acid 
• 693-58-3 1-Bromononane 
• 56555-02-3 methyl 9-chloro-9-oxononanoate 
• 2447-53-2 9-hydroxy-octadecanoic acid methyl ester 
• 71201-23-5 methyl 9-oxo-trans-10,trans-12-octadecadienoate 
• 95336-35-9 6-hexyl-3-(7-methoxycarbonylheptyl)-3,6-dihydro-1,2-dioxine 
• 64-19-7 acetic acid 
• 2500-59-6 (E)-9,10-epoxyoctadecanoic acid methyl ester 
• 2500-59-6 (Z)-9,10-epoxyoctadecanoic acid methyl ester 
• 1115-01-1 erythro-9,10-dihydroxyoctadecanoic acid methyl ester 
• 7664-93-9 sulfuric acid 

Downstream Products

• 4114-74-3 9-oxo-octadecanoic acid 
• 2097130-84-0 9-PAHSA 

Relevant academic research and scientific papers

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.

Fatty ketones from the rearrangement of epoxidized vegetable oils

The rearrangement of epoxidized vegetable oils to produce fatty ketones, catalyzed by acidic resins, is disclosed. The non-microbial production of fatty ketones from epoxidized vegetable oils has not been previously reported. Some of the variables affecti

Diethylene Glycol/NaBr Catalyzed CO2 Insertion into Terminal Epoxides: From Batch to Continuous Flow

CO2 insertion reactions on terminal epoxides (styrene oxide, 1,2-epoxyhexane and butyl glycidyl ether) were performed in a binary homogeneous mixture comprising NaBr as the nucleophilic catalyst and diethylene glycol (DEG) as both solvent and catalyst activator (cation coordinating agent). The reaction protocol was initially studied under batch conditions either in autoclaves and glass reactors: quantitative formation of the cyclic organic carbonate products (COCs) were achieved at T=100 °C and p0(CO2)=1–40 bar. The process was then transferred to continuous-flow (CF) mode. The effects of the reaction parameters (T, p(CO2), catalyst loading, and flow rates) were studied using microfluidic reactors of capacities variable from 7.85 ? 10?2 to 0.157 cm3. Albeit the CF reaction took place at T=220 °C and 120 bar, CF improved the productivity and allowed catalyst recycle through a semi-continuous extraction procedure. For the model case of 1,2-epoxyhexane, the (non-optimized) rate of formation of the corresponding carbonate, 4-butyl-1,3-dioxolan-2-one, was increased up to 27.6 mmol h?1 equiv.?1, a value 2.5 higher than in the batch mode. Moreover, the NaBr/DEG mixture was reusable without loss of performance for at least 4 subsequent CF-tests.

A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids

Herein, an operationally simple, environmentally benign and effective method for intermolecular radical hydroacylation of unactivated substrates by employing photo-induced hydrogen atom transfer (HAT) initiation is described. The use of commercially available and inexpensive photoinitiators (Ph2CO and NHPI) makes the process attractive. The olefin hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.

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.

A Two-Step Oxidative Cleavage of 1,2-Diol Fatty Esters into Acids or Nitriles by a Dehydrogenation–Oxidative Cleavage Sequence

Dehydrogenative oxidation of vicinal alcohols catalyzed by a commercially 64 wt.% Ni/SiO2 catalyst leads to the formation of α-hydroxyketone. This first step was developed without additional solvent according to two protocols: “under vacuum” or “with an olefin scavenger”. The synthesis of ketols was carried out with good conversions and selectivities. The recyclability of the supported nickel was also studied. Acyloin was then cleaved with oxidative reagent “formic acid/hydrogen peroxide”, which is cheap and can be used on a large scale for industrial oxidation processes. The global yield of this sequential system was up to 80 % to pelargonic acid and azelaic acid monomethyl ester without intermediate purification. By treating the acyloin intermediate with hydroxylamine, nitriles were obtained with a good selectivity.

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.

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.

Cooperative catalyst system for the synthesis of oleochemical cyclic carbonates from CO2 and renewables

Phosphonium salts and various (transition-) metals were studied as catalysts in the synthesis of carbonated oleochemicals from the corresponding epoxides and carbon dioxide. In combination with tetra-n-butylphosphonium bromide molybdenum compounds were identified as highly active co-catalysts for the formation of cyclic carbonates. The co-catalyst accelerates the conversion of the epoxidized fatty acid ester considerably. The chemo- as well as the stereoselectivity of the carbonated oleochemicals can be controlled by the choice of the catalyst and the reaction conditions. Under optimized reaction conditions this new catalyst system allows the conversion of both mono- and polyepoxidized oleo compounds into the corresponding carbonates in good to excellent yields up to >99% under comparatively mild reaction conditions. This procedure has been applied to the synthesis of a potential renewable plasticizer and works well even at larger scale (200 g).

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%.