33796-87-1

Usage

InChI:InChI=1/C9H18O3/c1-2-3-4-5-6-8(10)7-9(11)12/h8,10H,2-7H2,1H3,(H,11,12)

Upstream product

• 70367-35-0 cis-2-hydroxycyclohexanecarbonitrile 
• 141-22-0 Ricinoleic acid 
• 81212-19-3 (Z)-12-hydroxyoctadec-9-enoic acid 
• 498-15-7 (+)-Δ³-carene 
• 10028-15-6 ozone 
• 63301-31-5 trans-2-cyanocyclohexanol 

Downstream Products

• 694527-88-3 N-((3R)-3-hydroxynonanoyl)-N-Me-L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl 
• 694528-02-4 N-((3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-nonanoyl)-N-Me-L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl 
• 3760-11-0 2-nonenoic acid 
• 76904-91-1 (R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-nonanoic acid methyl ester 
• 121541-65-9 (R)-(-)-1,3-nonandiol 1 

Relevant academic research and scientific papers

Scalable, sustainable and catalyst-free continuous flow ozonolysis of fatty acids

A simple and efficient catalyst-free protocol for continuous flow synthesis of azelaic acid is developed from the renewable feedstock oleic acid. An ozone and oxygen mixture was used as the reagent for oxidative cleavage of double bond without using any metal catalyst or terminal oxidant. The target product was scaled up to more than 100 g with 86% yield in a white powder form. Complete recycling and reuse of the solvent were established making it a green method. The approach is significantly energy efficient and also has a very small chemical footprint. The methodology has been successfully tested with four fatty acids making it a versatile platform that gives value addition from renewable resources.

Simultaneous Enzyme/Whole-Cell Biotransformation of C18 Ricinoleic Acid into (R)-3-Hydroxynonanoic Acid, 9-Hydroxynonanoic Acid, and 1,9-Nonanedioic Acid

Regiospecific oxyfunctionalization of renewable long chain fatty acids into industrially relevant C9 carboxylic acids has been investigated. One example was biocatalytic transformation of 10,12-dihydroxyoctadecanoic acid, which was produced from ricinoleic acid ((9Z,12R)-12-hydroxyoctadec-9-enoic acid) by a fatty acid double bond hydratase, into (R)-3-hydroxynonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid with a high conversion yield of ca. 70%. The biotransformation was driven by enzyme/whole-cell biocatalysts, consisting of the esterase of Pseudomonas fluorescens and the recombinant Escherichia coli expressing the secondary alcohol dehydrogenase of Micrococcus luteus, the Baeyer-Villiger monooxygenase of Pseudomonas putida KT2440 and the primary alcohol/aldehyde dehydrogenases of Acinetobacter sp. NCIMB9871. The high conversion yields and the high product formation rates over 20 U/g dry cells with insoluble reactants indicated that various (poly-hydroxy) fatty acids could be converted into multi-functional products via the simultaneous enzyme/whole-cell biotransformations. This study will contribute to the enzyme-based functionalization of hydrophobic substances. (Figure presented.).

Transformation of peroxide products of olefin ozonolysis under treatment with hydroxylamine and semicarbazide hydrochlorides in acetic acid

Hydrochlorides of hydroxylamine and semicarbazide efficiently reduce peroxide products of olefin ozonolysis in a system CH2Cl2-AcOH leading to the formation of carboxylic acids and their derivatives. The application of water as the solvent component favors the increase in the fraction of nitrogen-containing organic compounds (semicarbazones, keto- and aldoximes, nitriles) and reduction in the yield of carboxylic acids.

METHOD OF OXIDATIVE MOLECULAR CLEAVAGE OF A FATTY COMPOUND

A method of oxidative molecular cleavage of a fatty compound, includes: —forming a liquid composition, referred to as a fatty composition, consisting of at least one aliphatic carboxylic acid, the fatty composition including the fatty compound; characterised in that it then involves: —adding, to the fatty composition, a solution of at least one quaternary ammonium salt in water capable of forming an emulsion from the fatty compound and water, then; —adding, to the emulsion, a liquid solution of at least one tungstophosphoric acid in a composition including hydrogen peroxide (H2O2), in such a way as to form, in situ in the emulsion, a quantity of a phase-transfer catalyst, formed from tungstophosphoric acid and at least one quaternary ammonium from the quaternary ammonium salt(s), and to allow the oxidative molecular cleavage of the fatty compound.

New environmentally friendly oxidative scission of oleic acid into azelaic acid and pelargonic acid

Oleic acid (OA) is a renewable monounsaturated fatty acid obtained from high oleic sunflower oil. This work was focused on the oxidative scission of OA, which yields a mono-acid (pelargonic acid, PA) and a di-acid (azelaic acid, AA) through an emulsifying system. The conventional method for producing AA and PA consists of the ozonolysis of oleic acid, a process which presents numerous drawbacks. Therefore, we proposed to study a new alternative process using a green oxidant and a solvent-free system. OA was oxidized in a batch reactor with a biphasic organic-aqueous system consisting of hydrogen peroxide (H 2O2, 30 %) as an oxidant and a peroxo-tungsten complex Q3{PO4[WO(O2)2]4} as a phase-transfer catalyst/co-oxidant. Several phase-transfer catalysts were prepared in situ from tungstophosphoric acid, H2O2 and different quaternary ammonium salts (Q+, Cl-). The catalyst [C5H5N(n-C16H33)] 3{PO4[WO(O2)2]4} was found to give the best results and was chosen for the optimization of the other parameters of the process. This optimization led to a complete conversion of OA into AA and PA with high yields (>80 %) using the system OA/H 2O2/[C5H5N(n-C16H 33)]3{PO4[WO(O2)2] 4} (1/5/0.02 molar ratio) at 85 C for 5 h. In addition, a new treatment was developed in order to recover the catalyst.

Catalytic oxidation of olefins and alcohols with hydrogen peroxide in a two-phase system giving mono- and dicarboxylic acids

The present study considered the influence of various factors on the catalytic activity of systems based on a combination of tetrakis(oxodiperoxotungsto)phosphate(3-) with quaternary ammonium cations, for example, with methyltri-n-octylammonium [Me(n-C8H17) 3N]+. The catalysts were tested in oxidation of cycloolefins (cyclohexene and cyclooctene), alcohols (octan-1-ol and phenylmethanol), and unsaturated fatty acids (cis-9-octadecenoic and 12-hydroxy-9Z-octadecenoic acids) with a 30% hydrogen peroxide solution. These reactions proceed under mild conditions (atmospheric pressure, 80-90°C) to give carboxylic acids. The catalytic systems were characterized by vibrational (IR and Raman) spectroscopy. The state of the systems formed from various precursors, viz., polyoxometallates and phase-transfer catalysts, was studied. It was demonstrated for the first time that the structure formation of peroxo complexes depends on the nature of the halide anion of the quaternary ammonium salt used. The melting points of individual catalytic complexes were determined. The optimal conditions for oxidation were found.

Chemoselective Enzymatic Hydrolysis of Aliphatic and Alicyclic Nitriles

Mild and selective hydrolysis of aliphatic and alicycic nitriles leading to carboxylic acids and amides was achieved under neutral conditions by an immobilized enzyme preparation from Rhodococcus sp.This method is particularly useful for the transformation of compounds containing other acid- or basesensitive groups.