2874-74-0

Usage

InChI:InChI=1/C13H26O2/c1-3-4-5-6-7-8-9-10-11-12(2)13(14)15/h12H,3-11H2,1-2H3,(H,14,15)

Upstream product

• 22149-06-0 (+/-)-7-oxo-2-methyl-dodecanoic acid-⁽¹⁾ 
• 4372-30-9 decyl-methyl-malonic acid 
• 112-41-4 1-dodecene 
• 201230-82-2 carbon monoxide 
• 143-07-7 lauric acid 
• 74-88-4 methyl iodide 
• 872-05-9 1-Decene 
• 64-19-7 acetic acid 
• 123-62-6 propionic acid anhydride 
• 124-38-9 carbon dioxide 
• 64-18-6 formic acid 
• 879553-83-0 (+/-)-5-iodo-2-methyl-valeric acid methyl ester 
• 112-29-8 1-bromo dodecane 

Downstream Products

• 52756-21-5 2-methylenedodecanoic acid 
• 140112-71-6 2-Methyl-dodecanoic acid (2,4,6-trimethoxy-phenyl)-amide 
• 53663-29-9 (E)-2-Methyl-2-dodecenoic Acid 

Relevant academic research and scientific papers

Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation

The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-to-success is the use of a built-in-base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost-competitive processes for the industrial production of carboxylic acids.

ALPHA-BRANCHED ALKENOIC ACIDS AND THE USE OF ALPHA-BRANCHED ALKANOIC AND ALKENOIC ACIDS AS A FRAGRANCE

The present invention refers to alpha branched alkanoic and alkenoic acids of formula (I) wherein X and R have the same meaning as given in the description. The invention further refers to perfume compositions and fragrance applications comprising them.

Manufacture of C13 higher fatty acids from their esters by carbonylation of dodecene-1 in ionic liquid medium

The effect of catalyst nature, temperature, acidity, promoters, and feedstock composition on dodecene-1 carbonylation in the presence of Pd compounds in an ionic liquid medium yielding higher fatty acid and their esters was studied. Palladium salts without phosphine ligands show high activity in tetrabutylammonium bromide. In systems of this kind, the catalyst is suspended in the reaction mass in the form of Pd particles with a size of 4-10 nm. It was shown that the catalytic system can be repeatedly used without loss of activity. It is acceptable to use synthesis gas instead of bare carbon monoxide with the selectivity for tride-canoic acid increasing.

Hydrocarboxylation of terminal alkenes in supercritical carbon dioxide

The catalytic hydrocarboxylation of linear alkenes to carboxylic acids using supercritical carbon dioxide as a solvent was studied. High selectivities in acids have been obtained. The best results were achieved when adding a perfluorinated surfactant to the reaction mixture (93% conversions and ca. 80% selectivity). Comparative multinuclear high-pressure NMR spectroscopic studies in [D8]THF and in supercritical CO2 show the formation of Pd0 species. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Addition of carboxyalkyl radicals to alkenes through a catalytic process, using a Mn(II)/Co(II)/O2 redox system

A novel strategy for production of mono- and dicarboxylic acids by the addition of carboxyalkyl radicals to alkenes and dienes, respectively, was successfully developed through a catalytic process with use of Mn(II)/Co(II)/O2 system. Thus, a variety of carboxylic acids were prepared by the reaction of alkenes and dienes with acid anhydrides in the presence of a very small amount of Mn(OAc)2 (0.5 mol %) and Co(OAc)2 (0.1 mol %) under dilute dioxygen.

Novel palladium(II) complex containing a chelating anionic N-O ligand: Efficient carbonylation catalyst

(matrix presented) A novel palladium(II) complex containing chelating anionic pyridine-2-carboxylato and labile tosylato ligands is a highly efficient catalyst for the carbonylation of organic alcohols and olefins to carboxylic acids/esters. Carbonylation of primary, secondary, and tertiary alcohols as well as linear and functionalized terminal olefins was studied. In all cases remarkable activity and selectivity were observed. The catalyst is stable under reaction conditions even in the absence of excess phosphine ligands.

Autopoietic self-reproduction of chiral fatty acid vesicles

The self-reproduction of vesicles formed by (S)- and (R)-2-methyldodecanoic acid (4) was investigated in order to relate the autocatalytic increase of the vesicle concentration with enantioselectivity. 4(R) and 4(S) were synthesized with an enantiomeric excess greater than 98%. 4 forms vesicles in aqueous solution in the pH region between 8.8 and 7.5. Chiral properties of the vesicles were studied by differential scanning calorimetry (DSC) and circular dichroism (CD). For self-reproduction studies, the hydrolysis of the water-insoluble 2-methyldodecanoic anhydride (8) was investigated in a biphasic system consisting of an aqueous solution and 8. The reaction rates of 8(RR) and 8(SS) catalyzed by 4(R) or 4(S) vesicles were the same within experimental errors, indicating that the chiral vesicles cannot induce significant enantioselectivity. However, a clear effect was observed at 10°C: racemic vesicles destabilized during hydrolysis, causing phase separation, whereas homochiral vesicles remained stable and continued to self-reproduce.

Two-phase hydroformylation of higher molecular olefins by ethoxylated tris(p-hydroxyphenyl)-phosphine as complex ligand for the rhodiumcarbonyl catalyst

Water-soluble rhodiumcarbonyl complexes with new nonionic complex ligands prepared by ethoxylation of tris(p-hydroxyphenyl)phosphine were successfully used in the two-phase hydroformylation of higher-molecular olefins. Their efficiency depends likely on a temperature controlled circulation of the catalyst complex between the organic and the water phase: At the temperature of the hydroformylation (100-130°C) the ethoxylated tri-(p-hydroxyphenyl)phosphine becomes water-insoluble (appearance of a miscibility gap) and is now available for the catalysis in the organic phase. After cooling to room temperature the catalyst system is dissolved again in the water phase and can be recovered by a simple phase separation. Johann Ambrosius Barth 1996.

Inhibitors of Acyl-CoA:cholesterol acyltransferase. I. Identification and structure-activity relationships of a novel series of fatty acid anilide hypocholesterolemic agents

A series of fatty acid anilides was prepared, and compounds were tested for their ability to inhibit the enzyme acyl-CoA:cholesterol acyltransferase (ACAT) in vitro and to lower plasma total cholesterol and elevate high- density lipoprotein cholesterol in cholesterol-fed rats in vivo. The compounds reported were found to fall into two subclasses with different anilide SAR. For nonbranched acyl analogues, inhibitory potency was found to be optimal with bulky 2,6-dialkyl substitution. For α-substituted acyl analogues, there was little dependence of in vitro potency on anilide substitution and 2,4,6-trimethoxy was uniquely preferred. Most of the potent inhibitors (IC50 50 nM) were found to produce significant reductions in plasma total cholesterol in cholesterol-fed rats. Additionally, in vivo activity could be improved significantly by the introduction of α,α- disubstitution into the fatty acid portion of the molecule. A narrow group of α,α-disubstituted trimethoxyanilides, exemplified by 2,2-dimethyl-N-(2,4,6- trimethoxyphenyl)dodecanamide (39), was found to not only lower plasma total cholesterol (-60%) in cholesterol-fed rats but also elevate levels of high- density lipoprotein cholesterol (+94%) in this model at the screening dose of 0.05% in the diet (ca. 50 mg/kg).