2009-59-8

Basic information

• Product Name: Dodecanoic acid, 12-oxo-, methyl ester
• CAS NO: 2009-59-8
• Molecular Formula: C13H24O3
• Molecular Weight: 228.332
• Mol File: 2009-59-8.mol

Chemical Properties

• CAS DataBase Reference: Dodecanoic acid, 12-oxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecanoic acid, 12-oxo-, methyl ester(2009-59-8)
• EPA Substance Registry System: Dodecanoic acid, 12-oxo-, methyl ester(2009-59-8)

Safety Data

• Hazardous Substances Data: 2009-59-8(Hazardous Substances Data)

Upstream product

• 111-82-0 methyl n-dodecanoate 
• 111-81-9 Methyl 10-undecenoate 
• 201230-82-2 carbon monoxide 
• 67-56-1 methanol 
• 1501-82-2 cyclododecene 

Downstream Products

• 693-23-2 1,12-dodecanedioic acid 
• 121269-67-8 methyl 15-(3-nitrophenyl)pentadec-12-enoate 
• 6114-39-2 methyl 12-hydroxyoctadecanoate 
• 593-50-0 melissyl alcohol 
• 506-50-3 melissic acid 
• 629-83-4 methyl 1-triacontanoate 
• 5129-59-9 methyl 13-methyltetradecanoate 
• 66054-36-2 tunicamycin V 
• 121269-70-3 15-(3-iodophenyl)pentadecanoic acid 
• 121269-68-9 methyl 15-(3-aminophenyl)pentadecanoate 
• 121269-69-0 methyl 15-(3-iodophenyl)pentadecanoate 
• 121269-63-4 1-acetyl-2-[15-(m-iodophenyl)pentadecanoyl]-rac-glycerol 
• 121269-64-5 1-[15-(m-iodophenyl)pentadecanoyl]-2-acetyl-rac-glycerol 
• 121269-74-7 1-O-<15-(3-iodophenyl)pentadecanoyl>-3-O-trityl-1,3-dihydroxy-2-propanone 

Relevant articles and documents

TRANSFORMATION OF PEROXYACETAL INTERMEDIATE

A method for transforming a compound of formula IIa: to a compound of formula III: is provided, wherein A is a C6-C10 alkene chain with at least one double bond, R1 is a C1-C10 alkyl, and R3 is an oxygen-containing functional group.

Rhodium versus iridium catalysts in the controlled tandem hydroformylation-isomerization of functionalized unsaturated fatty substrates

The hydroformylation of 10-undecenitrile (1) and related unsaturated fatty substrates (H2C=CH(CH2)7CH2R; R=CO2Me, CH2Br, CHO) has been studied with rhodium, iridium, ruthenium, and palladium biphephos catalysts. The reactions proceeded effectively with all four systems, with high selectivities for the linear aldehyde (ratio of linear/branched aldehydes=99:1). The biphephos-bis[chloro(cyclooctadiene)iridium] system showed a non-optimized hydroformylation turnover frequency (TOFHF) of 770h-1 that was only approximately 5times lower than that of the rhodium-based system (TOFHF=3320h-1); the palladium and ruthenium biphephos systems were less active (TOFHF=210 and 310h-1, respectively). Upon recycling, remarkable productivities were achieved in both cases (TON≈58-000mol(1/1-int)-mol(Ir)-1 and 250-000mol(1/1-int)-mol(Rh)-1, in which int=internal olefin). Competitive isomerization of terminal to internal olefins occurred with these catalysts. Iridium biphephos systems allowed slightly better control of the distribution of the internal isomers than the rhodium biphephos catalyst, with higher ratios of 9-/8-undecenitrile (1-int). Place your bets now: Iridium-biphephos catalysts are highly effective in the controlled tandem isomerization-hydroformylation of 10-undecenitrile and related functionalized unsaturated fatty substrates.

Rhodium-catalyzed tandem isomerization/hydroformylation of the bio-sourced 10-undecenenitrile: Selective and productive catalysts for production of polyamide-12 precursor

The hydroformylation of 10-undecenenitrile (1) - a substrate readily prepared from renewable castor oil - in the presence of rhodium-phosphane catalysts systems is reported. The corresponding linear aldehyde (2) can be prepared in high yields and regioselectivities with a (dicarbonyl)rhodium acetoacetonate-biphephos [Rh(acac)(CO)2-biphephos] catalyst. The hydroformylation process is accompanied by isomerization of 1 into internal isomers of undecenenitrile (1-int); yet, it is shown that the Rh-biphephos catalyst effectively isomerizes back 1-int into 1, eventually allowing high conversions of 1/1-int into 2. Recycling of the catalyst by vacuum distillation under a controlled atmosphere was demonstrated over 4-5 runs, leading to high productivities up to 230,000 mol (2)×mol (Rh)-1 and 5,750 mol (2)×mol (biphephos)-1. Attempted recycling of the catalyst using a thermomorphic multicomponent solvent (TMS) phase-separation procedure proved ineffective because the final product 2 and the Rh-biphephos catalyst were always found in the same polar phase. Auto-oxidation of the linear aldehyde 2 into the fatty 10-cyano-2-methyldecanoic acid (5) proceeds readily upon exposure to air at room temperature, opening a new effective entry toward polyamide-12. Copyright

Direct terminal alkylamino-functionalization via multistep biocatalysis in one recombinant whole-cell catalyst

Direct and regiospecific amino-functionalization of non-activated carbon could be achieved using one recombinant microbial catalyst. The presented proof of concept shows that heterologous pathway engineering allowed the construction of a whole-cell biocatalyst catalyzing the terminal amino-functionalization of fatty acid methyl esters (e.g., dodecanoic acid methyl ester) and alkanes (e.g., octane). By coupling oxygenase and transaminase catalysis in vivo, both substrates are converted with absolute regiospecificity to the terminal amine via two sequential oxidation reactions followed by an amination step. Such demanding chemical three-step reactions achieved with a single catalyst demonstrate the tremendous potential of whole-cell biocatalysts for the production of industrially relevant building blocks. Copyright