22663-09-8

Upstream product

• 79-21-0 peracetic acid 
• 111-81-9 Methyl 10-undecenoate 
• 91258-67-2 methyl 10-hydroxy-11-iodoundecanoic acid 
• 112-38-9 10-undecenoic acid 
• 123-05-7 d,l-2-ethylhexanal 

Downstream Products

• 111-81-9 Methyl 10-undecenoate 
• 15764-66-6 10,11-epoxyundecan-1-ol 
• 10596-05-1 undecane-1,10-diol 
• 765-04-8 undecane-1,11-diol 
• 129409-76-3 9-(2-Thioxo-oxazolidin-5-yl)-nonanoic acid methyl ester 
• 129409-77-4 9-{2-[(E)-4-Fluoro-phenylimino]-[1,3]oxathiolan-5-yl}-nonanoic acid methyl ester 
• 129409-78-5 9-[3-(4-Fluoro-phenyl)-2-thioxo-oxazolidin-5-yl]-nonanoic acid methyl ester 
• 133617-30-8 11-Hydroxy-10-phenyltellanyl-undecanoic acid methyl ester 
• 133617-24-0 10-Hydroxy-11-phenyltellanyl-undecanoic acid methyl ester 

Relevant academic research and scientific papers

"click" tetradentate ligands

A series of triazole-based N4 tetradenate ligands 1a-d are efficiently synthesized using CuI-catalyzed azide-alkyne "click" strategy and are readily coordinated to many metal ions (e.g. MnII, NiII, ZnII and FeII). The X-ray structures of the resultant metal-complexes (4a-d, 5a, 6a and 7a) reveal an octahedral mononuclear structure with two co-ligands bonded in cis sites and the two triazoles as nitrogen donors to the metal center. The MnII-complexes (4a-d) show efficient catalytic activities in the epoxidation of various aliphatic terminal olefins with peracetic acid, and feature with low catalyst loading, fast conversion and high yields. The Royal Society of Chemistry 2010.

Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes

Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2. Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.

Hyperbranched polyesters by polycondensation of fatty acid-based AB: N-type monomers

Widely available vegetable oils were readily derivatized into chemically pure ABn-type monomers (n = 2 or 3). Their polymerization led to unprecedented hyperbranched polyesters. Four different AB2/AB3-type monomers bearing one A-type methyl ester and two or three B-type alcohol functions were purposely synthesized via two elementary steps, i.e. epoxidation of the internal double bond of the vegetable oil precursors followed by ring-opening of the epoxy groups under acidic conditions. The polycondensation of these bio-sourced monomers was performed in bulk, in the presence of an appropriate catalyst, giving access to modular hyperbranched polyesters with tunable properties. Among the catalysts tested, zinc acetate, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and sodium methoxide proved the most effective, allowing the achievement of molar masses in the range 3000-10000 g mol-1 and dispersities varying from 2 to 15, depending on the initial conditions. The degree of branching, DB, as determined by 1H NMR spectroscopy, was found to be between 0.07 and 0.45. The as-devised hyperbranched polyesters displayed either amorphous or semi-crystalline properties, as a function of the selected AB2/AB3-type initial monomers, with a glass transition temperature, Tg, ranging from -33 to 9 °C and a decomposition temperature at 5 wt% of the sample, Td5%, varying from 204 to 340 °C.

Total Synthesis of Four Isomers of the Proposed Structures of Cryptorigidifoliol K

The first asymmetric convergent total synthesis of four isomers of proposed structures of cryptorigidifoliol K (1a, 1b, 1c, and 1d) has been achieved from commercially available starting materials. The key steps in this synthesis involve tandem isomerization followed by a C-O and C-C bond-forming reaction for the construction of trans-2,6-disubstituted dihydropyran, iodolactonization, isomerization of terminal alkene, and cross-metathesis reaction. The large discrepancies in the spectroscopic data (1H NMR) of synthetic cryptorigidifoliol K from the natural product suggest that the structure of the natural cryptorigidifoliol K requires revision.

Synthesis of fully alternating polycarbonate with low Tg from carbon dioxide and bio-based fatty acid

The selective copolymerization of CO2 and an epoxide to form fully alternating polycarbonates is a great challenge via catalysis with the zinc-cobalt(iii) double metal cyanide complex [Zn-Co(iii) DMCC]. We describe the first perfectly alternating copolymerization of CO2 with a bio-based epoxide. The resultant polycarbonate had a low Tgs of -38 to -44 °C and two end hydroxyl groups, which were then used to initiate ring-opening polymerization of l-lactide via metal-free catalysis, affording a biodegradable triblock copolymer. This study provides a new platform copolymer for making various advanced polymers with biodegradable properties. This journal is the Partner Organisations 2014.

An enzymatic approach to bifunctional chelating agents

Bifunctional chelating agents (BFCAs) combine the complexing properties of a multidentate ligand with the presence of a free reactive functional group, mainly devoted to conjugation purposes. Indeed, products obtained by conjugation of a BFCA to a biomolecule and coordination of a suitable metal ion are widely applied in medicine nowadays as diagnostic and therapeutic agents. BFCAs are generally prepared through multi-step syntheses and with extensive application of protection-deprotection strategies, due to the large number of functional groups involved. Hydrolytic enzymes, with their unique chemoselectivity, provided the best results in the preparation of three different BFCAs based on very useful and well known ligand platforms. This journal is the Partner Organisations 2014.

New cytotoxic annonaceous acetogenin mimetics having a nitrogen- heterocyclic terminal and their application to cell imaging

A terminal unsaturated lactone or its equivalent is commonly believed to be essential for the cytotoxicity of natural annonaceous acetogenins and their artificial mimetics. In this work, we discovered a series of new cytotoxic ethylene glycol ether-contai

Epoxidation of alkenes bearing a carboxylic acid group by iron complexes of the tetradentate ligand N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1, 2-diaminoethane and its derivatives

The addition of carboxylic acids enhances the rate and selectivity of alkene oxidations catalyzed by [(bpmen)Fe(OTf)2] (bpmen = N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1,2-diaminoethane). The syntheses and characterizations of four derivatives of this iron complex with varying substitutions on the pyridine ring and with a substituted piperazine backbone are reported. These [(L)Fe(OTf)2] complexes and [(bpmen)Fe(OTf)2] are employed as catalysts for the oxidation of alkenes bearing a carboxylic acid functional group, namely oleic acid, undecylenic acid, 5-hexenoic acid and 4-pentenoic acid, with hydrogen peroxide as the oxidant. Comparisons with the analogous ester substrates demonstrate the beneficial impact of the acid functional group on conversion and selectivity when using [(bpmen)Fe(OTf)2] as a catalyst. For the oleic and undecylenic acids, epoxide product is formed with moderate to high conversions and high selectivities. Under the conditions employed, 4-pentenoic acid is oxidized to a γ-lactone, most likely via the epoxide intermediate, and 5-hexenoic acid to a mixture of epoxide and δ-lactone. Of the iron complexes with bpmen derivatives as ligands, only the N,N′-dimethyl-N, N′-bis(5-chloropyridin-2-ylmethyl)-1,2-diaminoethane variant shows appreciable activity. The effect of solvent choice is also investigated.

Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives

Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C1, C4, and C6; isoalkyl, C3, C4, and C8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 85-90% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 °C) compared to butylated hydroxytoluene (BHT, 193.8 °C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.

Envirocat (K10-MX)-catalyzed regioselective transformation of alkenes into iodohydrins and β-iodo ethers and further conversion of iodohydrins to epoxides using Al2O3-Na2Co3 under MWI

Commercial K10 clay was converted to extremely efficient and environmentally friendly catalyst K10-MX for the preparation of iodohydrins and β-iodo ethers from alkenes (terminal as well as internal) using microwave irradiation. This method was further extended for the conversion of alkenes to epoxides via iodohydrin intermediate in a one-pot reaction system. Copyright Taylor & Francis Group, LLC.