19550-58-4

Usage

InChI:InChI=1/C10H18O4/c1-7(9(11)13-3)5-6-8(2)10(12)14-4/h7-8H,5-6H2,1-4H3/t7-,8-/m0/s1

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 186581-53-3 diazomethane 
• 4454-18-6 2,5-dimethyladipic acid 
• 32980-25-9 2-methylsuccinic acid 1-methyl ester 
• 4454-18-6 (S,S)-2,5-dimethyl-adipic acid 
• 111266-16-1 L-malic acid methyl ester 
• 4454-18-6 (R,R)-2,5-dimethyl-adipic acid 
• 83509-04-0 (R)-2-methylsuccinate-1-monomethyl ester 
• 503-74-2 3-methylbutyric acid 
• 56920-00-4 [1,6-dimethoxy-2,5-dimethyl-1,5-hexadien-1,6-diyl bis(oxy)] bis(trimethylsilane) 

Downstream Products

• 4041-09-2 2,5-dimethylcyclopentanone 
• 988-38-5 1,1,6,6-Tetraphenyl-2,5-dimethyl-1,5-hexadiene 
• 4454-18-6 2,5-dimethyladipic acid 

Relevant academic research and scientific papers

COMPOSITION OF THE COATS AND KERNELS OF THE SEEDS OF Nepeta pannonica and Lavandula vera

The lipid compositions of the coats and kernels of the seeds of Nepeta pannonica and Lavandula vera have been studied.It has been established that the lipids of the seed coats of the two species of plants differ substantially in their composition.The lipids of the kernels of Nepeta have been found to contain free fatty acids with chain lengths of from C20 to C35.Ursolic acid and its acetate have been isolated from extracts of the seed coats of Lavandula, and dimethyladipic acid from the seed oil of this species.

Isospecific polymerizations of alkyl methacrylates with a bis(alkyl)Yb complex and formation of stereocomplexes with syndiotactic poly(alkyl methacrylate)s

Yb[C(SiMe3)3]2 initiates the living polymerization of methyl methacrylate (MMA) at -78°C to give the polymer with Mn of 51.0×104 (Mw/M n=1.1) and high isotacticity (97%) in a quantitative yield. Mixing of the acetone solution of resulting polymer (Mn=16.3×10 4) with the acetone solution of syndiotactic poly(MMA) (M n=15.7×104) prepared by the (C5Me 5)2SmMe(THF) initiator produces desired stereocomplex in high yield bearing very high Tm whose tensile modulus is higher than the respective isotactic and syndiotactic poly(MMA)s. Yb[C(SiMe 3)3]2 also generated isotactic (98%) poly[2-(dimethylamino)ethyl methacrylate] (DMEMA), and (C5Me 5)2SmMe(THF) affords the syndiotactic (97%) polymer in high yields. The combination of isotactic poly(MMA)-block-poly(DMEMA) (97/3) and syndiotactic poly(MMA)-block-poly(DMEMA) (97/3) provides the amphiphathic stereocomplex. In sharp contrast to the catalysis of Yb[C(SiMe3) 3]2 in toluene, the addition of THF or HMPA resulted in the formation of syndio-rich poly(MMA).

Electrochemical cross-coupling of biogenic di-acids for sustainable fuel production

Direct electrocatalytic conversion of bio-derivable acids represents a promising technique for the production of value-added chemicals and tailor-made fuels from lignocellulosic biomass. In the present contribution, we report the electrochemical decarboxylation and cross-coupling of ethyl hydrogen succinate, methyl hydrogen methylsuccinate and methylhexanoic acid with isovaleric acid. The reactions were performed in aqueous solutions or methanol at ambient temperatures, following the principles of green chemistry. High conversions of the starting materials have been obtained with maximum yields between 42 and 61% towards the desired branched alkane products. Besides costly Pt electrodes also (RuxTi1-x)O2 on Ti electrodes exhibited a notable activity for cross-Kolbe electrolysis. As some of the products are insoluble in water, easy product isolation and reuse of the reaction solvent is enabled via phase separation. Several side products have been identified to evaluate the efficiency of the reaction and to elucidate the factors influencing the product selectivity. The yielded alkanes and esters were assessed with regard to their potential as fuels for internal combustion engines. While the longer alkanes constitute promising candidates for the compression-ignition engine, the smaller ester represents an interesting option for the spark-ignition engine.

Electrochemical Coupling of Biomass-Derived Acids: New C8 Platforms for Renewable Polymers and Fuels

Electrolysis of biomass-derived carbonyl compounds is an alternative to condensation chemistry for supplying products with chain length >C6for biofuels and renewable materials production. Kolbe coupling of biomass-derived levulinic acid is used to obtain 2,7-octanedione, a new platform molecule only two low process-intensity steps removed from raw biomass. Hydrogenation to 2,7-octanediol provides a chiral secondary diol largely unknown to polymer chemistry, whereas intramolecular aldol condensation followed by hydrogenation yields branched cycloalkanes suitable for use as high-octane, cellulosic gasoline. Analogous electrolysis of an itaconic acid-derived methylsuccinic monoester yields a chiral 2,5-dimethyladipic acid diester, another underutilized monomer owing to lack of availability.