Structural Characterization of Cyclic Isoprene Trimer

Tanaka, Yasuyuki; Sato, Hisaya; Nakafutami, Yasunobu; Iwasaki, Hitoshi; Taketomi, T.

doi:10.1295/polymj.14.713

Cited by 3 publications

(2 citation statements)

References 10 publications

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“…Figure 1 and 2 show the spectra of a PIP obtained in bulk at 20 °C. In the 1 H NMR, the signal at 5.0 ppm is assigned to the CH protons, and the signals at 2.0, 1.9, and 1.5 ppm are assigned to the CH 2  and CH 3 protons of oligoisoprenes in 1,4‐enchainment 6–8. They indicate the predominant insertion of IP in a 1,4 configuration.…”

Section: Resultsmentioning

confidence: 99%

Biomimetic processes. IV. Carbocationic polymerization of isoprene initiated by dimethyl allyl alcohol

Puskás¹,

Peres²,

Peruch³

et al. 2009

J. Polym. Sci. A Polym. Chem.

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In this article, we investigate a new bio-inspired synthetic route towards NR homologs based on the carbocationic polymerization of isoprene initiated by dimethyl allyl alcohol (DMAOH)/TiCl 4 or BF 3 .Et 2 O as the catalytic system. This study is the continuation of our studies related to the proof of principle that NR biosynthesis is based on a carbocationic mechanism. It is shown that using the biomimetic strategy of initiation by allylic carbocations, polyisoprene carrying a dimethyl allyl head group is produced almost exclusively via 1,4 addition, yielding repeating units with cis and trans configurations. V

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Section: Resultsmentioning

confidence: 99%

Biomimetic processes. IV. Carbocationic polymerization of isoprene initiated by dimethyl allyl alcohol

Puskás¹,

Peres²,

Peruch³

et al. 2009

J. Polym. Sci. A Polym. Chem.

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“…One promising route to SAF is the synthesis of fuel molecules from bio-based platform chemicals. − One of the most versatile and desirable platform chemicals is isoprene. This five-carbon conjugated hydrocarbon can be directly produced through fermentation or derived from other bio-based molecules including isoprenol, − mesaconic/itaconic acid, , and mevalanolactone. , Isoprene can be readily converted to jet fuel blendstocks through catalytic − and photochemical cycloadditions as well as oligomerization reactions. − Cycloalkanes prepared through these routes exhibit high densities and heats of combustion, while maintaining low viscosities. Although discrete molecules produced from isoprene are outstanding blendstocks, conventional jet fuel is a complex mixture of n -alkanes, isoalkanes, cycloalkanes, and aromatic compounds with carbon numbers ranging from about 9 to 14.…”

Section: Introductionmentioning

confidence: 99%

Designer Biosynthetic Jet Fuels Derived from Isoprene and α-Olefins

Keller

Walkling

Zhang

et al. 2023

ACS Sustainable Chem. Eng.

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Isoprene was hydrovinylated with a series of α-olefins (1-pentene, 1-hexene, 1-heptene, 1-octene) to produce acyclic branched C 10 −C 13 alkenes. The process utilized CoBr 2 (DPPE) as the precatalyst in loadings as low as 0.1 mol % and zinc as the reducing agent. Use of the cobalt catalyst resulted in primarily 1,4-addition, with carbon coupling at the 4-position of isoprene. A significant amount (∼20%) of the coupling products at the 1-position of isoprene was also observed. Each of the discrete C 10 , C 11 , C 12 , and C 13 products were then hydrogenated with 10% Pd/C (200 °C; 650 psi H 2 ) to yield jet fuel blendstocks. In addition to the reactions with pure α-olefins, an equimolar mixture of the C 5 −C 8 α-olefins was used to mimic a stream of olefins produced from ethanol dehydration/oligomerization or Fischer−Tropsch catalysis. The different fuel blends exhibited densities ranging from 0.73 to 0.76 g mL −1 , gravimetric net heats of combustion (NHOC) from 43.91 to 44.13 MJ kg −1 , and −20 °C kinematic viscosities from 2.4 to 6.3 mm 2 s −1 . The NHOC values were ∼2.9% higher than the lower limit for Jet-A, while the low-temperature viscosities were up to 70% lower than the upper limit for Jet-A. In addition to studying the suitability of the lightly branched hydrocarbons generated in this process as jet fuel blendstocks, it was of interest to explore their potential as diesel fuels. The equimolar C 10 −C 13 fuel mixture exhibited a derived cetane number (DCN) of 56, which is 16 units higher than that required for Diesel #2 (40). The outstanding fuel properties of the isoprene-derived fuels suggest that they have applications as replacements for both petroleum-derived Jet-A and Diesel #2.

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Physical Data of Oligomers

Rothe

1999

The Wiley Database of Polymer Properties

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Structural Characterization of Cyclic Isoprene Trimer

Cited by 3 publications

References 10 publications

Biomimetic processes. IV. Carbocationic polymerization of isoprene initiated by dimethyl allyl alcohol

Biomimetic processes. IV. Carbocationic polymerization of isoprene initiated by dimethyl allyl alcohol

Designer Biosynthetic Jet Fuels Derived from Isoprene and α-Olefins

Physical Data of Oligomers

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