An efficient initiator system containing AlCl3 and supported ionic-liquid for the synthesis of conventional grade polyisobutylene in mild conditions

Yousefi, Saleh; Bahri‐Laleh, Naeimeh; Nekoomanesh, Mehdi; Emami, Mehrsa; Sadjadi, Samahe; Mirmohammadi, Seyed Amin; Tomasini, Michele; Bardají, Eduard; Poater, Albert

doi:10.1016/j.molliq.2022.120381

Cited by 20 publications

(8 citation statements)

References 72 publications

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“…There have been many advanced researches, discoveries and patents in the field of ILs in recent years due to their significant features and great applicability, but their commercial exploitation is still limited. Ionic liquids have many unique properties, including low vapor pressure, high thermal stability, low toxicity, high ionic conductivity and almost unlimited tunability, which have already allowed them to find many applications in chemistry, electrochemistry, extraction and separation processes [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ]; however, the photonic application of these materials have so far been very limited, and their optical parameters have not been sufficiently explored. Their properties can be tuned either by anion and/or cation modification, making them photodefinable, transparent, colored or flexible.…”

Section: Introductionmentioning

confidence: 99%

Optical Fiber Grating-Prism Fabrication by Imprint Patterning of Ionic-Liquid-Based Resist

Turek

Pala

Szpecht

et al. 2023

IJMS

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We present a method of microstructure fabrication on the tip of the optical fiber using a UV soft-imprint process of polymerizable ionic liquid-based optical resist. Ionic liquid with two UV-sensitive vinylbenzyl groups in the structure was diluted in non-hazardous propylene glycol (PG) to obtain liquid material for imprinting. No additional organic solvent was required. The impact of propylene glycol amount and exposure dose on optical and mechanical properties was investigated. The final procedure of the UV imprint on the optical fiber tip was developed, including the mold preparation, setup building, UV exposure and post-laser cure. As the IL-containing vinylbenzyl groups can also be polymerized by the radical rearrangement of double bonds through thermal heating, the influence of the addition of 1–2% BHT polymerization inhibitor was verified. As a result, we present the fabricated diffraction gratings and the optical fiber spectrometer component—grism (grating-prism), which allows obtaining a dispersion spectrum at the output of an optical in line with the optical fiber long axis, as the main component in an optical fiber spectrometer. The process is very simple due to the fact that its optimization already starts in the process of molecule design, which is part of the trend of sustainable technologies. The final material can be designed by the tailoring of the anion and/or cation molecule, which in turn can lead to a more efficient fabrication procedure and additional functionalities of the final structure.

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Section: Introductionmentioning

confidence: 99%

Optical Fiber Grating-Prism Fabrication by Imprint Patterning of Ionic-Liquid-Based Resist

Turek

Pala

Szpecht

et al. 2023

IJMS

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“…In this line, some attempts were devoted to synthesize low viscosity PAOs using a less hazardous AlCl 3 initiator. [16,17,18] Recently, we have demonstrated high performance of the AlCl 3 /solvent system in the production of low viscosity PAOs, whose properties are comparable with the analogous commercial PAO4 and PAO6. [19] It was clarified that, the solvent, especially aromatic type, facilitates chain transfer reactions, thanks to the capability of aromatic solvents to perform the Friedel-Crafts reaction.…”

Section: Introductionmentioning

confidence: 99%

“…However, due to its extremely hazardous and corrosive nature, [13,14,15] the initiating system based on this compound is of considerable environmental concern and its use increases the risk and cost of PAO production. In this line, some attempts were devoted to synthesize low viscosity PAOs using a less hazardous AlCl 3 initiator [16,17,18] . Recently, we have demonstrated high performance of the AlCl 3 /solvent system in the production of low viscosity PAOs, whose properties are comparable with the analogous commercial PAO4 and PAO6 [19] .…”

Section: Introductionmentioning

confidence: 99%

Chain Walking in the AlCl₃ Catalyzed Cationic Polymerization of α‐Olefins

et al. 2023

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Continuing efforts aimed at performing the 1‐decene polymerization to low viscosity polyalphaolefins (PAO)s using a less hazardous AlCl3 catalyst than boron‐based analogs, the basic mechanisms of this system were revealed in this research. In this aspect, neat AlCl3 and AlCl3/toluene were carried out to perform 1‐decene polymerizations. Microstructure analyses of the as‐synthesized oils revealed low molecular weight (708 vs. 1529 g/mol), kinematic viscosity (KV100=6.4 vs. 22.2 cSt), and long chain branching (82.1 vs. 84.7) of PAO from the system containing toluene solvent. Furthermore, NMR analysis confirmed various types of short chain branch (SCB) with the inclusion of toluene ring in the structure of final PAO chains. Then, to shed light on the basic mechanisms of cationic polymerization of 1‐decene including: i) chain initiation, ii) chain transfer to the monomer, iii) isomerization of the carbocation via a chain walking mechanism (causes different SCB length), and iv) binding of toluene ring to the propagating PAO chain (to yield aromatic containing oligomers), molecular modeling at the DFT level was employed. The energies obtained confirmed the ease of carbocation isomerization and chain transfer mechanisms in toluene medium, which well confirms the highly branched structure experimentally obtained for related PAO.

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“…In this case, PIB can be used as a reactant with maleic anhydride to produce poly (isobutenyl succinic anhydride), a notable commercial intermediate for the manufacture of ashless dispersants, without involving any sort of chlorination step, which makes this product desirable 2–8 . Nevertheless, the increase of the exo‐olefin content of standard CPIB grades can also be very beneficial for posterior chemical modifications of these materials, enhancing reaction rates and double‐bond conversions in mild conditions 9 . For this reason, the manufacture of PIB grades with exo‐olefin contents ranging from 10 to 70 mol% (modified conventional PIB [MCPIB]) also raises commercial interest.…”

Section: Introductionmentioning

confidence: 99%

“…[2][3][4][5][6][7][8] Nevertheless, the increase of the exo-olefin content of standard CPIB grades can also be very beneficial for posterior chemical modifications of these materials, enhancing reaction rates and double-bond conversions in mild conditions. 9 For this reason, the manufacture of PIB grades with exo-olefin contents ranging from 10 to 70 mol% (modified conventional PIB [MCPIB]) also raises commercial interest.…”

Section: Introductionmentioning

confidence: 99%

Cationic polymerization of isobutylene by AlCl3 in n‐hexane and toluene at mild temperatures

Bentes,

Mangia,

Vasconcelos

et al. 2023

J of Applied Polymer Sci

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This study aims to find more efficient ways to manufacture highly reactive polyisobutylene (HRPIB) and modified conventional PIB materials (MCPIB) industrially with high vinyl exo‐group contents through cationic polymerization at mild temperatures. The study performed polymerizations using aluminum trichloride (AlCl3) as a catalyst with different nonpolar solvents (hexane and toluene), reaction temperatures (10 and 30°C), and co‐catalysts (water and dibutyl ether [DBE]). At 30°C, toluene can provide vinyl contents above 30 mol%. Particularly, an important synergetic effect was observed between toluene and ether, as corroborated by statistical analyses, resulting in vinyl contents above 50 mol%, while reactions performed in n‐hexane provided maximum vinyl content of 20 mol%. In all cases, number average molar masses ranged from 200 to 1000 Da, which are typical of CPIB and MCPIB materials. Moreover, addition of excess of ether indicated the likely inhibition of reaction rates in presence of high ether concentrations (≥1.18 × 10 −1 mol/L). The obtained results indicated that AlCl3 can be used successfully to manufacture MCPIB products with terminal vinyl contents above 50 mol% at mild temperatures in common nonpolar solvents (n‐hexane and toluene) and in presence of common co‐catalysts (water and DBE) with high rates of reactions.

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An efficient initiator system containing AlCl3 and supported ionic-liquid for the synthesis of conventional grade polyisobutylene in mild conditions

Cited by 20 publications

References 72 publications

Optical Fiber Grating-Prism Fabrication by Imprint Patterning of Ionic-Liquid-Based Resist

Optical Fiber Grating-Prism Fabrication by Imprint Patterning of Ionic-Liquid-Based Resist

Chain Walking in the AlCl₃ Catalyzed Cationic Polymerization of α‐Olefins

Cationic polymerization of isobutylene by AlCl3 in n‐hexane and toluene at mild temperatures

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An efficient initiator system containing AlCl3 and supported ionic-liquid for the synthesis of conventional grade polyisobutylene in mild conditions

Cited by 20 publications

References 72 publications

Optical Fiber Grating-Prism Fabrication by Imprint Patterning of Ionic-Liquid-Based Resist

Optical Fiber Grating-Prism Fabrication by Imprint Patterning of Ionic-Liquid-Based Resist

Chain Walking in the AlCl3 Catalyzed Cationic Polymerization of α‐Olefins

Cationic polymerization of isobutylene by AlCl3 in n‐hexane and toluene at mild temperatures

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Chain Walking in the AlCl₃ Catalyzed Cationic Polymerization of α‐Olefins