The Applications of
            <scp>DMSO</scp>

Xiang, Jia‐Chen; Gao, Qinghe; Wu, An‐Xin

doi:10.1002/9783527805624.ch7

Cited by 18 publications

(18 citation statements)

References 102 publications

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“…32 In addition to the ability of solubilizing nylons, DMSO has also been claimed as an environmentally friendly solvent as it can be prepared from renewable sources, exhibits toxicity lower than that of several other polar solvents, and is biodegradable. 33 Because of such unique properties, coupled with low cost, DMSO has been utilized in several industrial processes as a solvent or reagent. 33 Encouragingly, in the case of DMSO solvent, a mixture of a solution and a white precipitate was obtained at the end of the hydrogenation, suggestive of a partial solubilization or degradation of nylon-6.…”

Section: Resultsmentioning

confidence: 99%

“… 33 Because of such unique properties, coupled with low cost, DMSO has been utilized in several industrial processes as a solvent or reagent. 33 Encouragingly, in the case of DMSO solvent, a mixture of a solution and a white precipitate was obtained at the end of the hydrogenation, suggestive of a partial solubilization or degradation of nylon-6. Indeed, analysis of the reaction mixture by gas chromatography (GC) revealed the formation of 6-amino-1-hexanol in 14% yield.…”

Section: Resultsmentioning

confidence: 99%

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Hydrogenative Depolymerization of Nylons

et al. 2020

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The widespread crisis of plastic pollution demands discovery of new and sustainable approaches to degrade robust plastics such as nylons. Using a green and sustainable approach based on hydrogenation, in the presence of a ruthenium pincer catalyst at 150 °C and 70 bar H 2 , we report here the first example of hydrogenative depolymerization of conventional, widely used nylons and polyamides, in general. Under the same catalytic conditions, we also demonstrate the hydrogenation of a polyurethane to produce diol, diamine, and methanol. Additionally, we demonstrate an example where monomers (and oligomers) obtained from the hydrogenation process can be dehydrogenated back to a poly(oligo)amide of approximately similar molecular weight, thus completing a closed loop cycle for recycling of polyamides. Based on the experimental and density functional theory studies, we propose a catalytic cycle for the process that is facilitated by metal–ligand cooperativity. Overall, this unprecedented transformation, albeit at the proof of concept level, offers a new approach toward a cleaner route to recycling nylons.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Hydrogenative Depolymerization of Nylons

et al. 2020

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“…Under such conditions, the [Ru(NO)]

[Ru(NO 2 )] reaction cannot be strictly avoided, but it is not observed in other deuterated solvents (e.g., acetonitrile) containing the same amount of residual water, which seems to prove that the nature of the solvent is essential. At this point, it has to be considered that DMSO itself may be an alternative source of oxygen, according to the following equation [ 32 , 33 , 34 , 35 , 36 ]:

…”

Section: Resultsmentioning

confidence: 99%

Multistep Photochemical Reactions of Polypyridine-Based Ruthenium Nitrosyl Complexes in Dimethylsulfoxide

et al. 2020

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The photorelease of nitric oxide (NO·) has been investigated in dimethylsulfoxide (DMSO) on two compounds of formula [Ru(R-tpy)(bpy)(NO)](PF6)3, in which bpy stands for 2,2′-bipyridine and R-tpy for the 4′-R-2,2′:6′,2″-terpyridine with R = H and MeOPh. It is observed that both complexes are extremely sensitive to traces of water, leading to an equilibrium between [Ru(NO)] and [Ru(NO2)]. The photoproducts of formula [Ru(R-tpy)(bpy)(DMSO)](PF6)2 are further subjected to a photoreaction leading to a reversible linkage isomerization between the stable Ru-DMSO(S) (sulfur linked) and the metastable Ru-DMSO(O) (oxygen linked) species. A set of 4 [Ru(R-tpy)(bpy)(DMSO)]2+ complexes (R = H, MeOPh, BrPh, NO2Ph) is investigated to characterize the ratio and mechanism of the isomerization which is tentatively related to the difference in absorbance between the Ru-DMSO(S) and Ru-DMSO(O) forms. In addition, the X-ray crystal structures of [Ru(tpy)(bpy)(NO)](PF6)3 and [Ru(MeOPh-tpy)(bpy)(DMSO(S))](PF6)2 are presented.

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“…In the field of organic synthesis, solvents as reactants or reagents for the efficient installation of a methylene moiety have attracted the continuous attention of many chemists on the basis of cost and easy availability perspectives. 1 Therefore, the development of diversified reaction systems involving a 'CH 2 synthon' in the construction of functionalized molecules from purchased solvents would be highly valuable. Generally, CH 2 Cl 2 is one of the most common methylene bridges for carbon-heteroatom bond formation.…”

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confidence: 99%

“…Yield: 281 mg (88%); white solid; mp 136-137°C (recrystallized from hexanes/EtOAc) 1. H NMR (400 MHz, CDCl 3 ):  = 10.5 (br s, 1 H), 7.71 (d, J = 8.4 Hz, 2 H), 7.54 (dd, J = 1.6, 8.0 Hz, 1 H), 7.29 (d, J = 8.0 Hz, 2 H), 7.27 (dt, J = 1.2, 7.6 Hz, 1 H), 6.96 (d, J = 8.4 Hz, 1 H), 6.91 (t, J = 7.6 Hz, 1 H), 4.73 (s, 2 H), 3.61 (s, 3 H), 2.43 (s, 3 H).…”

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confidence: 99%