Poly[Ethylene Glycol] Derivatives as Phase Transfer Catalysts and Solvents for Organic Reactions

Totten, George E.; Clinton, Nye A.

doi:10.1080/15583728808085378

Cited by 45 publications

(7 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, despite their high activity as effective PT catalysts, crown ethers and cryptands are not feasible for most industrial applications due their high costs and toxicity. Open chain polyethers like polyethylene glycols (PEGs) and their many derivatives are also widely used as PT catalysts (Totten and Clinton, 1988). Although less active than quaternary ammonium salts and crown ethers, they are relatively less costly and environmentally safe.…”

Section: Pt Catalystmentioning

confidence: 99%

“…PEGs are good alternatives to onium salts as cheap and stable PT catalysts in reactions in basic media and at elevated temperatures. However, in comparison to crown ethers, cryptands, and onium salts, larger quantities of PEG are required due to their lower activity, though recovery via distillation is easily accomplished (Totten and Clinton, 1988).…”

Section: Choice Of Pt Catalystmentioning

confidence: 99%

See 1 more Smart Citation

Phase transfer catalysis: Chemistry and engineering

1998

View full text Add to dashboard Cite

Section: Pt Catalystmentioning

confidence: 99%

Section: Choice Of Pt Catalystmentioning

confidence: 99%

Phase transfer catalysis: Chemistry and engineering

1998

View full text Add to dashboard Cite

“…These tensides are soluble in the aqueous phase as well as in the oil phase. PEG is a well-known phase-transfer catalyst, capable of transporting positively charged molecules from the aqueous phase into the oil phase and vice versa (Kim et al 2003 b; Totten and Clinton 1988 ).…”

Section: Discussionmentioning

confidence: 99%

Chemical Analysis of a “Miller-Type” Complex Prebiotic Broth

Scherer

Wollrab

Codutti

et al. 2016

Orig Life Evol Biosph

View full text Add to dashboard Cite

We have analyzed the chemical variety obtained by Miller-Urey-type experiments using nuclear magnetic resonance (NMR) spectroscopy and coherent anti-Stokes Raman scattering (CARS) spectroscopy, gas chromatography followed by mass spectrometry (GC/MS) and two-dimensional gas chromatography followed by mass spectrometry (GCxGC/MS). In the course of a running Miller-Urey-type experiment, a hydrophobic organic layer emerged besides the hydrophilic aqueous phase and the gaseous phase that were initially present. The gas phase mainly consisted of aromatic compounds and molecules containing C≡C or C≡N triple bonds. The hydrophilic phase contained at least a few thousands of different molecules, primarily distributed in a range of 50 and 500 Da. The hydrophobic phase is characterized by carbon-rich, oil-like compounds and their amphiphilic derivatives containing oxygen with tensioactive properties. The presence of a wide range of oxidized molecules hints to the availability of oxygen radicals. We suggest that they intervene in the formation of alkylated polyethylene glycol (PEG) in the oil/water interface. CARS spectroscopy revealed distinct vibrational molecular signatures. In particular, characteristic spectral bands for cyanide compounds were observed if the broth was prepared with electric discharges in the gaseous phase. The characteristic spectral bands were absent if discharges were released onto the water surface. NMR spectroscopy on the same set of samples independently confirmed the observation. In addition, NMR spectroscopy revealed overall high chemical variability that suggests strong non-linearities due to interdependent, sequential reaction steps.Electronic supplementary materialThe online version of this article (doi:10.1007/s11084-016-9528-8) contains supplementary material, which is available to authorized users.

show abstract

“…For example, a number of publications have described the use of soluble polymers, such as PEG, to serve as both phase-transfer reagents and the solvent for a reaction [105][106][107][108][109][110][111][112][113][114][115] . PEG systems of low-average-molecular weight offer a number of unique attractions because of their relatively low-melting points (MW 400-800) 45-47 • C and facile separation from small organic compounds.…”

Section: Reaction Heating: Solvent Considerationsmentioning

confidence: 99%