Organic Carbonates. IV.<sup>1a,b,c</sup> Factors Affecting Formation of Homologous Cyclic Carbonates

Sarel, Shalom; Pohoryles, Leo A.; Ben-Shoshan, Raphael

doi:10.1021/jo01094a010

Cited by 43 publications

(12 citation statements)

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“…Mp 78 °C (lit. 6 mp 75 °C). 1 H NMR (CDCl3): δ 1.30 (-CH3, s, 3H), 2.12 (-OH, broad s, 2H), 3.96 (-CH2-, q, J ) 10.8 Hz, 4H), 7.24-7.44 (-C6H5, m, 5H) ppm.…”

Section: Methodsmentioning

confidence: 99%

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Substituent Effect on the Anionic Equilibrium Polymerization of Six-Membered Cyclic Carbonates

et al. 1998

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Anionic equilibrium polymerization behavior of several six-membered cyclic carbonates was examined. The conversions of the monomers reached a constant below 100%, and the final conversion decreased in the order of 1,3-dioxan-2-one (1) > 5,5-dimethyl-1,3-dioxan-2-one (2) > 5,5-diethyl-1,3-dioxan-2-one (3) ≥ 5-methyl-5-phenyl-1,3-dioxan-2-one (4) > 5-ethyl-5-phenyl-1,3-dioxan-2-one (5). The reactions of 2,2-disubstituted-1,3-propanediols were carried out with phosgene dimer to find that the cyclic carbonate (5) was formed quantitatively in the reaction of 2-ethyl-2-phenyl-1,3-propanediol, while the corresponding polycarbonate was formed in the reaction of 2,2-diethyl-1,3-propanediol in 24% yield besides 3. Thermodynamic parameters were estimated in the anionic ring-opening polymerizations of cyclic carbonates (1−5) by Dainton's equation. The obtained ΔH p value in the ring-opening polymerization of each cyclic carbonate reflected the polymerizability. Molecular orbital calculations of the model compounds of the polymers were carried out to find that the polymerizabilities of the cyclic carbonates correlated with the stabilities of the corresponding polymer structures. The concentrations of the monomers formed in the depolymerizations well agreed with the equilibrium monomer concentrations in the anionic ring-opening polymerizations.

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“…Mp 78 °C (lit. 6 mp 75 °C). 1 H NMR (CDCl3): δ 1.30 (-CH3, s, 3H), 2.12 (-OH, broad s, 2H), 3.96 (-CH2-, q, J ) 10.8 Hz, 4H), 7.24-7.44 (-C6H5, m, 5H) ppm.…”

Section: Methodsmentioning

confidence: 99%

“…Mp: 45 °C (lit. 6 mp 44-45 °C). 1 H NMR (CDCl3): δ 0.91 (-CH3, t, J ) 7.3 Hz, 6H), 1.49 (-CH2-, q, J ) 7.3 Hz, 4H), 4.14 (-CH2O-, s, 4H) ppm.…”

Section: Methodsmentioning

confidence: 99%

Substituent Effect on the Anionic Equilibrium Polymerization of Six-Membered Cyclic Carbonates

et al. 1998

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“…The alkylene carbonates are easily available through transesterification of dialkyl carbonates (usually dimethyl carbonate or diethyl carbonate) or diphenyl carbonate with appropriate 1,2‐diols in the presence of alkaline catalysts . This approach for the preparation of five‐membered cyclic carbonates was also described in the 1950s by Ludwig and Piech and Sarel et al Currently, this approach is frequently used for synthesis of a glycerol carbonate. Glycerol carbonate is one of the most valuable derivatives that could be obtained from glycerol and CO 2 , and it is considered as a green chemical with a broad spectrum of uses such as substitute for petro‐derivative compounds as ethylene carbonate or propylene carbonate.…”

Section: Synthesis Of Nipu By Step‐growth Polyadditionmentioning

confidence: 99%

“…Reaction of equimolar amounts of propane‐1,3‐diol and diethyl carbonate with stannous 2‐ethylhexanoate as a catalyst led to six‐membered cyclic carbonate with a yield of 53%. Also, Pohoryles and Sarel reported the synthesis of various six‐membered cyclic carbonates from propane‐1,3‐diols with different substituents …”

Section: Synthesis Of Nipu By Step‐growth Polyadditionmentioning

confidence: 99%

Non‐isocyanate polyurethanes: synthesis, properties, and applications

Rokicki

Parzuchowski

Mazurek

2015

Polymers for Advanced Techs

331

233

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Conventional polyurethanes are typically obtained from polyisocyanates, polyols, and chain extenders. The main starting materials-isocyanates used in this process-raise severe health hazard concerns. Therefore, there is a growing demand for environment-friendly processes and products. This review article summarizes progress that has been made in recent years in the development of alternative methods of polyurethane synthesis. In most of them, carbon dioxide is applied as a sustainable feedstock for polyurethane production directly or indirectly. The resulting nonisocyanate polyurethanes are characterized by a solvent-free synthesis, resistance to chemical degradation, 20% more wear resistance than conventional polyurethane, and can be applied on wet substrates and cured under cold conditions. Three general polymer synthetic methods, step-growth polyaddition, polycondensation, and ring-opening polymerization, are presented in the review. Much attention is given to the most popular and having potential industrial importance method of obtaining non-isocyanate polyurethanes, poly(hydroxy-urethane)s, based upon multicyclic carbonates and aliphatic amines. It is evident from the present review that considerable effort has been made during the last years to develop environmentally friendly methods of obtaining polyurethanes, especially those with the use of carbon dioxide or simple esters of carbonic acid. Scheme 1. [n,m]-Polyurethane synthesis from alkylene bis(chloroformate)s and diamines. Scheme 2. Synthesis of NIPU in the reaction of alkylene bis(phenyl carbonate) with diamine. Scheme 3. Synthesis of [n]-polyurethane from aminoalkyl chloroformate.Scheme 4. Synthesis of [6]-polyurethane from 6-amino-1-hexanol. Scheme 5. Synthesis of allylcarbamate monomer and poly(thioether-urethane).708 Scheme 8. Synthesis of NIPU via AB-type self-polycondensation.Scheme 7. Multistep synthesis of isosorbide-based polyurethane (polycondensation mode). Scheme 6. Multistep synthesis of isosorbide-based polyurethane (polyaddition mode).

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“…The choice of educts was limited to monohydric alcohols, because polyhydric alcohols tend to react to polycarbonates or cyclic carbonates of which the latter easily decarboxylate at temperatures above room temperature. 15,16 The microwave-assisted esterification of the selected alcohols was carried out via parallel syntheses in the homogeneous phase, and with BTAC as the catalyst. The rotor systems HPR 1000/10™ and MMR-8™ (Fig.…”

Section: Green Contextmentioning

confidence: 99%

Microwave assisted phosgenation – alcoholysis using triphosgene

2003

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Organic Carbonates. IV.^1a,b,c Factors Affecting Formation of Homologous Cyclic Carbonates

Cited by 43 publications

References 0 publications

Substituent Effect on the Anionic Equilibrium Polymerization of Six-Membered Cyclic Carbonates

Substituent Effect on the Anionic Equilibrium Polymerization of Six-Membered Cyclic Carbonates

Non‐isocyanate polyurethanes: synthesis, properties, and applications

Microwave assisted phosgenation – alcoholysis using triphosgene

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Organic Carbonates. IV.1a,b,c Factors Affecting Formation of Homologous Cyclic Carbonates

Cited by 43 publications

References 0 publications

Substituent Effect on the Anionic Equilibrium Polymerization of Six-Membered Cyclic Carbonates

Substituent Effect on the Anionic Equilibrium Polymerization of Six-Membered Cyclic Carbonates

Non‐isocyanate polyurethanes: synthesis, properties, and applications

Microwave assisted phosgenation – alcoholysis using triphosgene

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Organic Carbonates. IV.^1a,b,c Factors Affecting Formation of Homologous Cyclic Carbonates