Organotin phosphate condensates as a catalyst of selective ring-opening of oxiranes by alcohols

Otera, Junzo; Niibo, Y.; Tatsumi, N.; Nozaki, H.

doi:10.1021/jo00237a009

Cited by 37 publications

(13 citation statements)

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“…5, curve b). Etherification should take place, because similar etherification products have been reported in the literature 12. As alcohols are not reactive enough toward epoxy groups, the first exothermic peak did not appear in the absence of the catalyst (Fig.…”

Section: Resultssupporting

confidence: 78%

Novel dibutyltin oxide–tributyl phosphate condensate as accelerator for the curing of the epoxy resin/4,4′‐diamino diphenyl sulfone system. I. Chemical reactions and properties of the cured resin

Song

et al. 2001

J of Applied Polymer Sci

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A crystalline condensate of dibutyltin oxide and tributyl phosphate (Sn-P-c) was more effective than the stannous octoate and dibutyltin dilaurate in accelerating the curing of the epoxy resin/4,4Ј-diamino diphenyl sulfone (DDS) system, based on an equal tin concentration. Water took part in the reaction and played an important role in the morphology and mechanical properties of the cured resin when Sn-P-c was used as the accelerator. In the presence of Sn-P-c, water first reacted with glycidyl ether to yield glycerol ether; the yielded hydroxyl group may further catalyze the amino/epoxy group reaction. In the absence of water or polar hydroxyl additives, Sn-P-c did not completely dissolve in the resin systems, and the cured resin was translucent material with poor mechanical strength. In the presence of a small amount of water, the cured material became transparent. Both flexural strength and maximum deflection were increased greatly.

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Section: Resultssupporting

confidence: 78%

Novel dibutyltin oxide–tributyl phosphate condensate as accelerator for the curing of the epoxy resin/4,4′‐diamino diphenyl sulfone system. I. Chemical reactions and properties of the cured resin

Song

et al. 2001

J of Applied Polymer Sci

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“…The alcoholysis of epoxides to form β‐hydroxy ethers is an important intermediate step in the synthesis of many small molecules and is normally catalyzed by Brønsted or Lewis acids . Heterogeneous acidic catalysts that have been successfully employed for this purpose include sulfonated polymers (Amberlyst‐15 and Nafion‐H), neutral alumina, mesoporous aluminosilicate, organotin phosphate condensates (OPCs), and Fe 3+ ‐montmorillonite, but it is unlikely that they could achieve sufficient interaction with the pendant functionalities of polymers to efficiently promote functionalization. Soluble compounds or complexes of main group metals, transition metals, and lanthanides are well‐known for their Lewis acidity and have been investigated specifically for their ability to catalyze the alcoholysis of epoxides.…”

Section: Introductionmentioning

confidence: 99%

“…9 Heterogeneous acidic catalysts that have been successfully employed for this purpose include sulfonated polymers (Amberlyst-15 and Nafion-H), 10,11 Additional Supporting Information may be found in the online version of this article. neutral alumina, [12][13][14] mesoporous aluminosilicate, [15][16][17] organotin phosphate condensates (OPCs), [18][19][20] and Fe 31 -montmorillonite, 21 but it is unlikely that they could achieve sufficient interaction with the pendant functionalities of polymers to efficiently promote functionalization. Soluble compounds or complexes of main group metals, [22][23][24][25][26][27][28][29][30][31] transition metals, 22,25,27,29,[32][33][34][35][36][37][38][39][40][41][42][43][44][45] and lanthanides 22,27,[46][47][48]…”

mentioning

confidence: 99%

Well-defined epoxide-containing styrenic polymers and their functionalization with alcohols

McLeod

Tsarevsky

2015

J. Polym. Sci. Part A: Polym. Chem.

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Polymers containing electrophilic moieties, such as activated esters, epoxides, and alkyl halides, can be readily modified with a variety of nucleophiles to produce useful functional materials. The modification of epoxide-containing polymers with amines and other strong nucleophiles is welldocumented, but there are no reports on the modification of such polymers with alcohols. Using phenyloxirane and glycidyl butyrate as low molecular weight model compounds, it was determined that the acid-catalyzed ring-opening of arylsubstituted epoxides by alcohols to form b-hydroxy ether products was significantly more efficient than that of alkylsubstituted epoxides. An aryl epoxide-type styrenic monomer, 4-vinylphenyloxirane (4VPO), was synthesized in high yield using an improved procedure and then polymerized in a controlled manner under reversible addition-fragmentation chaintransfer (RAFT) polymerization conditions. A successful chain extension with styrene proved the high degree of chain-end functionalization of the poly4VPO-based macro chain transfer agent. Poly4VPO was modified with a library of alcohols and phenols, some of which contained reactive functionalities, e.g., azide, alkyne, allyl, etc., using either CBr 4 (in PhCN at 90 8C for 2-3 days) or BF 3 (in CH 2 Cl 2 at ambient temperature over 30 min) as the catalyst. The resulting b-hydroxy ether-functionalized homopolymers were characterized using size exclusion chromatography, 1 H NMR and IR spectroscopy, and thermal gravimetric analysis.

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“…[14][15][16] A catalytic amount of the catalyst (%10 mg) was dissolved in 1.2 mL (1 g) propylene oxide in a sealed vial. The polymerization mixture was allowed to react for 7 d at room temperature.…”

Section: Synthesis Of It-ppomentioning

confidence: 99%

FTIR Imaging of Poly(3‐hydroxybutyrate) and Isotactic Poly(propylene oxide) Spherulites

Merten¹,

Kowalik²,

Aßhoff³

et al. 2010

Macro Chemistry & Physics

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FTIR spectroscopic imaging is combined with linear dichroism measurements to investigate the structures of spherulites of poly(3‐hydroxybutyrate) and isotactic poly(propylene oxide). It is shown that this technique can be used to easily gain qualitative information about relative orientations of chemical bonds within a solid polymeric sample. Furthermore the imaging technique is shown to have the considerable advantage that the obtained images are easy to understand and easy to interpret even without deep knowledge of FTIR linear dichroism measurements.magnified image

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Organotin phosphate condensates as a catalyst of selective ring-opening of oxiranes by alcohols

Cited by 37 publications

References 0 publications

Novel dibutyltin oxide–tributyl phosphate condensate as accelerator for the curing of the epoxy resin/4,4′‐diamino diphenyl sulfone system. I. Chemical reactions and properties of the cured resin

Novel dibutyltin oxide–tributyl phosphate condensate as accelerator for the curing of the epoxy resin/4,4′‐diamino diphenyl sulfone system. I. Chemical reactions and properties of the cured resin

Well-defined epoxide-containing styrenic polymers and their functionalization with alcohols

FTIR Imaging of Poly(3‐hydroxybutyrate) and Isotactic Poly(propylene oxide) Spherulites

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