A NEW METHOD OF PREPARING SUBSTITUTED VINYL COMPOUNDS. DEPOLYMERIZATION STUDIES ON VINYL POLYMERS.<sup>1, 2</sup>

Bachman, G. Bryant; Hellman, Henry M.; Robinson, Kerry; Finholt, R. W.; Kähler, E.; Filar, L. J.; Heisey, Lowell V.; Lewis, LL; Micucci, D. Donald

doi:10.1021/jo01165a015

Cited by 45 publications

(5 citation statements)

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“…This has been fOlmd to be true by Bachman, et al [6], who recovered 66 percent of the styrene from such a copolymrr, whereas under the same conditions polystyrene yielded 60 to 65 percent of its styrene. In the case of a symmetrical disubstituted ethene polymerized with a monosubstituted or asymmetrically disubstituted ethene, we should again have a copolymer that has only one way of splitting out monomer if the monomer units considered are isolated from one another.…”

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confidence: 84%

“…This effect wou ld be appreciable only for rather low molecular weight polymers. Bachman et al [6] report that the pyrolytic yield of styrene from low molecular weight polystyrene decreases with decreasing molecular weight of the polymer.…”

Section: Polymers From Single Monomersmentioning

confidence: 99%

“…Probabilities P AB and P A A are similarly defined. They can be calculated from th e following expressions: (6) PAA rAA…”

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confidence: 99%

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Mass spectrometric investigation of the thermal decomposition of polymers

Wall¹

1948

J. RES. NATL. BUR. STAN.

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The application of t he mass spectrometer to the s tudy of the therm al decomposition of polymers is described . The relationships between the structure of polymers and yield of monomer s on decomposition are discussed . A quantitative treatment relating the composition s of certain coploymers and the yields of monomers is given. Data are presented showin g t he co mposition of the volatile hydrocarbons produced by the thermal decomposition of several vin yl a nd die ne p olymers.

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confidence: 84%

Section: Polymers From Single Monomersmentioning

confidence: 99%

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Mass spectrometric investigation of the thermal decomposition of polymers

Wall¹

1948

J. RES. NATL. BUR. STAN.

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“…Polymerization and subsequent pyrolysis of the resulting polymer have been proposed for the separation of styrene and substituted styrenes from nonpolymerizable liquids (IS!). Nuclear substituted styrenes have been obtained by Bachman et al (1) by depolymerization of the reaction products obtained by chlorination, nitration, and alkylation of polystyrene. Lebedev and Koblyanskil (5) obtained monoisobutylene and Volatile lowmolecular-weight polymers of isobutylene by the pyrolysis of polyisobutylene.…”

Section: Styrene Polymerizesmentioning

confidence: 99%

Pyrolysis of High Polymeric Hydrocarbons

Seymour¹

1948

Ind. Eng. Chem.

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700°C. calcination, the Mo/Al 0.05 sample had higher activity than the Mo/Al 0.15.The linear correlation of activity with surface area on calcination did not obtain for high-silica activated alumina H, although the activity of this surface has previously been shown to increase approximately linearly with amount of added molybdena to Mo / Al 0.15. The relation of activity to surface area on calcination for this material is shown in Figure 6 (upper). The sample impregnated to Mo/Al 0.15, a monolayer for this high surface area material, showed a linear decrease to area about 0.6 millimole of nbutane per gram and then another linear decrease of lesser slope. A possible explanation for this behavior is that the high-silica alumina surface is not homogeneous, and the most stable area is least effective in distributing molybdena in an active layer. Samples impregnated with lesser amounts of molybdena declined slowly in activity with area until they intersected the monolayer curve, after which they decreased with area at the same rate as the higher molybdena samples. The transition from the uniform activity to the rapid decline with loss of area was apparently not sharp for the Mo/Al 0.05 sample. There was a small loss of molybdena on calcination of these samples, but this wras much less than would be necessary to explain the break in Figure 5 (lower). Coke and gas yields were increased several per cent by the silica.COPRECIPITATED MOLYBDENA-ALUMINA Coprecipitated molybdena-alumina samples have shown low activity and low coke yield when calcined only at. 500°C. They had the unique property of a very rapid increase in activity on calcination to about 700°C ., and at this temperature had as high

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“…Since polystyrene is one of the most popular plastics, many chemical modifications of polystyrene, e.g., sulfonation, 1 acylation, 2 nitration, 3 and chloromethylation, 4 have been reported. Amidomethylation of styrene-divinylbenzene beads with N-methylol phthalimide was studied by Merrifield to obtain the aminomethylated beads.…”

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Amidomethylation of Vinyl Aromatic Polymers with N-Methylol-2-chloroacetamide

Teramoto

Nakamoto

2002

Polym J

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ABSTRACT:New vinyl aromatic compound polymers containing 2-chloroacetamidomethyl groups have been prepared from the corresponding polymers by amidomethylation with N-methylol-2-chloroacetamide (NMCA). The reaction proceeds in nitrobenzene or nitropropane in the presence of sulfuric acid as catalyst at temperature of 10 to 25• C.When 1.1 molar or less than 0.3 molar of NMCA to a molar of polystyrene is used, a soluble polymer is obtained. From poly(4-methylstyrene) or poly(4-tert-butylstyrene), soluble polymers containing 2-chloro-acetamidomethyl group are also obtained by the same reaction. 1 H NMR, 13 C NMR, FT-IR spectroscopy, and elemental analysis identifies the structures. These polymers are soluble in DMF or chloroform. In the case of poly(4-methylstyrene), NMR analysis shows that meta substituted product is exclusively obtained, although there are two possibilities of ortho-and meta-substituted products.KEY WORDS N-Methylol-2-chloroacetamide / Amidomethylation Reaction / Polystyrene / Poly(4-methylstyrene) / Poly(4-tert-butylstyrene) / 2-Chloro-acetamidomethyl Group / Since polystyrene is one of the most popular plastics, many chemical modifications of polystyrene, e.g., sulfonation, 1 acylation, 2 nitration, 3 and chloromethylation, 4 have been reported. Amidomethylation of styrene-divinylbenzene beads with N-methylol phthalimide was studied by Merrifield to obtain the aminomethylated beads. 5 On the other hand we developed the amidomethylation of polystyrene fibers 6 and dishes 7 using NMCA as amidomethylating reagent, by which the benzene ring of the polystyrene was quantitatively substituted by a chloroacetamidomethyl group that was easily converted into various functional groups. 8 The amidomethylation reaction could be performed at the temperature below 25 • C in a short time. Moreover, the preparation and the handling of NMCA were easy, because NMCA was liable to crystallize, and the crystal was nonhygroscopic. The replacement of the chlorine with amino compounds proceeded readily under mild condition. Thus, polymyxin B was immobilized on the chloroacetamidomethylated fiber, and the resulting fiber had an endotoxin adsorbing capacity. The fibers were packed in column for hemoperfusion, and used for the treatment against sepsis shock. 9

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A NEW METHOD OF PREPARING SUBSTITUTED VINYL COMPOUNDS. DEPOLYMERIZATION STUDIES ON VINYL POLYMERS.^{1, 2}

Cited by 45 publications

References 2 publications

Mass spectrometric investigation of the thermal decomposition of polymers

Mass spectrometric investigation of the thermal decomposition of polymers

Pyrolysis of High Polymeric Hydrocarbons

Amidomethylation of Vinyl Aromatic Polymers with N-Methylol-2-chloroacetamide

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A NEW METHOD OF PREPARING SUBSTITUTED VINYL COMPOUNDS. DEPOLYMERIZATION STUDIES ON VINYL POLYMERS.1, 2

Cited by 45 publications

References 2 publications

Mass spectrometric investigation of the thermal decomposition of polymers

Mass spectrometric investigation of the thermal decomposition of polymers

Pyrolysis of High Polymeric Hydrocarbons

Amidomethylation of Vinyl Aromatic Polymers with N-Methylol-2-chloroacetamide

Contact Info

Product

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A NEW METHOD OF PREPARING SUBSTITUTED VINYL COMPOUNDS. DEPOLYMERIZATION STUDIES ON VINYL POLYMERS.^{1, 2}