Properties of cyclodextrins. III. Cyclodextrin-epichlorhydrin resins. Preparation and analysis

N. Wiedenhof, J.N.J.J. Lammers, C.L. Panthaleon baron van Eck, van

Research output: Contribution to journalArticleAcademicpeer-review

59 Citations (Scopus)

Abstract

A bead polymn. process was used to prepare resins in a form useful for packing chromatographic columns from a-cyclodextrin (I) or b-cyclodextrin (II) and epichlorohydrin (III). A soln. of 2 ml. nonionic detergent (Nonidet P40) in 10 ml. o-xylene was added to 350 ml. o-xylene at 80 Deg , stirred 2 min., and mixed with a soln. prepd. by dissolving 9 g. finely powdered I in a mixt. of 5 g. water, 16 g. 30% NaOH, and 20 mg. NaBH4 at 30 Deg. After 5 min. vigorous stirring, 25 g. III was added. Beads formed in 30 min. The beads were then suspended in 100 ml. 1:1 vol. EtOH-water for 10 min., freed of excess liq., and suspended 30 min. in 96% EtOH. This procedure was repeated 2 times, and the beads were then dried 18 hrs. at 70 Deg. The bead polymn. of II was carried out similarly, using iso-BuCOMe instead of o-xylene solvent. Water-sol. resins were also prepd. by stirring the polymn. mixt. gently and omitting the surfactant. The apparent void concn. in the resins was detd. either by cleaving the a,1 -> 4 linkages by acid hydrolysis and then detg. the reducing groups liberated, or by utilizing the ability of cyclodextrin voids to form a sol. inclusion compd. with m-chlorobenzoic acid. The amt. of inclusion compd. was detd. spectrophotometrically and the apparent void concn. was read from a calibration curve. The results of degree of substitution calcns. indicated that the resins contained at least some polyoxyethene chains. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)119-123
JournalStarch - Staerke
Volume21
Issue number5
DOIs
Publication statusPublished - 1969

Fingerprint

Epichlorohydrin
cyclodextrins
Cyclodextrins
xylene
resins
Resins
Polymethyl Methacrylate
Water
Surface-Active Agents
Detergents
Calibration
water
Hydrolysis
acid hydrolysis
surfactants
detergents
Acids
calibration
Substitution reactions
2-xylene

Cite this

Wiedenhof, N., Lammers, J. N. J. J., & Panthaleon baron van Eck, van, C. L. (1969). Properties of cyclodextrins. III. Cyclodextrin-epichlorhydrin resins. Preparation and analysis. Starch - Staerke, 21(5), 119-123. https://doi.org/10.1002/star.19690210504
Wiedenhof, N. ; Lammers, J.N.J.J. ; Panthaleon baron van Eck, van, C.L. / Properties of cyclodextrins. III. Cyclodextrin-epichlorhydrin resins. Preparation and analysis. In: Starch - Staerke. 1969 ; Vol. 21, No. 5. pp. 119-123.
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abstract = "A bead polymn. process was used to prepare resins in a form useful for packing chromatographic columns from a-cyclodextrin (I) or b-cyclodextrin (II) and epichlorohydrin (III). A soln. of 2 ml. nonionic detergent (Nonidet P40) in 10 ml. o-xylene was added to 350 ml. o-xylene at 80 Deg , stirred 2 min., and mixed with a soln. prepd. by dissolving 9 g. finely powdered I in a mixt. of 5 g. water, 16 g. 30{\%} NaOH, and 20 mg. NaBH4 at 30 Deg. After 5 min. vigorous stirring, 25 g. III was added. Beads formed in 30 min. The beads were then suspended in 100 ml. 1:1 vol. EtOH-water for 10 min., freed of excess liq., and suspended 30 min. in 96{\%} EtOH. This procedure was repeated 2 times, and the beads were then dried 18 hrs. at 70 Deg. The bead polymn. of II was carried out similarly, using iso-BuCOMe instead of o-xylene solvent. Water-sol. resins were also prepd. by stirring the polymn. mixt. gently and omitting the surfactant. The apparent void concn. in the resins was detd. either by cleaving the a,1 -> 4 linkages by acid hydrolysis and then detg. the reducing groups liberated, or by utilizing the ability of cyclodextrin voids to form a sol. inclusion compd. with m-chlorobenzoic acid. The amt. of inclusion compd. was detd. spectrophotometrically and the apparent void concn. was read from a calibration curve. The results of degree of substitution calcns. indicated that the resins contained at least some polyoxyethene chains. [on SciFinder (R)]",
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Wiedenhof, N, Lammers, JNJJ & Panthaleon baron van Eck, van, CL 1969, 'Properties of cyclodextrins. III. Cyclodextrin-epichlorhydrin resins. Preparation and analysis', Starch - Staerke, vol. 21, no. 5, pp. 119-123. https://doi.org/10.1002/star.19690210504

Properties of cyclodextrins. III. Cyclodextrin-epichlorhydrin resins. Preparation and analysis. / Wiedenhof, N.; Lammers, J.N.J.J.; Panthaleon baron van Eck, van, C.L.

In: Starch - Staerke, Vol. 21, No. 5, 1969, p. 119-123.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Properties of cyclodextrins. III. Cyclodextrin-epichlorhydrin resins. Preparation and analysis

AU - Wiedenhof, N.

AU - Lammers, J.N.J.J.

AU - Panthaleon baron van Eck, van, C.L.

PY - 1969

Y1 - 1969

N2 - A bead polymn. process was used to prepare resins in a form useful for packing chromatographic columns from a-cyclodextrin (I) or b-cyclodextrin (II) and epichlorohydrin (III). A soln. of 2 ml. nonionic detergent (Nonidet P40) in 10 ml. o-xylene was added to 350 ml. o-xylene at 80 Deg , stirred 2 min., and mixed with a soln. prepd. by dissolving 9 g. finely powdered I in a mixt. of 5 g. water, 16 g. 30% NaOH, and 20 mg. NaBH4 at 30 Deg. After 5 min. vigorous stirring, 25 g. III was added. Beads formed in 30 min. The beads were then suspended in 100 ml. 1:1 vol. EtOH-water for 10 min., freed of excess liq., and suspended 30 min. in 96% EtOH. This procedure was repeated 2 times, and the beads were then dried 18 hrs. at 70 Deg. The bead polymn. of II was carried out similarly, using iso-BuCOMe instead of o-xylene solvent. Water-sol. resins were also prepd. by stirring the polymn. mixt. gently and omitting the surfactant. The apparent void concn. in the resins was detd. either by cleaving the a,1 -> 4 linkages by acid hydrolysis and then detg. the reducing groups liberated, or by utilizing the ability of cyclodextrin voids to form a sol. inclusion compd. with m-chlorobenzoic acid. The amt. of inclusion compd. was detd. spectrophotometrically and the apparent void concn. was read from a calibration curve. The results of degree of substitution calcns. indicated that the resins contained at least some polyoxyethene chains. [on SciFinder (R)]

AB - A bead polymn. process was used to prepare resins in a form useful for packing chromatographic columns from a-cyclodextrin (I) or b-cyclodextrin (II) and epichlorohydrin (III). A soln. of 2 ml. nonionic detergent (Nonidet P40) in 10 ml. o-xylene was added to 350 ml. o-xylene at 80 Deg , stirred 2 min., and mixed with a soln. prepd. by dissolving 9 g. finely powdered I in a mixt. of 5 g. water, 16 g. 30% NaOH, and 20 mg. NaBH4 at 30 Deg. After 5 min. vigorous stirring, 25 g. III was added. Beads formed in 30 min. The beads were then suspended in 100 ml. 1:1 vol. EtOH-water for 10 min., freed of excess liq., and suspended 30 min. in 96% EtOH. This procedure was repeated 2 times, and the beads were then dried 18 hrs. at 70 Deg. The bead polymn. of II was carried out similarly, using iso-BuCOMe instead of o-xylene solvent. Water-sol. resins were also prepd. by stirring the polymn. mixt. gently and omitting the surfactant. The apparent void concn. in the resins was detd. either by cleaving the a,1 -> 4 linkages by acid hydrolysis and then detg. the reducing groups liberated, or by utilizing the ability of cyclodextrin voids to form a sol. inclusion compd. with m-chlorobenzoic acid. The amt. of inclusion compd. was detd. spectrophotometrically and the apparent void concn. was read from a calibration curve. The results of degree of substitution calcns. indicated that the resins contained at least some polyoxyethene chains. [on SciFinder (R)]

U2 - 10.1002/star.19690210504

DO - 10.1002/star.19690210504

M3 - Article

VL - 21

SP - 119

EP - 123

JO - Starch - Staerke

JF - Starch - Staerke

SN - 0038-9056

IS - 5

ER -