Formaldehyde → Hydroxymethyl Oxazolidine Iodopropynyl Butylcarbamate

HRID 1241910

Reaktionsgleichung

Reaktionsgleichung von HRID 1241910
OCC[CH:4]([OH:6])[CH3:5].C=O.C(O)[C:10]([NH2:15])(CO)[CH2:11][OH:12].[CH3:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]#[C:27][I:28])=[O:23]>O>[OH:12][CH2:11][CH:10]1[NH:15][CH2:5][CH2:4][O:6]1.[CH2:20]([NH:21][C:22](=[O:23])[O:24][C:25]#[C:26][CH2:27][I:28])[CH2:19][CH2:18][CH3:17]

Komponenten

6

Edukt 4

HCID 712Formaldehyde3×HCID 6503Tris(hydroxymethyl)aminomethane3×HCID 78961,3-ButanediolHCID 620973-Iodo-2-propynyl butylcarbamate

Produkt 1

HCID 131725965Hydroxymethyl Oxazolidine Iodopropynyl Butylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A closed vessel is charged with 102 g of 1,3-dihydroxybutane and 62 g of prilled paraformaldehyde is added and mixed at room temperature until a uniform slurry is formed. The slurry is then heated to 60° C. and a 2% molar (or 1–5%) molar excess of tris(hydroxymethyl)aminomethane (THAM) is introduced. A total of 124 g of 99% pure tris(hydroxymethyl)aminomethane is gradually added in increasing increments until a 2% molar excess is obtained. The ensuing condensation reaction takes place over a period of 3 hours. During the reaction, soluble bicyclic hydroxymethyl oxazolidine is continuously formed. Since paraformaldehyde and tris(hydroxymethyl)-aminomethane are of low solubility in the reaction medium, completion of the reaction is indicated when a clear solution is formed with water by-product. When the mixture becomes clear, insuring that all of the formaldehyde has reacted, the resulting solution is allowed to cool to ambient temperature and 4.42 g of powdered IPBC (weight ratio of bicyclic hydroxymethyl oxazolidine HMBO to IPBC is 33:1) is added and stirred until a clear solution is obtained. No crystallization of IPBC is noted in the substantially colorless product and a pure clear, liquid composition containing less than 1000 ppm of formaldehyde is obtained.

Aufarbeitung

  1. additionis added
  2. additionmixed at room temperature until a uniform slurry
  3. customis formed
  4. temperaturein increasing increments until a 2% molar excess
  5. customis obtained
  6. customThe ensuing condensation reaction
  7. customof 3 hours
  8. customis continuously formed
  9. customhas reacted
  10. temperatureto cool to ambient temperature
  11. customis obtained
  12. customNo crystallization of IPBC
  13. additiona pure clear, liquid composition containing less than 1000 ppm of formaldehyde
  14. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-fe9ea3e7c1e64b9ebdf54cb27a449dcd
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115641B2

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