3-Cyanopyridine → Nicotinate

HRID 324688

Reaktionsgleichung

Reaktionsgleichung von HRID 324688
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:10]([O-:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1.[Na+].C(C1C=NC=CC=1)#N.[Na].C=CC1C=CC=CC=1.C(C1C=CC=CC=1C=C)=C.CNC>O>[C:10]([O-:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1.[C:10]([OH:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1.[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Komponenten

11

Edukt 7

HCID 793-Cyanopyridine2×HCID 674DimethylamineHCID 936Nicotinamide4×HCID 7501Styrene2×HCID 666661,2-Diethenylbenzene2×HCID 5360545Sodium2×HCID 23687810Niacin sodium2×

Produkt 3

HCID 936NicotinamideHCID 937NicotinateAusbeute 5,07 %HCID 938Nicotinic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Versuchsvorschrift

In this Example a USP grade nicotinamide product was recovered from a crude nicotinamide product medium. The crude contained 39.7% nicotinamide, 2.15% sodium nicotinate and 0.14% 3-cyanopyridine. These and all other percentages given in this Example are percentages by weight unless indicated otherwise. The total sodium content of the medium was 0.38%. On a dry basis, the reaction crude contained 93.7% nicotinamide, 5.07% sodium nicotinate, 0.33% 3-cyanopyridine, and 0.9% total sodium. Cation and weak base resins were utilized in the recovery process. The cation exchange resin was Dowex Marathon C, a sulfonated copolymer of styrene and divinylbenzene (gel form). The weak base resin was Dowex Marathon WBA, a dimethylamine-functionalized chloromethylated copolymer of styrene and divinylbenzene (macroporous form with a monodisperse size distribution). After washing with deionized water, these resins were loaded into columns each having an inner diameter of 15 mm and a height of 30 cm, leaving about 1.5 inches head space at the top of the columns. The reaction crude was then successively treated over the cation-exchange resin (at 28 ml/min), the weak base resin (20 ml/min), the cation-exchange resin (28 ml/min), and the weak base resin (20 ml/min). The cation-exchange resin was regenerated after every ten bed volumes of reaction crude, by a cycle that included a water wash (20 ml/min, 1.25 bed volumes), a 12% sulfuric acid strip (7 ml/min, 1 bed volume), and another water wash (20 ml/min, 1.25 bed volumes). The weak base resin was regenerated after every five bed volumes of reaction crude, by a cycle including a water wash (20 ml/min, 1.6 bed volumes), a 4% sodium hydroxide strip (20 ml/min, 1 bed volume), and another water wash (2.6 bed volumes). The feeds were analyzed by HPLC after the first pass cation-exchange and weak base, and second pass cation-exchange and weak base. Typical results from such experiments are presented in Table 1 below, top. The lower section of Table 1 gives a typical product analysis on a water free basis. The extreme right hand column of Table 1 sets out the results of an analysis of the product after recovery by evaporation (no crystallization performed). As can be seen, this processing reduced the 0.9% initial sodium to an undetectable level, and the initial 5.07% nicotinate to 0.13% (as nicotinic acid) on a dry weight basis, providing a USP grade nicotinamide.

Aufarbeitung

  1. customOn a dry basis, the reaction crude
  2. washAfter washing with deionized water
  3. customa height of 30 cm, leaving about 1.5 inches
  4. customThe reaction crude
  5. additionwas then successively treated over the cation-exchange resin (at 28 ml/min)
  6. customafter every ten bed volumes of reaction crude
  7. washwash (20 ml/min, 1.25 bed volumes)
  8. washa 12% sulfuric acid strip (7 ml/min, 1 bed volume), and another water wash (20 ml/min, 1.25 bed volumes)
  9. customafter every five bed volumes of reaction crude
  10. washwash (20 ml/min, 1.6 bed volumes)
  11. washa 4% sodium hydroxide strip (20 ml/min, 1 bed volume), and another water wash (2.6 bed volumes)
  12. customTypical results from such experiments
  13. customresults of an analysis of the product after recovery
  14. customby evaporation (
  15. customno crystallization

Quellen und Nachweise

ORD-Eintrag
ord-1eab9a573ee74171b5e5dd13981a3d81
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218543B1

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