Hydrochloric Acid → 2-Propanone, 1-(2-nitrophenoxy)-

HRID 489470

반응식

HRID 489470 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Cl[CH2:12][C:13](=[O:15])[CH3:14].[Br-].[Na+].C(=O)(O)[O-].[Na+].Cl>[Cl-].C([N+](CCCC)(CCCC)C)CCC.O.C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:12][C:13](=[O:15])[CH3:14])([O-:3])=[O:2]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6571Chloroacetone2회HCID 69472-NitrophenolHCID 253881Sodium BromideHCID 516892Sodium Bicarbonate

생성물 1

HCID 792392-Propanone, 1-(2-nitrophenoxy)-수율 354,046.594%

시약·촉매·용매 3

HCID 91822Tributylmethylammonium chloride촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
65 °C

실험 절차

The following materials are combined in a 1000 gallon vessel and heated at 65° C. for 6–8 hours: 499.0 kg (1.000 mole equiv.) of o-Nitrophenol (o-NP, 99%, 3.551 kg-moles), 359.7 kg (1.05 mole equiv.) of chloroacetone (CA, 96%, 3.733 kg-moles), 45.4 kg (0.124 mole equiv.) of sodium bromide (0.441 kg-moles), 328.9 kg (1.102 mole equiv.) of sodium bicarbonate (3.915 kg-moles), 27.2 kg (0.023 mole equiv.) of aqueous tributylmethylammonium chloride (TBMAC, 70%, 0.081 kg-moles), and 989 kg of toluene. The reaction is checked for completion and a trim charge of chloroacetone is added if necessary. Then 682 kg of water are added at 60° C. and the pH of the reaction mixture is adjusted to pH 6.5 –7.0 at 55 to 60° C. (about 66 kg of 10% HCl). The phases are separated and the heavier aqueous phase is removed. A 5–15% NaCl solution (725 kg) is added to the organic phase, the mixture is agitated at 55 to 60° C. and the phases are separated again by decantation. The remaining organic phase of crude o-NPA is vacuum stripped at 65–75° C. to remove toluene and volatile impurities. Toluene (about 70 kg) is added towards the end of the vacuum strip and stripped off again to improve the removal of volatile impurities. About 691 kg of crude o-NPA (96.9% assay, 3.428 kg-moles, 96.5% yield rel. o-NP) are obtained. Finally 339 kg of a toluene/isopropanol (8:2) mixture is added at 55–65° C. to the crude o-NPA melt to obtain approximately a 65% o-NPA solution. This solution is transferred to a hold vessel where it is held at 65° C. for step b.

후처리

  1. customThe following materials are combined in a 1000 gallon vessel
  2. additionis added if necessary
  3. customis adjusted to pH 6.5 –7.0 at 55 to 60° C.
  4. customThe phases are separated
  5. customthe heavier aqueous phase is removed
  6. additionA 5–15% NaCl solution (725 kg) is added to the organic phase
  7. customthe phases are separated again by decantation
  8. customstripped at 65–75° C.
  9. customto remove toluene and volatile impurities
  10. additionToluene (about 70 kg) is added towards the end of the vacuum strip
  11. customthe removal of volatile impurities

출처 및 근거

ORD 기록
ord-af6faccecfaf4e1eb76be130fd187807
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977299B2

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