Acetic Acid → 2-Butene-1,4-diol diacetate

HRID 839429

반응식

HRID 839429 반응식
[N+]([O-])([O-])=O.[Li+].[C:6]([O:9][C:10](=[O:12])[CH3:11])(=[O:8])[CH3:7].[CH2:13]=[CH:14][CH:15]=[CH2:16].O=O.[C:19]([OH:22])(=[O:21])[CH3:20]>>[C:19]([O:22][CH2:13][CH:14]([O:9][C:10](=[O:12])[CH3:11])[CH:15]=[CH2:16])(=[O:21])[CH3:20].[C:19]([O:22][CH2:15][CH:16]=[CH:11][CH2:10][O:9][C:6](=[O:8])[CH3:7])(=[O:21])[CH3:20]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 977Oxygen2회HCID 78451,3-ButadieneHCID 7918Acetic AnhydrideHCID 10129889Lithium nitrate

생성물 2

HCID 1404022-Butene-1,4-diol diacetateHCID 27350013,4-Diacetoxy-1-butene

실험 절차

Another control run was carried out, employing the same reaction vessel as that utilized in Examples I and II above. In this run, the reactor was charged with 3.9 grams (50 mmoles) of lithium nitrate, 50 ml of acetic acid, 25 ml of acetic anhydride, and 11.0 grams (204 mmoles) of butadiene charged from the vapor phase. The reactor was placed in an oil bath and pressured to 30 psig with oxygen, and heated to 140° C for 3 hours. Oxygen was added to the reactor intermittently in the same manner as in Example I. At the end of the reaction period, the reactor was vented and the contents fractionally distilled through an 18 inch Vigreaux column, fraction 1 boiling at 46° - 51° C at 55 mm Hg, weighed 88.4 grams while fraction 2 boiling at 74° - 78° C at 6 mm Hg, weighed 2.1 grams and the distillation residue fraction 3 weighed 17.7 grams and was a thick black tar. Fractions 1 and 2 were analyzed by gas-liquid phase chromatography, which indicated that there was obtained 1.16 grams (6.7 mmoles) of 1,2-diacetoxy-3-butene and 0.43 grams (2.5 mmoles) of 1,4-diacetoxy-2-butene for a total yield of 9.2 mmoles of the diacetoxy butenes. This represents a yield of 4.5% based on the butadiene charged. This result shows that a much lower yield of diacetoxy butenes was obtained when the bismuth catalyst component is omitted from the reaction mixture.

후처리

  1. additioncharged from the vapor phase
  2. customThe reactor was placed in an oil bath
  3. customAt the end of the reaction period
  4. distillationthe contents fractionally distilled through an 18 inch Vigreaux column, fraction 1 boiling at 46° - 51° C at 55 mm Hg

출처 및 근거

ORD 기록
ord-8d2ae470b13c467289a0dbfa0e7e983b
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04095037

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