Propionic Acid → Octocrylene

HRID 1640077노트

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HRID 1640077 반응식
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])#[N:2].[C:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(=O)C.[NH4+].C(O)(=O)CC>CCCCCCC.O>[C:1]([C:3](=[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])#[N:2]

참가 물질

7

반응물 4

HCID 1032Propionic Acid2회HCID 3102BenzophenoneHCID 963592-Ethylhexyl cyanoacetateHCID 517165Ammonium Acetate

생성물 1

HCID 22571Octocrylene

시약·촉매·용매 2

HCID 962Water용매HCID 8900Heptane용매2회

반응 조건

온도
90 °C

실험 절차

Into a 500 ml four-neck round-bottom flask, equipped with a mechanical stirrer, a thermometer and a condenser is charged with 62.2 g (0.32 mmol) of 2-Ethylhexyl cyanoacetate (EHCA) and 81.0 g (0.45 mol) of Benzophenone (BP) (molar ratio EHCA:BP=0.71:1) and 27.7 g (0.36 mol) of ammonium acetate and 81.0 g (1.1 mol) of propionic acid and 81.0 g of heptane. The mixture is heated under stirring. When the temperature reach 110° C., a mixture of propionic acid, water, heptane is distilled off over a period of 5 hours at normal pressure. Heptane phase is returned back to the flask. Then the reactant is cooled to 90° C., and 100 ml of hot water is added to the reaction mixture. The mixture is kept at 85° C. for 10 minutes, and then transferred to a funnel for separation. To a flask equipped with a column 256.0 g of crude 2-ethylhexyl 2-cyano-3,3-diphenylacrylate solution is added. Rectification is carried out at 1 mbar. 2-Ethylhexyl 2-cyano-3,3-diphenylacrylate is distilled out at 210° C. (vapor). After distillation, light yellow 2-ethylhexyl 2-cyano-3,3-diphenylacrylate is obtained. Reaction yields are as indicated in table 1 and assume recycle of unreacted benzophenone and 2-EHCA.

후처리

  1. customInto a 500 ml four-neck round-bottom flask, equipped with a mechanical stirrer
  2. temperatureThe mixture is heated
  3. customreach 110° C.
  4. distillationis distilled off over a period of 5 hours at normal pressure
  5. addition100 ml of hot water is added to the reaction mixture
  6. customtransferred to a funnel for separation
  7. customTo a flask equipped with a column 256.0 g of crude 2-ethylhexyl 2-cyano-3,3-diphenylacrylate solution
  8. additionis added
  9. distillation2-Ethylhexyl 2-cyano-3,3-diphenylacrylate is distilled out at 210° C. (vapor)
  10. distillationAfter distillation

출처 및 근거

ORD 기록
ord-4f3ba922594d40518039311d7b82be31
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110702B2

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