2-Benzyltoluene → Methoxycarbonylaminohexyl isocyanate

HRID 1424746

反応式

HRID 1424746 の反応式
C[O:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][CH3:16])=[O:14])=O.C(C1C=CC=CC=1C)C1C=CC=CC=1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C[N+]1C=CNC=1.CCCS([O-])(=O)=O>>[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][CH3:16])=[O:14])=[C:3]=[O:2]

参加物

5

反応物 4

HCID 697382-BenzyltolueneHCID 235165methyl N-[6-(methoxycarbonylamino)hexyl]carbamateHCID 9809426Di-n-butyldilauryltinHCID 1297396711-Methylimidazolium 3-propanesulfonate

生成物 1

HCID 20588398Methoxycarbonylaminohexyl isocyanate収率 5.2%

反応条件

温度
240 °C

実験手順

500 mL 3-necked flask equipped with a reflux apparatus, cooler, thermometer and sampling device was charged with 1,6-bis(methoxycarbonylamino)hexane (HDC, 50 g), benzyltoluene (250 g), di-n-butyltin dilaurate (0.05 g), and 1-methylimidazolium-3-propanesulfonate (0.1 g) as a zwitterionic compound, which were heated to 240° C. under 20 mmHg pressure. The reaction time was 2 hours, and the temperature of the reflux and cooling condenser was kept at 60° C. or more to prevent the reverse reaction. The resulting 1,6-diisocyanatohexane (HDI) and methanol were separately collected into a flask and dry ice-acetone trap. After the completion of the reaction, the product collected in the flask was analyzed with gas chromatography, which showed 94.1% yield of HDI, 5.2% yield of 1-isocyanato-6-methoxycarbonylaminohexane (HMI), and only 1.3 g of high-boiling polymer precipitates.

後処理

  1. custom500 mL 3-necked flask equipped with a reflux apparatus
  2. aliquotcooler, thermometer and sampling device
  3. temperaturethe temperature of the reflux
  4. temperaturecooling condenser
  5. customwas kept at 60° C. or more
  6. customthe reverse reaction
  7. customThe resulting 1,6-diisocyanatohexane (HDI) and methanol were separately collected into a flask and dry ice-acetone trap
  8. customAfter the completion of the reaction
  9. customthe product collected in the flask

出典と根拠

ORDレコード
ord-5efdbf0fbcd7454ba8fe159ee90aae54
出典データセット
uspto-grants-2015_01
特許番号
US08927763B2

関連ノート

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