Benzoic Acid → Nonylbenzoate, branched and linear

HRID 1869568

反応式

HRID 1869568 の反応式
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17].CC(C(O)=O)C1C=CC(CC2C(=O)CCC2)=CC=1.[OH-].[K+].[OH-].[Na+]>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4].O>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 243Benzoic AcidHCID 3965LoxoprofenHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 17072Isononanol

生成物 1

HCID 53673956Nonylbenzoate, branched and linear

試薬・触媒・溶媒 2

HCID 21801Titanium tetrabutoxide触媒HCID 962Water溶媒3 回

反応条件

温度
80 °C

実験手順

A 4 liter distillation flask with top-mounted water separator and reflux condenser and also with a sampling port and thermometer was charged with 976 g of benzoic acid (8 mol), 1728 g of isononanol from Oxeno Olefinchemie GmbH (12 mol) and 0.59 g of butyl titanate (0.06% by weight based on the amount of acid) and this initial charge was heated at boiling under a nitrogen atmosphere. The water of reaction produced during the esterification was taken off at regular intervals. When the acid number fell below 0.1 mg KOH/g (after about 3 hours) the mixture was first cooled to below 60° C. and a 20 cm packed column was mounted. Thereafter the pressure was reduced to 2 mbar and first of all the excess alcohol was removed by distillation (temperature at the top of the column about 120° C.). Thereafter the batch was cooled to 80° C. and transferred to a 4 liter reaction flask with dip tube, top-mounted dropping funnel and column, and attached to a Claisen bridge. It was then neutralized with 5% strength by weight aqueous sodium hydroxide solution (5-fold excess of alkali) and stirred for 30 minutes more. Subsequently it was heated to 190° C. under reduced pressure (about 10 mbar). Then 8% by weight of fully demineralized water, based on the amount of crude ester employed, was added dropwise at constant temperature through the dropping funnel. Care was taken during this procedure to ensure that the overhead temperature did not climb above 120° C. Following the addition of water the heating was shut off and the mixture was cooled under reduced pressure. The ester was filtered off at room temperature on a suction filter with filter paper and filter aid. Gas chromatography indicated a purity for the ester of 99.7%.

後処理

  1. distillationA 4 liter distillation flask with top-mounted water separator
  2. temperaturereflux condenser
  3. additionthis initial charge
  4. temperaturewas heated
  5. customproduced during the esterification
  6. custom(after about 3 hours)
  7. temperaturewas first cooled to below 60° C.
  8. customwas removed by distillation (temperature at the top of the column about 120° C.)
  9. customtransferred to a 4 liter reaction flask with dip tube
  10. temperatureSubsequently it was heated to 190° C. under reduced pressure (about 10 mbar)
  11. additionwas added dropwise at constant temperature through the dropping funnel
  12. customdid not climb above 120° C
  13. temperaturethe mixture was cooled under reduced pressure
  14. filtrationThe ester was filtered off at room temperature on a suction
  15. filtrationfilter
  16. filtrationwith filter paper
  17. filtrationfilter aid

出典と根拠

ORDレコード
ord-1668cf07d3294fd8be456ef80cd10c8d
出典データセット
uspto-grants-2009_12
特許番号
US07638568B2

関連ノート

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