Bromide ion → Tetrabromobisphenol A

HRID 1582846

反応式

HRID 1582846 の反応式
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([Br:9])[C:5](Br)=[C:4]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])[C:3]=1Br.OC1C=CC(C(C2C=CC(O)=CC=2)(C)C)=CC=1.[Br-:39].[Br-:40].[Na+].Br([O-])(=O)=O.[Na+].Cl>C(Cl)Cl.O.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+]>[CH3:13][C:11]([C:14]1[CH:15]=[C:16]([Br:39])[C:17]([OH:20])=[C:18]([Br:40])[CH:19]=1)([C:4]1[CH:5]=[C:6]([Br:9])[C:7]([OH:8])=[C:2]([Br:1])[CH:3]=1)[CH3:12]

参加物

10

反応物 6

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 6623Bisphenol A2 回HCID 253881Sodium BromideHCID 23668195Sodium BromateHCID 54240982HCID 54240982、化合物

生成物 1

HCID 6618Tetrabromobisphenol A

試薬・触媒・溶媒 3

HCID 3423265Sodium Lauryl Sulfate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

Ramachandraiah, P. K. Ghosh, A. S. Mehta, R. P. Pandya, A. D. Jethva, S. S. Vaghela, S. N. Misra (pending U.S. pat. appln. Ser. No. 09/767,667 [2001]) have prepared tetrabromobisphenol-A from bisphenol-A using 2:1 molar ratio of bromide and bromate salts as brominating agent. To 0.50 kg (2.19 moles) of bisphenol-A in 1.50 liters of methylene chloride, a solution of 0.63 kg (6.14 moles) of sodium bromide, 0.44 kg (2.93 moles) of sodium bromate and 1 g of sodium lauryl sulfate in 2.5 liters of water was added. The flask was cooled to 10° C. by placing it in a cold water bath. To it, 0.90 liters (10.8 moles) of 12 N hydrochloric acid was added over 3 h under stirring. The contents were stirred for another 0.5 h and the separated solid product was filtered, washed twice with deionized water and dried in oven at 100° C. to give a yield of 0.85 kg of TBBPA. The organic layer was recycled in subsequent batches. The isolated yield of TBBPA (m.p. 178-180° C.) over three batches was 85.4%. Although the method has several advantages in that the brominating reagent is easy to handle, no catalyst is required, the bromine atom efficiency for the aromatic substitution reaction studied is as high as 95-100%, the main drawback of this method is that alkali bromide and bromate salts are individually much costlier than liquid bromine. Moreover the 4:2 stoichiometry of bromide:bromate is suitable for substitution reactions but not for addition of bromine across double bonds.

後処理

  1. stirringThe contents were stirred for another 0.5 h
  2. filtrationthe separated solid product was filtered
  3. washwashed twice with deionized water
  4. customdried in oven at 100° C.

出典と根拠

ORDレコード
ord-3d9ed992a8c8463da085ea7dd200d5fb
出典データセット
uspto-grants-2004_05
特許番号
US06740253B2

関連ノート

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