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Sulfuric Acid → Quinoline, sulfate (1:1)

HRID 1376258
Notes
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Reaction equation

HRID 1376258 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O.O=[O+][O-].[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1>O=O.O=[O+][O-]>[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.[S:1](=[O:3])(=[O:2])([OH:5])[OH:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7047QuinolineHCID 24823OzoneHCID 2724130Cornforth reagent

Product 1

HCID 10744Quinoline, sulfate (1:1)

Reagents, catalysts & solvents 1

HCID 131711318Oxygen ozoneSolvent

Procedure

4 kg of an aquoeus sulfuric acid solution of quinoline (composition: 6% by weight of quinoline, 9.1% by weight of sulfuric acid, remainder water as in Example 29) are ozonized with 2500 l (STP) of O2/O3 with 100 g of O3/Nm3 in a batchwise manner until the quinoline content had dropped to 0.9 g/l. Ozonization is then continued with the same amount of gas and ozone concentration, and the quinoline concentration is maintained between 0.7 g/l and 0.9 g./l as a result of the metered addition of aqueous sulfuric acid quinoline solution. The offgas comprised 63 g of 3/Nm3 at the start of the continuous procedure, and 59 g of O3/Nm3 at the end of the experiment. The ozone consumption was measured and was 230% of theory, calculated on the basis of quinoline, which suggests massive secondary reactions and further reactions of the cleavage products. Finally, PDC began to precipitate out of the solution, which blocked the absorption column.

Workup

  1. additionhad dropped to 0.9 g/l
  2. concentrationOzonization is then continued with the same amount of gas and ozone concentration
  3. concentrationthe quinoline concentration
  4. temperatureis maintained between 0.7 g/l and 0.9 g

Sources & evidence

ORD record
ord-7c7be3d36d504b468a154c8bdfaec8dd
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169950B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes