Citric Acid → HCID 86744195, compound

HRID 1031316Notes

Reaction equation

HRID 1031316 reaction equation
O.[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[OH:15][CH2:16][C@@H:17]([C@H:19]([C@@H:21]([C@@H:23]([CH2:25][OH:26])[OH:24])[OH:22])[OH:20])[OH:18].[Cl:27][Ti:28]([Cl:31])([Cl:30])[Cl:29].[OH-].[Na+].[Ti].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[Cl:27][Ti:28]([Cl:31])([Cl:30])[Cl:29].[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[OH:26][CH2:25][C@@H:23]([C@H:21]([C@@H:19]([C@@H:17]([CH2:16][OH:15])[OH:18])[OH:20])[OH:22])[OH:24]

Participants

8

Reactant 6

HCID 311Citric AcidHCID 5780Sorbitol2×HCID 14798Sodium HydroxideHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 23963TitaniumHCID 24193Titanium Tetrachloride

Product 1

HCID 86744195HCID 86744195, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Citric acid monohydrate (945 g) and sorbitol (819 g) were dissolved in deionized water (1620 g) and swept slowly with nitrogen. At 22-24°, TiCl4 (855 g) was added dropwise over a two hour and eight minute period, and stirring was continued at 25° for an additional 32 minutes. Aqueous NaOH (4033 g of a 30.3% solution) was added dropwise at 21-28° over a period of about five hours resulting in a pH of 7.5. The product was an aqueous solution which weighed 8240 g and contained 2.62% by weight of titanium. A portion of the product (78.2 g) was withdrawn for density measurement. The remainder of the product was heated to 60±2° over a 35 minute period and maintained at that temperature for two hours. It was cooled to about 25°, giving a pH of 7.1. The aqueous product had a Ti:citric acid:sorbitol mol ratio of 1:1:1.

Workup

  1. customresulting in a pH of 7.5
  2. customA portion of the product (78.2 g) was withdrawn for density measurement
  3. temperatureThe remainder of the product was heated to 60±2° over a 35 minute period
  4. temperaturemaintained at that temperature for two hours
  5. temperatureIt was cooled to about 25°
  6. customgiving a pH of 7.1

Sources & evidence

ORD record
ord-af522ac87caa49efb3159843c1a77ea8
Source dataset
uspto-grants-1990_09
Patent number
US04953621

Reaction notes

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