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1. WO1992018449 - SELECTIVE HYDROXYLATION OF PHENOL OR PHENOLIC ETHERS

Publication Number WO/1992/018449
Publication Date 29.10.1992
International Application No. PCT/GB1992/000639
International Filing Date 09.04.1992
Chapter 2 Demand Filed 11.11.1992
IPC
B01J 27/16 2006.1
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
27Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
14Phosphorus; Compounds thereof
16containing oxygen
C01B 25/37 2006.1
CCHEMISTRY; METALLURGY
01INORGANIC CHEMISTRY
BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF
25Phosphorus; Compounds thereof
16Oxyacids of phosphorus; Salts thereof
26Phosphates
37Phosphates of heavy metals
C07C 37/60 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
37Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
60by oxidation reactions introducing directly a hydroxy group on a CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
CPC
B01J 27/16
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
27Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
14Phosphorus; Compounds thereof
16containing oxygen ; , i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
C01B 25/372
CCHEMISTRY; METALLURGY
01INORGANIC CHEMISTRY
BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; ; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
25Phosphorus; Compounds thereof
16Oxyacids of phosphorus; Salts thereof
26Phosphates
37Phosphates of heavy metals
372of titanium, vanadium, zirconium, niobium, hafnium or tantalum
C07C 37/60
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
37Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
60by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
C07C 41/26
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
41Preparation of ethers; Preparation of compounds having groups, groups or groups
01Preparation of ethers
18by reactions not forming ether-oxygen bonds
26by introduction of hydroxy or O-metal groups
Applicants
  • SOLVAY INTEROX LIMITED [GB]/[GB] (AllExceptUS)
  • WASSON, Robert, Craig [GB]/[GB] (UsOnly)
  • JOHNSTONE, Alexander [GB]/[GB] (UsOnly)
  • SANDERSON, William, Ronald [GB]/[GB] (UsOnly)
Inventors
  • WASSON, Robert, Craig
  • JOHNSTONE, Alexander
  • SANDERSON, William, Ronald
Agents
  • PEARCE, Timothy
Priority Data
9107655.411.04.1991GB
Publication Language English (en)
Filing Language English (EN)
Designated States
Title
(EN) SELECTIVE HYDROXYLATION OF PHENOL OR PHENOLIC ETHERS
(FR) HYDROXYLATION SELECTIVE DE PHENOL OU D'ETHERS PHENOLIQUES
Abstract
(EN) Phenols, and related aromatic compounds, phenolic ethers, can be hydroxylated selectively using hydrogen peroxide in the presence of an amorphous or microcrystalline zirconium phosphate catalyst in a solvent containing an aliphatic carboxylic acid. The process is particularly suitable for phenol itself, and advantageously employs a partially dehydrated microcrystalline catalyst obtained by heating an hydrated microcrystalline zirconium phosphate for example at about 100 °C. A convenient reaction temperature is 50 to 90 °C, and convenient solvent is acetic acid. In an improved method of producing the catalyst, zirconium phosphate is precipitated from an aqueous phosphoric acid solution of zirconium oxychloride in the presence of a cationic phase transfer agent such as an alkylpyridinium salt or tetraalkylquaternary ammonium salt or a nonionic surfactant such as an alcohol ethoxylate.
(FR) On peut hydroxyler de manière sélective les phénols, et les composés aromatiques associés tels que les éthers phénoliques, à l'aide de peroxyde d'hydrogène et en présence d'un catalyseur en phosphate de zirconium amorphe ou monocristallin dans un solvant contenant un acide carboxylique aliphatique. Ce procédé est adapté notamment au phénol lui-même, et emploie avantageusement un catalyseur monocristallin partiellement déshydraté obtenu par le chauffage, par exemple à une température de 100 °C, d'un phosphate de zirconium monocristallin et hydraté. Une température réactionnelle appropriée est comprise entre 50 et 90 °C, et un solvant approprié est l'acide acétique. Suivant un procédé amélioré de production du catalyseur, on provoque la précipitation du phosphate de zirconium à partir d'une solution aqueuse en acide phosphorique d'oxychlorure de zirconium en présence d'un agent cationique de transfert de phase tel qu'un sel d'alkylpyridinium ou un sel d'ammonium tétraalkylquaternaire, ou d'un tensioactif non ionique tel qu'un éthoxylat alcoolique.
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