GB708593A - Improvements in the catalytic production of hydroquinone - Google Patents

Improvements in the catalytic production of hydroquinone

Info

Publication number
GB708593A
GB708593A GB13241/52A GB1324152A GB708593A GB 708593 A GB708593 A GB 708593A GB 13241/52 A GB13241/52 A GB 13241/52A GB 1324152 A GB1324152 A GB 1324152A GB 708593 A GB708593 A GB 708593A
Authority
GB
United Kingdom
Prior art keywords
salt
complex
cobalt carbonyl
heavy metal
amine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB13241/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB708593A publication Critical patent/GB708593A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/08Dihydroxy benzenes; Alkylated derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Hydroquinone is produced by the reaction of carbon monoxide and acetylene in the presence of water and/or an alcohol at an elevated temperature and superatmospheric pressure, e.g. at 80-150 DEG C., at a pressure exceeding 5 atmospheres, in the presence of a catalyst which comprises a salt of an ammonium or amino complex of a heavy metal with cobalt carbonyl hydride. The cation of the catalyst may be derived from ammonia or a primary amine and cadmium, zinc or copper, or a metal of the iron group, for example [Fe(NH3)6]++, [Fe(NH3)6]+++, [Co(NH3)6]++, [Ni(NH3)6]++, [Co(NH2.CH2.CH2.NH2)3]++, [Cd(NH3)2]++. In forming the catalysts, the complex cation replaces the hydrogen atoms of the equivalent number of molecules of cobalt carbonyl hydride, HCo(CO)4. In examples: (1) acetylene and carbon monoxide are reacted with ethanol in the presence of a complex salt of the formula [Fe(NH3)6] [Co(CO)4]2 to give hydroquinone, and, if desired, the complex ferrous ammonium cation might be replaced by complex ferrous cations with ethylene diamine, hexamethylene diamine or pyridine; (2) a mixture of ethanol, hydroquinone and the ferrous ammonium cobalt carbonyl compound of (1) are treated with carbon monoxide and acetylene under pressure at 90-100 DEG C. to give an increased amount of hydroquinone. Metal-amine complex salts of cobalt carbonyl hydride are prepared by introducing cobalt carbonyl into an aqueous solution of an alkali or alkaline earth metal hydroxide or an amino compound, e.g. by treating an aqueous solution or suspension of a cobalt salt oxide or hydroxide in the presence of ammonia or an amine at 50-250 DEG C. at superatmospheric pressure with carbon monoxide, and treating the resultant solution of a salt of cobalt carbonyl hydride with a complex amine salt of a heavy metal, or when there is already a sufficient excess of amine present, with the simple salt of a heavy metal. The preparation of the complex salts of cobalt carbonyl hydride with the iron complex of ethylene diamine of the formula [Fe(NH2.CH2.CH2.NH2)3] [Co(CO)4]2 the corresponding hexamethylene diamine compound of the formula [Fe(NH2(CH2)6NH2)3] [Co(CO)4]2 and the corresponding pyridine compound is described.ALSO:Salts of ammonium complexes of heavy metals with cobalt carbonyl hydride are prepared by introducing cobalt carbonyl into an aqueous solution of an alkali or alkaline earth metal hydroxide or an amino compound to form the corresponding salt of cobalt carbonyl hydride which is then treated with a complex heavy metal salt obtained by the action of ammonia on a solution of the ordinary mineral acid salt of the heavy metal to give by double decomposition the desired heavy metal complex ammonium salt of cobalt carbonyl hydride. These salts may also be obtained by treating an aqueous solution or suspension of a cobalt salt, oxide or hydroxde with carbon monoxide at 50-250 DEG C. in the presence of ammonia or an amine at superatmospheric pressure and treating the resulting solution of an ammonium or amine salt of cobalt carbonyl hydride with a complex ammonium salt of a heavy metal or, where the reaction mixture already contains a sufficient excess of ammonia, with a simple salt of a heavy metal. The above reactions are preferably carried out with the exclusion of air. Specified heavy metal complex cations are those derived from cadmium, zinc or copper or metals of the iron group such as [Fe(NH3)6]++, [Fe(NH3)6+++], [Co(NH3)6++, [Ni(NH3)6++ and [Cd(NH3)2]++. In an example the preparation of the compound of the formula [Fe(NH3)6] [Co(CO)4]2 is described.
GB13241/52A 1951-05-31 1952-05-26 Improvements in the catalytic production of hydroquinone Expired GB708593A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE708593X 1951-05-31

Publications (1)

Publication Number Publication Date
GB708593A true GB708593A (en) 1954-05-05

Family

ID=6617655

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13241/52A Expired GB708593A (en) 1951-05-31 1952-05-26 Improvements in the catalytic production of hydroquinone

Country Status (1)

Country Link
GB (1) GB708593A (en)

Similar Documents

Publication Publication Date Title
GB312717A (en) Improvements in the manufacture and production of hydrocarbons
GB518614A (en) Synthesis of hydrocarbons which are solid, liquid or readily liquefiable from carbon monoxide and hydrogen
CA1130265A (en) Process for the production of amorphous aluminosilicates and their use as catalysts
CA1248512A (en) Process for the preparation of a cayalyst mixture and its use
US1984884A (en) Process for producing oxygeanted organic compounds
GB708593A (en) Improvements in the catalytic production of hydroquinone
Pregaglia et al. Catalysis by cobalto-cyano complexes in non-aqueous solvents
CN111036284B (en) Catalyst, preparation method thereof and method for preparing light olefins from synthesis gas
Shultz et al. STUDIES OF THE FISCHER—TROPSCH SYNTHESIS. PREPOISONING OF IRON CATALYSTS BY SULFUR COMPOUNDS
KR910019958A (en) Process for preparing secondary amines and catalyst system for same
Kölbel et al. Model studies of the interaction of CO and H2 on transition metals: II. On the role of chemisorption complexes in primary reactions
GB718386A (en) Catalysts for carbon monoxide hydrogenation
US2590078A (en) Process for the manufacture of the carbonyls of nickel
DE69107896D1 (en) Process for the preparation of a precipitation catalyst precursor for ammonia synthesis.
SU709163A1 (en) Method of obtaining catalyst for carbon monoxide conversion
US4521394A (en) Conversion of gases to useable products
GB1245036A (en) Improvements in or relating to the preparation of catalysts
Ebert et al. More on the reaction of graphite/potassium with water
CN102026962A (en) A process for the production of nitrogen or phosphorus containing compounds from synthesis gas
US3567655A (en) Method of producing a low-temperature catalyst for the conversion of carbon monoxide with steam
GB1382468A (en) Process for making tetraalkylpyrazines
GB337409A (en) Improvements in or relating to the manufacture of oxygenated organic compounds
US1977633A (en) Process for producing alcohols
JPH02251245A (en) Preparation of copper-iron-aluminum catalyst
US2467282A (en) Hydrocarbon synthesis