GB1222216A - Hydrogenation process - Google Patents

Hydrogenation process

Info

Publication number
GB1222216A
GB1222216A GB3167067A GB3167067A GB1222216A GB 1222216 A GB1222216 A GB 1222216A GB 3167067 A GB3167067 A GB 3167067A GB 3167067 A GB3167067 A GB 3167067A GB 1222216 A GB1222216 A GB 1222216A
Authority
GB
United Kingdom
Prior art keywords
irh
ooc
groups
acetic acid
group
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
GB3167067A
Inventor
Robert Stevenson Coffey
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB3167067A priority Critical patent/GB1222216A/en
Publication of GB1222216A publication Critical patent/GB1222216A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1895—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/20—Carbonyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/827—Iridium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,222,216. Preparing alcohols; iridium complexes. IMPERIAL CHEMICAL INDUSTRIES Ltd. 24 June, 1968 [10 July, 1967], No. 31670/67. Addition to 1,135,979. Heading C2C. Primary or secondary alcohols are prepared by catalytic reduction of aldehydes or ketones, by contacting with hydrogen in the presence of a carboxylic acid containing at least two carbon atoms and a catalytic iridium complex of formula IrHY(OOC.R)L n wherein n is 2 or 3; Y is an anionic element or group, or hydrogen; R is an alkyl, cycloalkyl, aryl, alkaryl, aralkyl, alkenyl, cyclo - alkenyl, alkoxy, aryloxy, or heterocyclic group; and L is a ligand, both L groups being Z[R 1 R 2 R 3 ] when n is 2, and at least two L groups being Z[R 1 R 2 R 3 ] when n is 3, the remaining L group being CO or Z[R 1 R 2 R 3 ], the groups Z[R 1 R 2 R 3 ] being the same or different and Z being phosphorus, antimony or arsenic and R 1 , R 2 and R 3 being as for R above. Y and the group (OOC.R) are preferably each C 1 -C 6 alkyl mono-carboxylate groups, or Y may alternatively be halogen or -CN. R 1 , R 2 and R 3 may be C 1 -C 12 alkyl, phenyl, benzyl or pyridyl groups. The hydrogenation is carried out at room temperature and pressure or above, using 10<SP>-4</SP> to 10-1 molar amounts of the iridium complex. In an example, n-butyraldehyde is hydrogenated in acetic acid to a mixture of n - butanol and n - butyl acetate. A mixture of the iridium complexes IrH(OOC. - CH 3 ) 2 (P.Ph 3 ) 3 and IrH 2 (OOC.CH 3 )(P.Ph. 3 ) 3 is prepared by dissolving IrH 3 (P.Ph 3 ) 3 in acetic acid and distilling off the acetic acid under reduced pressure. A similar mixture is obtained by refluxing IrH 3 (P.Ph 3 ) 3 in acetic acid. Other complexes described are IrH 2 (OOC.CH 3 )(P.- Ph 3 ) 2 CO and IrH 2 (OOC.C 2 H 5 )(AsPh 3 ) 2 .
GB3167067A 1967-07-10 1967-07-10 Hydrogenation process Expired GB1222216A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3167067A GB1222216A (en) 1967-07-10 1967-07-10 Hydrogenation process

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3167067A GB1222216A (en) 1967-07-10 1967-07-10 Hydrogenation process

Publications (1)

Publication Number Publication Date
GB1222216A true GB1222216A (en) 1971-02-10

Family

ID=10326651

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3167067A Expired GB1222216A (en) 1967-07-10 1967-07-10 Hydrogenation process

Country Status (1)

Country Link
GB (1) GB1222216A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0405956A1 (en) * 1989-06-29 1991-01-02 BP Chemicals Limited Hydrogenation of alpha-hydroxy ketones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0405956A1 (en) * 1989-06-29 1991-01-02 BP Chemicals Limited Hydrogenation of alpha-hydroxy ketones

Similar Documents

Publication Publication Date Title
US3574716A (en) Hydrogenation of aldehydes and ketones
GB1197847A (en) Hydroformylation Process
US3849480A (en) Catalytic asymmetric hydrogenation
EP0564406A1 (en) Ferrocenyldiphosphine as ligands for homogeneous catalysts
ES8101080A1 (en) Platinum-diamine complexes, a method for the preparation of a medicine using such a platinum-diamine complex for the treatment of malignant tumor in mice
Manatt et al. Small-ring compounds. XXIV. Molecular orbital calculations of the delocalization energies of some small-Ring systems
GB1002429A (en) Process for the preparation of alcohols
ES453389A1 (en) Amino-alcohol derivatives and their preparation
Alyea et al. Crystal and molecular structures of bis (. mu.-chloro) bis [o-(dimesitylphosphino)-3, 5-dimethylbenzyl] dipalladium (II) acetone solvate,[Pd (P (mes) 2C6H2 (CH3) 2CH2) Cl] 2. cntdot. 2 (CH3COCH3), and its platinum analog [Pt (P (mes) 2C6H2 (CH3) 2CH2) Cl] 2. cntdot. 2 (CH3COCH3). Cyclometalated complexes of the bulkiest known phosphine trimesitylphosphine
GB1222216A (en) Hydrogenation process
JPS5561937A (en) Catalyst for asymmetric hydrogenation
GB1451409A (en) Process for the manufacture of 2-2-hydroxyphenyl-benztriazoles
ES443320A1 (en) Process for the production of n-phosphonomethyl glycine and its derivatives
GB971771A (en) Improvements in the preparation of organo-metal compounds
ES380098A1 (en) Organo-metallic compounds and uses thereof
ES410155A1 (en) 2-formyl-(6-methoxy-2-naphthyl) acetic acid
US2849470A (en) Oxy-dicyclopentadienyl compounds of transition metals of groups vi to viii and theirpreparation
KR860001780A (en) Method for preparing carboxylic anhydride using rhodium complex catalyst
Chatt et al. 625. Complexes of iridium (III) halides with tertiary phosphines and tertiary arsines
Okamoto et al. Structure of aqua (ethylenediaminetetraacetato) ruthenium (III)
GB1368434A (en) Hydroformylation of propylene
US2980741A (en) Di-valent nickel acetylene reactions
GB1414662A (en) Complexes containing phosphorus
ES295661A1 (en) Procedure for the preparation of O-hidroxifenil-s-triazines (Machine-translation by Google Translate, not legally binding)
GB1367623A (en) Hydroformylation using iridium catalyst