GB781405A - Hydrogenation of unsaturated carbonyl compounds - Google Patents
Hydrogenation of unsaturated carbonyl compoundsInfo
- Publication number
- GB781405A GB781405A GB27880/55A GB2788055A GB781405A GB 781405 A GB781405 A GB 781405A GB 27880/55 A GB27880/55 A GB 27880/55A GB 2788055 A GB2788055 A GB 2788055A GB 781405 A GB781405 A GB 781405A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copper
- oxide
- catalyst
- hydrogenated
- carbonyl compounds
- 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
Links
- 150000001728 carbonyl compounds Chemical class 0.000 title abstract 6
- 238000005984 hydrogenation reaction Methods 0.000 title abstract 3
- 239000003054 catalyst Substances 0.000 abstract 11
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 8
- 239000010949 copper Substances 0.000 abstract 8
- 229910052802 copper Inorganic materials 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 6
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 4
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
- 229910000431 copper oxide Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 abstract 2
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 abstract 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 2
- 239000005751 Copper oxide Substances 0.000 abstract 2
- 239000004115 Sodium Silicate Substances 0.000 abstract 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052788 barium Inorganic materials 0.000 abstract 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 abstract 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052911 sodium silicate Inorganic materials 0.000 abstract 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- 239000011701 zinc Substances 0.000 abstract 2
- PYLMCYQHBRSDND-SOFGYWHQSA-N (E)-2-ethyl-2-hexenal Chemical compound CCC\C=C(/CC)C=O PYLMCYQHBRSDND-SOFGYWHQSA-N 0.000 abstract 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 abstract 1
- 239000005750 Copper hydroxide Substances 0.000 abstract 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- -1 aliphatic aldehydes Chemical class 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 229910000423 chromium oxide Inorganic materials 0.000 abstract 1
- 229940117916 cinnamic aldehyde Drugs 0.000 abstract 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910001956 copper hydroxide Inorganic materials 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
- B01J2208/00176—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles outside the reactor
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
- B01J2208/00274—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant vapours
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/0053—Controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Mycology (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Catalysts for use in the hydrogenation of unsaturated carbonyl compounds comprise copper with or without an oxide of an element such as chromium, barium or zinc which acts as a promoter and stabilizer. Such catalysts may be prepared by the reduction of pellets of copper oxide or hydroxide mixed with one or more of the other oxides or the corresponding hydroxides. Alternatively the catalyst may be prepared by reducing with hydrogen a coating, comprising a mixture of the oxide or hydroxide of copper and of one of the metals specified above, previously deposited on an inactive carrier, such as inert alumina or kieselguhr. Other copper catalysts may be used, e.g. the product obtained by reducing with hydrogen mixtures of copper oxide and sodium silicate containing, for example, 10-20 per cent of sodium silicate. In an example unsaturated carbonyl compounds are hydrogenated using as catalyst porous inert alumina tablets coated with a mixture of freshly reduced copper and chromium oxide.ALSO:Ethylenically unsaturated carbonyl compounds are hydrogenated to saturated carbonyl compounds or alcohols or both by a process comprising continuously passing a feed of hydrogen and the unsaturated compound into contact with a hydrogenation catalyst, recycling part of the reacted mixture which has left the catalyst by mixing it with the feed and withdrawing the remainder of the mixture from the system. Suitable unsaturated carbonyl compounds are, for example, aliphatic aldehydes such as crotonaldehyde, acrolein, methacrolein and 2-ethylhex-2-enal; aromatic aldehydes such as cinnamaldehyde; and ketones such as mesityl oxide, methyl vinyl ketone and methyl isopropenyl ketone. Preferably a copper base catalyst is used, e.g. a copper catalyst which contains an oxide of an element such as chromium, barium or zinc, which acts as a promoter and stabilizer. In the examples: (a) crotonaldehyde is hydrogenated in the presence of a catalyst consisting of alumina coated with freshly-reduced copper and chromic oxide, some of the product being recycled, to give a mixture of butyraldehyde and butanol; (b) mesityl oxide is similarly hydrogenated to methyl isobutyl ketone; (c) crotonaldehyde is hydrogenated in the presence of a copper catalyst to give butyraldehyde and butanol, all of the butyraldehyde being recycled to the feed; and (d) crotonaldehyde is similarly hydrogenated to give butyraldehyde and butanol, all of the butanol being recycled to the feed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US781405XA | 1954-10-01 | 1954-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB781405A true GB781405A (en) | 1957-08-21 |
Family
ID=22142161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27880/55A Expired GB781405A (en) | 1954-10-01 | 1955-09-30 | Hydrogenation of unsaturated carbonyl compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB781405A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2982789A (en) * | 1957-12-13 | 1961-05-02 | Allied Chem | Manufacture of trifluoroethanol |
| DE1152398B (en) * | 1958-08-06 | 1963-08-08 | Engelhard Ind Inc | Process for the selective catalytic hydrogenation of the olefin bond of ª ‡, ª ‰ -unsaturated ketones with hydrogen in the presence of a noble metal catalyst |
| DE1196632B (en) * | 1963-04-27 | 1965-07-15 | Scholven Chemie Ag | Process for the production of saturated ketones |
| FR2489304A1 (en) * | 1980-09-03 | 1982-03-05 | Alexeeva Klavdia | 2-Ethyl:hexanol prodn. from 2-ethyl-hexenal - by hydrogenation over zinc, copper and chromium contg. catalyst (CS 31.3.81) |
| EP0073129A1 (en) * | 1981-08-20 | 1983-03-02 | DAVY McKEE (LONDON) LIMITED | Hydrogenation process |
| US4451677A (en) * | 1981-08-20 | 1984-05-29 | Davy Mckee (London) Limited | Multistage aldehyde hydrogenation |
| US4762817A (en) * | 1986-11-03 | 1988-08-09 | Union Carbide Corporation | Aldehyde hydrogenation catalyst |
| US4876402A (en) * | 1986-11-03 | 1989-10-24 | Union Carbide Chemicals And Plastics Company Inc. | Improved aldehyde hydrogenation process |
| EP0753496A3 (en) * | 1995-07-08 | 1997-04-02 | Huels Chemische Werke Ag | Process for the catalytic selective hydrogenation of multiple unsaturated organic substances |
| US5728891A (en) * | 1990-07-08 | 1998-03-17 | Huels Aktiengesellschaft | Process for the preparation of 3,3,5-trimethylcyclohexanone |
| US5756856A (en) * | 1995-07-08 | 1998-05-26 | Huels Aktiengesellschaft | Process for the preparation of 2-ethylhexanal |
| GB2630183A (en) * | 2023-05-15 | 2024-11-20 | Johnson Matthey Davy Technologies Ltd | Process for hydrongenating a substrate |
-
1955
- 1955-09-30 GB GB27880/55A patent/GB781405A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2982789A (en) * | 1957-12-13 | 1961-05-02 | Allied Chem | Manufacture of trifluoroethanol |
| DE1152398B (en) * | 1958-08-06 | 1963-08-08 | Engelhard Ind Inc | Process for the selective catalytic hydrogenation of the olefin bond of ª ‡, ª ‰ -unsaturated ketones with hydrogen in the presence of a noble metal catalyst |
| DE1196632B (en) * | 1963-04-27 | 1965-07-15 | Scholven Chemie Ag | Process for the production of saturated ketones |
| FR2489304A1 (en) * | 1980-09-03 | 1982-03-05 | Alexeeva Klavdia | 2-Ethyl:hexanol prodn. from 2-ethyl-hexenal - by hydrogenation over zinc, copper and chromium contg. catalyst (CS 31.3.81) |
| EP0073129A1 (en) * | 1981-08-20 | 1983-03-02 | DAVY McKEE (LONDON) LIMITED | Hydrogenation process |
| US4451677A (en) * | 1981-08-20 | 1984-05-29 | Davy Mckee (London) Limited | Multistage aldehyde hydrogenation |
| US4762817A (en) * | 1986-11-03 | 1988-08-09 | Union Carbide Corporation | Aldehyde hydrogenation catalyst |
| US4876402A (en) * | 1986-11-03 | 1989-10-24 | Union Carbide Chemicals And Plastics Company Inc. | Improved aldehyde hydrogenation process |
| US5728891A (en) * | 1990-07-08 | 1998-03-17 | Huels Aktiengesellschaft | Process for the preparation of 3,3,5-trimethylcyclohexanone |
| EP0753496A3 (en) * | 1995-07-08 | 1997-04-02 | Huels Chemische Werke Ag | Process for the catalytic selective hydrogenation of multiple unsaturated organic substances |
| US5756856A (en) * | 1995-07-08 | 1998-05-26 | Huels Aktiengesellschaft | Process for the preparation of 2-ethylhexanal |
| US5831135A (en) * | 1995-07-08 | 1998-11-03 | Huels Aktiengesellschaft | Process for the catalytic selective hydrogenation of polyunsaturated organic substances |
| GB2630183A (en) * | 2023-05-15 | 2024-11-20 | Johnson Matthey Davy Technologies Ltd | Process for hydrongenating a substrate |
| WO2024236286A1 (en) * | 2023-05-15 | 2024-11-21 | Johnson Matthey Davy Technologies Limited | Process for hydrogenating a substrate |
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