CA1090829A - Process for the partial catalytic hydrogenation of butynediol to butenediol in high yield - Google Patents
Process for the partial catalytic hydrogenation of butynediol to butenediol in high yieldInfo
- Publication number
- CA1090829A CA1090829A CA299,445A CA299445A CA1090829A CA 1090829 A CA1090829 A CA 1090829A CA 299445 A CA299445 A CA 299445A CA 1090829 A CA1090829 A CA 1090829A
- Authority
- CA
- Canada
- Prior art keywords
- butynediol
- catalyst
- lead
- weight
- butenediol
- 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
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title claims abstract description 33
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 13
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 title abstract description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 20
- 239000000243 solution Substances 0.000 claims abstract description 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 239000000843 powder Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 23
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 claims description 18
- OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000001241 acetals Chemical class 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- -1 brom1de Chemical compound 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229940046892 lead acetate Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910000464 lead oxide Inorganic materials 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 206010042618 Surgical procedure repeated Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
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
- C07C29/17—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
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/628—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with lead
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79880777A | 1977-05-20 | 1977-05-20 | |
| US798,807 | 1977-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1090829A true CA1090829A (en) | 1980-12-02 |
Family
ID=25174331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA299,445A Expired CA1090829A (en) | 1977-05-20 | 1978-03-21 | Process for the partial catalytic hydrogenation of butynediol to butenediol in high yield |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS53144511A (enExample) |
| CA (1) | CA1090829A (enExample) |
| DE (1) | DE2818260C2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521139A (en) * | 1993-09-30 | 1996-05-28 | Basf Aktiengesellschaft | Palladium-containing fixed-bed catalyst for the hydrogenation of butyne-1,4-diol to butene-2-diol-1,2 |
| US5714644A (en) * | 1994-07-06 | 1998-02-03 | Basf Aktiengesellschaft | Process and catalyst for the selective hydrogenation of butynediol to butenediol |
-
1978
- 1978-03-21 CA CA299,445A patent/CA1090829A/en not_active Expired
- 1978-04-26 DE DE2818260A patent/DE2818260C2/de not_active Expired
- 1978-05-19 JP JP5901978A patent/JPS53144511A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521139A (en) * | 1993-09-30 | 1996-05-28 | Basf Aktiengesellschaft | Palladium-containing fixed-bed catalyst for the hydrogenation of butyne-1,4-diol to butene-2-diol-1,2 |
| US5714644A (en) * | 1994-07-06 | 1998-02-03 | Basf Aktiengesellschaft | Process and catalyst for the selective hydrogenation of butynediol to butenediol |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53144511A (en) | 1978-12-15 |
| JPS627178B2 (enExample) | 1987-02-16 |
| DE2818260A1 (de) | 1978-11-30 |
| DE2818260C2 (de) | 1982-03-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4113662A (en) | Catalyst for ester hydrogenation | |
| KR920001303B1 (ko) | 개선된 알데하이드 수소화 방법 | |
| US4628129A (en) | Process for the preparation of ethylene glycol | |
| US4398039A (en) | Hydrogenation of carboxylic acids | |
| US5714644A (en) | Process and catalyst for the selective hydrogenation of butynediol to butenediol | |
| US3350439A (en) | Process for preparing aminoalkanenitriles | |
| EP0175558A1 (en) | Process for the vapor phase hydrogenation of carboxylic acids to esters and alcohols | |
| US4795733A (en) | Hydrogenation catalyst and process for its preparation | |
| US4677234A (en) | Process for the preparation of ethylene glycol | |
| US4149021A (en) | Ester hydrogenation using cobalt, zinc and copper oxide catalyst | |
| EP0484800B1 (en) | Process for producing neopentyl glycol | |
| US4885410A (en) | Hydrogenation catalyst | |
| GB1599598A (en) | Process for the preparation of ethylene glycol | |
| EP0204046B1 (en) | Process and catalyst for the conversion of cyclohexanol to cyclohexanone | |
| US3118954A (en) | Graduated hydrogenation of aldox aldehydes to alcohols | |
| EP0266976B1 (en) | Catalytic removal of peroxide contaminants from tertiary butyl alcohol | |
| US4628128A (en) | Process for the preparation of ethylene glycol by catalytic hydrogenation | |
| US5395989A (en) | Process for producing neopentyl glycol | |
| EP0011439B1 (en) | Method for selective preparation of cis isomers of ethylenically unsaturated compounds | |
| CA2194097C (en) | Preparation of 1,4-butanediol | |
| US3032583A (en) | Process for obtaining alpha-beta, deltaepsilon unsaturated esters | |
| CA1319710C (en) | Process for the preparation of alkanediols | |
| EP0376182B1 (en) | Process for preparing glycol aldehyde | |
| JP2955866B2 (ja) | ジアルキルカーボネートの製造方法 | |
| US4161616A (en) | Acrolein conversion to butanediol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |