NL8703157A - Werkwijze voor het selectief hydrogeneren van acetylenen. - Google Patents
Werkwijze voor het selectief hydrogeneren van acetylenen. Download PDFInfo
- Publication number
- NL8703157A NL8703157A NL8703157A NL8703157A NL8703157A NL 8703157 A NL8703157 A NL 8703157A NL 8703157 A NL8703157 A NL 8703157A NL 8703157 A NL8703157 A NL 8703157A NL 8703157 A NL8703157 A NL 8703157A
- Authority
- NL
- Netherlands
- Prior art keywords
- catalyst
- process according
- hydrogen
- butadiene
- alkynes
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 41
- 238000005984 hydrogenation reaction Methods 0.000 title description 34
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title description 8
- 239000003054 catalyst Substances 0.000 claims description 75
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 150000001345 alkine derivatives Chemical class 0.000 claims description 30
- 229910052763 palladium Inorganic materials 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 235000013305 food Nutrition 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 2
- 229910001020 Au alloy Inorganic materials 0.000 claims 1
- 239000003353 gold alloy Substances 0.000 claims 1
- JUWSSMXCCAMYGX-UHFFFAOYSA-N gold platinum Chemical compound [Pt].[Au] JUWSSMXCCAMYGX-UHFFFAOYSA-N 0.000 claims 1
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 19
- 150000002430 hydrocarbons Chemical class 0.000 description 18
- 229930195733 hydrocarbon Natural products 0.000 description 16
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 150000000475 acetylene derivatives Chemical class 0.000 description 10
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 10
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 230000004913 activation Effects 0.000 description 9
- 235000013844 butane Nutrition 0.000 description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000010931 gold Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 235000016709 nutrition Nutrition 0.000 description 5
- 230000035764 nutrition Effects 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 4
- 238000004230 steam cracking Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- 239000005061 synthetic rubber Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000570 Cupronickel Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010338 mechanical breakdown Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B01J23/48—Silver or gold
- B01J23/52—Gold
-
- 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
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/06—Washing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8631017A GB2199588B (en) | 1986-12-30 | 1986-12-30 | Process for the selective hydrogenation of acetylenes |
| GB8631017 | 1986-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8703157A true NL8703157A (nl) | 1988-07-18 |
Family
ID=10609665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8703157A NL8703157A (nl) | 1986-12-30 | 1987-12-29 | Werkwijze voor het selectief hydrogeneren van acetylenen. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JP2560056B2 (de) |
| BE (1) | BE1000871A4 (de) |
| CA (1) | CA1290354C (de) |
| DE (1) | DE3744086C2 (de) |
| FI (1) | FI87453C (de) |
| FR (1) | FR2609023B1 (de) |
| GB (1) | GB2199588B (de) |
| IT (1) | IT1223624B (de) |
| NL (1) | NL8703157A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19500366C1 (de) * | 1995-01-09 | 1996-05-02 | Basf Ag | Palladium-Trägerkatalysator und seine Verwendung |
| US6509292B1 (en) | 2001-03-30 | 2003-01-21 | Sud-Chemie Inc. | Process for selective hydrogenation of acetylene in an ethylene purification process |
| DE102008043344A1 (de) | 2008-10-31 | 2010-05-06 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 1-Alkoxyocta-2,7-dien |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB510343A (en) * | 1936-10-22 | 1939-07-26 | Ig Farbenindustrie Ag | A process of hydrogenating monovinylacetylene |
| FR1217305A (fr) * | 1957-12-17 | 1960-05-03 | Bayer Ag | Procédé pour éliminer l'acétylène, le méthylacétylène et l'allène à partirde mélanges d'hydrocarbures |
| DE1184336B (de) * | 1963-07-10 | 1964-12-31 | Huels Chemische Werke Ag | Verfahren zur Entfernung von Methylacetylen und Propadien aus einem ueberwiegend Propen enthaltenden C-Kohlenwasserstoffgemisch |
| DE1210795B (de) * | 1964-11-14 | 1966-02-17 | Huels Chemische Werke Ag | Verfahren zur Entfernung von Butadien und bzw. oder Acetylenen aus einem ueberwiegend Butene bzw. Butadien enthaltenden C-Kohlenwasserstoffgemisch |
| DE1568542C3 (de) * | 1966-06-15 | 1974-07-18 | Bayer Ag, 5090 Leverkusen | Verfahren zur katalytischen Umwandlung von Butadien- und n-Buten-1-haltigen C tief 4 - Kohlenwasserstoffen |
| US3842137A (en) * | 1973-01-02 | 1974-10-15 | Monsanto Co | Selective hydrogenation of c4 acetylenic hydrocarbons |
| US3898298A (en) * | 1973-04-13 | 1975-08-05 | Atlantic Richfield Co | Selective hydrogenation of vinyl acetylene |
| US3859377A (en) * | 1973-12-13 | 1975-01-07 | Monsanto Co | Selective hydrogenation of c' 4 'acetylenic hydrocarbons |
| FR2421858A1 (fr) * | 1978-04-05 | 1979-11-02 | Inst Francais Du Petrole | Procede d'hydrogenation selective d'une fraction d'hydrocarbures renfermant au moins un hydrocarbure diolefinique et au moins un hydrocarbure acetylenique |
| JPS54141706A (en) * | 1978-04-21 | 1979-11-05 | Nippon Oil Co Ltd | Removal of acetylenes in 4c hydrocarbon mixture containing butadiene |
| US4247745A (en) * | 1978-09-13 | 1981-01-27 | Westinghouse Electric Corp. | Vacuum-type contactor assembly |
| FR2460989A1 (fr) * | 1979-07-06 | 1981-01-30 | Inst Francais Du Petrole | Procede de purification d'une coupe d'hydrocarbures aromatiques contenant des hydrocarbures insatures olefiniques et acetyleniques |
| DE3143647A1 (de) * | 1981-11-04 | 1983-05-11 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur selektiven hydrierung von mehrfach ungesaettigten kohlenwasserstoffen in kohlenwasserstoff-gemischen |
| JPS58149987A (ja) * | 1982-03-02 | 1983-09-06 | Sumitomo Chem Co Ltd | 炭化水素類の選択的水素添加の方法 |
-
1986
- 1986-12-30 GB GB8631017A patent/GB2199588B/en not_active Expired - Fee Related
-
1987
- 1987-12-24 DE DE3744086A patent/DE3744086C2/de not_active Revoked
- 1987-12-26 JP JP62328448A patent/JP2560056B2/ja not_active Expired - Lifetime
- 1987-12-28 FR FR878718223A patent/FR2609023B1/fr not_active Expired
- 1987-12-29 NL NL8703157A patent/NL8703157A/nl active Search and Examination
- 1987-12-30 IT IT23273/87A patent/IT1223624B/it active
- 1987-12-30 BE BE8701501A patent/BE1000871A4/fr not_active IP Right Cessation
- 1987-12-30 CA CA000555579A patent/CA1290354C/en not_active Expired - Lifetime
- 1987-12-30 FI FI875774A patent/FI87453C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2609023A1 (fr) | 1988-07-01 |
| GB8631017D0 (en) | 1987-02-04 |
| DE3744086A1 (de) | 1988-07-14 |
| CA1290354C (en) | 1991-10-08 |
| FI87453B (fi) | 1992-09-30 |
| BE1000871A4 (fr) | 1989-04-25 |
| FI875774A0 (fi) | 1987-12-30 |
| IT8723273A0 (it) | 1987-12-30 |
| IT1223624B (it) | 1990-09-29 |
| FI87453C (fi) | 1993-01-11 |
| GB2199588B (en) | 1990-12-05 |
| GB2199588A (en) | 1988-07-13 |
| FR2609023B1 (fr) | 1989-10-20 |
| JP2560056B2 (ja) | 1996-12-04 |
| JPS63185935A (ja) | 1988-08-01 |
| DE3744086C2 (de) | 2000-05-04 |
| FI875774L (fi) | 1988-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BN | A decision not to publish the application has become irrevocable |