DE2158555A1 - Verfahren zur Herstellung von Alkalimetall-Katalysatoren auf Graphit und ihre Verwendung zur Herstellung von 4-Methyl-lpenten durch Dimerisieren von Propylen - Google Patents
Verfahren zur Herstellung von Alkalimetall-Katalysatoren auf Graphit und ihre Verwendung zur Herstellung von 4-Methyl-lpenten durch Dimerisieren von PropylenInfo
- Publication number
- DE2158555A1 DE2158555A1 DE19712158555 DE2158555A DE2158555A1 DE 2158555 A1 DE2158555 A1 DE 2158555A1 DE 19712158555 DE19712158555 DE 19712158555 DE 2158555 A DE2158555 A DE 2158555A DE 2158555 A1 DE2158555 A1 DE 2158555A1
- Authority
- DE
- Germany
- Prior art keywords
- graphite
- alkali metal
- heated
- methyl
- production
- 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.)
- Pending
Links
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims description 34
- 229910002804 graphite Inorganic materials 0.000 title claims description 34
- 239000010439 graphite Substances 0.000 title claims description 34
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 title claims description 24
- 239000003054 catalyst Substances 0.000 title claims description 17
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 16
- 150000001340 alkali metals Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims description 11
- 230000000447 dimerizing effect Effects 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 8
- 239000012670 alkaline solution Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LGAQJENWWYGFSN-SNAWJCMRSA-N (e)-4-methylpent-2-ene Chemical compound C\C=C\C(C)C LGAQJENWWYGFSN-SNAWJCMRSA-N 0.000 description 1
- LGAQJENWWYGFSN-PLNGDYQASA-N (z)-4-methylpent-2-ene Chemical compound C\C=C/C(C)C LGAQJENWWYGFSN-PLNGDYQASA-N 0.000 description 1
- RYPKRALMXUUNKS-HYXAFXHYSA-N (z)-hex-2-ene Chemical compound CCC\C=C/C RYPKRALMXUUNKS-HYXAFXHYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-HWKANZROSA-N 2E-hexene Chemical compound CCC\C=C\C RYPKRALMXUUNKS-HWKANZROSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- ZQDPJFUHLCOCRG-WAYWQWQTSA-N cis-3-hexene Chemical compound CC\C=C/CC ZQDPJFUHLCOCRG-WAYWQWQTSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ZQDPJFUHLCOCRG-AATRIKPKSA-N trans-3-hexene Chemical compound CC\C=C\CC ZQDPJFUHLCOCRG-AATRIKPKSA-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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/22—Carbides
-
- 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
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/24—Catalytic processes with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/18—Carbon
-
- 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
- C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
- C07C2523/04—Alkali metals
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3221070 | 1970-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2158555A1 true DE2158555A1 (de) | 1972-06-08 |
Family
ID=11235015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712158555 Pending DE2158555A1 (de) | 1970-11-26 | 1971-11-25 | Verfahren zur Herstellung von Alkalimetall-Katalysatoren auf Graphit und ihre Verwendung zur Herstellung von 4-Methyl-lpenten durch Dimerisieren von Propylen |
Country Status (9)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57126426A (en) * | 1981-01-27 | 1982-08-06 | Nippon Oil Co Ltd | Preparation of 4-methyl-1-pentene |
| CA1198409A (en) * | 1981-12-28 | 1985-12-24 | Keiji Kawamoto | Catalyst composition suitable for the dimerization or codimerization of alpha-olefins |
| DE3470877D1 (en) * | 1983-10-29 | 1988-06-09 | Nippon Oil Co Ltd | Process for preparing 4-methyl-1-pentene |
| US4656154A (en) * | 1985-06-24 | 1987-04-07 | Phillips Petroleum Co. | Potassium carbonate with carbon supports and catalysts with elemental alkali metal |
| US4595787A (en) * | 1985-06-24 | 1986-06-17 | Phillips Petroleum Company | Potassium carbonate supports, catalysts and olefin dimerization processes therewith |
| US4661466A (en) * | 1985-12-23 | 1987-04-28 | Phillips Petroleum Company | Potassium carbonate supports, catalysts and processes therewith |
| US4727213A (en) * | 1985-12-23 | 1988-02-23 | Phillips Petroleum Company | Potassium carbonate supports, catalysts and processes therewith |
-
1971
- 1971-11-16 GB GB5314571A patent/GB1310476A/en not_active Expired
- 1971-11-19 US US00200508A patent/US3758416A/en not_active Expired - Lifetime
- 1971-11-24 CH CH1711471A patent/CH545756A/xx not_active IP Right Cessation
- 1971-11-25 FR FR7142309A patent/FR2116059A5/fr not_active Expired
- 1971-11-25 DE DE19712158555 patent/DE2158555A1/de active Pending
- 1971-11-25 NL NL7116199A patent/NL7116199A/xx unknown
- 1971-11-25 CA CA128,558A patent/CA955234A/en not_active Expired
- 1971-11-26 JP JP46094577A patent/JPS511233B1/ja active Pending
- 1971-11-26 YU YU2994/71A patent/YU34360B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU34360B (en) | 1979-07-10 |
| CH545756A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-15 |
| NL7116199A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-05-30 |
| FR2116059A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-07-07 |
| CA955234A (en) | 1974-09-24 |
| YU299471A (en) | 1978-12-31 |
| US3758416A (en) | 1973-09-11 |
| GB1310476A (en) | 1973-03-21 |
| JPS511233B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-01-14 |
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