GB917358A - Process for the catalytic conversion of unsaturated hydrocarbons - Google Patents
Process for the catalytic conversion of unsaturated hydrocarbonsInfo
- Publication number
- GB917358A GB917358A GB37453/60A GB3745360A GB917358A GB 917358 A GB917358 A GB 917358A GB 37453/60 A GB37453/60 A GB 37453/60A GB 3745360 A GB3745360 A GB 3745360A GB 917358 A GB917358 A GB 917358A
- Authority
- GB
- United Kingdom
- Prior art keywords
- metal
- alkali metal
- alkali
- promoted
- catalyst
- 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
- 238000006243 chemical reaction Methods 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 230000003197 catalytic effect Effects 0.000 title 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 8
- 229910052783 alkali metal Inorganic materials 0.000 abstract 8
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 abstract 7
- 229910052751 metal Inorganic materials 0.000 abstract 6
- 239000002184 metal Substances 0.000 abstract 6
- 150000001336 alkenes Chemical class 0.000 abstract 5
- 239000003054 catalyst Substances 0.000 abstract 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical group [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 150000001340 alkali metals Chemical class 0.000 abstract 3
- 230000029936 alkylation Effects 0.000 abstract 3
- 238000005804 alkylation reaction Methods 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 238000006317 isomerization reaction Methods 0.000 abstract 3
- 238000006116 polymerization reaction Methods 0.000 abstract 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000008020 evaporation Effects 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract 2
- 150000004706 metal oxides Chemical class 0.000 abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 238000010924 continuous production Methods 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000539 dimer Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 238000005470 impregnation Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/107—Alkenes with six carbon atoms
- C07C11/113—Methylpentenes
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
-
- 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
- B01J27/24—Nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
-
- 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
-
- 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
- C07C2/10—Catalytic processes with metal oxides
-
- 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
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
-
- 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
-
- 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/72—Addition to a non-aromatic carbon atom of hydrocarbons containing a six-membered aromatic ring
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/2213—Catalytic processes not covered by C07C5/23 - C07C5/31 with metal oxides
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/2266—Catalytic processes not covered by C07C5/23 - C07C5/31 with hydrides or organic compounds
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2518—Catalytic processes with crystalline alumino-silicates, e.g. molecular sieves
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2556—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
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/24—Nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A catalyst for polymerizing or isomerizing olefins or for the side chain alkylation of alkyl aromatic hydrocarbons with an olefin comprises an alkali metal amide supported on an anhydrous metal oxide having a surface area of 25-500 square metres per gram and which has been promoted by an alkali or alkaline earth metal or compound thereof. The preferred support is gamma-, eta-, or theta-alumina which may be impregnated with an alkali metal at 3 DEG -53 DEG C. above the melting point of the metal, e.g. by dropping the molten metal on the support or by passing an inert gas through the metal and the result vapours over the support. Promotion by alkali or alkaline earth metal oxides, hydroxides or salts can be effected conventionally by impregnation followed by decomposition if necessary. The alkali metal amide may be added by immersing the promoted support in a dispersion of alkali metal or alkali metal amide in liquid ammonia at the refluxing temperature followed by evaporation of the ammonia or by adding an alkali metal to the promoted support and refluxing in liquid ammonia followed by evaporation of the ammonia and/or reacting the metal with gaseous ammonia. The catalyst preferably contains 2-20% by weight of alkali metal amide (calculated as the metal).ALSO:The polymerization, copolymerization or isomerisation of olefins or the side chain alkylation of alkyl aromatic hydrocarbons with olefins is effected in the presence of an alkali metal amide supported on an anhydrous metal oxide having a surface area of 25-500 square metres per gram and promoted with an alkali or alkaline earth metal or compound thereof. The olefin may be a mono-, poly- or cyclic-olefin, several being specified; polymerization results mostly in dimers, isomerisation shifts only the double bond, usually to a more central position. The process may be effected batchwise or continuously in the liquid phase in the presence of a diluent hydrocarbon if desired, e.g. a paraffin, cycloparaffin or non-alkylated aromatic hydrocarbon. Polymerization or alkylation is effected at 50-300 DEG C. and 5-250 atmospheres using a reactant LHSV in continuous processes of 0.1-20. In dimerisation processes undesired product isomers may be recycled to the reaction zone to effect isomerisation or may be separately isomerised at a lower reaction temperature but a similar catalyst e.g. at 0.75 DEG C. and 1-136 atmospheres. The catalyst is particularly suitable for the conversion of propylene to 2-methly-2-pentene. The catalyst is preferably a promoted gamma-alumina, e.g. containing lithium hydroxide on which is dispersed 2-20% by weight of sodium or potassium amide (calculated as the metal).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DENDAT1248640D DE1248640B (en) | 1960-11-01 | Process for the oligomerization or mixed oligomerization of olefinic hydrocarbons with 2 to 4 carbon atoms | |
| GB37453/60A GB917358A (en) | 1960-11-01 | 1960-11-01 | Process for the catalytic conversion of unsaturated hydrocarbons |
| DEU10611A DE1253263B (en) | 1960-11-01 | 1960-11-08 | Process for the preparation of 2-methyl-pentene-2 from propylene |
| DEP1269A DE1270008B (en) | 1960-11-01 | 1960-11-08 | Process for preparing a catalyst for olefin conversion reactions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37453/60A GB917358A (en) | 1960-11-01 | 1960-11-01 | Process for the catalytic conversion of unsaturated hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB917358A true GB917358A (en) | 1963-02-06 |
Family
ID=10396599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37453/60A Expired GB917358A (en) | 1960-11-01 | 1960-11-01 | Process for the catalytic conversion of unsaturated hydrocarbons |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1248640B (en) |
| GB (1) | GB917358A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3383378A (en) * | 1964-04-22 | 1968-05-14 | Universal Oil Prod Co | Polymerization of ethylene |
| US3398131A (en) * | 1964-04-22 | 1968-08-20 | Universal Oil Prod Co | Homopolymerization of ethylene for the production of solid and liquid polymers |
| US3856877A (en) * | 1972-11-15 | 1974-12-24 | Nippon Oil Co Ltd | Method for isomerization of lower polymers of butadiene |
| EP0057971A1 (en) * | 1981-01-27 | 1982-08-18 | Nippon Oil Co. Ltd. | Process for preparing 4-methyl-1-pentene |
| CN115109246A (en) * | 2022-07-01 | 2022-09-27 | 佳化化学科技发展（上海）有限公司 | Alkynyl alcohol ether and preparation method and application thereof |
| CN118702539A (en) * | 2024-06-26 | 2024-09-27 | 大连凯飞化学股份有限公司 | A method for preparing 2,3-dimethyl-2-butene |
-
0
- DE DENDAT1248640D patent/DE1248640B/en active Pending
-
1960
- 1960-11-01 GB GB37453/60A patent/GB917358A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3383378A (en) * | 1964-04-22 | 1968-05-14 | Universal Oil Prod Co | Polymerization of ethylene |
| US3398131A (en) * | 1964-04-22 | 1968-08-20 | Universal Oil Prod Co | Homopolymerization of ethylene for the production of solid and liquid polymers |
| US3856877A (en) * | 1972-11-15 | 1974-12-24 | Nippon Oil Co Ltd | Method for isomerization of lower polymers of butadiene |
| EP0057971A1 (en) * | 1981-01-27 | 1982-08-18 | Nippon Oil Co. Ltd. | Process for preparing 4-methyl-1-pentene |
| CN115109246A (en) * | 2022-07-01 | 2022-09-27 | 佳化化学科技发展（上海）有限公司 | Alkynyl alcohol ether and preparation method and application thereof |
| CN115109246B (en) * | 2022-07-01 | 2023-07-14 | 佳化化学科技发展（上海）有限公司 | Alkynyl alcohol ether and preparation method and application thereof |
| CN118702539A (en) * | 2024-06-26 | 2024-09-27 | 大连凯飞化学股份有限公司 | A method for preparing 2,3-dimethyl-2-butene |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1248640B (en) | 1967-08-31 |
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