DE1543129C3 - Verfahren zur Herstellung von Monovinylacetylen - Google Patents
Verfahren zur Herstellung von MonovinylacetylenInfo
- Publication number
- DE1543129C3 DE1543129C3 DE1543129A DE1543129A DE1543129C3 DE 1543129 C3 DE1543129 C3 DE 1543129C3 DE 1543129 A DE1543129 A DE 1543129A DE 1543129 A DE1543129 A DE 1543129A DE 1543129 C3 DE1543129 C3 DE 1543129C3
- Authority
- DE
- Germany
- Prior art keywords
- acetylene
- solution
- monovinylacetylene
- catalyst
- reaction
- 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
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 49
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 47
- 239000003054 catalyst Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000007789 gas Substances 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- -1 monovinyl ethylene glycol monoalkyl ether Chemical class 0.000 claims description 3
- SWZDPOQDVXVJOR-UHFFFAOYSA-M chlorocopper;hydrochloride Chemical compound Cl.[Cu]Cl SWZDPOQDVXVJOR-UHFFFAOYSA-M 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims 1
- 240000003834 Triticum spelta Species 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- AUBDSFLQOBEOPX-UHFFFAOYSA-N hexa-1,5-dien-3-yne Chemical group C=CC#CC=C AUBDSFLQOBEOPX-UHFFFAOYSA-N 0.000 claims 1
- 239000003350 kerosene Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000012495 reaction gas Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- MTUKGUHFXPYUBQ-UHFFFAOYSA-M C(=C)C#C.[Cl-].[K+] Chemical compound C(=C)C#C.[Cl-].[K+] MTUKGUHFXPYUBQ-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07C2/38—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 dienes or alkynes
-
- 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
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/122—Compounds comprising a halogen and copper
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0057510 | 1965-10-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1543129A1 DE1543129A1 (de) | 1969-07-31 |
| DE1543129B2 DE1543129B2 (de) | 1974-02-28 |
| DE1543129C3 true DE1543129C3 (de) | 1974-10-03 |
Family
ID=7228281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1543129A Expired DE1543129C3 (de) | 1965-10-28 | 1965-10-28 | Verfahren zur Herstellung von Monovinylacetylen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3409694A (cg-RX-API-DMAC10.html) |
| BE (1) | BE689022A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1543129C3 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1109610A (cg-RX-API-DMAC10.html) |
| NL (1) | NL6615153A (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101492340B (zh) * | 2009-02-26 | 2012-06-13 | 华东师范大学 | 1,3-烯炔类化合物的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA640262A (en) * | 1962-04-24 | Vogt Wilhelm | Process for the manufacture of monovinyl acetylene of high purity | |
| US2934576A (en) * | 1958-05-16 | 1960-04-26 | Du Pont | Improved process for the manufacture of monovinylacetylene from acetylene |
-
1965
- 1965-10-28 DE DE1543129A patent/DE1543129C3/de not_active Expired
-
1966
- 1966-10-17 US US587201A patent/US3409694A/en not_active Expired - Lifetime
- 1966-10-26 GB GB48058/66A patent/GB1109610A/en not_active Expired
- 1966-10-26 NL NL6615153A patent/NL6615153A/xx unknown
- 1966-10-28 BE BE689022D patent/BE689022A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE689022A (cg-RX-API-DMAC10.html) | 1967-03-31 |
| DE1543129A1 (de) | 1969-07-31 |
| GB1109610A (en) | 1968-04-10 |
| DE1543129B2 (de) | 1974-02-28 |
| US3409694A (en) | 1968-11-05 |
| NL6615153A (cg-RX-API-DMAC10.html) | 1967-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |