DE1264435B - Verfahren zur Herstellung von Methylacetylen und Allen - Google Patents
Verfahren zur Herstellung von Methylacetylen und AllenInfo
- Publication number
- DE1264435B DE1264435B DEN20412A DEN0020412A DE1264435B DE 1264435 B DE1264435 B DE 1264435B DE N20412 A DEN20412 A DE N20412A DE N0020412 A DEN0020412 A DE N0020412A DE 1264435 B DE1264435 B DE 1264435B
- Authority
- DE
- Germany
- Prior art keywords
- isobutylene
- reaction
- allene
- methylacetylene
- moles
- 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
- 238000000034 method Methods 0.000 title claims description 26
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 title claims description 26
- 150000001361 allenes Chemical class 0.000 title claims description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 239000007789 gas Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 238000000197 pyrolysis Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 238000004227 thermal cracking Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 238000007086 side reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 3
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- 238000005336 cracking Methods 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 229910001220 stainless steel Inorganic materials 0.000 claims 2
- 239000010935 stainless steel Substances 0.000 claims 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 241000827140 Euroscaptor micrura Species 0.000 claims 1
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 claims 1
- 241000270295 Serpentes Species 0.000 claims 1
- 238000013459 approach Methods 0.000 claims 1
- 229910010293 ceramic material Inorganic materials 0.000 claims 1
- 238000002485 combustion reaction Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- NAHDKUILRATFAH-UHFFFAOYSA-N prop-1-yne Chemical group CC#C.CC#C NAHDKUILRATFAH-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- -1 B. isobutylene Chemical class 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010891 electric arc Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/10—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from acyclic hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4886460A | 1960-08-11 | 1960-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1264435B true DE1264435B (de) | 1968-03-28 |
Family
ID=21956862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN20412A Pending DE1264435B (de) | 1960-08-11 | 1961-08-04 | Verfahren zur Herstellung von Methylacetylen und Allen |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH395061A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1264435B (cg-RX-API-DMAC7.html) |
| DK (1) | DK106276C (cg-RX-API-DMAC7.html) |
| GB (1) | GB911597A (cg-RX-API-DMAC7.html) |
| NL (1) | NL268013A (cg-RX-API-DMAC7.html) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2752405A (en) * | 1952-12-10 | 1956-06-26 | Happel John | Manufacturing process for acetylenic hydrocarbons |
-
0
- NL NL268013D patent/NL268013A/xx unknown
-
1961
- 1961-08-03 CH CH908961A patent/CH395061A/de unknown
- 1961-08-04 DE DEN20412A patent/DE1264435B/de active Pending
- 1961-08-09 DK DK323761A patent/DK106276C/da active
- 1961-08-10 GB GB2894261A patent/GB911597A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2752405A (en) * | 1952-12-10 | 1956-06-26 | Happel John | Manufacturing process for acetylenic hydrocarbons |
Also Published As
| Publication number | Publication date |
|---|---|
| CH395061A (de) | 1965-07-15 |
| GB911597A (en) | 1962-11-28 |
| DK106276C (da) | 1967-01-16 |
| NL268013A (cg-RX-API-DMAC7.html) |
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