DE1568362A1 - Verfahren zur Herstellung von Adamantan - Google Patents
Verfahren zur Herstellung von AdamantanInfo
- Publication number
- DE1568362A1 DE1568362A1 DE19661568362 DE1568362A DE1568362A1 DE 1568362 A1 DE1568362 A1 DE 1568362A1 DE 19661568362 DE19661568362 DE 19661568362 DE 1568362 A DE1568362 A DE 1568362A DE 1568362 A1 DE1568362 A1 DE 1568362A1
- Authority
- DE
- Germany
- Prior art keywords
- adamantane
- catalyst
- dealkylation
- temperature
- hydrogen
- 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.)
- Withdrawn
Links
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title claims description 62
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
- 230000020335 dealkylation Effects 0.000 claims description 11
- 238000006900 dealkylation reaction Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 1
- UZUCFTVAWGRMTQ-UHFFFAOYSA-N 1-methyladamantane Chemical compound C1C(C2)CC3CC2CC1(C)C3 UZUCFTVAWGRMTQ-UHFFFAOYSA-N 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000006317 isomerization reaction Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000017858 demethylation Effects 0.000 description 3
- 238000010520 demethylation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LXTHCCWEYOKFSR-UHFFFAOYSA-N 1-ethyladamantane Chemical compound C1C(C2)CC3CC2CC1(CC)C3 LXTHCCWEYOKFSR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GVJFFQYXVOJXFI-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a,9,9a,10,10a-tetradecahydroanthracene Chemical compound C1C2CCCCC2CC2C1CCCC2 GVJFFQYXVOJXFI-UHFFFAOYSA-N 0.000 description 1
- HBIKNLNXSSBQCT-UHFFFAOYSA-N 1,2,5,7-tetramethyladamantane Chemical compound C1C(C2)(C)CC3(C)CC1C(C)C2(C)C3 HBIKNLNXSSBQCT-UHFFFAOYSA-N 0.000 description 1
- RTPQXHZLCUUIJP-UHFFFAOYSA-N 1,2-dimethyladamantane Chemical compound C1C(C2)CC3CC1C(C)C2(C)C3 RTPQXHZLCUUIJP-UHFFFAOYSA-N 0.000 description 1
- UJSORZVCMMYGBS-UHFFFAOYSA-N 1,3,5,7-tetramethyladamantane Chemical compound C1C(C2)(C)CC3(C)CC1(C)CC2(C)C3 UJSORZVCMMYGBS-UHFFFAOYSA-N 0.000 description 1
- WCACLGXPFTYVEL-UHFFFAOYSA-N 1,3,5-trimethyladamantane Chemical compound C1C(C2)CC3(C)CC1(C)CC2(C)C3 WCACLGXPFTYVEL-UHFFFAOYSA-N 0.000 description 1
- FTNPDAKMYKMVKB-UHFFFAOYSA-N 1-ethyl-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC2(C)CC1(CC)C3 FTNPDAKMYKMVKB-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- -1 alkyl adamantane Chemical compound 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 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
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/26—Chromium
-
- 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
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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 |
|---|---|---|---|
| CS779065 | 1965-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1568362A1 true DE1568362A1 (de) | 1970-04-30 |
Family
ID=5427639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661568362 Withdrawn DE1568362A1 (de) | 1965-12-28 | 1966-12-27 | Verfahren zur Herstellung von Adamantan |
Country Status (5)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3489817A (en) * | 1968-06-21 | 1970-01-13 | Atlantic Richfield Co | Method for the production of adamantane |
| US3944626A (en) * | 1973-04-26 | 1976-03-16 | Kosaku Honna | Process for producing adamantane compounds |
| US4301043A (en) * | 1976-12-25 | 1981-11-17 | Idemitsu Kosan Company Limited | Sublimable perfume compositions |
| US4398978A (en) * | 1982-04-26 | 1983-08-16 | The United States Of America As Represented By The Secretary Of The Navy | High density, low viscosity airbreather fuel (RJ-4-I) |
| JP4931590B2 (ja) * | 2004-07-15 | 2012-05-16 | 出光興産株式会社 | アダマンタンの固結防止方法 |
| CN111701600B (zh) * | 2020-07-02 | 2023-06-06 | 沧州那瑞化学科技有限公司 | 一种用于制备1-溴-3,5-二甲基金刚烷的催化剂及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2422671A (en) * | 1943-07-08 | 1947-06-24 | Universal Oil Prod Co | Process for lowering the molecular weight of nonaromatic hydrocarbons |
| US2422674A (en) * | 1944-10-31 | 1947-06-24 | Universal Oil Prod Co | Selective demethylation of saturated hydrocarbons |
-
1966
- 1966-12-27 NL NL6618212A patent/NL6618212A/xx unknown
- 1966-12-27 DE DE19661568362 patent/DE1568362A1/de not_active Withdrawn
- 1966-12-28 FR FR89072A patent/FR1513451A/fr not_active Expired
- 1966-12-28 GB GB58002/66A patent/GB1123320A/en not_active Expired
- 1966-12-28 US US605232A patent/US3418387A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3418387A (en) | 1968-12-24 |
| NL6618212A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-29 |
| GB1123320A (en) | 1968-08-14 |
| FR1513451A (fr) | 1968-02-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3340711A1 (de) | Verfahren zur herstellung von paraffin-kohlenwasserstoff-loesungsmitteln aus pflanzlichen oelen | |
| DE1283212B (de) | Verfahren zum hydrierenden Entalkylieren von Toluol | |
| DE1568362A1 (de) | Verfahren zur Herstellung von Adamantan | |
| DE2127625A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE1568362C (de) | Verfahren zur Herstellung von Adaman tan | |
| DE2425290C3 (de) | Verfahren zur Herstellung von Cyclopentadien durch Spaltung von i Dicyclopentadien in flüssiger Phase | |
| DE1568362B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE912928C (de) | Verfahren zur Abtrennung konjugierte Doppelbindungen enthaltender aliphatischer und alicyclischer Diene | |
| AT204669B (de) | Verfahren zur katalytischen Reformierung von Benzinkohlenwasserstoffen | |
| AT231414B (de) | Verfahren zur Herstellung von Isopren-haltigem Material | |
| DE2139043A1 (de) | Kontinuierliches Verfahren zur Be handlung eines Kohlenwasserstoffstromes aus einem Gemisch alkylaromatischer Kohlen Wasserstoffe | |
| AT92090B (de) | Verfahren zur Herstellung von Diolefinen und ihren Polymerisationsprodukten. | |
| AT214458B (de) | Verfahren zur Herstellung von Schwefelkohlenstoff | |
| DE1184756B (de) | Verfahren zur katalytischen Hydrierung von aromatischen Kohlenwasserstoffen | |
| DE646327C (de) | Verfahren zur Herstellung von aromatischen Kohlenwasserstoffen und bzw. oder Acetylen | |
| DE2005820C3 (de) | 21.08.69 Japan 65778-69 Verfahren zur Herstellung von Xylole n | |
| DE1793448B1 (de) | Verfahren zur Herstellung von Benzol durch thermische hydrierende Entmethylierung von Toluol | |
| DE1036847B (de) | Verfahren zur Herstellung von Halogenkohlenwasserstoffen aus ungesaettigten cyclischen Kohlenwasserstoffen | |
| DE1493025C3 (de) | Verfahren zur Herstellung von Alkyladamantanen mit 12 bis 15 Kohlenstoffatomen durch katalytische Isomerisierung von bestimmten tricyclischen perhydroaromatischen Kohlenwasserstoffen mit 12 bis 15 Kohlenstoffatomen und Unterbrechen der Reaktion vor Abschluß der Isomerisierung | |
| DE944489C (de) | Verfahren zur UEberfuehrung von í¸-Caren in vorzugsweise monocyclische Terpene | |
| DE634330C (de) | Verfahren zur Herstellung von niedrigsiedenden Kohlenwasserstoffen | |
| DE1567777B1 (de) | Verfahren zur kontinuierlichen Herstellung von Schwefelkohlenstoff | |
| DE706934C (de) | Verfahren zur katalytischen Umwandlung von geradkettigen Kohlenwasserstoffen | |
| DE1952976C3 (de) | Verfahren zur Herstellung von Methacrylsäureestern | |
| DE1199761B (de) | Verfahren zur Herstellung von Oligomeren des Isobutens |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |