DE2602965C2 - - Google Patents
Info
- Publication number
- DE2602965C2 DE2602965C2 DE2602965A DE2602965A DE2602965C2 DE 2602965 C2 DE2602965 C2 DE 2602965C2 DE 2602965 A DE2602965 A DE 2602965A DE 2602965 A DE2602965 A DE 2602965A DE 2602965 C2 DE2602965 C2 DE 2602965C2
- Authority
- DE
- Germany
- Prior art keywords
- palladium
- platinum
- carbon atoms
- reaction mixture
- dehydrogenation
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- -1 3,5-disubstituted pyrazoles Chemical class 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims description 2
- 150000003738 xylenes Chemical class 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 3
- 239000000377 silicon dioxide Substances 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VJFQJTFADLQQNS-UHFFFAOYSA-N 3,5-diphenyl-4,5-dihydro-1h-pyrazole Chemical compound C1C(C=2C=CC=CC=2)NN=C1C1=CC=CC=C1 VJFQJTFADLQQNS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/549,219 US3952010A (en) | 1973-09-17 | 1975-02-12 | Catalytic dehydrogenation process for the preparation of 3,5-disubstituted pyrazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2602965A1 DE2602965A1 (de) | 1976-08-26 |
| DE2602965C2 true DE2602965C2 (en:Method) | 1988-11-17 |
Family
ID=24192112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762602965 Granted DE2602965A1 (de) | 1975-02-12 | 1976-01-27 | Verfahren zur herstellung von 3,5- diphenylpyrazolen |
Country Status (19)
| Country | Link |
|---|---|
| JP (2) | JPS51101979A (en:Method) |
| AT (1) | AT350549B (en:Method) |
| BE (1) | BE838408R (en:Method) |
| BR (1) | BR7600847A (en:Method) |
| CA (1) | CA1060455A (en:Method) |
| CH (1) | CH608004A5 (en:Method) |
| CS (1) | CS192554B2 (en:Method) |
| DD (1) | DD124249A6 (en:Method) |
| DE (1) | DE2602965A1 (en:Method) |
| DK (1) | DK55276A (en:Method) |
| ES (1) | ES445094A2 (en:Method) |
| FR (1) | FR2300763A2 (en:Method) |
| GB (1) | GB1537859A (en:Method) |
| IL (1) | IL48724A (en:Method) |
| IT (1) | IT1053296B (en:Method) |
| NL (1) | NL178075C (en:Method) |
| SE (1) | SE7601544L (en:Method) |
| SU (1) | SU799657A3 (en:Method) |
| ZA (1) | ZA757986B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029160A1 (de) * | 1980-08-01 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von pyrazolen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5855148A (ja) * | 1981-09-29 | 1983-04-01 | Hino Motors Ltd | 成形用金型の製造方法 |
-
1975
- 1975-12-22 CA CA242,256A patent/CA1060455A/en not_active Expired
- 1975-12-23 ZA ZA00757986A patent/ZA757986B/xx unknown
- 1975-12-24 IL IL48724A patent/IL48724A/xx unknown
-
1976
- 1976-01-09 IT IT47573/76A patent/IT1053296B/it active
- 1976-01-16 NL NLAANVRAGE7600445,A patent/NL178075C/xx not_active IP Right Cessation
- 1976-01-27 DE DE19762602965 patent/DE2602965A1/de active Granted
- 1976-02-03 DD DD191069A patent/DD124249A6/xx unknown
- 1976-02-10 BE BE164196A patent/BE838408R/xx not_active IP Right Cessation
- 1976-02-10 JP JP51012890A patent/JPS51101979A/ja active Pending
- 1976-02-10 FR FR7603642A patent/FR2300763A2/fr active Granted
- 1976-02-11 SU SU762319859A patent/SU799657A3/ru active
- 1976-02-11 SE SE7601544A patent/SE7601544L/xx unknown
- 1976-02-11 DK DK55276*#A patent/DK55276A/da unknown
- 1976-02-11 CS CS76899A patent/CS192554B2/cs unknown
- 1976-02-11 BR BR7600847A patent/BR7600847A/pt unknown
- 1976-02-11 CH CH166976A patent/CH608004A5/xx not_active IP Right Cessation
- 1976-02-11 AT AT96276A patent/AT350549B/de not_active IP Right Cessation
- 1976-02-12 GB GB5650/76A patent/GB1537859A/en not_active Expired
- 1976-02-12 ES ES445094A patent/ES445094A2/es not_active Expired
-
1985
- 1985-02-27 JP JP60036705A patent/JPS60222463A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES445094A2 (es) | 1977-06-16 |
| DK55276A (da) | 1976-08-13 |
| ZA757986B (en) | 1976-12-29 |
| AT350549B (de) | 1979-06-11 |
| GB1537859A (en) | 1979-01-04 |
| IL48724A (en) | 1979-07-25 |
| DE2602965A1 (de) | 1976-08-26 |
| IT1053296B (it) | 1981-08-31 |
| NL178075B (nl) | 1985-08-16 |
| SE7601544L (sv) | 1976-08-13 |
| CH608004A5 (en) | 1978-12-15 |
| FR2300763A2 (fr) | 1976-09-10 |
| AU8790475A (en) | 1977-06-30 |
| JPS51101979A (en:Method) | 1976-09-08 |
| CS192554B2 (en) | 1979-08-31 |
| BR7600847A (pt) | 1976-09-14 |
| JPS6227068B2 (en:Method) | 1987-06-12 |
| FR2300763B2 (en:Method) | 1982-09-03 |
| CA1060455A (en) | 1979-08-14 |
| JPS60222463A (ja) | 1985-11-07 |
| SU799657A3 (ru) | 1981-01-23 |
| NL178075C (nl) | 1986-01-16 |
| NL7600445A (nl) | 1976-08-16 |
| IL48724A0 (en) | 1976-02-29 |
| DD124249A6 (en:Method) | 1977-02-09 |
| BE838408R (fr) | 1976-08-10 |
| ATA96276A (de) | 1978-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| AF | Is addition to no. |
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| 8172 | Supplementary division/partition in: |
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| Q171 | Divided out to: |
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| Q161 | Has additional application no. |
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| AF | Is addition to no. |
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| AG | Has addition no. |
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| AH | Division in |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8340 | Patent of addition ceased/non-payment of fee of main patent |