JPS60163875A - １−シクロヘキセン−１，２−ジカルボン酸無水物の製造方法 - Google Patents
１−シクロヘキセン−１，２−ジカルボン酸無水物の製造方法Info
- Publication number
- JPS60163875A JPS60163875A JP59017818A JP1781884A JPS60163875A JP S60163875 A JPS60163875 A JP S60163875A JP 59017818 A JP59017818 A JP 59017818A JP 1781884 A JP1781884 A JP 1781884A JP S60163875 A JPS60163875 A JP S60163875A
- Authority
- JP
- Japan
- Prior art keywords
- palladium
- copper
- catalyst
- cyclohexene
- catalyst containing
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 title description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 19
- 239000010949 copper Substances 0.000 claims abstract description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052802 copper Inorganic materials 0.000 claims abstract description 12
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
- 238000006317 isomerization reaction Methods 0.000 abstract description 7
- 150000001879 copper Chemical class 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 238000001354 calcination Methods 0.000 abstract 1
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 8
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59017818A JPS60163875A (ja) | 1984-02-03 | 1984-02-03 | １−シクロヘキセン−１，２−ジカルボン酸無水物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59017818A JPS60163875A (ja) | 1984-02-03 | 1984-02-03 | １−シクロヘキセン−１，２−ジカルボン酸無水物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60163875A true JPS60163875A (ja) | 1985-08-26 |
| JPH0527633B2 JPH0527633B2 (enrdf_load_html_response) | 1993-04-21 |
Family
ID=11954310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59017818A Granted JPS60163875A (ja) | 1984-02-03 | 1984-02-03 | １−シクロヘキセン−１，２−ジカルボン酸無水物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60163875A (enrdf_load_html_response) |
-
1984
- 1984-02-03 JP JP59017818A patent/JPS60163875A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0527633B2 (enrdf_load_html_response) | 1993-04-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6045938B2 (ja) | シュウ酸ジエステルの水素添加触媒の製造法 | |
| JPH0729962B2 (ja) | フェノール類の製造方法 | |
| JPH0242032A (ja) | メタクリル酸および／またはメタクロレインの製造法 | |
| JP4081824B2 (ja) | アクリル酸の製造方法 | |
| IL35991A (en) | Iodine 131 radioactive and a method for its production | |
| JPH0242033A (ja) | メタクリル酸および／またはメタクロレインの製造方法 | |
| US4263175A (en) | Catalyst for the production of pyrrolidone | |
| JPS60163875A (ja) | １−シクロヘキセン−１，２−ジカルボン酸無水物の製造方法 | |
| JPH05177141A (ja) | メタクリル酸の製造法 | |
| JP2000237592A (ja) | メタクロレインおよびメタクリル酸合成用触媒およびメタクロレインおよびメタクリル酸の製造方法 | |
| JPH026414A (ja) | イソブチレンの製造法 | |
| CA2114635C (en) | Process for preparing adipic acid | |
| JP3485622B2 (ja) | アンモニア合成触媒およびアンモニア合成方法 | |
| WO2005003073A1 (ja) | ５－ヨード－２－メチル安息香酸の製造方法 | |
| JP4599780B2 (ja) | 含フッ素アルコール化合物の製造用触媒及び含フッ素アルコールの製造方法 | |
| US3873595A (en) | Production of o-phthalodinitrile | |
| JP2623008B2 (ja) | メタクロレイン及びメタクリル酸の製造法 | |
| JP2759376B2 (ja) | メタクロレイン及びメタクリル酸の製造法 | |
| JP2001002604A (ja) | ジオール類の製法 | |
| SU475765A3 (ru) | Способ получени непредельных алифатических динитрилов | |
| JP3282488B2 (ja) | 高純度スカンジュウム・トリフラートの製造方法 | |
| DE2444004A1 (de) | Verfahren zur herstellung von buten2-diol-1,4-diacetat | |
| JPH0338542A (ja) | カルボニル化合物の製法 | |
| JP3541448B2 (ja) | アセトアミドの製造方法 | |
| JPH08217712A (ja) | フェノールの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |