JPH0460456B2 - - Google Patents
Info
- Publication number
- JPH0460456B2 JPH0460456B2 JP59218790A JP21879084A JPH0460456B2 JP H0460456 B2 JPH0460456 B2 JP H0460456B2 JP 59218790 A JP59218790 A JP 59218790A JP 21879084 A JP21879084 A JP 21879084A JP H0460456 B2 JPH0460456 B2 JP H0460456B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogenation
- stage
- tbcol
- carried out
- tbphol
- 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 - Lifetime
Links
- 238000005984 hydrogenation reaction Methods 0.000 claims description 65
- 239000003054 catalyst Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- FDZSOJOJVCBNNI-UHFFFAOYSA-N 1-tert-butylcyclohexan-1-ol Chemical class CC(C)(C)C1(O)CCCCC1 FDZSOJOJVCBNNI-UHFFFAOYSA-N 0.000 claims description 6
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- DLTWBMHADAJAAZ-RKDXNWHRSA-N (1r,2s)-2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)[C@@H]1CCCC[C@H]1O DLTWBMHADAJAAZ-RKDXNWHRSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- DLTWBMHADAJAAZ-BDAKNGLRSA-N (1s,2s)-2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)[C@@H]1CCCC[C@@H]1O DLTWBMHADAJAAZ-BDAKNGLRSA-N 0.000 description 18
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 13
- XTVMZZBLCLWBPM-UHFFFAOYSA-N tert-butylcyclohexane Chemical compound CC(C)(C)C1CCCCC1 XTVMZZBLCLWBPM-UHFFFAOYSA-N 0.000 description 13
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- ZRYDPLOWJSFQAE-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-one Chemical compound CC(C)(C)C1CCCCC1=O ZRYDPLOWJSFQAE-UHFFFAOYSA-N 0.000 description 4
- CCOQPGVQAWPUPE-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-ol Chemical class CC(C)(C)C1CCC(O)CC1 CCOQPGVQAWPUPE-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical group CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DLTWBMHADAJAAZ-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCCCC1O DLTWBMHADAJAAZ-UHFFFAOYSA-N 0.000 description 1
- MQSXUKPGWMJYBT-UHFFFAOYSA-N 3-butylphenol Chemical compound CCCCC1=CC=CC(O)=C1 MQSXUKPGWMJYBT-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical class CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3338437 | 1983-10-22 | ||
| DE3338437.1 | 1983-10-22 | ||
| DE3401343.1 | 1984-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60104032A JPS60104032A (ja) | 1985-06-08 |
| JPH0460456B2 true JPH0460456B2 (OSRAM) | 1992-09-28 |
Family
ID=6212507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59218790A Granted JPS60104032A (ja) | 1983-10-22 | 1984-10-19 | シス異性体の割合の多い２‐および４‐第３‐ブチルシクロヘキサノール類を、相応する第３‐ブチルフエノール類の接触的水素化によつて製造する方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60104032A (OSRAM) |
-
1984
- 1984-10-19 JP JP59218790A patent/JPS60104032A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60104032A (ja) | 1985-06-08 |
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