CA1045141A - 7-substituted alkylates of 8-hydroxyquinoline and process for the preparation thereof - Google Patents
7-substituted alkylates of 8-hydroxyquinoline and process for the preparation thereofInfo
- Publication number
- CA1045141A CA1045141A CA270,276A CA270276A CA1045141A CA 1045141 A CA1045141 A CA 1045141A CA 270276 A CA270276 A CA 270276A CA 1045141 A CA1045141 A CA 1045141A
- Authority
- CA
- Canada
- Prior art keywords
- accordance
- ketone
- gpl
- alkylates
- hydroxyquinoline
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 title claims description 17
- 229960003540 oxyquinoline Drugs 0.000 title claims description 15
- 239000005725 8-Hydroxyquinoline Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 150000002576 ketones Chemical class 0.000 claims abstract description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 abstract description 16
- 229910052751 metal Inorganic materials 0.000 abstract description 12
- 239000002184 metal Substances 0.000 abstract description 12
- 238000000605 extraction Methods 0.000 abstract description 7
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract description 6
- 150000004325 8-hydroxyquinolines Chemical class 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005804 alkylation reaction Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 3
- 230000029936 alkylation Effects 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 239000010949 copper Substances 0.000 description 21
- 239000012071 phase Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- 238000005191 phase separation Methods 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- NIOYUNMRJMEDGI-UHFFFAOYSA-N hexadecanal Chemical compound CCCCCCCCCCCCCCCC=O NIOYUNMRJMEDGI-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- -1 2-ethylhexyl Chemical group 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- CYIFVRUOHKNECG-UHFFFAOYSA-N tridecan-2-one Chemical compound CCCCCCCCCCCC(C)=O CYIFVRUOHKNECG-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- JANNLFXZQKAKEF-UHFFFAOYSA-N 2,4-diethyloctanal Chemical compound CCCCC(CC)CC(CC)C=O JANNLFXZQKAKEF-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- BUGODZVINXTXEH-UHFFFAOYSA-N 5-ethylnonan-2-one Chemical compound CCCCC(CC)CCC(C)=O BUGODZVINXTXEH-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/665,467 US4045441A (en) | 1976-03-10 | 1976-03-10 | 7-(Alpha-methyl-alpha-alkenyl)substituted 8-hydroxyquinolines and process for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045141A true CA1045141A (en) | 1978-12-26 |
Family
ID=24670226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA270,276A Expired CA1045141A (en) | 1976-03-10 | 1977-01-24 | 7-substituted alkylates of 8-hydroxyquinoline and process for the preparation thereof |
Country Status (7)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0063137A1 (en) * | 1980-10-22 | 1982-10-27 | Sherex Chemical Company, Inc. | Stabilization of substituted 8-hydroxyquinoline hydrometallurgical reagents |
| SE8206377A0 (sv) * | 1982-11-10 | 1984-05-11 | Madan Khorshed | Nya kelatbildande biskinolinföreningar |
| SE8206378L (sv) * | 1982-11-10 | 1984-05-11 | Sverker Hogberg | Nya kelatbildande kinolinforeningar |
| US4698429A (en) * | 1985-12-03 | 1987-10-06 | Henkel Corporation | Alkylated 8-hydroxyquinoline derivatives via a diels-alder cycloaddition to 5,7-diallyl or 7-allyl substituents thereon |
| US7585475B2 (en) * | 2006-08-11 | 2009-09-08 | Cognis Ip Management Gmbh | Highly-conductive copper extractant formulations |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637711A (en) * | 1968-03-25 | 1972-01-25 | Ashland Oil Inc | Beta-alkenyl substituted 8-hydroxyquinolines |
-
1976
- 1976-03-10 US US05/665,467 patent/US4045441A/en not_active Expired - Lifetime
-
1977
- 1977-01-24 CA CA270,276A patent/CA1045141A/en not_active Expired
- 1977-01-31 BE BE174534A patent/BE850936A/xx not_active IP Right Cessation
- 1977-02-11 AU AU22217/77A patent/AU509588B2/en not_active Expired
- 1977-03-09 GB GB9998/77A patent/GB1525550A/en not_active Expired
- 1977-03-10 JP JP2554877A patent/JPS52108981A/ja active Granted
- 1977-03-10 DE DE19772710491 patent/DE2710491A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE850936A (fr) | 1977-08-01 |
| JPS566418B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-02-10 |
| GB1525550A (en) | 1978-09-20 |
| AU509588B2 (en) | 1980-05-15 |
| DE2710491A1 (de) | 1977-09-15 |
| AU2221777A (en) | 1978-08-17 |
| JPS52108981A (en) | 1977-09-12 |
| US4045441A (en) | 1977-08-30 |
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