DE4005515A1 - Verfahren zur herstellung von (alpha)-alkyllactonen - Google Patents
Verfahren zur herstellung von (alpha)-alkyllactonenInfo
- Publication number
- DE4005515A1 DE4005515A1 DE4005515A DE4005515A DE4005515A1 DE 4005515 A1 DE4005515 A1 DE 4005515A1 DE 4005515 A DE4005515 A DE 4005515A DE 4005515 A DE4005515 A DE 4005515A DE 4005515 A1 DE4005515 A1 DE 4005515A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- hydrogenation
- lactone
- reaction
- 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- Withdrawn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
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 53
- 150000008044 alkali metal hydroxides Chemical class 0.000 title claims abstract description 23
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 33
- 150000001299 aldehydes Chemical class 0.000 title description 19
- 150000002596 lactones Chemical class 0.000 title description 17
- -1 alkylidene lactone Chemical class 0.000 title description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 15
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000003701 inert diluent Substances 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000007142 ring opening reaction Methods 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims 2
- 239000012895 dilution Substances 0.000 claims 2
- 239000003337 fertilizer Substances 0.000 claims 2
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 239000003085 diluting agent Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- SPOJRVXZEMNXKH-UHFFFAOYSA-N 3-heptylidene-5-methyloxolan-2-one Chemical compound CCCCCCC=C1CC(C)OC1=O SPOJRVXZEMNXKH-UHFFFAOYSA-N 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- GSLDEZOOOSBFGP-UHFFFAOYSA-N alpha-methylene gamma-butyrolactone Chemical compound C=C1CCOC1=O GSLDEZOOOSBFGP-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HJLVPHHUURFMLO-UHFFFAOYSA-N 3-(cyclohexylmethylidene)-5-methyloxolan-2-one Chemical compound O=C1OC(C)CC1=CC1CCCCC1 HJLVPHHUURFMLO-UHFFFAOYSA-N 0.000 description 4
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZFKUTGNRVJOCIO-UHFFFAOYSA-N 3-Heptyldihydro-5-methyl-2(3H)-furanone Chemical compound CCCCCCCC1CC(C)OC1=O ZFKUTGNRVJOCIO-UHFFFAOYSA-N 0.000 description 3
- PNRIRUUSCZDXEP-UHFFFAOYSA-N 3-acetyl-5-methyloxolan-2-one Chemical compound CC1CC(C(C)=O)C(=O)O1 PNRIRUUSCZDXEP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NEBMUHXPHLFPGQ-DTWKUNHWSA-N (3r,5s)-3-acetyl-5-butyloxolan-2-one Chemical compound CCCC[C@H]1C[C@H](C(C)=O)C(=O)O1 NEBMUHXPHLFPGQ-DTWKUNHWSA-N 0.000 description 2
- MBNMGGKBGCIEGF-UHFFFAOYSA-N 1,1-diethoxypropane Chemical compound CCOC(CC)OCC MBNMGGKBGCIEGF-UHFFFAOYSA-N 0.000 description 2
- SWTCCCJQNPGXLQ-UHFFFAOYSA-N 1-(1-butoxyethoxy)butane Chemical compound CCCCOC(C)OCCCC SWTCCCJQNPGXLQ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- NEBMUHXPHLFPGQ-UHFFFAOYSA-N 3-acetyl-5-butyloxolan-2-one Chemical compound CCCCC1CC(C(C)=O)C(=O)O1 NEBMUHXPHLFPGQ-UHFFFAOYSA-N 0.000 description 2
- KRCFMTREVNAMCY-UHFFFAOYSA-N 3-acetyl-5-ethyloxolan-2-one Chemical compound CCC1CC(C(C)=O)C(=O)O1 KRCFMTREVNAMCY-UHFFFAOYSA-N 0.000 description 2
- YHGLGIHEAKQUOG-UHFFFAOYSA-N 3-benzylidene-5-butyloxolan-2-one Chemical compound O=C1OC(CCCC)CC1=CC1=CC=CC=C1 YHGLGIHEAKQUOG-UHFFFAOYSA-N 0.000 description 2
- TWDMVZSYTMJVEK-UHFFFAOYSA-N 3-benzylideneoxolan-2-one Chemical compound O=C1OCCC1=CC1=CC=CC=C1 TWDMVZSYTMJVEK-UHFFFAOYSA-N 0.000 description 2
- PMIJCDYTQGCTNJ-UHFFFAOYSA-N 3-butan-2-yl-5-ethyl-4-methylideneoxolan-2-one Chemical compound CC(CC)C1C(OC(C1=C)CC)=O PMIJCDYTQGCTNJ-UHFFFAOYSA-N 0.000 description 2
- XDCLCGHGDRDLPR-UHFFFAOYSA-N 3-pentylideneoxolan-2-one Chemical compound CCCCC=C1CCOC1=O XDCLCGHGDRDLPR-UHFFFAOYSA-N 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
- UYHAOVWDFLWADN-UHFFFAOYSA-N 5-butyl-3-methylideneoxolan-2-one Chemical compound CCCCC1CC(=C)C(=O)O1 UYHAOVWDFLWADN-UHFFFAOYSA-N 0.000 description 2
- FZCKLBIPLUKLSU-UHFFFAOYSA-N 5-butyl-3-pentylideneoxolan-2-one Chemical compound CCCCC=C1CC(CCCC)OC1=O FZCKLBIPLUKLSU-UHFFFAOYSA-N 0.000 description 2
- YMSOFQXWTJLCTF-UHFFFAOYSA-N 5-ethyl-3-heptylideneoxolan-2-one Chemical compound CCCCCCC=C1CC(CC)OC1=O YMSOFQXWTJLCTF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N delta-Valerolactone Natural products O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- MISTZQJSHHTDCF-UHFFFAOYSA-N 1-(1-propoxyethoxy)propane Chemical compound CCCOC(C)OCCC MISTZQJSHHTDCF-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- OSWDNIFICGLKEE-UHFFFAOYSA-N 2-acetylcyclopentan-1-one Chemical compound CC(=O)C1CCCC1=O OSWDNIFICGLKEE-UHFFFAOYSA-N 0.000 description 1
- JQYFSFNSNVRUPY-UHFFFAOYSA-N 2-chloro-2-nitropropane Chemical compound CC(C)(Cl)[N+]([O-])=O JQYFSFNSNVRUPY-UHFFFAOYSA-N 0.000 description 1
- JNPHXXOADOMUQP-UHFFFAOYSA-N 2-propan-2-ylidenecyclopentan-1-one Chemical compound CC(C)=C1CCCC1=O JNPHXXOADOMUQP-UHFFFAOYSA-N 0.000 description 1
- YGVNNINOXJVBJG-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-methyloxolan-2-one Chemical compound O=C1OC(C)CC1CC1CCCCC1 YGVNNINOXJVBJG-UHFFFAOYSA-N 0.000 description 1
- FHPAJUFBBWADPL-UHFFFAOYSA-N 3-benzyl-5-butyloxolan-2-one Chemical compound O=C1OC(CCCC)CC1CC1=CC=CC=C1 FHPAJUFBBWADPL-UHFFFAOYSA-N 0.000 description 1
- DYCIOBMGECOFOG-UHFFFAOYSA-N 5-butyl-3-methyloxolan-2-one Chemical compound CCCCC1CC(C)C(=O)O1 DYCIOBMGECOFOG-UHFFFAOYSA-N 0.000 description 1
- IAKNFYBJJWSXSU-UHFFFAOYSA-N 5-butyl-3-pentyloxolan-2-one Chemical compound CCCCCC1CC(CCCC)OC1=O IAKNFYBJJWSXSU-UHFFFAOYSA-N 0.000 description 1
- IJQWFNWVLSICLC-UHFFFAOYSA-N 5-ethyl-3-(2-methylbutyl)oxolan-2-one Chemical compound CCC(C)CC1CC(CC)OC1=O IJQWFNWVLSICLC-UHFFFAOYSA-N 0.000 description 1
- NAXZWHLYHOASKL-UHFFFAOYSA-N 5-ethyl-3-heptyloxolan-2-one Chemical compound CCCCCCCC1CC(CC)OC1=O NAXZWHLYHOASKL-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WXIPNVLTINMRNH-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C1C(OC(C1=C)CCCC)=O Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1C(OC(C1=C)CCCC)=O WXIPNVLTINMRNH-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- JVRMSXLSEPWFIT-UHFFFAOYSA-N ethyl 2-oxooxolane-3-carboxylate Chemical compound CCOC(=O)C1CCOC1=O JVRMSXLSEPWFIT-UHFFFAOYSA-N 0.000 description 1
- IRLLCGNUJLJIGN-UHFFFAOYSA-N ethyl 3-oxobutanoate;2-methyloxirane Chemical compound CC1CO1.CCOC(=O)CC(C)=O IRLLCGNUJLJIGN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002241 furanones Chemical class 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31510989A | 1989-02-24 | 1989-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4005515A1 true DE4005515A1 (de) | 1990-08-30 |
Family
ID=23222929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4005515A Withdrawn DE4005515A1 (de) | 1989-02-24 | 1990-02-22 | Verfahren zur herstellung von (alpha)-alkyllactonen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPH02273667A (ja) |
| BE (1) | BE1003310A5 (ja) |
| DE (1) | DE4005515A1 (ja) |
| FR (1) | FR2643635A1 (ja) |
| GB (1) | GB2228481B (ja) |
| IT (1) | IT9067138A1 (ja) |
| NL (1) | NL9000443A (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231192A (en) * | 1989-02-24 | 1993-07-27 | Henkel Corporation | Process for the preparation of alpha-alkyl lactones |
| US6770658B2 (en) | 1998-09-09 | 2004-08-03 | Inflazyme Pharmaceuticals Ltd. | Substituted γ-phenyl-Δ-lactams and uses related thereto |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3617177A1 (de) * | 1986-05-22 | 1987-11-26 | Basf Ag | Verfahren zur herstellung von (alpha)-substituierten (gamma)-butyrolactonen |
-
1990
- 1990-02-22 DE DE4005515A patent/DE4005515A1/de not_active Withdrawn
- 1990-02-23 IT IT067138A patent/IT9067138A1/it unknown
- 1990-02-23 JP JP2044309A patent/JPH02273667A/ja active Pending
- 1990-02-23 BE BE9000200A patent/BE1003310A5/fr not_active IP Right Cessation
- 1990-02-23 NL NL9000443A patent/NL9000443A/nl not_active Application Discontinuation
- 1990-02-23 GB GB9004142A patent/GB2228481B/en not_active Expired - Fee Related
- 1990-02-26 FR FR9002350A patent/FR2643635A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2228481A (en) | 1990-08-29 |
| GB2228481B (en) | 1992-04-15 |
| IT9067138A1 (it) | 1990-08-25 |
| NL9000443A (nl) | 1990-09-17 |
| JPH02273667A (ja) | 1990-11-08 |
| IT9067138A0 (it) | 1990-02-23 |
| BE1003310A5 (fr) | 1992-02-25 |
| GB9004142D0 (en) | 1990-04-18 |
| FR2643635A1 (fr) | 1990-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |