BE525128A - - Google Patents
Info
- Publication number
- BE525128A BE525128A BE525128DA BE525128A BE 525128 A BE525128 A BE 525128A BE 525128D A BE525128D A BE 525128DA BE 525128 A BE525128 A BE 525128A
- Authority
- BE
- Belgium
- Prior art keywords
- yne
- compound
- dimethyl
- dial
- diene
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 17
- 229910052744 lithium Inorganic materials 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 7
- GQVGTWFEGUJKDT-UHFFFAOYSA-N 2,7-dimethylocta-2,6-dien-4-ynedial Chemical compound O=CC(C)=CC#CC=C(C)C=O GQVGTWFEGUJKDT-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- 150000004291 polyenes Polymers 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 150000002642 lithium compounds Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- 238000006680 Reformatsky reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 230000005494 condensation Effects 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 22
- 238000009833 condensation Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 239000007859 condensation product Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- NUJOXMJBOLGQSY-UHFFFAOYSA-N Manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- -1 diethyl ester Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000017105 transposition Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000000746 allylic group Chemical group 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- PANKHBYNKQNAHN-MQQNZMFNSA-N crocetin Chemical compound OC(=O)C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)C(O)=O PANKHBYNKQNAHN-MQQNZMFNSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WDDOQHLJFOUQMW-UHFFFAOYSA-N lithium;ethynyl(trimethyl)silane Chemical compound [Li+].C[Si](C)(C)C#[C-] WDDOQHLJFOUQMW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MEAONJBNSODGKA-UHFFFAOYSA-N 2,7-dimethylocta-2,6-dien-4-yne-1,8-diol Chemical compound OCC(C)=CC#CC=C(C)CO MEAONJBNSODGKA-UHFFFAOYSA-N 0.000 description 2
- PXSBSBDNZRLRLK-UHFFFAOYSA-N 2-(2H-pyran-2-yloxy)-2H-pyran Chemical compound O1C=CC=CC1OC1OC=CC=C1 PXSBSBDNZRLRLK-UHFFFAOYSA-N 0.000 description 2
- ZSJHASYJQIRSLE-UHFFFAOYSA-N 3-methylpent-2-en-4-yn-1-ol Chemical compound C#CC(C)=CCO ZSJHASYJQIRSLE-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- AUPXBVDHVRZMIB-UHFFFAOYSA-M C[Mg]I Chemical compound C[Mg]I AUPXBVDHVRZMIB-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PANKHBYNKQNAHN-JTBLXSOISA-N Crocetin Natural products OC(=O)C(\C)=C/C=C/C(/C)=C\C=C\C=C(\C)/C=C/C=C(/C)C(O)=O PANKHBYNKQNAHN-JTBLXSOISA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N Decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- ARNWQMJQALNBBV-UHFFFAOYSA-N Lithium carbide Chemical class [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- FILUFGAZMJGNEN-UHFFFAOYSA-N pent-1-en-3-yne Chemical compound CC#CC=C FILUFGAZMJGNEN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- PSOPUECGKNQIPH-UHFFFAOYSA-N 2,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCCC=C(C)C PSOPUECGKNQIPH-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-Methyl-2-butene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N 3,4-dihydro-2H-pyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- HSIXEMVQMLIQLA-UHFFFAOYSA-N 3,8-dimethyldeca-3,7-dien-5-yne-2,9-dione Chemical compound CC(=O)C(C)=CC#CC=C(C)C(C)=O HSIXEMVQMLIQLA-UHFFFAOYSA-N 0.000 description 1
- BOTPFNAEWCOIDS-UHFFFAOYSA-N 5-bromo-3-methylpent-3-en-1-yne Chemical compound C#CC(C)=CCBr BOTPFNAEWCOIDS-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- RAFGELQLHMBRHD-BLOCSRKMSA-N Annatto Chemical compound COC(=O)\C=C\C(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC(O)=O RAFGELQLHMBRHD-BLOCSRKMSA-N 0.000 description 1
- 241000347356 Belonidae Species 0.000 description 1
- 229960002747 Betacarotene Drugs 0.000 description 1
- RAFGELQLHMBRHD-FTZHHOJMSA-N Bixin Natural products O=C(OC)/C=C/C(=C/C=C/C(=C\C=C\C=C(/C=C/C=C(\C=C\C(=O)O)/C)\C)/C)/C RAFGELQLHMBRHD-FTZHHOJMSA-N 0.000 description 1
- 241001269524 Dura Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N Lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- SPAGIJMPHSUYSE-UHFFFAOYSA-N Magnesium peroxide Chemical compound [Mg+2].[O-][O-] SPAGIJMPHSUYSE-UHFFFAOYSA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N Methyl vinyl ketone Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N Methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 229950004497 Transcrocetin Drugs 0.000 description 1
- 238000006621 Wurtz reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000001670 anatto Substances 0.000 description 1
- 235000012665 annatto Nutrition 0.000 description 1
- OENHQHLEOONYIE-VYAWBVGESA-N beta-Carotene Natural products CC=1CCCC(C)(C)C=1\C=C\C(\C)=C/C=C/C(/C)=C\C=C\C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-VYAWBVGESA-N 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- OYICOGPBEIHJEO-UHFFFAOYSA-L magnesium;acetylene;dibromide Chemical compound [Mg+2].[Br-].[Br-].C#C OYICOGPBEIHJEO-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940100888 zinc compounds Drugs 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE525128A true BE525128A (de) |
Family
ID=159520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE525128D BE525128A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE525128A (de) |
-
0
- BE BE525128D patent/BE525128A/fr unknown
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