CA2392049C - Metathesis syntheses of pheromones or their components - Google Patents
Metathesis syntheses of pheromones or their components Download PDFInfo
- Publication number
- CA2392049C CA2392049C CA2392049A CA2392049A CA2392049C CA 2392049 C CA2392049 C CA 2392049C CA 2392049 A CA2392049 A CA 2392049A CA 2392049 A CA2392049 A CA 2392049A CA 2392049 C CA2392049 C CA 2392049C
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- acetate
- dichloro
- ruthenium
- bis
- 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
- 238000005649 metathesis reaction Methods 0.000 title claims abstract description 132
- 238000003786 synthesis reaction Methods 0.000 title abstract description 108
- 239000003016 pheromone Substances 0.000 title abstract description 93
- 239000003054 catalyst Substances 0.000 claims abstract description 293
- 238000000034 method Methods 0.000 claims abstract description 154
- 238000006243 chemical reaction Methods 0.000 claims abstract description 110
- 150000001336 alkenes Chemical class 0.000 claims abstract description 94
- SPOXUSGCKOQPRB-DLBZAZTESA-N [(1s)-1-[(2r)-6-oxooxan-2-yl]undecyl] acetate Chemical compound CCCCCCCCCC[C@H](OC(C)=O)[C@H]1CCCC(=O)O1 SPOXUSGCKOQPRB-DLBZAZTESA-N 0.000 claims abstract description 29
- YJINQJFQLQIYHX-SNAWJCMRSA-N 11E-Tetradecenyl acetate Chemical compound CC\C=C\CCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-SNAWJCMRSA-N 0.000 claims abstract description 18
- YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 claims abstract description 16
- VTUFOIHYMMMNOM-VOTSOKGWSA-N 5E-Decenyl acetate Chemical compound CCCC\C=C\CCCCOC(C)=O VTUFOIHYMMMNOM-VOTSOKGWSA-N 0.000 claims abstract description 12
- YLYWMNJAJOQSGH-UHFFFAOYSA-N (9E,11E)-hexadecadienal Natural products CCCCC=CC=CCCCCCCCC=O YLYWMNJAJOQSGH-UHFFFAOYSA-N 0.000 claims abstract description 11
- MAOWSVNIDSZOBR-AATRIKPKSA-N [(e)-tetradec-9-enyl] formate Chemical compound CCCC\C=C\CCCCCCCCOC=O MAOWSVNIDSZOBR-AATRIKPKSA-N 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 96
- 239000000047 product Substances 0.000 claims description 83
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 80
- VTUFOIHYMMMNOM-UHFFFAOYSA-N dec-5-enyl acetate Chemical compound CCCCC=CCCCCOC(C)=O VTUFOIHYMMMNOM-UHFFFAOYSA-N 0.000 claims description 80
- 238000005686 cross metathesis reaction Methods 0.000 claims description 72
- 239000000376 reactant Substances 0.000 claims description 70
- -1 carboxylate ester Chemical class 0.000 claims description 68
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 62
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 claims description 54
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 53
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 31
- 229940069096 dodecene Drugs 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- MPLWNENKBSBMFN-UHFFFAOYSA-N hex-5-enyl acetate Chemical compound CC(=O)OCCCCC=C MPLWNENKBSBMFN-UHFFFAOYSA-N 0.000 claims description 30
- 235000019198 oils Nutrition 0.000 claims description 27
- 241001072282 Limnanthes Species 0.000 claims description 26
- XNOVSIYQBIDVRG-QURGRASLSA-N (e)-docos-11-ene Chemical compound CCCCCCCCCC\C=C\CCCCCCCCCC XNOVSIYQBIDVRG-QURGRASLSA-N 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- ATTQOHBPGJEQNM-ONEGZZNKSA-N [(e)-10-acetyloxydec-5-enyl] acetate Chemical compound CC(=O)OCCCC\C=C\CCCCOC(C)=O ATTQOHBPGJEQNM-ONEGZZNKSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000006227 byproduct Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 15
- 239000005977 Ethylene Substances 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- UJUXUEKQHBXUEM-AATRIKPKSA-N 5-Decenoic acid Chemical compound CCCC\C=C\CCCC(O)=O UJUXUEKQHBXUEM-AATRIKPKSA-N 0.000 claims description 14
- 150000004820 halides Chemical class 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- 150000001299 aldehydes Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 10
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- 238000005872 self-metathesis reaction Methods 0.000 claims description 10
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 claims description 9
- HHRKFGMMAHZWIM-UHFFFAOYSA-N ethenoxyboronic acid Chemical compound OB(O)OC=C HHRKFGMMAHZWIM-UHFFFAOYSA-N 0.000 claims description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 8
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical group OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- PYVDPRZZYPCYBD-ZHACJKMWSA-N CCCCCCCC\C=C\CCCCCCCCCCOC(C)=O Chemical compound CCCCCCCC\C=C\CCCCCCCCCCOC(C)=O PYVDPRZZYPCYBD-ZHACJKMWSA-N 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- 239000004711 α-olefin Substances 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- QBGNQGGJSCRVJJ-UHFFFAOYSA-N 1,6-dibromohex-3-ene Chemical compound BrCCC=CCCBr QBGNQGGJSCRVJJ-UHFFFAOYSA-N 0.000 claims description 6
- JXKKTNIUHNDXCH-UHFFFAOYSA-N 8-chlorooct-5-enyl acetate Chemical group CC(=O)OCCCCC=CCCCl JXKKTNIUHNDXCH-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- OKJUOWUYZJEYMS-ONEGZZNKSA-N [(e)-8-acetyloxyoct-4-enyl] acetate Chemical compound CC(=O)OCCC\C=C\CCCOC(C)=O OKJUOWUYZJEYMS-ONEGZZNKSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- WYPQHXVMNVEVEB-UHFFFAOYSA-N dec-5-en-1-ol Chemical compound CCCCC=CCCCCO WYPQHXVMNVEVEB-UHFFFAOYSA-N 0.000 claims description 6
- ASKDFGVMJZMYEM-UHFFFAOYSA-N methyl hex-5-enoate Chemical compound COC(=O)CCCC=C ASKDFGVMJZMYEM-UHFFFAOYSA-N 0.000 claims description 6
- IPFUCPILAVBTPZ-UHFFFAOYSA-N methyl hexadec-5-enoate Chemical compound CCCCCCCCCCC=CCCCC(=O)OC IPFUCPILAVBTPZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- KVXIRQZWCOAYRD-VAWYXSNFSA-N (Z)-5-Hexadecenoic acid Chemical compound CCCCCCCCCC\C=C\CCCC(O)=O KVXIRQZWCOAYRD-VAWYXSNFSA-N 0.000 claims description 5
- JYPUYHQUARVUER-UHFFFAOYSA-N 1,6-dichlorohex-3-ene Chemical compound ClCCC=CCCCl JYPUYHQUARVUER-UHFFFAOYSA-N 0.000 claims description 5
- KVXIRQZWCOAYRD-UHFFFAOYSA-N 16:1omega5 fatty acid Natural products CCCCCCCCCCC=CCCCC(O)=O KVXIRQZWCOAYRD-UHFFFAOYSA-N 0.000 claims description 5
- WRDVRNIPMDDMJM-UHFFFAOYSA-N 6,6-diethoxyhex-1-ene Chemical compound CCOC(OCC)CCCC=C WRDVRNIPMDDMJM-UHFFFAOYSA-N 0.000 claims description 5
- ISNYRMWYYORWMN-UHFFFAOYSA-N [Ru]=C Chemical compound [Ru]=C ISNYRMWYYORWMN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- CSWBSLXBXRFNST-UHFFFAOYSA-N dodeca-8,10-dien-1-ol Chemical compound CC=CC=CCCCCCCCO CSWBSLXBXRFNST-UHFFFAOYSA-N 0.000 claims description 5
- GSAAJQNJNPBBSX-UHFFFAOYSA-N tetradec-9-en-1-ol Chemical compound CCCCC=CCCCCCCCCO GSAAJQNJNPBBSX-UHFFFAOYSA-N 0.000 claims description 5
- HSNQNPCNYIJJHT-ISLYRVAYSA-N trans-octadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCC HSNQNPCNYIJJHT-ISLYRVAYSA-N 0.000 claims description 5
- DUCVQKMNGSZPAV-UHFFFAOYSA-N tridec-4-enyl acetate Chemical compound CCCCCCCCC=CCCCOC(C)=O DUCVQKMNGSZPAV-UHFFFAOYSA-N 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- HSNATJOWAYTBGM-ONEGZZNKSA-N (e)-1-bromohex-3-ene Chemical compound CC\C=C\CCBr HSNATJOWAYTBGM-ONEGZZNKSA-N 0.000 claims description 4
- FCFJANPVDCPCQF-UHFFFAOYSA-N 1,8-dichlorooct-4-ene Chemical compound ClCCCC=CCCCCl FCFJANPVDCPCQF-UHFFFAOYSA-N 0.000 claims description 4
- ABPSHLJXBCKNLR-UHFFFAOYSA-N 14-chlorotetradec-3-ene Chemical compound CCC=CCCCCCCCCCCCl ABPSHLJXBCKNLR-UHFFFAOYSA-N 0.000 claims description 4
- NBIDGUDYWIMVDZ-UHFFFAOYSA-N 14-chlorotetradec-5-ene Chemical compound CCCCC=CCCCCCCCCCl NBIDGUDYWIMVDZ-UHFFFAOYSA-N 0.000 claims description 4
- LVHDNIMNOMRZMF-UHFFFAOYSA-N 4-penten-1-yl acetate Chemical compound CC(=O)OCCCC=C LVHDNIMNOMRZMF-UHFFFAOYSA-N 0.000 claims description 4
- GMXIEASXPUEOTG-UHFFFAOYSA-N 8-bromooctan-1-ol Chemical compound OCCCCCCCCBr GMXIEASXPUEOTG-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- YUCXRZJMTCTYDG-UHFFFAOYSA-N hexadec-5-enyl acetate Chemical compound CCCCCCCCCCC=CCCCCOC(C)=O YUCXRZJMTCTYDG-UHFFFAOYSA-N 0.000 claims description 4
- QYOZAXQSDUAPDS-UHFFFAOYSA-N icos-11-en-1-ol Natural products CCCCCCCCC=CCCCCCCCCCCO QYOZAXQSDUAPDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- BDWJRABOFNWETH-SNAWJCMRSA-N methyl (e)-tetradec-11-enoate Chemical compound CC\C=C\CCCCCCCCCC(=O)OC BDWJRABOFNWETH-SNAWJCMRSA-N 0.000 claims description 4
- YYRDDAPQDPABPZ-UHFFFAOYSA-N methyl dec-5-enoate Chemical compound CCCCC=CCCCC(=O)OC YYRDDAPQDPABPZ-UHFFFAOYSA-N 0.000 claims description 4
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 3
- ODDBBUZTMLEZBW-ONEGZZNKSA-N (e)-1-chlorohex-3-ene Chemical compound CC\C=C\CCCl ODDBBUZTMLEZBW-ONEGZZNKSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- UPOBJNRMUDPATE-UHFFFAOYSA-N 5-chloropent-1-ene Chemical compound ClCCCC=C UPOBJNRMUDPATE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- HLNHLSMPPPSBDK-UHFFFAOYSA-N icos-5-enyl acetate Chemical compound CCCCCCCCCCCCCCC=CCCCCOC(C)=O HLNHLSMPPPSBDK-UHFFFAOYSA-N 0.000 claims description 3
- DCELZGFMHKOOJH-WUKNDPDISA-N methyl (E)-icos-5-enoate Chemical compound CCCCCCCCCCCCCC\C=C\CCCC(=O)OC DCELZGFMHKOOJH-WUKNDPDISA-N 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 claims description 2
- KJDZDTDNIULJBE-UHFFFAOYSA-N 11-Docosenoic acid Natural products CCCCCCCCCCC=CCCCCCCCCCC(O)=O KJDZDTDNIULJBE-UHFFFAOYSA-N 0.000 claims description 2
- KJDZDTDNIULJBE-VAWYXSNFSA-N 11-docosenoic acid Chemical compound CCCCCCCCCC\C=C\CCCCCCCCCC(O)=O KJDZDTDNIULJBE-VAWYXSNFSA-N 0.000 claims description 2
- BLMIXWDJHNJWDT-UHFFFAOYSA-N 6-chlorohex-1-ene Chemical compound ClCCCCC=C BLMIXWDJHNJWDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 claims description 2
- RJLJOXJZWMGEFD-UHFFFAOYSA-N ethyl 5-hexenoate Chemical compound CCOC(=O)CCCC=C RJLJOXJZWMGEFD-UHFFFAOYSA-N 0.000 claims description 2
- 235000021299 gondoic acid Nutrition 0.000 claims description 2
- AIRPJJGSWHWBKS-UHFFFAOYSA-N hydroxymethylphosphanium;chloride Chemical compound [Cl-].OC[PH3+] AIRPJJGSWHWBKS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229940119170 jojoba wax Drugs 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- FWWOMPFHMRPXIH-ONEGZZNKSA-N trans-11-tetradecenoic acid Chemical compound CC\C=C\CCCCCCCCCC(O)=O FWWOMPFHMRPXIH-ONEGZZNKSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 64
- 229910052707 ruthenium Inorganic materials 0.000 claims 64
- RAENQLVVMVSUNF-UHFFFAOYSA-N ClP(C(P(C1CCCCC1)(C1CCCCC1)(C1CCCCC1)Cl)C1=CC=CC=C1)(C1CCCCC1)(C1CCCCC1)C1CCCCC1 Chemical compound ClP(C(P(C1CCCCC1)(C1CCCCC1)(C1CCCCC1)Cl)C1=CC=CC=C1)(C1CCCCC1)(C1CCCCC1)C1CCCCC1 RAENQLVVMVSUNF-UHFFFAOYSA-N 0.000 claims 10
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 8
- RGQUMMXAGXSHCL-UHFFFAOYSA-N ClP(C(C=C(C)C)P(C1CCCCC1)(C1CCCCC1)(C1CCCCC1)Cl)(C1CCCCC1)(C1CCCCC1)C1CCCCC1 Chemical compound ClP(C(C=C(C)C)P(C1CCCCC1)(C1CCCCC1)(C1CCCCC1)Cl)(C1CCCCC1)(C1CCCCC1)C1CCCCC1 RGQUMMXAGXSHCL-UHFFFAOYSA-N 0.000 claims 7
- MZLRLIAQRLDZPF-UHFFFAOYSA-N [2-benzylidene-4-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-1,3-dichlorocyclohexyl]-dicyclohexylphosphane Chemical compound CC1=C(C(=CC(=C1)C)C)N1C(N(CC1)C1=C(C=C(C=C1C)C)C)=C1C(C(C(CC1)(P(C1CCCCC1)C1CCCCC1)Cl)=CC1=CC=CC=C1)Cl MZLRLIAQRLDZPF-UHFFFAOYSA-N 0.000 claims 7
- PPMJJYFUKKWEPB-UHFFFAOYSA-N ClC1C(C(C(C1)(P(C1CCCC1)C1CCCC1)Cl)=CC=C(C)C)=C1N(CCN1C1=C(C=C(C=C1C)C)C)C1=C(C=C(C=C1C)C)C Chemical compound ClC1C(C(C(C1)(P(C1CCCC1)C1CCCC1)Cl)=CC=C(C)C)=C1N(CCN1C1=C(C=C(C=C1C)C)C)C1=C(C=C(C=C1C)C)C PPMJJYFUKKWEPB-UHFFFAOYSA-N 0.000 claims 6
- CQKXVIOHEWHEBB-UHFFFAOYSA-N [2-benzylidene-3-[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]-1,4-dichlorocyclohexyl]-dicyclohexylphosphane Chemical compound ClC1C(C(C(CC1)(P(C1CCCCC1)C1CCCCC1)Cl)=CC1=CC=CC=C1)=C1N(C=CN1C1=C(C=C(C=C1C)C)C)C1=C(C=C(C=C1C)C)C CQKXVIOHEWHEBB-UHFFFAOYSA-N 0.000 claims 6
- RNYILAYKSQHQEM-UHFFFAOYSA-N [3-[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]-1,4-dichloro-2-(3-methylbut-2-enylidene)cyclohexyl]-dicyclohexylphosphane Chemical compound ClC1C(C(C(CC1)(P(C1CCCCC1)C1CCCCC1)Cl)=CC=C(C)C)=C1N(C=CN1C1=C(C=C(C=C1C)C)C)C1=C(C=C(C=C1C)C)C RNYILAYKSQHQEM-UHFFFAOYSA-N 0.000 claims 6
- NENRAFFRCRBHPP-UHFFFAOYSA-N [3-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-1,4-dichloro-2-(3-methylbut-2-enylidene)cyclohexyl]-dicyclohexylphosphane Chemical compound ClC1C(C(C(CC1)(P(C1CCCCC1)C1CCCCC1)Cl)=CC=C(C)C)=C1N(CCN1C1=C(C=C(C=C1C)C)C)C1=C(C=C(C=C1C)C)C NENRAFFRCRBHPP-UHFFFAOYSA-N 0.000 claims 6
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- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 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
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000010887 waste solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5086—Preparation; Separation; Purification; Stabilisation from phosphonium salts as starting materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/44—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon double or triple bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/12—Preparation of carboxylic acid esters from asymmetrical anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16654399P | 1999-11-18 | 1999-11-18 | |
| US60/166,543 | 1999-11-18 | ||
| PCT/US2000/031549 WO2001036368A2 (en) | 1999-11-18 | 2000-11-17 | Metathesis syntheses of pheromones or their components |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2392049A1 CA2392049A1 (en) | 2001-05-25 |
| CA2392049C true CA2392049C (en) | 2012-01-31 |
Family
ID=22603759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2392049A Expired - Lifetime CA2392049C (en) | 1999-11-18 | 2000-11-17 | Metathesis syntheses of pheromones or their components |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1230207B1 (enExample) |
| JP (2) | JP4943612B2 (enExample) |
| CN (1) | CN100528829C (enExample) |
| AT (1) | ATE298318T1 (enExample) |
| AU (1) | AU1921201A (enExample) |
| BR (1) | BR0015712B1 (enExample) |
| CA (1) | CA2392049C (enExample) |
| DE (1) | DE60020987T2 (enExample) |
| IL (2) | IL149720A0 (enExample) |
| WO (1) | WO2001036368A2 (enExample) |
| ZA (1) | ZA200204712B (enExample) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2002020395A (ja) * | 2000-07-04 | 2002-01-23 | Sekisui Chem Co Ltd | 新規な高メタセシス活性の有機金属錯体化合物、これを含有してなるメタセシス反応触媒、この触媒を用いた重合方法、並びにこの重合方法により得られた樹脂組成物 |
| WO2002079126A1 (en) | 2001-03-30 | 2002-10-10 | California Institute Of Technology | Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts |
| BRPI0406756A (pt) | 2003-01-13 | 2005-12-20 | Cargill Inc | Método para fabricação de agentes quìmicos industriais |
| BRPI0606718A2 (pt) | 2005-01-10 | 2009-07-14 | Cargill Inc | vela e cera para vela contendo produtos de metátese e semelhantes a metátese |
| KR101269568B1 (ko) * | 2005-07-04 | 2013-06-04 | 자난 사이텍 컴퍼니 리미티드 | 루테늄 착물 리간드, 루테늄 착물, 고정 루테늄 착물 촉매및 그의 제조방법과 용도 |
| WO2007081987A2 (en) * | 2006-01-10 | 2007-07-19 | Elevance Renewable Sciences, Inc. | Method of making hydrogenated metathesis products |
| US8888908B2 (en) | 2006-03-07 | 2014-11-18 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
| CN102525829B (zh) | 2006-03-07 | 2014-08-06 | 埃莱文斯可更新科学公司 | 含有复分解不饱和多元醇酯的组合物 |
| EP2046908B1 (en) | 2006-07-12 | 2017-01-11 | Elevance Renewable Sciences, Inc. | Hot melt adhesive compositions comprising metathesized unsaturated polyol ester wax |
| WO2008010961A2 (en) | 2006-07-13 | 2008-01-24 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
| CN101129138B (zh) * | 2006-08-25 | 2010-06-23 | 北京中捷四方生物科技有限公司 | 一种思茅松毛虫性引诱剂和诱芯及其制备方法 |
| CN106083579A (zh) | 2006-10-13 | 2016-11-09 | 埃莱文斯可更新科学公司 | 通过烯烃复分解由内烯烃合成末端烯烃的方法 |
| WO2008048520A2 (en) | 2006-10-13 | 2008-04-24 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
| DK2121546T3 (en) | 2006-10-13 | 2018-03-12 | Elevance Renewable Sciences | Process for preparing omega-dicarboxylic acid olefin derivative by metathesis |
| ATE519725T1 (de) | 2006-10-13 | 2011-08-15 | Elevance Renewable Sciences | Metatheseverfahren mit hydrierung, und damit in zusammenhang stehende zusammensetzungen |
| BRPI0814994A2 (pt) * | 2007-08-09 | 2015-02-03 | Elevance Renewable Sciences | Métodos químicos para tratamento de uma matéria-prima de metátese |
| FR2921363B1 (fr) * | 2007-09-20 | 2009-11-06 | Arkema France | Procedes de synthese de diacides gras par metathese de diacides insatures obtenus par fermentation d'acides gras naturels |
| JP4594371B2 (ja) * | 2007-11-30 | 2010-12-08 | 信越化学工業株式会社 | （ｅ３，ｚ５）−３，５−アルカジエニルアセタートの製造方法 |
| CN101502262B (zh) * | 2009-03-20 | 2012-06-20 | 中国农业科学院草原研究所 | 草地螟性诱剂的合成及其应用 |
| EP2473038A4 (en) * | 2009-09-04 | 2013-10-23 | United Paragon Associates Inc | COMPOSITIONS FOR TREATING SUFFICIENT OR ILLNESSES PROVIDED BY NEUROKININ-2-RECEPTOR ACTIVITY |
| US8735640B2 (en) | 2009-10-12 | 2014-05-27 | Elevance Renewable Sciences, Inc. | Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks |
| US9175231B2 (en) | 2009-10-12 | 2015-11-03 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils and methods of producing fuel compositions |
| US9000246B2 (en) | 2009-10-12 | 2015-04-07 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
| US9382502B2 (en) | 2009-10-12 | 2016-07-05 | Elevance Renewable Sciences, Inc. | Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks |
| US9365487B2 (en) | 2009-10-12 | 2016-06-14 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
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| US9169447B2 (en) | 2009-10-12 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
| US9222056B2 (en) | 2009-10-12 | 2015-12-29 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
| US8957268B2 (en) | 2009-10-12 | 2015-02-17 | Elevance Renewable Sciences, Inc. | Methods of refining natural oil feedstocks |
| ES2608556T3 (es) * | 2011-01-14 | 2017-04-12 | Basf Se | Composición atrayente que contiene etil 3-metilbutanoato y (E,E)-8-,10-dodecadien-1-ol |
| US9150468B2 (en) * | 2011-09-28 | 2015-10-06 | Nalco Company | Method of producing olefins via metathesis |
| US9133416B2 (en) | 2011-12-22 | 2015-09-15 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
| MX348233B (es) | 2011-12-22 | 2017-05-30 | Elevance Renewable Sciences | Metodos para suprimir la isomerizacion de productos de metatesis de olefina, metodos de refinación de aceites naturales, y metodos de producción de composiciones de combustible. |
| US9139493B2 (en) | 2011-12-22 | 2015-09-22 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
| US9169174B2 (en) | 2011-12-22 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
| EP2804936B1 (en) | 2012-01-10 | 2016-03-23 | Elevance Renewable Sciences, Inc. | Renewable fatty acid waxes and methods of making |
| EP2859068A1 (en) * | 2012-06-12 | 2015-04-15 | Elevance Renewable Sciences, Inc. | Methods for suppressing dehydrogenation |
| EP2864447B3 (en) | 2012-06-20 | 2019-07-17 | Elevance Renewable Sciences, Inc. | Natural oil metathesis compositions |
| US9388098B2 (en) | 2012-10-09 | 2016-07-12 | Elevance Renewable Sciences, Inc. | Methods of making high-weight esters, acids, and derivatives thereof |
| ES2662827T3 (es) * | 2013-04-12 | 2018-04-09 | Shin-Etsu Chemical Co., Ltd | Omega-halo-2-alquinal, procedimiento de producción del mismo y procedimiento de producción de acetato de Z-alquen-in-ilo conjugado usando el mismo |
| GB201404468D0 (en) | 2014-03-13 | 2014-04-30 | Givaudan Sa | Process |
| JP6572966B2 (ja) * | 2015-03-03 | 2019-09-11 | Ａｇｃ株式会社 | 含フッ素オレフィン化合物の製造方法 |
| AU2016357756B2 (en) * | 2015-11-18 | 2021-09-30 | Provivi, Inc. | Production of fatty olefin derivatives via olefin metathesis |
| WO2017100585A1 (en) * | 2015-12-10 | 2017-06-15 | Materia, Inc. | Olefin metathesis catalysts |
| CN105794775B (zh) * | 2016-03-30 | 2018-05-08 | 中国检验检疫科学研究院 | 一种长小蠹科昆虫引诱剂及其制备方法与应用 |
| WO2018069146A1 (fr) | 2016-10-11 | 2018-04-19 | Demeta | Procede de synthese de pheromones |
| CN110603240B (zh) * | 2017-02-17 | 2022-11-15 | 普罗维维公司 | 通过烯烃复分解合成信息素和相关物质 |
| JP7023166B2 (ja) * | 2018-04-18 | 2022-02-21 | 信越化学工業株式会社 | （９ｅ，１１ｚ）－９，１１－ヘキサデカジエナールの製造方法 |
| WO2020123534A1 (en) | 2018-12-10 | 2020-06-18 | Provivi, Inc. | Synthesis of conjugated diene pheromones and related compounds |
| FR3098515B1 (fr) * | 2019-07-12 | 2022-11-04 | Melchior Material & Life Science France | Nouvelles formulations stables de composés 1-Z-bromo alcènes-1 et leur utilisation dans la fabrication de phéromones |
| WO2021247583A1 (en) * | 2020-06-01 | 2021-12-09 | Provivi, Inc. | Synthesis of pheromone derivatives via z-selective olefin metathesis |
| JP7291105B2 (ja) * | 2020-06-24 | 2023-06-14 | 信越化学工業株式会社 | （９ｚ，１１ｅ）－９，１１－ヘキサデカジエナールの製造方法 |
| CN112782309B (zh) * | 2020-12-29 | 2022-10-28 | 常州大学 | 一种稳定长链不饱和烯醛的方法 |
| CN114507122B (zh) * | 2022-01-28 | 2024-07-05 | 宜都市华阳化工有限责任公司 | 3-(4-甲基苯亚甲基)-樟脑合成副产物的回收利用方法 |
| KR102473703B1 (ko) | 2022-07-12 | 2022-12-01 | 전종열 | 사피엔산과 그 트랜스 이성질체 및 사피엔산 에스터를 제조하는 방법 |
| CN115452991B (zh) * | 2022-09-15 | 2024-07-12 | 江苏科技大学 | 十四碳烯酸和十六碳烯醛在检测检疫性害虫中的应用 |
| CN117682940A (zh) * | 2023-11-13 | 2024-03-12 | 中捷四方生物科技股份有限公司 | 无患子在制备昆虫信息素中的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2196061C (en) * | 1992-04-03 | 2000-06-13 | Robert H. Grubbs | High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof |
| US5916983A (en) * | 1997-05-27 | 1999-06-29 | Bend Research, Inc. | Biologically active compounds by catalytic olefin metathesis |
| JP3942122B2 (ja) * | 1997-12-26 | 2007-07-11 | 高砂香料工業株式会社 | ルテニウムメタセシス触媒およびそれを用いたメタセ シス反応によるオレフィン反応生成物を製造する方法 |
| DE19815275B4 (de) * | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
| JP2002535297A (ja) * | 1999-01-26 | 2002-10-22 | カリフォルニア インスティチュート オブ テクノロジー | 末端オレフィンのクロスメタセシスのための方法 |
| DE19907519A1 (de) * | 1999-02-22 | 2000-08-31 | Basf Ag | Verfahren zur Herstellung von substituierten Olefinen |
| JP4410422B2 (ja) * | 1999-05-24 | 2010-02-03 | カリフォルニア インスティチュート オブ テクノロジー | イミダゾリジンに基づく金属カルベンメタセシス触媒 |
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2000
- 2000-11-17 CN CNB008181101A patent/CN100528829C/zh not_active Expired - Lifetime
- 2000-11-17 BR BRPI0015712-0A patent/BR0015712B1/pt not_active IP Right Cessation
- 2000-11-17 DE DE60020987T patent/DE60020987T2/de not_active Expired - Lifetime
- 2000-11-17 EP EP00982144A patent/EP1230207B1/en not_active Expired - Lifetime
- 2000-11-17 CA CA2392049A patent/CA2392049C/en not_active Expired - Lifetime
- 2000-11-17 JP JP2001538323A patent/JP4943612B2/ja not_active Expired - Lifetime
- 2000-11-17 AU AU19212/01A patent/AU1921201A/en not_active Abandoned
- 2000-11-17 AT AT00982144T patent/ATE298318T1/de not_active IP Right Cessation
- 2000-11-17 WO PCT/US2000/031549 patent/WO2001036368A2/en not_active Ceased
- 2000-11-17 IL IL14972000A patent/IL149720A0/xx active IP Right Grant
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2002
- 2002-05-19 IL IL149720A patent/IL149720A/en unknown
- 2002-06-12 ZA ZA200204712A patent/ZA200204712B/en unknown
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2011
- 2011-04-05 JP JP2011084025A patent/JP5687114B2/ja not_active Expired - Lifetime
Also Published As
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|---|---|
| BR0015712B1 (pt) | 2011-01-25 |
| CN1423629A (zh) | 2003-06-11 |
| ZA200204712B (en) | 2004-04-08 |
| BR0015712A (pt) | 2004-04-27 |
| JP2003531818A (ja) | 2003-10-28 |
| CN100528829C (zh) | 2009-08-19 |
| ATE298318T1 (de) | 2005-07-15 |
| JP2011178789A (ja) | 2011-09-15 |
| EP1230207A2 (en) | 2002-08-14 |
| JP5687114B2 (ja) | 2015-03-18 |
| JP4943612B2 (ja) | 2012-05-30 |
| DE60020987D1 (de) | 2005-07-28 |
| IL149720A (en) | 2008-03-20 |
| EP1230207B1 (en) | 2005-06-22 |
| IL149720A0 (en) | 2002-11-10 |
| DE60020987T2 (de) | 2006-05-11 |
| WO2001036368A3 (en) | 2002-01-10 |
| AU1921201A (en) | 2001-05-30 |
| WO2001036368A2 (en) | 2001-05-25 |
| CA2392049A1 (en) | 2001-05-25 |
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