AU2004285852A1 - Process for preparing functional group-containing olefinic compounds - Google Patents
Process for preparing functional group-containing olefinic compounds Download PDFInfo
- Publication number
- AU2004285852A1 AU2004285852A1 AU2004285852A AU2004285852A AU2004285852A1 AU 2004285852 A1 AU2004285852 A1 AU 2004285852A1 AU 2004285852 A AU2004285852 A AU 2004285852A AU 2004285852 A AU2004285852 A AU 2004285852A AU 2004285852 A1 AU2004285852 A1 AU 2004285852A1
- Authority
- AU
- Australia
- Prior art keywords
- group
- olefinic
- reacting
- compound
- carbonyl
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 88
- 125000000524 functional group Chemical group 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- -1 alkylidene phosphorane Chemical compound 0.000 claims abstract description 53
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 36
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000012038 nucleophile Substances 0.000 claims abstract description 19
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 16
- 150000002576 ketones Chemical class 0.000 claims abstract description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 70
- 230000008569 process Effects 0.000 claims description 62
- 239000003016 pheromone Substances 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 150000004714 phosphonium salts Chemical class 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
- DETKMHVWNMOSRN-UHFFFAOYSA-N 8-bromooctanal Chemical compound BrCCCCCCCC=O DETKMHVWNMOSRN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000004419 alkynylene group Chemical group 0.000 claims description 8
- 150000003462 sulfoxides Chemical class 0.000 claims description 8
- XDMCURSJJKHDCO-UHFFFAOYSA-N 12-bromododeca-2,4-diene Chemical compound CC=CC=CCCCCCCCBr XDMCURSJJKHDCO-UHFFFAOYSA-N 0.000 claims description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
- CSWBSLXBXRFNST-UHFFFAOYSA-N dodeca-8,10-dien-1-ol Chemical compound CC=CC=CCCCCCCCO CSWBSLXBXRFNST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001632 sodium acetate Substances 0.000 claims description 7
- 235000017281 sodium acetate Nutrition 0.000 claims description 7
- YJINQJFQLQIYHX-SNAWJCMRSA-N 11E-Tetradecenyl acetate Chemical compound CC\C=C\CCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-SNAWJCMRSA-N 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- SUCYDSJQVVGOIW-UHFFFAOYSA-N dodec-8-enyl acetate Chemical compound CCCC=CCCCCCCCOC(C)=O SUCYDSJQVVGOIW-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 claims description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 4
- TXIFFCXBKFWXFJ-UHFFFAOYSA-N 11-bromoundecanal Chemical compound BrCCCCCCCCCCC=O TXIFFCXBKFWXFJ-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 4
- MVLWUDKKPUDRIZ-UHFFFAOYSA-N 2-bromooctanal Chemical compound CCCCCCC(Br)C=O MVLWUDKKPUDRIZ-UHFFFAOYSA-N 0.000 claims description 3
- DOQLCJMCQWQQHK-UHFFFAOYSA-N 4-chlorobutanal Chemical compound ClCCCC=O DOQLCJMCQWQQHK-UHFFFAOYSA-N 0.000 claims description 3
- HTZJFSSXTWXAMP-UHFFFAOYSA-N 9-bromononanal Chemical compound BrCCCCCCCCC=O HTZJFSSXTWXAMP-UHFFFAOYSA-N 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- RIGUTONFWSZQSU-UHFFFAOYSA-N butylidene(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCCC)C1=CC=CC=C1 RIGUTONFWSZQSU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- DDMOZUBZYFKJDS-UHFFFAOYSA-N triphenyl(propylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCC)C1=CC=CC=C1 DDMOZUBZYFKJDS-UHFFFAOYSA-N 0.000 claims description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims description 2
- WIGLPAZBNNFHSK-UHFFFAOYSA-N 12-bromododec-4-ene Chemical compound CCCC=CCCCCCCCBr WIGLPAZBNNFHSK-UHFFFAOYSA-N 0.000 claims 2
- SYAFMCQKFHDZMO-UHFFFAOYSA-N 14-bromotetradec-3-ene Chemical compound CCC=CCCCCCCCCCCBr SYAFMCQKFHDZMO-UHFFFAOYSA-N 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- AEPMMTRERWOSHG-HULFFUFUSA-N (1E,3E)-dodeca-1,3-dien-1-ol Chemical compound CCCCCCCC\C=C\C=C\O AEPMMTRERWOSHG-HULFFUFUSA-N 0.000 claims 1
- NTKDSWPSEFZZOZ-UHFFFAOYSA-N dodeca-8,10-dienyl acetate Chemical compound CC=CC=CCCCCCCCOC(C)=O NTKDSWPSEFZZOZ-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000007858 starting material Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000000796 flavoring agent Substances 0.000 description 8
- 235000019634 flavors Nutrition 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 230000013011 mating Effects 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 6
- SUCYDSJQVVGOIW-WAYWQWQTSA-N 8Z-Dodecenyl acetate Chemical compound CCC\C=C/CCCCCCCOC(C)=O SUCYDSJQVVGOIW-WAYWQWQTSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003620 semiochemical Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241001635274 Cydia pomonella Species 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241001441330 Grapholita molesta Species 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- AHKZTVQIVOEVFO-UHFFFAOYSA-N oxide(2-) Chemical compound [O-2] AHKZTVQIVOEVFO-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- SMGSPBKMKYMJPQ-UHFFFAOYSA-M tetrapropylphosphanium;bromide Chemical compound [Br-].CCC[P+](CCC)(CCC)CCC SMGSPBKMKYMJPQ-UHFFFAOYSA-M 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- WIGLPAZBNNFHSK-SNAWJCMRSA-N (e)-12-bromododec-4-ene Chemical compound CCC\C=C\CCCCCCCBr WIGLPAZBNNFHSK-SNAWJCMRSA-N 0.000 description 3
- YJINQJFQLQIYHX-PLNGDYQASA-N 11Z-Tetradecenyl acetate Chemical compound CC\C=C/CCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-PLNGDYQASA-N 0.000 description 3
- SUCYDSJQVVGOIW-AATRIKPKSA-N 8E-Dodecenyl acetate Chemical compound CCC\C=C\CCCCCCCOC(C)=O SUCYDSJQVVGOIW-AATRIKPKSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 241000255901 Tortricidae Species 0.000 description 3
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- CQMJEZQEVXQEJB-UHFFFAOYSA-N 1-hydroxy-1,3-dioxobenziodoxole Chemical compound C1=CC=C2I(O)(=O)OC(=O)C2=C1 CQMJEZQEVXQEJB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000400431 Keiferia lycopersicella Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241001608848 Platynota idaeusalis Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241001341014 Sparganothis Species 0.000 description 2
- 241001528590 Synanthedon exitiosa Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RGOJAIVQEOCMJU-UHFFFAOYSA-N tri(nonyl)-nonylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCP(CCCCCCCCC)(CCCCCCCCC)=CCCCCCCCC RGOJAIVQEOCMJU-UHFFFAOYSA-N 0.000 description 2
- DUCVQKMNGSZPAV-UHFFFAOYSA-N tridec-4-enyl acetate Chemical compound CCCCCCCCC=CCCCOC(C)=O DUCVQKMNGSZPAV-UHFFFAOYSA-N 0.000 description 2
- NPFVOOAXDOBMCE-PLNGDYQASA-N (3Z)-hex-3-en-1-yl acetate Chemical compound CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
- CSWBSLXBXRFNST-MQQKCMAXSA-N (8e,10e)-dodeca-8,10-dien-1-ol Chemical compound C\C=C\C=C\CCCCCCCO CSWBSLXBXRFNST-MQQKCMAXSA-N 0.000 description 1
- GPINUUWEKPNDBB-CMDGGOBGSA-N (E)-2-Octenyl butyrate Chemical compound CCCCC\C=C\COC(=O)CCC GPINUUWEKPNDBB-CMDGGOBGSA-N 0.000 description 1
- DXAFFKRBQLZTCN-MDZDMXLPSA-N (E)-nonadec-10-enal Chemical compound CCCCCCCC\C=C\CCCCCCCCC=O DXAFFKRBQLZTCN-MDZDMXLPSA-N 0.000 description 1
- IUXHPSPHPKXTPA-ONEGZZNKSA-N (e)-1-bromobut-1-ene Chemical compound CC\C=C\Br IUXHPSPHPKXTPA-ONEGZZNKSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- VVGOCOMZRGWHPI-ARJAWSKDSA-N (z)-4-heptenal Chemical compound CC\C=C/CCC=O VVGOCOMZRGWHPI-ARJAWSKDSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- XFGANBYCJWQYBI-UHFFFAOYSA-N 11-bromoundecan-1-ol Chemical compound OCCCCCCCCCCCBr XFGANBYCJWQYBI-UHFFFAOYSA-N 0.000 description 1
- SPFYVVCZIOLVOK-ONEGZZNKSA-N 11E-Tetradecenal Chemical compound CC\C=C\CCCCCCCCCC=O SPFYVVCZIOLVOK-ONEGZZNKSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- MFFQOUCMBNXSBK-UHFFFAOYSA-N 16(R and S)-3,13Z-kolavadien-16,15-olide-2-one Natural products CCC=CCCCCCCCCOC(C)=O MFFQOUCMBNXSBK-UHFFFAOYSA-N 0.000 description 1
- UAEYWQLQNGPGFL-UHFFFAOYSA-N 2-bromoundecanal Chemical compound CCCCCCCCCC(Br)C=O UAEYWQLQNGPGFL-UHFFFAOYSA-N 0.000 description 1
- VVJPJXKHBZNADP-QQIRETTESA-N 3E,13E-Octadecadienyl acetate Chemical compound CCCC\C=C\CCCCCCCC\C=C\CCOC(C)=O VVJPJXKHBZNADP-QQIRETTESA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 description 1
- QSEJFJRCQSBQMS-UHFFFAOYSA-N 4-oxobutyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCC=O)C=C1 QSEJFJRCQSBQMS-UHFFFAOYSA-N 0.000 description 1
- LFMJSESKMXLPPR-UHFFFAOYSA-N 4-oxobutyl methanesulfonate Chemical compound CS(=O)(=O)OCCCC=O LFMJSESKMXLPPR-UHFFFAOYSA-N 0.000 description 1
- UXHBEJHWPUSRJH-UHFFFAOYSA-N 7-bromoheptanal Chemical compound BrCCCCCCC=O UXHBEJHWPUSRJH-UHFFFAOYSA-N 0.000 description 1
- TXAVTGHUCGFTCW-UHFFFAOYSA-N 7-oxoheptyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCCCCC=O)C=C1 TXAVTGHUCGFTCW-UHFFFAOYSA-N 0.000 description 1
- XXHMQGCNRMGNQG-UHFFFAOYSA-N 7-oxoheptyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCCCC=O XXHMQGCNRMGNQG-UHFFFAOYSA-N 0.000 description 1
- GMXIEASXPUEOTG-UHFFFAOYSA-N 8-bromooctan-1-ol Chemical compound OCCCCCCCCBr GMXIEASXPUEOTG-UHFFFAOYSA-N 0.000 description 1
- OFYUCKRZVKYNMU-UHFFFAOYSA-N 8-chlorooctanal Chemical compound ClCCCCCCCC=O OFYUCKRZVKYNMU-UHFFFAOYSA-N 0.000 description 1
- QVZMFFAALNTSJI-UHFFFAOYSA-N 9-chlorononanal Chemical compound ClCCCCCCCCC=O QVZMFFAALNTSJI-UHFFFAOYSA-N 0.000 description 1
- NGLMSXQPCHRUHO-UHFFFAOYSA-N 9-oxononyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCCCCCCC=O)C=C1 NGLMSXQPCHRUHO-UHFFFAOYSA-N 0.000 description 1
- UBBMYLYZADBJBB-UHFFFAOYSA-N 9-oxononyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCCCCCC=O UBBMYLYZADBJBB-UHFFFAOYSA-N 0.000 description 1
- MFFQOUCMBNXSBK-SNAWJCMRSA-N 9E-Dodecenyl acetate Chemical compound CC\C=C\CCCCCCCCOC(C)=O MFFQOUCMBNXSBK-SNAWJCMRSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- UYOVPRNBYIZHMW-UHFFFAOYSA-N C(=CCCC)=P(CCCC)(CCCC)CCCC Chemical compound C(=CCCC)=P(CCCC)(CCCC)CCCC UYOVPRNBYIZHMW-UHFFFAOYSA-N 0.000 description 1
- ICQKSRLBGRWQCK-UHFFFAOYSA-N C=1C=CC=CC=1P(=CCC)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1P(=CCC)C1=CC=CC=C1 ICQKSRLBGRWQCK-UHFFFAOYSA-N 0.000 description 1
- 241000255942 Choristoneura fumiferana Species 0.000 description 1
- 241001124562 Choristoneura rosaceana Species 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 1
- 241000498255 Enterobius vermicularis Species 0.000 description 1
- 241000801160 Euura alaskensis Species 0.000 description 1
- AWCPMVVOGVEPRC-VOTSOKGWSA-N Hept-trans-2-en-1-yl acetate Chemical compound CCCC\C=C\COC(C)=O AWCPMVVOGVEPRC-VOTSOKGWSA-N 0.000 description 1
- 241000581835 Monodora junodii Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241001201823 Rhopobota naevana Species 0.000 description 1
- 238000006280 Rosenmund reaction Methods 0.000 description 1
- 239000000877 Sex Attractant Substances 0.000 description 1
- IOUUIFSIQMVYKP-UHFFFAOYSA-N Tetradecanoyl acetate Natural products CCCCCCCCCCCCCCOC(C)=O IOUUIFSIQMVYKP-UHFFFAOYSA-N 0.000 description 1
- 241001238452 Tortrix Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- UECPLNNAVLEZGO-CCEZHUSRSA-N [(e)-tetradec-1-enyl] acetate Chemical compound CCCCCCCCCCCC\C=C\OC(C)=O UECPLNNAVLEZGO-CCEZHUSRSA-N 0.000 description 1
- DUCVQKMNGSZPAV-ZHACJKMWSA-N [(e)-tridec-4-enyl] acetate Chemical compound CCCCCCCC\C=C\CCCOC(C)=O DUCVQKMNGSZPAV-ZHACJKMWSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002411 allomone Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000031902 chemoattractant activity Effects 0.000 description 1
- JKKGTSUICJWEKB-SREVYHEPSA-N cis-3-Hexenyl 2-methylbutanoate Chemical compound CC\C=C/CCOC(=O)C(C)CC JKKGTSUICJWEKB-SREVYHEPSA-N 0.000 description 1
- LKNXTZXOBHAYSR-PLNGDYQASA-N cis-3-Hexenyl pyruvate Chemical compound CC\C=C/CCOC(=O)C(C)=O LKNXTZXOBHAYSR-PLNGDYQASA-N 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 206010014881 enterobiasis Diseases 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- BXJHOKLLMOYSRQ-UHFFFAOYSA-N hexadeca-7,11-dienyl acetate Chemical compound CCCCC=CCCC=CCCCCCCOC(C)=O BXJHOKLLMOYSRQ-UHFFFAOYSA-N 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 238000004920 integrated pest control Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002410 kairomone Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- RMNSMAQVNXMUQL-UHFFFAOYSA-N pentyl-pentylidene-diphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=CCCCC)(CCCCC)C1=CC=CC=C1 RMNSMAQVNXMUQL-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DDFXAFPWFJDMPS-UHFFFAOYSA-M tetra(nonyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCC[P+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC DDFXAFPWFJDMPS-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- YGHAIPJLMYTNAI-UHFFFAOYSA-N tetradec-11-en-1-ol Chemical compound CCC=CCCCCCCCCCCO YGHAIPJLMYTNAI-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YJJIVDCKSZMHGZ-VOTSOKGWSA-N trans-3-Octen-2-ol Chemical compound CCCC\C=C\C(C)O YJJIVDCKSZMHGZ-VOTSOKGWSA-N 0.000 description 1
- SEPBBMLUGLQMPY-UHFFFAOYSA-N tributyl(butylidene)-$l^{5}-phosphane Chemical compound CCCCP(CCCC)(CCCC)=CCCC SEPBBMLUGLQMPY-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- 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
- C07C29/12—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 mineral acids
- C07C29/124—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 mineral acids of halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Closures For Containers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/692,358 US6838576B1 (en) | 2003-10-23 | 2003-10-23 | Process for preparing functional group-containing olefinic compounds |
| US10/692,358 | 2003-10-23 | ||
| PCT/US2004/030461 WO2005042462A2 (en) | 2003-10-23 | 2004-09-16 | Process for preparing functional group-containing olefinic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004285852A1 true AU2004285852A1 (en) | 2005-05-12 |
Family
ID=33541617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004285852A Abandoned AU2004285852A1 (en) | 2003-10-23 | 2004-09-16 | Process for preparing functional group-containing olefinic compounds |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6838576B1 (enExample) |
| EP (2) | EP2314559A3 (enExample) |
| JP (1) | JP2007509142A (enExample) |
| AT (1) | ATE533742T1 (enExample) |
| AU (1) | AU2004285852A1 (enExample) |
| CA (2) | CA2457586A1 (enExample) |
| ES (1) | ES2377014T3 (enExample) |
| WO (1) | WO2005042462A2 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7838708B2 (en) * | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
| US20050171393A1 (en) * | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
| MXPA06000470A (es) * | 2003-07-15 | 2006-08-23 | Grt Inc | Sintesis de hidrocarburos. |
| US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US7674941B2 (en) * | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| EP1993951B1 (en) * | 2006-02-03 | 2014-07-30 | GRT, Inc. | Separation of light gases from bromine |
| CN101817720A (zh) | 2006-02-03 | 2010-09-01 | Grt公司 | 天然气转化为液体烃的连续方法 |
| CN101687725A (zh) * | 2007-05-14 | 2010-03-31 | Grt公司 | 使烃类原料转化同时电解回收卤素的方法 |
| AU2008256606A1 (en) | 2007-05-24 | 2008-12-04 | Grt, Inc. | Zone reactor incorporating reversible hydrogen halide capture and release |
| US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
| NZ591207A (en) * | 2008-07-18 | 2013-03-28 | Grt Inc | Continuous process for converting natural gas to liquid hydrocarbons |
| WO2010124041A1 (en) * | 2009-04-22 | 2010-10-28 | Grt, Inc. | Process for converting hydrocarbon feedstocks with electrolytic and photoelectrocatalytic recovery of halogens |
| US8198495B2 (en) | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8367884B2 (en) * | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8815050B2 (en) | 2011-03-22 | 2014-08-26 | Marathon Gtf Technology, Ltd. | Processes and systems for drying liquid bromine |
| US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
| US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
| US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
| US9193641B2 (en) | 2011-12-16 | 2015-11-24 | Gtc Technology Us, Llc | Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems |
| MD4247C1 (ro) * | 2012-10-19 | 2014-03-31 | Институт По Защите Растений И Экологического Сельского Хозяйства Анм | Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. |
| CN103044247A (zh) * | 2012-12-15 | 2013-04-17 | 黑龙江大学 | 鳞翅目类昆虫性信息素(e/z)8-十二烯乙酸酯及其类似物的合成方法 |
| CN104478930B (zh) * | 2014-11-19 | 2016-05-25 | 上海泰坦科技股份有限公司 | 磷配体类化合物的合成工艺 |
| CN105330696A (zh) * | 2015-12-08 | 2016-02-17 | 山东维天精细化工科技有限公司 | 一种三苯基丁基溴化膦的合成方法 |
| 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 |
| CN114940690A (zh) * | 2022-07-07 | 2022-08-26 | 昆明理工大学 | 一种四丙基氢氧化鏻及其制备方法和应用 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1299691A (en) | 1971-04-26 | 1972-12-13 | Wendell Roelofs | Dodeca-8,10-dien-1-ols |
| US3818049A (en) | 1971-07-26 | 1974-06-18 | Zoecon Corp | Synthesis of codling moth attractant |
| US3943157A (en) | 1971-07-26 | 1976-03-09 | Zoecon Corporation | Synthesis of codling moth attractant |
| US3783135A (en) | 1971-08-20 | 1974-01-01 | Zoecon Corp | Synthesis of codling moth attractant |
| US3805607A (en) | 1971-08-27 | 1974-04-23 | Zellweger Uster Ag | Yarn changing mechanism |
| US3752843A (en) | 1971-10-08 | 1973-08-14 | Zoecon Corp | Aliphatic di olefinic nitriles |
| US3875243A (en) | 1972-01-17 | 1975-04-01 | Zoecon Corp | 1-Cyclopropyl-trans-2-buten-1-ol |
| US4057593A (en) * | 1973-11-07 | 1977-11-08 | Hoechst Aktiengesellschaft | Process for preparing cis-olefins |
| DE2355534A1 (de) | 1973-11-07 | 1975-09-11 | Hoechst Ag | Verfahren zur herstellung von cisolefinen |
| RO64550A2 (fr) | 1976-02-13 | 1978-12-15 | Inst De Chimie | Procede pour la preparation du z-11-tetradecen-1-ile acetate |
| US4130709A (en) | 1977-12-08 | 1978-12-19 | Eli Lilly And Company | Pleuromutilin glycoside derivatives |
| RO76824A2 (ro) | 1978-01-19 | 1981-08-17 | Institutul De Chimie,Ro | Procedeu de preparare a 8,10-trans,trans-dodecadien-1-olului |
| FR2417487A1 (fr) | 1978-02-15 | 1979-09-14 | Agronomique Inst Nat Rech | Nouveau procede de preparation stereoselectif de pheromones sexuelles |
| EP0038052B1 (en) | 1980-04-14 | 1984-03-07 | Shin-Etsu Chemical Co., Ltd. | Method for the preparation of cis-alkenyl bromide and acetate |
| HU181328B (en) * | 1981-05-15 | 1983-07-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives |
| JPS58177924A (ja) | 1982-04-12 | 1983-10-18 | Shin Etsu Chem Co Ltd | シス−アルケニルクロライドの製造方法 |
| CS233069B1 (cs) | 1983-05-04 | 1985-02-14 | Ladislav Kalvoda | Způsob přípravy (8E, l0E)-8,10-dodekadien-l-olu |
| JPS62212347A (ja) | 1986-03-12 | 1987-09-18 | Nitto Electric Ind Co Ltd | シス−１１−テトラデセニルアセテ−トの製造方法 |
| JPS62223136A (ja) | 1986-03-19 | 1987-10-01 | Shin Etsu Chem Co Ltd | １―ハロ―（ｅ，ｚ）―７，９―アルカジエン化合物 |
| DE3729225A1 (de) | 1987-09-02 | 1989-03-23 | Basf Ag | 9-hydroxydodec-10-enyl-1-t-butylether und seine verwendung als zwischenprodukt zur synthese von 8,10-dodecadienol |
| DE3817399A1 (de) | 1988-05-21 | 1989-11-30 | Basf Ag | Verfahren zur herstellung von e7/z9-alkadien-1-olen und deren an der hydroxylgruppe geschuetzten derivaten |
| JPH07116075B2 (ja) | 1988-06-06 | 1995-12-13 | 信越化学工業株式会社 | 不飽和アルコール化合物の製造方法 |
| DE3829979A1 (de) | 1988-09-03 | 1990-03-15 | Basf Ag | Vinylsubstituierte alkohole und deren oh-geschuetzte derivate und ihre verwendung zur bekaempfung von insekten der ordnung lepidoptera |
| JP2693615B2 (ja) | 1990-02-16 | 1997-12-24 | 信越化学工業株式会社 | １‐ハロ‐４，６，１０‐ヘキサデカトリエン化合物およびその製造方法 |
| US5599848A (en) | 1991-10-24 | 1997-02-04 | Basf Aktiengesellschaft | Preparation, intermediates for the preparation and the use of a mixture of dodecdienol isomers |
| DE4142515A1 (de) | 1991-12-21 | 1993-06-24 | Basf Ag | Verfahren zur herstellung von alkenolen |
| DE4215747A1 (de) | 1992-05-13 | 1993-11-18 | Basf Ag | Verfahren und Zwischenprodukte zur Herstellung von 2,13-Octadecadienylacetat sowie dessen Verwendung |
| DE4303079A1 (de) | 1993-02-04 | 1994-08-11 | Basf Ag | (E,Z)8-Tetradecenylacetat, Verfahren zu dessen Herstellung sowie dessen Verwendung zur Bekämpfung von Lepidopteren |
| JP3240752B2 (ja) | 1993-06-18 | 2001-12-25 | ソニー株式会社 | 固体撮像素子 |
| EP0630877B1 (en) | 1993-06-21 | 1997-03-12 | Shin-Etsu Chemical Co., Ltd. | Workup of Wittig reaction products |
| JP3467307B2 (ja) | 1994-03-31 | 2003-11-17 | 信越化学工業株式会社 | ホスホニウム塩の製造方法 |
| US6248364B1 (en) | 1997-04-07 | 2001-06-19 | 3M Innovative Properties Company | Encapsulation process and encapsulated products |
| US6471975B1 (en) | 1998-05-01 | 2002-10-29 | 3M Innovative Properties Company | Microspheres as a delivery vehicle for bio-active agents useful in agricultural applications |
-
2003
- 2003-10-23 US US10/692,358 patent/US6838576B1/en not_active Expired - Lifetime
-
2004
- 2004-02-12 CA CA002457586A patent/CA2457586A1/en not_active Abandoned
- 2004-09-16 EP EP10013203A patent/EP2314559A3/en not_active Withdrawn
- 2004-09-16 WO PCT/US2004/030461 patent/WO2005042462A2/en not_active Ceased
- 2004-09-16 ES ES04784349T patent/ES2377014T3/es not_active Expired - Lifetime
- 2004-09-16 AU AU2004285852A patent/AU2004285852A1/en not_active Abandoned
- 2004-09-16 AT AT04784349T patent/ATE533742T1/de active
- 2004-09-16 EP EP04784349A patent/EP1678115B1/en not_active Expired - Lifetime
- 2004-09-16 JP JP2006536628A patent/JP2007509142A/ja not_active Withdrawn
- 2004-09-16 CA CA002542857A patent/CA2542857A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1678115B1 (en) | 2011-11-16 |
| EP2314559A3 (en) | 2011-09-07 |
| CA2457586A1 (en) | 2005-04-23 |
| EP2314559A2 (en) | 2011-04-27 |
| WO2005042462A3 (en) | 2005-07-28 |
| ES2377014T3 (es) | 2012-03-21 |
| WO2005042462A2 (en) | 2005-05-12 |
| US6838576B1 (en) | 2005-01-04 |
| EP1678115A2 (en) | 2006-07-12 |
| ATE533742T1 (de) | 2011-12-15 |
| JP2007509142A (ja) | 2007-04-12 |
| CA2542857A1 (en) | 2005-05-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1678115B1 (en) | Process for preparing functional group-containing olefinic compounds | |
| Buss et al. | The stereocontrolled Horner-Wittig reaction: synthesis of disubstituted alkenes | |
| US20020151742A1 (en) | Process for producing vitamin a ester | |
| CN106660928B (zh) | 用于制备(e,z)-7,9-十二碳二烯基-1-乙酸酯的新方法 | |
| US5166445A (en) | Method for the manufacture of carotinoids and the novel intermediates | |
| EP0069761B1 (en) | (+)-4-substituted-2-indanols and insecticidal ester derivatives | |
| US5208381A (en) | Method for the manufacture of carotinoids and novel intermediates | |
| GB1587390A (en) | Process for the preparation of four-membered cyclic ketones | |
| EP3037404B1 (en) | 1-(2-acyloxyethyl)cyclopropyl sulfonate compound and method for producing 4-alkyl-3-methylenebutyl carboxylate | |
| Fujiwara et al. | Highly stereoselective syntheses of alkenylsilanes and germanes utilizing cyclobutyl ketones | |
| EP3037405A1 (en) | 3-acyloxymethyl-3-butenyl carboxylate compound and method for producing 4-alkyl-3-methylenebutyl carboxylate | |
| EP3214063B1 (en) | Terminal conjugated trienal acetal compound and method for producing terminal conjugated trienal compound using the same | |
| Shakhmaev et al. | Stereoselective synthesis of 11 (E)-tetradecen-1-yl acetate—Sex pheromone of sod webworm (Loxostege sticticalis) | |
| JP7145166B2 (ja) | 新規な７，９－ドデカジエニル－１－アセテート異性体組成物、およびその製造方法 | |
| EP0002849B1 (en) | Process for the preparation of di-(halo)-vinyl compounds and di-(halo)-vinyl compounds produced thereby | |
| US5681977A (en) | Method for the production of (3-alkoxycarbonyl-2-butenyl) triphenylphosphonium salts | |
| US5382732A (en) | 2,5-bis(1,1-dialkoxy-2-propyl)-2,5-dihydrofurans, the preparation thereof and the use thereof for the preparation of carotenoids | |
| JP6772290B2 (ja) | ノートカトン、ジヒドロノートカトン、およびテトラヒドロノートカトンの合成のための反応シーケンス | |
| EP0007142B1 (en) | Novel intermediates in the preparation of cyclopropanecarboxylate esters and process for their manufacture | |
| EP4588911A1 (en) | Process for preparing alpha-farnesenes and 4-substituted 3-methyl-1,3-butadiene compound having related structure, and synthetic intermediate compound thereof | |
| EP0002850B1 (en) | Novel intermediates in the preparation of cyclopropylcarboxylate esters and process for their manufacture | |
| Kasradze et al. | Synthesis of dicyclopropanes from 4, 7, 7-Trimethyl-3-oxabicyclo [4.1. 0] hept-4-en-2-one | |
| EP4588912A1 (en) | Process for preparing beta-farnesenes and 2-(3-alkenyl)-1,3-butadiene compound having related structure, and synthetic intermediate compound thereof | |
| KR100374688B1 (ko) | 싸이클로프로판에스테르의제조방법 | |
| GB2073754A (en) | Preparation of 3,7,11- Trimethyl-2,4-dodecadienoates and Starting Materials Therefor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |