NL1002998C2 - Werkwijze voor het substitueren van cyclopentadieen. - Google Patents
Werkwijze voor het substitueren van cyclopentadieen. Download PDFInfo
- Publication number
- NL1002998C2 NL1002998C2 NL1002998A NL1002998A NL1002998C2 NL 1002998 C2 NL1002998 C2 NL 1002998C2 NL 1002998 A NL1002998 A NL 1002998A NL 1002998 A NL1002998 A NL 1002998A NL 1002998 C2 NL1002998 C2 NL 1002998C2
- Authority
- NL
- Netherlands
- Prior art keywords
- mol
- cyclopentadiene
- compound
- added
- stirring
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title abstract description 48
- 150000001875 compounds Chemical group 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 150000004820 halides Chemical class 0.000 claims abstract description 14
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 85
- 238000006467 substitution reaction Methods 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 28
- 238000002360 preparation method Methods 0.000 abstract description 14
- -1 cyclopentadiene compound Chemical class 0.000 abstract description 6
- 238000003756 stirring Methods 0.000 description 34
- 238000004817 gas chromatography Methods 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 125000001424 substituent group Chemical group 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 238000012512 characterization method Methods 0.000 description 13
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 13
- 238000004821 distillation Methods 0.000 description 11
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 10
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000005191 phase separation Methods 0.000 description 9
- UMAHMMJKEZXFRU-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)cyclopenta-1,3-diene Chemical compound CC(C)C1=C(C(C)C)C(C(C)C)=CC1 UMAHMMJKEZXFRU-UHFFFAOYSA-N 0.000 description 8
- ZVDDKNWZQSDQNX-UHFFFAOYSA-N 5,5-di(propan-2-yl)cyclopenta-1,3-diene Chemical compound CC(C)C1(C(C)C)C=CC=C1 ZVDDKNWZQSDQNX-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000003518 caustics Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- DFODTWUFWMTZID-UHFFFAOYSA-N 2-propylcyclopenta-1,3-diene Chemical compound CCCC1=CCC=C1 DFODTWUFWMTZID-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HYKLMSLCZHLCMQ-UHFFFAOYSA-N (2,3-dicyclohexylcyclopenta-1,3-dien-1-yl)cyclohexane Chemical compound C1CCCCC1C1=C(C2CCCCC2)CC=C1C1CCCCC1 HYKLMSLCZHLCMQ-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- ZISCLASKNKBKTH-UHFFFAOYSA-N 1,2,3-tri(butan-2-yl)cyclopenta-1,3-diene Chemical compound CCC(C)C1=C(C(C)CC)C(C(C)CC)=CC1 ZISCLASKNKBKTH-UHFFFAOYSA-N 0.000 description 2
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 2
- HILJWHUIEBFFEW-UHFFFAOYSA-N 2-butylcyclopenta-1,3-diene Chemical compound CCCCC1=CCC=C1 HILJWHUIEBFFEW-UHFFFAOYSA-N 0.000 description 2
- WKZUZGPZSXUBFQ-UHFFFAOYSA-N 2-pentylcyclopenta-1,3-diene Chemical compound CCCCCC1=CCC=C1 WKZUZGPZSXUBFQ-UHFFFAOYSA-N 0.000 description 2
- HDLXPNDSLDLJHF-UHFFFAOYSA-N 4,7,13,16,21-pentaoxa-1,10-diazabicyclo[8.8.5]tricosane Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCC2 HDLXPNDSLDLJHF-UHFFFAOYSA-N 0.000 description 2
- LVNQVIZBPSRXAN-UHFFFAOYSA-N 4,7,13,18-tetraoxa-1,10-diazabicyclo[8.5.5]icosane Chemical compound C1COCCOCCN2CCOCCN1CCOCC2 LVNQVIZBPSRXAN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- AQHXALDLCNTRII-UHFFFAOYSA-N cyclopenta-1,3-dien-1-ylcyclohexane Chemical compound C1C=CC=C1C1CCCCC1 AQHXALDLCNTRII-UHFFFAOYSA-N 0.000 description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- TTXDTKOSGXSEGK-UHFFFAOYSA-N (1-cyclohexylcyclopenta-2,4-dien-1-yl)cyclohexane Chemical compound C1(CCCCC1)C1(C=CC=C1)C1CCCCC1 TTXDTKOSGXSEGK-UHFFFAOYSA-N 0.000 description 1
- AGWRAAIQXVWVLJ-UHFFFAOYSA-N 1,2,3,4,5-pentaethylcyclopenta-1,3-diene Chemical compound CCC1C(CC)=C(CC)C(CC)=C1CC AGWRAAIQXVWVLJ-UHFFFAOYSA-N 0.000 description 1
- AIPFLCWRUBQAEA-UHFFFAOYSA-N 1,2,3,4,5-pentaoctylcyclopenta-1,3-diene Chemical compound CCCCCCCCC1C(CCCCCCCC)=C(CCCCCCCC)C(CCCCCCCC)=C1CCCCCCCC AIPFLCWRUBQAEA-UHFFFAOYSA-N 0.000 description 1
- ZMNDIYBMNRKMFS-UHFFFAOYSA-N 1,2,3,4,5-pentapropylcyclopenta-1,3-diene Chemical compound CCCC1C(CCC)=C(CCC)C(CCC)=C1CCC ZMNDIYBMNRKMFS-UHFFFAOYSA-N 0.000 description 1
- XGELKYQHJDZVLR-UHFFFAOYSA-N 1,2,3,4-tetra(butan-2-yl)cyclopenta-1,3-diene Chemical compound CCC(C)C1=C(C(C)CC)C(C(C)CC)=C(C(C)CC)C1 XGELKYQHJDZVLR-UHFFFAOYSA-N 0.000 description 1
- MBRJEKTWCTVQKS-UHFFFAOYSA-N 1,2,3,4-tetraethylcyclopenta-1,3-diene Chemical compound CCC1=C(CC)C(CC)=C(CC)C1 MBRJEKTWCTVQKS-UHFFFAOYSA-N 0.000 description 1
- CDKZBGBETFWWPT-UHFFFAOYSA-N 1,2,3,4-tetraoctylcyclopenta-1,3-diene Chemical compound CCCCCCCCC1=C(CCCCCCCC)C(CCCCCCCC)=C(CCCCCCCC)C1 CDKZBGBETFWWPT-UHFFFAOYSA-N 0.000 description 1
- JKVMDWCVUHVDHY-UHFFFAOYSA-N 1,2,3,4-tetrapropylcyclopenta-1,3-diene Chemical compound CCCC1=C(CCC)C(CCC)=C(CCC)C1 JKVMDWCVUHVDHY-UHFFFAOYSA-N 0.000 description 1
- GQLKKRKODOLPST-UHFFFAOYSA-N 1,2,3-tri(pentan-2-yl)cyclopenta-1,3-diene Chemical compound CCCC(C)C1=C(C(C)CCC)C(C(C)CCC)=CC1 GQLKKRKODOLPST-UHFFFAOYSA-N 0.000 description 1
- GALAFVYMXSKXPQ-UHFFFAOYSA-N 1,2,3-tri(pentan-3-yl)cyclopenta-1,3-diene Chemical compound CCC(CC)C1=C(C(CC)CC)C(C(CC)CC)=CC1 GALAFVYMXSKXPQ-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- FTFYDDRPCCMKBT-UHFFFAOYSA-N 1-butylcyclopenta-1,3-diene Chemical compound CCCCC1=CC=CC1 FTFYDDRPCCMKBT-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- LGAJYTCRJPCZRJ-UHFFFAOYSA-N 2-bromopentane Chemical compound CCCC(C)Br LGAJYTCRJPCZRJ-UHFFFAOYSA-N 0.000 description 1
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 1
- VTOQFOCYBTVOJZ-UHFFFAOYSA-N 3-bromopentane Chemical compound CCC(Br)CC VTOQFOCYBTVOJZ-UHFFFAOYSA-N 0.000 description 1
- PGKZNDZDZDYMFJ-UHFFFAOYSA-N 5,5-di(butan-2-yl)cyclopenta-1,3-diene Chemical compound CC(CC)C1(C=CC=C1)C(C)CC PGKZNDZDZDYMFJ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BAEQXSKHFROEFS-UHFFFAOYSA-N C(CC)C1C(CCCC1)C1=CC=CC1 Chemical compound C(CC)C1C(CCCC1)C1=CC=CC1 BAEQXSKHFROEFS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- QSXVYHHWZVPHNW-UHFFFAOYSA-N [5,5-di(propan-2-yl)cyclopenta-1,3-dien-1-yl]cyclohexane Chemical compound CC(C)C1(C=CC=C1C1CCCCC1)C(C)C QSXVYHHWZVPHNW-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229940090047 auto-injector Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- JOZHCQBYRBGYAJ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 JOZHCQBYRBGYAJ-UHFFFAOYSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- YRPWLKVCRKAUAO-UHFFFAOYSA-N bismuthonium Chemical compound [BiH4+] YRPWLKVCRKAUAO-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical class NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- UCQHUEOREKHIBP-UHFFFAOYSA-N heptacyclo[9.6.1.14,7.113,16.02,10.03,8.012,17]icosa-5,14-diene Chemical compound C1C(C23)C4C(C=C5)CC5C4C1C3CC1C2C2C=CC1C2 UCQHUEOREKHIBP-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXLUTPDNMOEWGG-UHFFFAOYSA-N kryptand 222b Chemical compound C1COCCOCCN2CCOCCOCCN1CCOC1=CC=CC=C1OCC2 QXLUTPDNMOEWGG-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 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
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000913 palmityl 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])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
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-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
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1002998A NL1002998C2 (nl) | 1996-05-03 | 1996-05-03 | Werkwijze voor het substitueren van cyclopentadieen. |
| JP9142873A JPH1081636A (ja) | 1996-05-03 | 1997-04-25 | シクロペンタジエン置換のための方法 |
| ES97201280T ES2124102T3 (es) | 1996-05-03 | 1997-04-28 | Procedimiento de sustitucion de ciclopentadieno. |
| EP97201280A EP0805133B1 (de) | 1996-05-03 | 1997-04-28 | Verfahren zur Substitution von Cyclopentadien |
| AT97201280T ATE171928T1 (de) | 1996-05-03 | 1997-04-28 | Verfahren zur substitution von cyclopentadien |
| DE69700036T DE69700036T2 (de) | 1996-05-03 | 1997-04-28 | Verfahren zur Substitution von Cyclopentadien |
| CN97109765A CN1170706A (zh) | 1996-05-03 | 1997-04-30 | 环戊二烯取代的方法 |
| CA002204202A CA2204202A1 (en) | 1996-05-03 | 1997-05-01 | Process for cyclopentadiene substitution |
| US08/850,930 US6232516B1 (en) | 1996-05-03 | 1997-05-02 | Process for cyclopentadiene substitution |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1002998 | 1996-05-03 | ||
| NL1002998A NL1002998C2 (nl) | 1996-05-03 | 1996-05-03 | Werkwijze voor het substitueren van cyclopentadieen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1002998C2 true NL1002998C2 (nl) | 1997-11-06 |
Family
ID=19762769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1002998A NL1002998C2 (nl) | 1996-05-03 | 1996-05-03 | Werkwijze voor het substitueren van cyclopentadieen. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0805133B1 (de) |
| JP (1) | JPH1081636A (de) |
| CN (1) | CN1170706A (de) |
| AT (1) | ATE171928T1 (de) |
| CA (1) | CA2204202A1 (de) |
| DE (1) | DE69700036T2 (de) |
| ES (1) | ES2124102T3 (de) |
| NL (1) | NL1002998C2 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945444A (zh) * | 2014-03-26 | 2015-09-30 | 广东丹邦科技有限公司 | 用于制备钡金属茂合物的原料及钡金属茂合物的制备方法 |
| US11274069B2 (en) * | 2020-08-13 | 2022-03-15 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Mono-substituted cyclopentadienes and metal cyclopentadienyl complexes and synthesis methods thereof |
| CN119930380A (zh) * | 2023-11-06 | 2025-05-06 | 江苏南大光电材料股份有限公司 | 一种取代环戊二烯及其制备方法和应用 |
-
1996
- 1996-05-03 NL NL1002998A patent/NL1002998C2/nl not_active IP Right Cessation
-
1997
- 1997-04-25 JP JP9142873A patent/JPH1081636A/ja not_active Withdrawn
- 1997-04-28 AT AT97201280T patent/ATE171928T1/de not_active IP Right Cessation
- 1997-04-28 EP EP97201280A patent/EP0805133B1/de not_active Expired - Lifetime
- 1997-04-28 ES ES97201280T patent/ES2124102T3/es not_active Expired - Lifetime
- 1997-04-28 DE DE69700036T patent/DE69700036T2/de not_active Expired - Fee Related
- 1997-04-30 CN CN97109765A patent/CN1170706A/zh active Pending
- 1997-05-01 CA CA002204202A patent/CA2204202A1/en not_active Abandoned
Non-Patent Citations (3)
| Title |
|---|
| CLIFFORD G. VENIER ET AL.: "D-tert-butylcyclopentadiene and Tri-tert-butylcyclopentadiene", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 112, no. 7, 28 March 1990 (1990-03-28), DC US, pages 2808 - 2809, XP002021660 * |
| ECKEHARD V. DEHMLOW ET AL.: "Phase Transfer Catalyzed Tert-Alkylations of Cyclopentadiene and Indene: Indications for Set Processes", TETRAHEDRON LETTERS, vol. 32, no. 41, 7 October 1991 (1991-10-07), OXFORD GB, pages 5773 - 5776, XP002021661 * |
| R. ALLEN WILLIAMS ET AL.: "Encapsulated Alkaline-Earth Metallocenes. Synthesis, Solution, Behavior, and Solid-State Structures of Bis(tetraisopropylcyclopentadienyl)calcium and -barium, [(C3H7)4C5]2Ca and [(C3H7)4C5H]2Ba", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 113, no. 13, 19 June 1991 (1991-06-19), DC US, pages 4843 - 4851, XP002021659 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0805133B1 (de) | 1998-10-07 |
| CA2204202A1 (en) | 1997-11-03 |
| EP0805133A1 (de) | 1997-11-05 |
| JPH1081636A (ja) | 1998-03-31 |
| ES2124102T3 (es) | 1999-01-16 |
| ATE171928T1 (de) | 1998-10-15 |
| DE69700036T2 (de) | 1999-06-24 |
| CN1170706A (zh) | 1998-01-21 |
| DE69700036D1 (de) | 1998-11-12 |
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