TW466221B - The preparation of mixtures of monoolefinic C5 mononitriles by catalytic hydrocyanation in the presence of a catalyst comprising at least one metallocene-phosphorus (III)-nickel(0) complex - Google Patents
The preparation of mixtures of monoolefinic C5 mononitriles by catalytic hydrocyanation in the presence of a catalyst comprising at least one metallocene-phosphorus (III)-nickel(0) complex Download PDFInfo
- Publication number
- TW466221B TW466221B TW087112745A TW87112745A TW466221B TW 466221 B TW466221 B TW 466221B TW 087112745 A TW087112745 A TW 087112745A TW 87112745 A TW87112745 A TW 87112745A TW 466221 B TW466221 B TW 466221B
- Authority
- TW
- Taiwan
- Prior art keywords
- patent application
- item
- butadiene
- mixture
- scope
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000003054 catalyst Substances 0.000 title claims abstract description 57
- 238000005669 hydrocyanation reaction Methods 0.000 title claims abstract description 46
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 22
- 239000011574 phosphorus Substances 0.000 title claims abstract description 22
- 229910052759 nickel Inorganic materials 0.000 title claims abstract description 18
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 82
- 239000003446 ligand Substances 0.000 claims abstract description 51
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 39
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 18
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000006317 isomerization reaction Methods 0.000 claims description 14
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 238000011049 filling Methods 0.000 claims description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 12
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 11
- 150000004696 coordination complex Chemical group 0.000 claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- 150000005673 monoalkenes Chemical class 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 241000208125 Nicotiana Species 0.000 claims description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- ISBHMJZRKAFTGE-ONEGZZNKSA-N (e)-pent-2-enenitrile Chemical compound CC\C=C\C#N ISBHMJZRKAFTGE-ONEGZZNKSA-N 0.000 claims description 2
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 claims description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229960004448 pentamidine Drugs 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000002079 cooperative effect Effects 0.000 claims 4
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 150000001409 amidines Chemical class 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 150000001925 cycloalkenes Chemical class 0.000 claims 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
- 150000004714 phosphonium salts Chemical class 0.000 claims 2
- IHXNSHZBFXGOJM-HWKANZROSA-N (e)-2-methylbut-2-enenitrile Chemical compound C\C=C(/C)C#N IHXNSHZBFXGOJM-HWKANZROSA-N 0.000 claims 1
- IHXNSHZBFXGOJM-UHFFFAOYSA-N 2-methylbut-2-enenitrile Chemical compound CC=C(C)C#N IHXNSHZBFXGOJM-UHFFFAOYSA-N 0.000 claims 1
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 claims 1
- VOKXPKSMYJLAIW-UHFFFAOYSA-N nickel;phosphane Chemical compound P.[Ni] VOKXPKSMYJLAIW-UHFFFAOYSA-N 0.000 claims 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 235000015170 shellfish Nutrition 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- -1 3-pentadienyl isocyanate Chemical group 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
- 150000003624 transition metals Chemical class 0.000 description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 229910052723 transition metal Inorganic materials 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000007883 cyanide addition reaction Methods 0.000 description 4
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 125000006178 methyl benzyl group Chemical group 0.000 description 4
- 239000002574 poison Substances 0.000 description 4
- 231100000614 poison Toxicity 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 3
- 238000007333 cyanation reaction Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 238000007172 homogeneous catalysis Methods 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 2
- AUGKLUNRHYPDAM-UHFFFAOYSA-N 3-methylbut-2-enenitrile Chemical compound CC(C)=CC#N AUGKLUNRHYPDAM-UHFFFAOYSA-N 0.000 description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000000475 acetylene derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 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 2
- 238000011161 development Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002816 nickel compounds Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- KLKTYTBUBMARFC-UHFFFAOYSA-N 2-(9H-fluoren-1-yl)but-3-enenitrile Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)C(C#N)C=C KLKTYTBUBMARFC-UHFFFAOYSA-N 0.000 description 1
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 1
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 1
- MVLRILUUXLBENA-UHFFFAOYSA-N 4-methylheptan-3-one Chemical compound CCCC(C)C(=O)CC MVLRILUUXLBENA-UHFFFAOYSA-N 0.000 description 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical group CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- PHJJWPXKTFKKPD-UHFFFAOYSA-N [Ni+3].[O-]P([O-])[O-] Chemical compound [Ni+3].[O-]P([O-])[O-] PHJJWPXKTFKKPD-UHFFFAOYSA-N 0.000 description 1
- RXGWEOPUMUXXTN-UHFFFAOYSA-N [Ni].P(O)(O)O Chemical class [Ni].P(O)(O)O RXGWEOPUMUXXTN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VINGIKPSOPUKBC-UHFFFAOYSA-N argon cyanic acid Chemical compound N#CO.[Ar] VINGIKPSOPUKBC-UHFFFAOYSA-N 0.000 description 1
- AUUYKEQHADNQCO-UHFFFAOYSA-N argon cyanide Chemical compound [Ar].[C-]#N AUUYKEQHADNQCO-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([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
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- WDIIYWASEVHBBT-UHFFFAOYSA-N di(propan-2-yl)phosphane Chemical compound CC(C)PC(C)C WDIIYWASEVHBBT-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- HDULBKVLSJEMGN-UHFFFAOYSA-N dicyclohexylphosphane Chemical compound C1CCCCC1PC1CCCCC1 HDULBKVLSJEMGN-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000011982 enantioselective catalyst Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NLEUXPOVZGDKJI-UHFFFAOYSA-N nickel(2+);dicyanide Chemical compound [Ni+2].N#[C-].N#[C-] NLEUXPOVZGDKJI-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 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 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19733682A DE19733682A1 (de) | 1997-08-04 | 1997-08-04 | Verfahren zur Herstellung von Gemischen monoolefinischer C¶5¶-Mononitrile durch katalytische Hydrocyanierung in Gegenwart eines katalysators, umfassend wenigstens einen Metallocenphosphor(III)-Nickel(0)-Komplex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW466221B true TW466221B (en) | 2001-12-01 |
Family
ID=7837954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087112745A TW466221B (en) | 1997-08-04 | 1998-08-03 | The preparation of mixtures of monoolefinic C5 mononitriles by catalytic hydrocyanation in the presence of a catalyst comprising at least one metallocene-phosphorus (III)-nickel(0) complex |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6169198B1 (https=) |
| EP (1) | EP1003716B1 (https=) |
| JP (1) | JP2001513528A (https=) |
| KR (1) | KR20010022579A (https=) |
| CN (1) | CN1266424A (https=) |
| AR (1) | AR010428A1 (https=) |
| AU (1) | AU9257098A (https=) |
| BR (1) | BR9810978A (https=) |
| CA (1) | CA2298585A1 (https=) |
| DE (2) | DE19733682A1 (https=) |
| ES (1) | ES2216308T3 (https=) |
| ID (1) | ID24307A (https=) |
| MY (1) | MY126401A (https=) |
| RU (1) | RU2228329C2 (https=) |
| TR (1) | TR200000327T2 (https=) |
| TW (1) | TW466221B (https=) |
| WO (1) | WO1999007671A1 (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10033982A1 (de) * | 2000-07-13 | 2002-01-24 | Basf Ag | Verfahren zur Herstellung von Additionsprodukten ethylenisch ungesättigter Verbindungen |
| DE10136488A1 (de) * | 2001-07-27 | 2003-02-06 | Basf Ag | Ni(O) enthaltendes Katalysatorsystem |
| EP1344770A1 (en) * | 2002-03-12 | 2003-09-17 | E.I. du Pont de Nemours and Company | Process for the hydrocyanation of butadiene |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| DE102004004671A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von linearem Pentennitril |
| DE102004004673A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung von Butadien |
| WO2005073174A1 (de) * | 2004-01-29 | 2005-08-11 | Basf Aktiengesellschaft | Verfahren zur herstellung von linearem pentennitril |
| DE102004004696A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von linearen Pentennitrilen |
| DE102004004697A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Pentennitrilen aus n-Butan |
| DE102004004721A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Trennung von Pentennitril-Isomeren |
| DE102004004682A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Adipodinitril durch Hydrocyanierung von 1,3-Butadien |
| DE102004004718A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| DE102004004672A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| US8685118B2 (en) * | 2005-01-10 | 2014-04-01 | Elevance Renewable Sciences, Inc. | Candle and candle wax containing metathesis and metathesis-like products |
| ES2532982T3 (es) | 2005-10-18 | 2015-04-06 | Invista Technologies S.À.R.L. | Proceso de preparación de 3-aminopentanonitrilo |
| WO2007081987A2 (en) | 2006-01-10 | 2007-07-19 | Elevance Renewable Sciences, Inc. | Method of making hydrogenated metathesis products |
| 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 |
| WO2007103460A2 (en) * | 2006-03-07 | 2007-09-13 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
| WO2007109005A2 (en) | 2006-03-17 | 2007-09-27 | Invista Technologies S.A R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| EP2046719B1 (en) * | 2006-07-12 | 2013-09-04 | Elevance Renewable Sciences, Inc. | Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like |
| WO2008010961A2 (en) | 2006-07-13 | 2008-01-24 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
| US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7919646B2 (en) | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7880028B2 (en) | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| WO2008140468A2 (en) | 2006-10-13 | 2008-11-20 | Elevance Renewable Sciences, Inc. | METHODS OF MAKING α, ω -DICARBOXYLIC ACID ALKENE DERIVATIVES BY METATHESIS |
| WO2008048520A2 (en) * | 2006-10-13 | 2008-04-24 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
| WO2008046106A2 (en) | 2006-10-13 | 2008-04-17 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
| EP2146930A2 (en) | 2007-05-14 | 2010-01-27 | INVISTA Technologies S.à.r.l. | High efficiency reactor and process |
| WO2008157218A1 (en) | 2007-06-13 | 2008-12-24 | Invista Technologies S.A.R.L. | Process for improving adiponitrile quality |
| CN101918356B (zh) | 2008-01-15 | 2013-09-25 | 因温斯特技术公司 | 戊烯腈的氢氰化 |
| WO2009091771A2 (en) | 2008-01-15 | 2009-07-23 | Invista Technologies S.A R.L | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| US20090240068A1 (en) * | 2008-03-19 | 2009-09-24 | Invista North America S.A.R.L. | Methods of making cyclododecatriene and methods of making laurolactone |
| US8247621B2 (en) | 2008-10-14 | 2012-08-21 | Invista North America S.A.R.L. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
| FR2937321B1 (fr) * | 2008-10-21 | 2010-10-22 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
| CN102471218B (zh) | 2009-08-07 | 2014-11-05 | 因温斯特技术公司 | 用于形成二酯的氢化并酯化 |
| ES2542430T3 (es) | 2010-07-07 | 2015-08-05 | Invista Technologies S.À.R.L. | Proceso para hacer nitrilos |
| CN103080119B (zh) | 2010-09-07 | 2015-04-08 | 因温斯特技术公司 | 用于制备镍金属的镍组合物和镍配合物 |
| CN104619711B (zh) | 2012-06-01 | 2018-02-13 | 英威达纺织（英国）有限公司 | 水解催化剂及方法 |
| KR20150021545A (ko) | 2012-06-01 | 2015-03-02 | 인비스타 테크놀러지스 에스.에이 알.엘. | 안정한 리간드 혼합물 및 그의 제조 방법 |
| CN108997167B (zh) * | 2018-08-09 | 2021-05-07 | 大连微凯化学有限公司 | 一种利用丁二烯氢氰化制备己二腈和甲基戊二腈的方法 |
| CN116120207B (zh) * | 2021-11-15 | 2025-06-06 | 中国科学院上海有机化学研究所 | 一种手性单齿膦配体催化丁二烯制备己二腈的方法 |
| CN114105817B (zh) * | 2021-12-10 | 2022-10-28 | 北京道思克矿山装备技术有限公司 | 1,3-丁二烯氢氰化连续制备己二腈的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4714773A (en) * | 1987-01-09 | 1987-12-22 | E. I. Du Pont De Nemours And Company | Hydrocyanation of butadiene |
| BE1008343A3 (nl) | 1994-05-06 | 1996-04-02 | Dsm Nv | Bidentaat fosfineligand |
-
1997
- 1997-08-04 DE DE19733682A patent/DE19733682A1/de not_active Withdrawn
-
1998
- 1998-07-31 AR ARP980103803A patent/AR010428A1/es unknown
- 1998-08-03 TW TW087112745A patent/TW466221B/zh not_active IP Right Cessation
- 1998-08-04 EP EP98945143A patent/EP1003716B1/de not_active Expired - Lifetime
- 1998-08-04 ES ES98945143T patent/ES2216308T3/es not_active Expired - Lifetime
- 1998-08-04 CA CA002298585A patent/CA2298585A1/en not_active Abandoned
- 1998-08-04 CN CN98807985A patent/CN1266424A/zh active Pending
- 1998-08-04 DE DE59810804T patent/DE59810804D1/de not_active Expired - Fee Related
- 1998-08-04 ID IDW20000229A patent/ID24307A/id unknown
- 1998-08-04 AU AU92570/98A patent/AU9257098A/en not_active Abandoned
- 1998-08-04 MY MYPI98003554A patent/MY126401A/en unknown
- 1998-08-04 BR BR9810978-2A patent/BR9810978A/pt not_active IP Right Cessation
- 1998-08-04 US US09/463,820 patent/US6169198B1/en not_active Expired - Fee Related
- 1998-08-04 WO PCT/EP1998/004851 patent/WO1999007671A1/de not_active Ceased
- 1998-08-04 JP JP2000507207A patent/JP2001513528A/ja not_active Withdrawn
- 1998-08-04 RU RU2000106067/04A patent/RU2228329C2/ru not_active IP Right Cessation
- 1998-08-04 KR KR1020007001170A patent/KR20010022579A/ko not_active Ceased
- 1998-08-04 TR TR2000/00327T patent/TR200000327T2/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1266424A (zh) | 2000-09-13 |
| BR9810978A (pt) | 2000-08-08 |
| JP2001513528A (ja) | 2001-09-04 |
| RU2228329C2 (ru) | 2004-05-10 |
| WO1999007671A1 (de) | 1999-02-18 |
| DE59810804D1 (de) | 2004-03-25 |
| US6169198B1 (en) | 2001-01-02 |
| CA2298585A1 (en) | 1999-02-18 |
| TR200000327T2 (tr) | 2000-11-21 |
| ID24307A (id) | 2000-07-13 |
| ES2216308T3 (es) | 2004-10-16 |
| MY126401A (en) | 2006-09-29 |
| EP1003716A1 (de) | 2000-05-31 |
| EP1003716B1 (de) | 2004-02-18 |
| KR20010022579A (ko) | 2001-03-26 |
| DE19733682A1 (de) | 1999-02-11 |
| AU9257098A (en) | 1999-03-01 |
| AR010428A1 (es) | 2000-06-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW466221B (en) | The preparation of mixtures of monoolefinic C5 mononitriles by catalytic hydrocyanation in the presence of a catalyst comprising at least one metallocene-phosphorus (III)-nickel(0) complex | |
| TW519496B (en) | Catalyst comprising a complex of a metal of subgroup VIII based on a bidentate phosphonite ligand and preparation of nitriles. | |
| TW400249B (en) | A catalyst comprising at least one nickel (0)complex based on a phosphonite ligand, and the preparation of nitriles | |
| Bhawal et al. | Catalytic isofunctional reactions—expanding the repertoire of shuttle and metathesis reactions | |
| van Leeuwen et al. | Featuring xantphos | |
| TW570839B (en) | Ni(0)-containing catalyst system | |
| TW387874B (en) | Monoolefinic C5-mononitriles, having nonconjugated bonding preparation thereof and use thereof | |
| Beller et al. | Catalytic Markovnikov and anti‐Markovnikov functionalization of alkenes and alkynes: recent developments and trends | |
| Hartwig | Development of catalysts for the hydroamination of olefins | |
| TW453983B (en) | Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor | |
| TWI235144B (en) | Multidentate phosphite ligands, catalytic compositions containing such ligands and catalytic processes utilizing such catalytic compositions | |
| JP4479925B2 (ja) | 立体規制ホスフィニット・ホスフィットキレート配位子で安定化された少なくとも１個のニッケル（０）錯体を含む触媒、およびニトリルの製造 | |
| JP2001513528A5 (https=) | ||
| JP2006511591A (ja) | エチレン性不飽和化合物からのニトリル官能基含有化合物の合成方法 | |
| Salah et al. | Hydroamination and Alcoholysis of Acrylonitrile Promoted by the Pincer Complex {κ P, κ C, κ P-2, 6-(Ph2PO) 2C6H3} Ni (OSO2CF3) | |
| JP2004535929A5 (https=) | ||
| EP1090905B1 (en) | Use of ruthenium hydrogenation catalysts | |
| TW527340B (en) | Separation of pentene nitrile isomers | |
| EP1031379B1 (en) | Catalyst comprising rutheniumcomplex, and use thereof in hydrogenation of unsaturated substrates, especially organic nitriles | |
| MXPA04002139A (es) | Fosfonitos. | |
| BR0212966B1 (pt) | fosfonita, uso da mesma, complexo de metal de transição, processo para a preparação e uso do mesmo, e, processos para a adição de ácido cianìdrico a uma ligação dupla olefìnica na presença de um catalisador, e para a isomerização de nitrilas orgánicas na presença de um catalisador. | |
| JPH10513448A (ja) | ルテニウム水素化触媒 | |
| Tauchert et al. | Highly efficient nickel-catalyzed 2-methyl-3-butenenitrile isomerization: applications and mechanistic studies employing the TTP ligand family | |
| JP5378412B2 (ja) | ニトリル化合物の製造方法 | |
| CN104968433B (zh) | 改进的戊烯腈制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |