NO761797L - - Google Patents
Info
- Publication number
- NO761797L NO761797L NO761797A NO761797A NO761797L NO 761797 L NO761797 L NO 761797L NO 761797 A NO761797 A NO 761797A NO 761797 A NO761797 A NO 761797A NO 761797 L NO761797 L NO 761797L
- Authority
- NO
- Norway
- Prior art keywords
- phthalocyanine
- hydroformylation
- unsaturated compound
- catalyst
- liquid
- Prior art date
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 53
- 239000003054 catalyst Substances 0.000 claims description 45
- 238000007037 hydroformylation reaction Methods 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 33
- 239000002184 metal Substances 0.000 claims description 33
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 28
- -1 2-methyltridecanol-1 Chemical compound 0.000 claims description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052703 rhodium Inorganic materials 0.000 claims description 20
- 239000010948 rhodium Substances 0.000 claims description 20
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 229910017052 cobalt Inorganic materials 0.000 claims description 13
- 239000010941 cobalt Substances 0.000 claims description 13
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 13
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 13
- 229910052741 iridium Inorganic materials 0.000 claims description 13
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 229910052702 rhenium Inorganic materials 0.000 claims description 13
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 13
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims description 12
- 229910052762 osmium Inorganic materials 0.000 claims description 10
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 6
- RQZBCUNQDJDCGV-UHFFFAOYSA-N 2-butylheptanal Chemical compound CCCCCC(C=O)CCCC RQZBCUNQDJDCGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003610 charcoal Substances 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- WZHKDGJSXCTSCK-FNORWQNLSA-N (E)-Hept-3-ene Chemical compound CCC\C=C\CC WZHKDGJSXCTSCK-FNORWQNLSA-N 0.000 claims description 2
- LWWJDXKGQVEZKT-UHFFFAOYSA-N 3-ethylhexan-1-ol Chemical compound CCCC(CC)CCO LWWJDXKGQVEZKT-UHFFFAOYSA-N 0.000 claims description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
- SBAZXXVUILTVKK-UHFFFAOYSA-N 2-Ethyl-1-dodecanol Chemical compound CCCCCCCCCCC(CC)CO SBAZXXVUILTVKK-UHFFFAOYSA-N 0.000 claims 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- XJUCCGJZENLZSA-UHFFFAOYSA-M [Rh]Cl Chemical group [Rh]Cl XJUCCGJZENLZSA-UHFFFAOYSA-M 0.000 description 22
- 150000001299 aldehydes Chemical class 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000001030 gas--liquid chromatography Methods 0.000 description 7
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003517 fume Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- HSSMNYDDDSNUKH-UHFFFAOYSA-K trichlororhodium;hydrate Chemical compound O.Cl[Rh](Cl)Cl HSSMNYDDDSNUKH-UHFFFAOYSA-K 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- XJGIDGNLXAJIOA-UHFFFAOYSA-N 2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(36),2,4,6,8,10(40),11,13,15,17,19,21(38),22,24,26,28,30,32,34-nonadecaen-37-amine Chemical compound Nn1c2nc3nc(nc4[nH]c(nc5nc(nc1c1ccccc21)c1ccccc51)c1ccccc41)c1ccccc31 XJGIDGNLXAJIOA-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011609 ammonium molybdate Substances 0.000 description 2
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 2
- 229940010552 ammonium molybdate Drugs 0.000 description 2
- 235000018660 ammonium molybdate Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- FAQAIHMZMAIJCR-BUHFOSPRSA-N (7e)-tetradeca-1,7-diene Chemical compound CCCCCC\C=C\CCCCC=C FAQAIHMZMAIJCR-BUHFOSPRSA-N 0.000 description 1
- 239000001602 (E)-hex-3-enoic acid Substances 0.000 description 1
- KFXPOIKSDYRVKS-UHFFFAOYSA-N (Z)-4-Heptenoic acid Natural products CCC=CCCC(O)=O KFXPOIKSDYRVKS-UHFFFAOYSA-N 0.000 description 1
- NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 description 1
- XKZKQTCECFWKBN-VOTSOKGWSA-N (e)-dec-4-enoic acid Chemical compound CCCCC\C=C\CCC(O)=O XKZKQTCECFWKBN-VOTSOKGWSA-N 0.000 description 1
- IJBFSOLHRKELLR-BQYQJAHWSA-N (e)-dodec-5-enoic acid Chemical compound CCCCCC\C=C\CCCC(O)=O IJBFSOLHRKELLR-BQYQJAHWSA-N 0.000 description 1
- RVUCYJXFCAVHNC-VAWYXSNFSA-N (e)-octadec-7-enoic acid Chemical compound CCCCCCCCCC\C=C\CCCCCC(O)=O RVUCYJXFCAVHNC-VAWYXSNFSA-N 0.000 description 1
- MZDYAVCNKNXCIS-ONEGZZNKSA-N (e)-pent-2-enamide Chemical compound CC\C=C\C(N)=O MZDYAVCNKNXCIS-ONEGZZNKSA-N 0.000 description 1
- ZVXDGKJSUPWREP-BQYQJAHWSA-N (e)-tetradec-7-enoic acid Chemical compound CCCCCC\C=C\CCCCCC(O)=O ZVXDGKJSUPWREP-BQYQJAHWSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OMXANELYEWRDAW-UHFFFAOYSA-N 1-Hexacosene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC=C OMXANELYEWRDAW-UHFFFAOYSA-N 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 description 1
- IFVMAGPISVKRAR-UHFFFAOYSA-N 1-ethylcyclohexene Chemical compound CCC1=CCCCC1 IFVMAGPISVKRAR-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
- XNPPJWUCJFXDEP-UHFFFAOYSA-N 12-methoxyheptadec-4-ene Chemical compound CCCCCC(OC)CCCCCCC=CCCC XNPPJWUCJFXDEP-UHFFFAOYSA-N 0.000 description 1
- WPFKWXGBVGMREU-UHFFFAOYSA-N 2-(4-aminobutyl)octanal Chemical compound CCCCCCC(C=O)CCCCN WPFKWXGBVGMREU-UHFFFAOYSA-N 0.000 description 1
- ZKPFRIDJMMOODR-UHFFFAOYSA-N 2-Methyloctanal Chemical compound CCCCCCC(C)C=O ZKPFRIDJMMOODR-UHFFFAOYSA-N 0.000 description 1
- PPVGIYDGIOTKTB-UHFFFAOYSA-N 2-butylheptan-1-ol Chemical compound CCCCCC(CO)CCCC PPVGIYDGIOTKTB-UHFFFAOYSA-N 0.000 description 1
- LSYROLKFWITOGT-UHFFFAOYSA-N 2-ethoxyoct-1-ene Chemical compound CCCCCCC(=C)OCC LSYROLKFWITOGT-UHFFFAOYSA-N 0.000 description 1
- LURDBVVSMHYBQQ-UHFFFAOYSA-N 2-formylhexadecyl acetate Chemical compound CCCCCCCCCCCCCCC(C=O)COC(C)=O LURDBVVSMHYBQQ-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
- ZNTNHMNCCVITMC-UHFFFAOYSA-N 3-formylicosyl acetate Chemical compound CCCCCCCCCCCCCCCCCC(C=O)CCOC(C)=O ZNTNHMNCCVITMC-UHFFFAOYSA-N 0.000 description 1
- ZIKZSSQIWASYQT-UHFFFAOYSA-N 3-formylnonanoic acid Chemical compound CCCCCCC(C=O)CC(O)=O ZIKZSSQIWASYQT-UHFFFAOYSA-N 0.000 description 1
- PPSGQPFQMOEOKU-UHFFFAOYSA-N 3-methoxyhex-2-ene Chemical compound CCCC(OC)=CC PPSGQPFQMOEOKU-UHFFFAOYSA-N 0.000 description 1
- MUBFXOOYJPHVJT-UHFFFAOYSA-N 3-methoxynonanal Chemical compound CCCCCCC(OC)CC=O MUBFXOOYJPHVJT-UHFFFAOYSA-N 0.000 description 1
- XHFREDZYXIAWQS-UHFFFAOYSA-N 3-propoxytridec-3-ene Chemical compound CCCCCCCCCC=C(CC)OCCC XHFREDZYXIAWQS-UHFFFAOYSA-N 0.000 description 1
- NPFVOOAXDOBMCE-SNAWJCMRSA-N 3E-Hexenyl acetate Chemical compound CC\C=C\CCOC(C)=O NPFVOOAXDOBMCE-SNAWJCMRSA-N 0.000 description 1
- KFXPOIKSDYRVKS-ONEGZZNKSA-N 4-Heptenoic acid Chemical compound CC\C=C\CCC(O)=O KFXPOIKSDYRVKS-ONEGZZNKSA-N 0.000 description 1
- AMIMBVVTTZXHBC-UHFFFAOYSA-N 4-ethoxyheptadec-1-ene Chemical compound CCCCCCCCCCCCCC(CC=C)OCC AMIMBVVTTZXHBC-UHFFFAOYSA-N 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- ZDLBWMYNYNATIW-UHFFFAOYSA-N tetracos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCC=C ZDLBWMYNYNATIW-UHFFFAOYSA-N 0.000 description 1
- AHUCFTLAWXSFON-UHFFFAOYSA-N tetracos-10-enyl acetate Chemical compound CCCCCCCCCCCCCC=CCCCCCCCCCOC(C)=O AHUCFTLAWXSFON-UHFFFAOYSA-N 0.000 description 1
- KKTSESTYYCNZHO-UHFFFAOYSA-N tetracos-6-en-8-ol Chemical compound CCCCCCCCCCCCCCCCC(O)C=CCCCCC KKTSESTYYCNZHO-UHFFFAOYSA-N 0.000 description 1
- GYCFTCKCVMKQSY-UHFFFAOYSA-N tetracos-6-enamide Chemical compound CCCCCCCCCCCCCCCCCC=CCCCCC(N)=O GYCFTCKCVMKQSY-UHFFFAOYSA-N 0.000 description 1
- XFZHOMZPIDALKJ-UHFFFAOYSA-N tetracos-6-enoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CCCCCC(O)=O XFZHOMZPIDALKJ-UHFFFAOYSA-N 0.000 description 1
- PHOHWWHIGSNYQZ-UHFFFAOYSA-N tetracos-7-enenitrile Chemical compound CCCCCCCCCCCCCCCCC=CCCCCCC#N PHOHWWHIGSNYQZ-UHFFFAOYSA-N 0.000 description 1
- SBLGLBNKXWHUFO-UHFFFAOYSA-N tetradec-6-enyl acetate Chemical compound CCCCCCCC=CCCCCCOC(C)=O SBLGLBNKXWHUFO-UHFFFAOYSA-N 0.000 description 1
- KWANPMBTUOMANR-UHFFFAOYSA-N tetradec-7-enamide Chemical compound CCCCCCC=CCCCCCC(N)=O KWANPMBTUOMANR-UHFFFAOYSA-N 0.000 description 1
- XOOFGZMOXVWJBD-UHFFFAOYSA-N tetradec-7-enenitrile Chemical compound CCCCCCC=CCCCCCC#N XOOFGZMOXVWJBD-UHFFFAOYSA-N 0.000 description 1
- 229910003438 thallium oxide Inorganic materials 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- XKZKQTCECFWKBN-UHFFFAOYSA-N trans-4-decenoic acid Natural products CCCCCC=CCCC(O)=O XKZKQTCECFWKBN-UHFFFAOYSA-N 0.000 description 1
- IWPOSDLLFZKGOW-AATRIKPKSA-N trans-beta-octenoic acid Chemical compound CCCC\C=C\CC(O)=O IWPOSDLLFZKGOW-AATRIKPKSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- XXHDAWYDNSXJQM-ONEGZZNKSA-N trans-hex-3-enoic acid Chemical compound CC\C=C\CC(O)=O XXHDAWYDNSXJQM-ONEGZZNKSA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- DVFJLLYIPAZJGG-UHFFFAOYSA-N triaconta-3,5-diene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC=CC=CCC DVFJLLYIPAZJGG-UHFFFAOYSA-N 0.000 description 1
- SJDSOBWGZRPKSB-UHFFFAOYSA-N tricos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=C SJDSOBWGZRPKSB-UHFFFAOYSA-N 0.000 description 1
- UTJQPYZOOFAPKI-UHFFFAOYSA-N tricos-4-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCC=CCCC(O)=O UTJQPYZOOFAPKI-UHFFFAOYSA-N 0.000 description 1
- LUQBNMYIWSJINE-UHFFFAOYSA-N tridec-1-en-5-one Chemical compound CCCCCCCCC(=O)CCC=C LUQBNMYIWSJINE-UHFFFAOYSA-N 0.000 description 1
- MBIHQLXWBNNOBC-UHFFFAOYSA-N tridec-4-en-6-ol Chemical compound CCCCCCCC(O)C=CCCC MBIHQLXWBNNOBC-UHFFFAOYSA-N 0.000 description 1
- WABHOBUTCSSXRO-UHFFFAOYSA-N tridec-4-enamide Chemical compound CCCCCCCCC=CCCC(N)=O WABHOBUTCSSXRO-UHFFFAOYSA-N 0.000 description 1
- MPAJTYAEHHKMLA-UHFFFAOYSA-N tridec-5-enenitrile Chemical compound CCCCCCCC=CCCCC#N MPAJTYAEHHKMLA-UHFFFAOYSA-N 0.000 description 1
- FHABDPOJOOAJRJ-UHFFFAOYSA-N undec-3-en-4-ol Chemical compound CCCCCCCC(O)=CCC FHABDPOJOOAJRJ-UHFFFAOYSA-N 0.000 description 1
- JYKJHHNMJOZQHX-UHFFFAOYSA-N undec-4-en-1-amine Chemical compound CCCCCCC=CCCCN JYKJHHNMJOZQHX-UHFFFAOYSA-N 0.000 description 1
- GQRWQKNTCJFDNC-UHFFFAOYSA-N undec-4-enamide Chemical compound CCCCCCC=CCCC(N)=O GQRWQKNTCJFDNC-UHFFFAOYSA-N 0.000 description 1
- DGWXCKOENZVCHY-UHFFFAOYSA-N undec-5-enyl acetate Chemical compound CCCCCC=CCCCCOC(C)=O DGWXCKOENZVCHY-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/025—Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/825—Osmium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/580,648 US3984478A (en) | 1975-05-27 | 1975-05-27 | Hydroformylation process |
Publications (1)
Publication Number | Publication Date |
---|---|
NO761797L true NO761797L (fr) | 1976-11-30 |
Family
ID=24321937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO761797A NO761797L (fr) | 1975-05-27 | 1976-05-26 |
Country Status (22)
Country | Link |
---|---|
US (1) | US3984478A (fr) |
JP (1) | JPS51143603A (fr) |
AT (1) | AT344673B (fr) |
AU (1) | AU1429976A (fr) |
BE (1) | BE842282A (fr) |
BR (1) | BR7603371A (fr) |
DE (1) | DE2623867A1 (fr) |
EG (1) | EG12141A (fr) |
ES (1) | ES448240A1 (fr) |
FR (1) | FR2312481A1 (fr) |
GB (1) | GB1540114A (fr) |
GR (1) | GR60387B (fr) |
IL (1) | IL49642A0 (fr) |
IN (1) | IN144560B (fr) |
IT (1) | IT1063377B (fr) |
NL (1) | NL7605642A (fr) |
NO (1) | NO761797L (fr) |
PL (1) | PL97862B1 (fr) |
PT (1) | PT65136B (fr) |
SE (1) | SE7605931L (fr) |
TR (1) | TR18892A (fr) |
ZA (1) | ZA763059B (fr) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4183872A (en) * | 1978-02-13 | 1980-01-15 | Conoco, Inc. | Polymer bound (pentahaptocyclopentadienyl)biscarbonyl rhodium hydroformylation catalyst |
US4306084A (en) * | 1978-12-06 | 1981-12-15 | The University Of Texas | Alcohol and aldehyde production using ruthenium carbonyl catalysts |
US4226845A (en) * | 1978-12-06 | 1980-10-07 | S R I International | Water gas shift reaction and in the hydroformylation and hydrohydroxyformylation reactions |
US4219684A (en) * | 1979-04-02 | 1980-08-26 | Uop Inc. | Synthesis of alcohols by hydroformylation with nitrile promoter |
ZA814841B (en) * | 1980-07-23 | 1983-02-23 | British Petroleum Co | Process for the production of lower hydrocarbons and oxygenated derivatives thereof by the catalytic conversion of carbon monoxide and hydrogen |
US4374277A (en) * | 1981-02-12 | 1983-02-15 | International Flavors & Fragrances Inc. | Aliphatic C11 branched chain aldehydes and alcohols, process for preparing same and uses thereof in augmenting or enhancing the aroma of perfumes, colognes and/or perfumed articles |
US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
DE4316180A1 (de) * | 1992-09-16 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
DE4408950A1 (de) * | 1994-03-16 | 1995-09-21 | Basf Ag | Verfahren zur Herstellung von Alkoholen und/oder Aldehyden |
DE4427428A1 (de) * | 1994-08-03 | 1996-02-29 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
DE4440801A1 (de) * | 1994-11-17 | 1996-05-23 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
US5689010A (en) * | 1995-05-04 | 1997-11-18 | Basf Aktiengesellschaft | Preparation of higher aldehydes |
DE19817043A1 (de) | 1998-04-17 | 1999-10-21 | Henkel Kgaa | Verwendung von monocyclischen Aldehyden als Riechstoffe |
DE10155237A1 (de) * | 2001-11-09 | 2003-05-22 | Starck H C Gmbh | Verfahren zur Gewinnung von Rhenium |
CN106970030B (zh) * | 2017-02-21 | 2019-06-18 | 上海师范大学 | 一种酞菁-铱金属配合物在银离子检测中的应用 |
CN109395784B (zh) * | 2018-11-19 | 2021-09-21 | 中国科学院兰州化学物理研究所 | 一种酚醛树脂修饰载体担载的金属催化剂的制备及应用 |
-
1975
- 1975-05-27 US US05/580,648 patent/US3984478A/en not_active Expired - Lifetime
-
1976
- 1976-05-24 ZA ZA763059A patent/ZA763059B/xx unknown
- 1976-05-24 IL IL49642A patent/IL49642A0/xx unknown
- 1976-05-25 IN IN913/CAL/76A patent/IN144560B/en unknown
- 1976-05-25 SE SE7605931A patent/SE7605931L/xx unknown
- 1976-05-26 IT IT23686/76A patent/IT1063377B/it active
- 1976-05-26 NL NL7605642A patent/NL7605642A/xx not_active Application Discontinuation
- 1976-05-26 ES ES448240A patent/ES448240A1/es not_active Expired
- 1976-05-26 AU AU14299/76A patent/AU1429976A/en not_active Expired
- 1976-05-26 BE BE167387A patent/BE842282A/fr unknown
- 1976-05-26 FR FR7615958A patent/FR2312481A1/fr active Granted
- 1976-05-26 NO NO761797A patent/NO761797L/no unknown
- 1976-05-26 PT PT65136A patent/PT65136B/pt unknown
- 1976-05-26 GB GB21804/76A patent/GB1540114A/en not_active Expired
- 1976-05-27 PL PL1976189916A patent/PL97862B1/pl unknown
- 1976-05-27 JP JP51061721A patent/JPS51143603A/ja active Pending
- 1976-05-27 BR BR7603371A patent/BR7603371A/pt unknown
- 1976-05-27 GR GR50826A patent/GR60387B/el unknown
- 1976-05-28 DE DE19762623867 patent/DE2623867A1/de active Pending
- 1976-05-28 AT AT392976A patent/AT344673B/de not_active IP Right Cessation
- 1976-05-28 TR TR18892A patent/TR18892A/xx unknown
- 1976-05-29 EG EG319/76A patent/EG12141A/xx active
Also Published As
Publication number | Publication date |
---|---|
NL7605642A (nl) | 1976-11-30 |
SE7605931L (sv) | 1976-11-28 |
FR2312481A1 (fr) | 1976-12-24 |
JPS51143603A (en) | 1976-12-10 |
ATA392976A (de) | 1977-12-15 |
AT344673B (de) | 1978-08-10 |
PT65136A (en) | 1976-06-01 |
ES448240A1 (es) | 1977-07-01 |
ZA763059B (en) | 1977-04-27 |
US3984478A (en) | 1976-10-05 |
BE842282A (fr) | 1976-09-16 |
GB1540114A (en) | 1979-02-07 |
IT1063377B (it) | 1985-02-11 |
GR60387B (en) | 1978-05-24 |
AU1429976A (en) | 1977-12-01 |
PL97862B1 (pl) | 1978-03-30 |
TR18892A (tr) | 1977-11-10 |
DE2623867A1 (de) | 1976-12-02 |
IN144560B (fr) | 1978-05-13 |
FR2312481B1 (fr) | 1979-05-04 |
PT65136B (en) | 1977-10-12 |
IL49642A0 (en) | 1976-07-30 |
EG12141A (en) | 1978-06-30 |
BR7603371A (pt) | 1977-02-15 |
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