NL8020079A - Werkwijze ter bereiding van aldehyden. - Google Patents
Werkwijze ter bereiding van aldehyden. Download PDFInfo
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- NL8020079A NL8020079A NL8020079A NL8020079A NL8020079A NL 8020079 A NL8020079 A NL 8020079A NL 8020079 A NL8020079 A NL 8020079A NL 8020079 A NL8020079 A NL 8020079A NL 8020079 A NL8020079 A NL 8020079A
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- Prior art keywords
- rhodium
- reaction
- process according
- complex
- containing catalyst
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- 150000001299 aldehydes Chemical class 0.000 title claims description 77
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 122
- 239000003054 catalyst Substances 0.000 claims abstract description 101
- 239000010948 rhodium Substances 0.000 claims abstract description 97
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 85
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 81
- 230000008569 process Effects 0.000 claims abstract description 51
- 239000003446 ligand Substances 0.000 claims abstract description 41
- 239000011541 reaction mixture Substances 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 28
- 239000002585 base Substances 0.000 claims description 24
- 239000004711 α-olefin Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 238000001704 evaporation Methods 0.000 claims description 17
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 16
- 230000008020 evaporation Effects 0.000 claims description 15
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- FEFNFOUJRMDJFO-UHFFFAOYSA-N 2-propylheptanal Chemical compound CCCCCC(C=O)CCC FEFNFOUJRMDJFO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002879 Lewis base Substances 0.000 claims description 8
- 150000007527 lewis bases Chemical class 0.000 claims description 8
- PYLMCYQHBRSDND-UHFFFAOYSA-N 2-ethyl-2-hexenal Chemical compound CCCC=C(CC)C=O PYLMCYQHBRSDND-UHFFFAOYSA-N 0.000 claims description 6
- GADNZGQWPNTMCH-UHFFFAOYSA-N 2-propylhept-2-enal Chemical compound CCCCC=C(C=O)CCC GADNZGQWPNTMCH-UHFFFAOYSA-N 0.000 claims description 6
- 235000019256 formaldehyde Nutrition 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007037 hydroformylation reaction Methods 0.000 abstract description 24
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 21
- 239000001257 hydrogen Substances 0.000 abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract description 17
- 229910052799 carbon Inorganic materials 0.000 abstract description 7
- 230000036961 partial effect Effects 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 65
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 48
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 40
- 239000007789 gas Substances 0.000 description 32
- 150000001336 alkenes Chemical class 0.000 description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 15
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 14
- 229910017052 cobalt Inorganic materials 0.000 description 14
- 239000010941 cobalt Substances 0.000 description 14
- 238000005882 aldol condensation reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 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 12
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 12
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 11
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 10
- 239000000539 dimer Substances 0.000 description 10
- 230000002779 inactivation Effects 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- -1 for example Chemical group 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- NQQJIBHSTRRTIU-UHFFFAOYSA-N diphenyl(2-trimethylsilylethyl)phosphane Chemical compound C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1 NQQJIBHSTRRTIU-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- DTCCTIQRPGSLPT-UHFFFAOYSA-N 2-pentenal Chemical compound CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 description 2
- RKYGQIPMFUIIHZ-UHFFFAOYSA-N 3-methyl-2-propylhex-2-enal Chemical compound CCCC(C)=C(C=O)CCC RKYGQIPMFUIIHZ-UHFFFAOYSA-N 0.000 description 2
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
- 239000004435 Oxo alcohol Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- RPYUWYHQEDMHLE-UHFFFAOYSA-N diphenyl(2-trimethylsilylethyl)phosphane formaldehyde rhodium Chemical compound [Rh].O=C.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1.C=1C=CC=CC=1P(CC[Si](C)(C)C)C1=CC=CC=C1 RPYUWYHQEDMHLE-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- BAUHZKXBGXCLBO-UHFFFAOYSA-N 2-propylpentanal Chemical compound CCCC(C=O)CCC BAUHZKXBGXCLBO-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 description 1
- 101100244625 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-1 gene Proteins 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
- DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 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
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 101150089353 cdaS gene Proteins 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- RMLOZYVMENRVSS-UHFFFAOYSA-N formaldehyde;rhodium Chemical compound [Rh].O=C RMLOZYVMENRVSS-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002903 organophosphorus compounds Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
-
- 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
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
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- 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
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- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5004—Acyclic saturated phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5013—Acyclic unsaturated phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
- C07F9/5414—Acyclic saturated phosphonium compounds substituted by B, Si, P or a metal
- C07F9/5421—Acyclic saturated phosphonium compounds substituted by B, Si, P or a metal substituted by a phosphorus atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- 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
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- 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)
- Catalysts (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/011,238 US4298541A (en) | 1979-02-12 | 1979-02-12 | Trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes and their use as homogeneous catalysts |
| US1123879 | 1979-02-12 | ||
| US4354879A | 1979-05-29 | 1979-05-29 | |
| US4354879 | 1979-05-29 | ||
| US11462780 | 1980-01-23 | ||
| US06/114,627 US4302401A (en) | 1980-01-23 | 1980-01-23 | Tetraalkyl phosphonium substituted phosphine and amine transition metal complexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8020079A true NL8020079A (nl) | 1980-12-31 |
Family
ID=27359388
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8020079A NL8020079A (nl) | 1979-02-12 | 1980-02-12 | Werkwijze ter bereiding van aldehyden. |
| NL8020087A NL8020087A (nl) | 1979-02-12 | 1980-02-12 | Carbonyleringswerkwijze en nieuwe overgangs- metaalkatalysatoren. |
| NL8020086A NL8020086A (nl) | 1979-02-12 | 1980-02-12 | Fosfine- en fosforniumverbindingen en katalysator. |
| NL8020088A NL8020088A (nl) | 1979-02-12 | 1980-02-12 | Tetraaelkylfosfonium-gesubstitueerde overgangsmetaal- complexen. |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8020087A NL8020087A (nl) | 1979-02-12 | 1980-02-12 | Carbonyleringswerkwijze en nieuwe overgangs- metaalkatalysatoren. |
| NL8020086A NL8020086A (nl) | 1979-02-12 | 1980-02-12 | Fosfine- en fosforniumverbindingen en katalysator. |
| NL8020088A NL8020088A (nl) | 1979-02-12 | 1980-02-12 | Tetraaelkylfosfonium-gesubstitueerde overgangsmetaal- complexen. |
Country Status (8)
| Country | Link |
|---|---|
| EP (6) | EP0159460A1 (enExample) |
| JP (3) | JPS56500167A (enExample) |
| BR (3) | BR8006680A (enExample) |
| DE (4) | DE3034353A1 (enExample) |
| GB (3) | GB2057906B (enExample) |
| NL (4) | NL8020079A (enExample) |
| SE (6) | SE439439B (enExample) |
| WO (4) | WO1980001691A1 (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450299A (en) * | 1980-10-01 | 1984-05-22 | Exxon Research And Engineering Co. | Homogeneous hydroformylation catalysis with silyl substituted alkyl diaryl phosphine metal complexes |
| US4440634A (en) * | 1981-08-03 | 1984-04-03 | Exxon Research And Engineering Co. | Organic salt compositions in extraction processes |
| US4522933A (en) * | 1981-08-17 | 1985-06-11 | Union Carbide Corporation | Hydroformylation catalyst containing bisphosphine monooxide ligands |
| US4491675A (en) * | 1981-08-17 | 1985-01-01 | Union Carbide Corporation | Hydroformylation process using triarylphosphine and bisphosphine monooxide ligands |
| US4400548A (en) * | 1981-08-17 | 1983-08-23 | Union Carbide Corporation | Hydroformylation process using bisphosphine monooxide ligands |
| US4429161A (en) * | 1981-08-17 | 1984-01-31 | Union Carbide Corporation | Process for preparing organic tertiary polyphosphine monooxides |
| US4593011A (en) * | 1981-08-17 | 1986-06-03 | Union Carbide Corporation | Hydroformylation process using triarylphosphine and bisphosphine monooxide ligands |
| DE3264581D1 (en) * | 1981-10-28 | 1985-08-08 | Monsanto Co | Synthesis of isoprene from linear butenes |
| DE3365327D1 (en) * | 1982-10-21 | 1986-09-18 | Texaco Development Corp | Method for the preparation of alcohols and aldehydes by reacting olefins with carbon monoxide and hydrogen |
| US5110990A (en) * | 1984-03-30 | 1992-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Process for recovery of phosphorus ligand from vaporized aldehyde |
| US4608444A (en) * | 1984-04-05 | 1986-08-26 | The Halcon Sd Group, Inc. | Process and accompanying catalysts for the hydroformylation of formaldehyde to glycol-aldehyde |
| US4927967A (en) * | 1984-07-20 | 1990-05-22 | Union Carbide Chemicals And Plastics Company Inc. | Production of carboxylic acids from organic formate esters using rhodium complex catalysts |
| CA1237728A (en) * | 1984-07-20 | 1988-06-07 | Anthony G. Abatjoglou | Production of carboxylic acids from alcohols using rhodium complex catalysts |
| CA1248549A (en) * | 1984-08-16 | 1989-01-10 | Richard W. Wegman | Production of anhydrous carboxylic acids from alcohols using rhodium complex catalysts and organic ester source |
| US4593127A (en) * | 1985-01-11 | 1986-06-03 | Union Carbide Corporation | Hydroformylation process |
| US4633021A (en) * | 1985-11-29 | 1986-12-30 | National Distillers And Chemical Corporation | Olefin hydroformylation |
| DE3546123A1 (de) * | 1985-12-24 | 1987-06-25 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| GB8614910D0 (en) * | 1986-06-19 | 1986-07-23 | British Petroleum Co Plc | Preparation of ketones |
| EP0320546A1 (en) * | 1987-12-15 | 1989-06-21 | Council of Scientific and Industrial Research | Hydrogenation catalyst |
| US4948870A (en) * | 1988-05-27 | 1990-08-14 | Shell Oil Company | Polymerization process |
| US5001274A (en) * | 1989-06-23 | 1991-03-19 | Union Carbide Chemicals And Plastics Company Inc. | Hydroformylation process |
| JPH0520984U (ja) * | 1991-03-04 | 1993-03-19 | 日本フルハーフ株式会社 | 貨物自動車における煽 |
| IT1256601B (it) * | 1992-10-16 | 1995-12-12 | Eniricerche Spa | Composizioni supportate a base di tungsteno o molibdeno,procedimento per il loro ottenimento e proprieta' come catalizzatori eterogenei di ossidazione |
| DE4242723A1 (de) * | 1992-12-17 | 1994-06-23 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden |
| DE4431528A1 (de) * | 1994-09-03 | 1996-03-07 | Basf Ag | Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol |
| US5689010A (en) * | 1995-05-04 | 1997-11-18 | Basf Aktiengesellschaft | Preparation of higher aldehydes |
| FR2743010B1 (fr) * | 1995-12-29 | 1998-02-20 | Rhone Poulenc Fibres | Procede de preparation par hydrogenation de catalyseurs a base de metal de transition et de phosphine |
| US7173138B2 (en) * | 2001-03-29 | 2007-02-06 | Basf Aktiengesellschaft | Ligands for pnicogen chelate complexes with a metal of subgroup VIII and use of the complexes as catalysts for hydroformylation, carbonylation, hydrocyanation or hydrogenation |
| WO2003018192A2 (de) * | 2001-08-24 | 2003-03-06 | Basf Aktiengesellschaft | Verfahren zur herstellung von 2-propylheptanol sowie dafür geeignete hydroformylierungskatalysatoren und deren weitere verwendung zur carbonylierung, hydrocyanierung und hydrierung |
| DE10313319A1 (de) | 2003-03-25 | 2004-10-07 | Basf Ag | Verfahren zur Hydroformylierung |
| DE10355066A1 (de) | 2003-11-25 | 2005-06-23 | Basf Ag | Verfahren zur asymmetrischen Synthese |
| KR101141634B1 (ko) * | 2004-07-20 | 2012-05-04 | 엘지전자 주식회사 | 세탁장치 |
| US7294745B2 (en) | 2004-12-30 | 2007-11-13 | Council Of Scientific And Industrial Research | Process for preparing aldol derivatives from alkenes using catalyst |
| CN101094826B (zh) * | 2004-12-31 | 2011-02-09 | 科学与工业研究委员会 | 使用催化剂从烯烃制备羟醛衍生物的方法 |
| FR2894251B1 (fr) * | 2005-12-05 | 2008-01-04 | Air Liquide | Procede de synthese de methanol permettant un recyclage du gaz residuaire |
| US9224416B2 (en) | 2012-04-24 | 2015-12-29 | Seagate Technology Llc | Near field transducers including nitride materials |
| US8427925B2 (en) | 2010-02-23 | 2013-04-23 | Seagate Technology Llc | HAMR NFT materials with improved thermal stability |
| US9251837B2 (en) | 2012-04-25 | 2016-02-02 | Seagate Technology Llc | HAMR NFT materials with improved thermal stability |
| DE102011081074A1 (de) * | 2011-08-17 | 2013-02-21 | Areva Np Gmbh | Verfahren zur Herstellung eines Uranoxid als aktive Komponente enthaltenden Katalysators |
| JP5890535B2 (ja) | 2011-12-20 | 2016-03-22 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 改良されたヒドロホルミル化プロセス |
| US9245573B2 (en) | 2013-06-24 | 2016-01-26 | Seagate Technology Llc | Methods of forming materials for at least a portion of a NFT and NFTs formed using the same |
| JP6038843B2 (ja) | 2013-06-24 | 2016-12-07 | シーゲイト テクノロジー エルエルシーSeagate Technology LLC | 少なくとも1つの相互混合層を含む装置 |
| US9058824B2 (en) | 2013-06-24 | 2015-06-16 | Seagate Technology Llc | Devices including a gas barrier layer |
| US20140376351A1 (en) | 2013-06-24 | 2014-12-25 | Seagate Technology Llc | Materials for near field transducers and near field transducers containing same |
| US9570098B2 (en) | 2013-12-06 | 2017-02-14 | Seagate Technology Llc | Methods of forming near field transducers and near field transducers formed thereby |
| US9697856B2 (en) | 2013-12-06 | 2017-07-04 | Seagate Techology LLC | Methods of forming near field transducers and near field transducers formed thereby |
| CN106103399B (zh) | 2013-12-19 | 2019-07-09 | 陶氏技术投资有限责任公司 | 氢甲酰化方法 |
| DE102014201122A1 (de) * | 2014-01-22 | 2015-07-23 | Leibniz-Institut Für Katalyse E.V. An Der Universität Rostock (Likat) | Verfahren zur katalytischen Herstellung von ungesättigten Aldehyden |
| US9552833B2 (en) | 2014-11-11 | 2017-01-24 | Seagate Technology Llc | Devices including a multilayer gas barrier layer |
| US9822444B2 (en) | 2014-11-11 | 2017-11-21 | Seagate Technology Llc | Near-field transducer having secondary atom higher concentration at bottom of the peg |
| US9620150B2 (en) | 2014-11-11 | 2017-04-11 | Seagate Technology Llc | Devices including an amorphous gas barrier layer |
| US10510364B2 (en) | 2014-11-12 | 2019-12-17 | Seagate Technology Llc | Devices including a near field transducer (NFT) with nanoparticles |
| TWI788364B (zh) | 2017-06-23 | 2023-01-01 | 美商陶氏科技投資有限公司 | 氫甲醯化反應製程 |
| CN110975941B (zh) * | 2019-12-17 | 2022-08-05 | 万华化学集团股份有限公司 | 一种氢甲酰化反应催化剂组合物及丙烯氢甲酰化反应制备醛的方法 |
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| JP2024500349A (ja) | 2020-12-22 | 2024-01-09 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化反応方法 |
| US11980875B2 (en) | 2022-08-23 | 2024-05-14 | King Fahd University Of Petroleum And Minerals | Method for making magnetic nanoparticle supported catalysts |
| GB202307175D0 (en) | 2023-05-15 | 2023-06-28 | Johnson Matthey Davy Technologies Ltd | Process for hydrogenating a substrate |
| GB202404300D0 (en) | 2024-03-26 | 2024-05-08 | Johnson Matthey Davy Technologies Ltd | Process for the production of 2-alkylalkanol |
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-
1980
- 1980-02-12 DE DE803034353T patent/DE3034353A1/de not_active Withdrawn
- 1980-02-12 WO PCT/US1980/000216 patent/WO1980001691A1/en not_active Ceased
- 1980-02-12 BR BR8006680A patent/BR8006680A/pt unknown
- 1980-02-12 JP JP50065180A patent/JPS56500167A/ja active Pending
- 1980-02-12 EP EP85100028A patent/EP0159460A1/en not_active Withdrawn
- 1980-02-12 JP JP50065080A patent/JPS55501178A/ja active Pending
- 1980-02-12 GB GB8031135A patent/GB2057906B/en not_active Expired
- 1980-02-12 BR BR8006679A patent/BR8006679A/pt unknown
- 1980-02-12 GB GB8031137A patent/GB2056989B/en not_active Expired
- 1980-02-12 NL NL8020079A patent/NL8020079A/nl not_active Application Discontinuation
- 1980-02-12 NL NL8020087A patent/NL8020087A/nl not_active Application Discontinuation
- 1980-02-12 BR BR8006681A patent/BR8006681A/pt unknown
- 1980-02-12 DE DE803034351T patent/DE3034351A1/de not_active Ceased
- 1980-02-12 GB GB8031136A patent/GB2086906B/en not_active Expired
- 1980-02-12 WO PCT/US1980/000215 patent/WO1980001692A1/en not_active Ceased
- 1980-02-12 DE DE803034354T patent/DE3034354A1/de not_active Ceased
- 1980-02-12 NL NL8020086A patent/NL8020086A/nl not_active Application Discontinuation
- 1980-02-12 WO PCT/US1980/000213 patent/WO1980001690A1/en not_active Ceased
- 1980-02-12 WO PCT/US1980/000212 patent/WO1980001689A1/en not_active Ceased
- 1980-02-12 JP JP55500652A patent/JPS6332079B2/ja not_active Expired
- 1980-02-12 NL NL8020088A patent/NL8020088A/nl not_active Application Discontinuation
- 1980-02-12 DE DE803034352T patent/DE3034352A1/de not_active Withdrawn
- 1980-02-12 EP EP82107978A patent/EP0071281B1/en not_active Expired
- 1980-08-25 EP EP80900541A patent/EP0023924B1/en not_active Expired
- 1980-08-25 EP EP80900539A patent/EP0023923B1/en not_active Expired
- 1980-08-25 EP EP80900540A patent/EP0024091B1/en not_active Expired
- 1980-08-25 EP EP80900484A patent/EP0024088A1/en not_active Withdrawn
- 1980-10-09 SE SE8007080A patent/SE439439B/sv not_active IP Right Cessation
- 1980-10-09 SE SE8007079A patent/SE8007079L/xx not_active Application Discontinuation
- 1980-10-10 SE SE8007140A patent/SE449093B/sv not_active IP Right Cessation
- 1980-10-10 SE SE8007139A patent/SE449750B/sv not_active IP Right Cessation
-
1982
- 1982-01-22 SE SE8200371A patent/SE8200371L/xx not_active Application Discontinuation
- 1982-07-23 SE SE8204443A patent/SE8204443L/xx not_active Application Discontinuation
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| Date | Code | Title | Description |
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| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BV | The patent application has lapsed |