SE444311B - Forfarande for hydroformylering av en alfa-olefin med 2-20 kolatomer for framstellning av aldehyder - Google Patents
Forfarande for hydroformylering av en alfa-olefin med 2-20 kolatomer for framstellning av aldehyderInfo
- Publication number
- SE444311B SE444311B SE7800872A SE7800872A SE444311B SE 444311 B SE444311 B SE 444311B SE 7800872 A SE7800872 A SE 7800872A SE 7800872 A SE7800872 A SE 7800872A SE 444311 B SE444311 B SE 444311B
- Authority
- SE
- Sweden
- Prior art keywords
- carbon monoxide
- olefin
- catalyst
- alpha
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 72
- 150000001299 aldehydes Chemical class 0.000 title claims description 50
- 238000002360 preparation method Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 124
- 239000010948 rhodium Substances 0.000 claims description 92
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 86
- 229910052703 rhodium Inorganic materials 0.000 claims description 85
- 238000006243 chemical reaction Methods 0.000 claims description 81
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 69
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 69
- 239000007789 gas Substances 0.000 claims description 57
- 230000008569 process Effects 0.000 claims description 57
- 230000000694 effects Effects 0.000 claims description 49
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 239000004711 α-olefin Substances 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 27
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 22
- 239000007859 condensation product Substances 0.000 claims description 21
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- -1 hydrogen carbon monoxide Chemical class 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 44
- 150000001336 alkenes Chemical class 0.000 description 33
- 239000000047 product Substances 0.000 description 30
- 230000009849 deactivation Effects 0.000 description 28
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 27
- 239000006227 byproduct Substances 0.000 description 25
- 239000003446 ligand Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 16
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 15
- 239000012429 reaction media Substances 0.000 description 15
- 239000013638 trimer Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- 239000003053 toxin Substances 0.000 description 10
- 231100000765 toxin Toxicity 0.000 description 10
- 108700012359 toxins Proteins 0.000 description 10
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012808 vapor phase Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 238000011027 product recovery Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 4
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 230000002596 correlated effect Effects 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 238000010960 commercial process Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- WQVMDOAYQORMRB-UHFFFAOYSA-N 1,1'-biphenyl;phosphane Chemical compound P.C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 WQVMDOAYQORMRB-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- GOEGBJDTWXTPHP-UHFFFAOYSA-N 4-diphenylphosphanyl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GOEGBJDTWXTPHP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100536695 Gallus gallus TENP gene Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- FQSDTIQFGVAWNS-UHFFFAOYSA-N rhodium;(triphenyl-$l^{5}-phosphanylidene)methanone Chemical compound [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C=O)C1=CC=CC=C1 FQSDTIQFGVAWNS-UHFFFAOYSA-N 0.000 description 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76233677A | 1977-01-25 | 1977-01-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7800872L SE7800872L (sv) | 1978-09-15 |
| SE444311B true SE444311B (sv) | 1986-04-07 |
Family
ID=25064757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7800872A SE444311B (sv) | 1977-01-25 | 1978-01-24 | Forfarande for hydroformylering av en alfa-olefin med 2-20 kolatomer for framstellning av aldehyder |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5857413B2 (is") |
| AT (1) | AT368122B (is") |
| AU (1) | AU522597B2 (is") |
| BE (1) | BE863268R (is") |
| BR (1) | BR7800396A (is") |
| CA (1) | CA1105946A (is") |
| DE (1) | DE2802923C2 (is") |
| ES (3) | ES466292A1 (is") |
| FR (1) | FR2377992A2 (is") |
| GB (1) | GB1599922A (is") |
| IT (1) | IT1093322B (is") |
| MX (1) | MX148047A (is") |
| NL (1) | NL186444C (is") |
| SE (1) | SE444311B (is") |
| ZA (1) | ZA78147B (is") |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016285B2 (en) * | 1979-03-21 | 1986-03-05 | DAVY McKEE (LONDON) LIMITED | Process for the production of valeraldehydes by hydroformylation of butene-1 |
| EP0016286B1 (en) * | 1979-03-21 | 1983-04-06 | DAVY McKEE (LONDON) LIMITED | Hydroformylation process |
| FR2459683A1 (fr) | 1979-06-22 | 1981-01-16 | Ugine Kuhlmann | Procede de stabilisation et de regeneration du catalyseur d'hydroformylation du propene |
| JPS606630A (ja) * | 1983-06-24 | 1985-01-14 | Kuraray Co Ltd | アリルアルコ−ルの連続ヒドロホルミル化方法 |
| JPS60174723U (ja) * | 1984-04-27 | 1985-11-19 | 安本 重一 | タイトフレ−ム |
| KR950000635B1 (ko) * | 1988-07-14 | 1995-01-26 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 캄파니 인코포레이티드 | 비수성 하이드로포르밀화 반응 생성물 조성물로부터 알데히드 생성물을 분리회수하는 방법 |
| DE102005046250B4 (de) * | 2005-09-27 | 2020-10-08 | Evonik Operations Gmbh | Anlage zur Abtrennung von organischen Übergangsmetallkomplexkatalysatoren |
| JP2013181004A (ja) * | 2012-03-02 | 2013-09-12 | Jnc Corp | オキソ反応触媒寿命改良法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3487112A (en) * | 1967-04-27 | 1969-12-30 | Monsanto Co | Vapor phase hydroformylation process |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US3555098A (en) * | 1967-12-13 | 1971-01-12 | Union Oil Co | Hydroformylation |
| CA918673A (en) * | 1969-12-22 | 1973-01-09 | L. Pruett Roy | Hydroformylation process |
| JPS50123611A (is") * | 1974-03-12 | 1975-09-29 | ||
| JPS511687A (en) * | 1974-06-27 | 1976-01-08 | Sadao Ukita | Tenpura hanbaagunadono nenseizairyono katakeiseinisaishiteno atsumichoseisochi |
| JPS516124A (en) * | 1974-07-05 | 1976-01-19 | Hitachi Chemical Co Ltd | Kikinzoku oyobi ryusandono kaishuhoho |
-
1978
- 1978-01-10 ZA ZA00780147A patent/ZA78147B/xx unknown
- 1978-01-19 CA CA295,310A patent/CA1105946A/en not_active Expired
- 1978-01-23 AU AU32629/78A patent/AU522597B2/en not_active Expired
- 1978-01-24 ES ES466292A patent/ES466292A1/es not_active Expired
- 1978-01-24 IT IT19576/78A patent/IT1093322B/it active
- 1978-01-24 SE SE7800872A patent/SE444311B/sv not_active IP Right Cessation
- 1978-01-24 AT AT0049178A patent/AT368122B/de not_active IP Right Cessation
- 1978-01-24 MX MX172157A patent/MX148047A/es unknown
- 1978-01-24 BE BE184600A patent/BE863268R/xx active
- 1978-01-24 JP JP53005880A patent/JPS5857413B2/ja not_active Expired
- 1978-01-24 GB GB2907/78A patent/GB1599922A/en not_active Expired
- 1978-01-24 FR FR7801867A patent/FR2377992A2/fr active Granted
- 1978-01-24 NL NLAANVRAGE7800856,A patent/NL186444C/xx not_active IP Right Cessation
- 1978-01-24 BR BR7800396A patent/BR7800396A/pt unknown
- 1978-01-24 DE DE2802923A patent/DE2802923C2/de not_active Expired
- 1978-10-31 ES ES474699A patent/ES474699A1/es not_active Expired
- 1978-10-31 ES ES474698A patent/ES474698A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT368122B (de) | 1982-09-10 |
| MX148047A (es) | 1983-03-09 |
| ATA49178A (de) | 1982-01-15 |
| CA1105946A (en) | 1981-07-28 |
| JPS5857413B2 (ja) | 1983-12-20 |
| ES474698A1 (es) | 1979-04-01 |
| NL7800856A (nl) | 1978-07-27 |
| ZA78147B (en) | 1978-11-29 |
| DE2802923C2 (de) | 1986-03-13 |
| FR2377992B2 (is") | 1984-02-03 |
| DE2802923A1 (de) | 1978-07-27 |
| AU522597B2 (en) | 1982-06-17 |
| NL186444B (nl) | 1990-07-02 |
| BE863268R (fr) | 1978-07-24 |
| IT7819576A0 (it) | 1978-01-24 |
| NL186444C (nl) | 1990-12-03 |
| JPS5392706A (en) | 1978-08-15 |
| IT1093322B (it) | 1985-07-19 |
| SE7800872L (sv) | 1978-09-15 |
| FR2377992A2 (fr) | 1978-08-18 |
| BR7800396A (pt) | 1978-08-22 |
| ES474699A1 (es) | 1979-04-01 |
| AU3262978A (en) | 1979-08-02 |
| GB1599922A (en) | 1981-10-07 |
| ES466292A1 (es) | 1979-01-16 |
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