RU2002728C1 - Способ получени @ -альдегидов - Google Patents
Способ получени @ -альдегидовInfo
- Publication number
- RU2002728C1 RU2002728C1 SU874203758A SU4203758A RU2002728C1 RU 2002728 C1 RU2002728 C1 RU 2002728C1 SU 874203758 A SU874203758 A SU 874203758A SU 4203758 A SU4203758 A SU 4203758A RU 2002728 C1 RU2002728 C1 RU 2002728C1
- Authority
- RU
- Russia
- Prior art keywords
- mixture
- rhodium
- ligand
- polyethylene
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 150000001299 aldehydes Chemical class 0.000 title description 34
- 239000003446 ligand Substances 0.000 claims abstract description 69
- 239000010948 rhodium Substances 0.000 claims abstract description 67
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 66
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 40
- 239000002904 solvent Substances 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 8
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004698 Polyethylene Substances 0.000 claims abstract description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 239000011574 phosphorus Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 3
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- ZEDPQIJYJCPIRM-UHFFFAOYSA-N dimethyl benzonitrile Natural products CC1=CC=CC(C#N)=C1C ZEDPQIJYJCPIRM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002314 glycerols Chemical class 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 51
- 150000001336 alkenes Chemical class 0.000 abstract description 11
- -1 alkaline earth metal cation Chemical class 0.000 abstract description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 8
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract description 7
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract description 3
- 229920000573 polyethylene Polymers 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 125000000746 allylic group Chemical group 0.000 abstract 1
- 239000006260 foam Substances 0.000 abstract 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 45
- 239000000047 product Substances 0.000 description 24
- 239000007788 liquid Substances 0.000 description 22
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 21
- 239000007789 gas Substances 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 18
- 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 17
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 16
- 239000012018 catalyst precursor Substances 0.000 description 14
- 239000002243 precursor Substances 0.000 description 12
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 238000002360 preparation method Methods 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 4
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ISZREKMLQKLUDD-UHFFFAOYSA-N 2-methyldodecanal Chemical compound CCCCCCCCCCC(C)C=O ISZREKMLQKLUDD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical class C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 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
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- ZKPFRIDJMMOODR-UHFFFAOYSA-N 2-Methyloctanal Chemical compound CCCCCCC(C)C=O ZKPFRIDJMMOODR-UHFFFAOYSA-N 0.000 description 1
- ITPOKAFWZBFZCV-UHFFFAOYSA-N 3-diphenylphosphanylbenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 ITPOKAFWZBFZCV-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102100035593 POU domain, class 2, transcription factor 1 Human genes 0.000 description 1
- 101710084414 POU domain, class 2, transcription factor 1 Proteins 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- RVKBVKYHZDEUCT-UHFFFAOYSA-N [Ca].[Rh] Chemical compound [Ca].[Rh] RVKBVKYHZDEUCT-UHFFFAOYSA-N 0.000 description 1
- TWWSMHPNERSWRN-UHFFFAOYSA-N acetaldehyde diisopropyl acetal Natural products CC(C)OC(C)OC(C)C TWWSMHPNERSWRN-UHFFFAOYSA-N 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- GPMUMMNTAZMBEC-UHFFFAOYSA-N bis(oxomethylidene)rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-] GPMUMMNTAZMBEC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZXKWUYWWVSKKQZ-UHFFFAOYSA-N cyclohexyl(diphenyl)phosphane Chemical class C1CCCCC1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZXKWUYWWVSKKQZ-UHFFFAOYSA-N 0.000 description 1
- ZBCKWHYWPLHBOK-UHFFFAOYSA-N cyclohexylphosphane Chemical class PC1CCCCC1 ZBCKWHYWPLHBOK-UHFFFAOYSA-N 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- UEMSXAXBVXSKSZ-UHFFFAOYSA-N lithium;triphenylphosphane Chemical class [Li].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UEMSXAXBVXSKSZ-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003297 rubidium Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/932,002 US4731486A (en) | 1986-11-18 | 1986-11-18 | Hydroformylation using low volatile phosphine ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2002728C1 true RU2002728C1 (ru) | 1993-11-15 |
Family
ID=25461633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU874203758A RU2002728C1 (ru) | 1986-11-18 | 1987-11-17 | Способ получени @ -альдегидов |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4731486A (enExample) |
| EP (1) | EP0268268B1 (enExample) |
| JP (1) | JPH0667868B2 (enExample) |
| KR (1) | KR920003556B1 (enExample) |
| CN (1) | CN1017145B (enExample) |
| AR (1) | AR248390A1 (enExample) |
| AT (1) | ATE77075T1 (enExample) |
| AU (1) | AU611867B2 (enExample) |
| BE (1) | BE1000619A5 (enExample) |
| BR (1) | BR8706223A (enExample) |
| CA (1) | CA1307296C (enExample) |
| DE (2) | DE3739064A1 (enExample) |
| DK (1) | DK605887A (enExample) |
| ES (3) | ES2009221A6 (enExample) |
| FI (1) | FI90858C (enExample) |
| FR (1) | FR2606771B1 (enExample) |
| GB (1) | GB2197867B (enExample) |
| HU (1) | HU202177B (enExample) |
| IN (1) | IN170369B (enExample) |
| IT (1) | IT1223147B (enExample) |
| MX (1) | MX166784B (enExample) |
| NL (1) | NL8702752A (enExample) |
| NO (1) | NO166440C (enExample) |
| PL (1) | PL153062B1 (enExample) |
| RU (1) | RU2002728C1 (enExample) |
| SE (1) | SE8704533L (enExample) |
| YU (1) | YU45074B (enExample) |
| ZA (1) | ZA878638B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2135456C1 (ru) * | 1994-01-14 | 1999-08-27 | Басф Аг | Способ получения н-бутиральдегида и/или н-бутанола |
| RU2296739C2 (ru) * | 2000-07-14 | 2007-04-10 | Оксено Олефинхеми Гмбх | Способ многоступенчатого гидроформилирования олефинов c6-c24 в альдегиды и/или спирты |
| RU2546110C2 (ru) * | 2009-12-22 | 2015-04-10 | Дау Текнолоджи Инвестментс Ллс | Регулирование соотношения альдегид нормального строения: альдегид изо-строения в процессе гидроформилирования со смешанным лигандом регулированием парциального давления синтез-газа |
| RU2561171C1 (ru) * | 2014-09-12 | 2015-08-27 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ непрерывного двухступенчатого гидроформилирования олефинов с3, с4 и технологическая установка для его осуществления |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1328281C (en) * | 1988-07-14 | 1994-04-05 | Anthony George Abatjoglou | Process for catalyst aldehyde product separation |
| US5180854A (en) * | 1988-07-14 | 1993-01-19 | Union Carbide Chemicals & Plastics Technology Corporation | Process for catalyst aldehyde product separation |
| ZA895346B (en) * | 1988-07-14 | 1990-10-31 | Union Carbide Chem Plastic | Process for producing alcohols and aldehydes |
| US5113022A (en) * | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
| US5059710A (en) * | 1988-08-05 | 1991-10-22 | Union Carbide Chemicals And Plastics Technology Corporation | Ionic phosphites and their use in homogeneous transition metal catalyzed processes |
| US4965404A (en) * | 1989-03-09 | 1990-10-23 | Kuraray Company, Ltd. | Process for the preparation of lithium diphenylphosphinobenzene-m-monosulfonate |
| DE3942954A1 (de) * | 1989-12-23 | 1991-06-27 | Hoechst Ag | Verfahren zur herstellung von aldehyden |
| EP0545997B1 (en) * | 1990-08-31 | 1995-11-02 | The Governors Of The University Of Alberta | Carbonylation of methanol using a novel transition metal catalyst precursor |
| US5087763A (en) * | 1990-11-09 | 1992-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5196596A (en) * | 1991-12-26 | 1993-03-23 | Union Carbide Chemicals & Plastics Technology Corporation | Higher aldehyde separation process |
| US5300617A (en) * | 1993-01-21 | 1994-04-05 | Exxon Chemical Patents Inc. | Potassium para-diphenyl phosphino benzene sulfonate ligand |
| US6143211A (en) * | 1995-07-21 | 2000-11-07 | Brown University Foundation | Process for preparing microparticles through phase inversion phenomena |
| DE19532393A1 (de) * | 1995-09-02 | 1997-03-06 | Hoechst Ag | Verfahren zur Hydroformylierung olefinisch ungesättigter Verbindungen |
| WO1997011931A1 (en) * | 1995-09-26 | 1997-04-03 | Kuraray Co., Ltd. | Hydroformylation method |
| DE19700805C1 (de) * | 1997-01-13 | 1998-08-06 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung olefinischer Verbindungen mit 3 bis 5 Kohlenstoffatomen in Anwesenheit einer Rhodium und sulfonierte Triarylphosphine als Katalysator enthhaltenden wäßrigen Phase |
| DE19700804C1 (de) * | 1997-01-13 | 1998-08-06 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung olefinischer Verbindungen mit 6 bis 16 Kohlenstoffatomen in Anwesenheit einer Rhodium und sulfonierte Triarylphosphine als Katalysator enthaltenden wäßrigen Phase |
| DE19742305A1 (de) * | 1997-09-25 | 1999-04-01 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung in Gegenwart von Kronenether |
| FI20002807A0 (fi) * | 2000-09-05 | 2000-12-20 | Neste Chemicals Oy | Menetelmä alkeenien hydroformyloimiseksi |
| KR20040007650A (ko) * | 2001-06-07 | 2004-01-24 | 가부시키가이샤 구라레 | 파라-디아릴포스피노벤젠설폰산 리튬염, 이의 제조방법 및이의 용도 |
| CA2456806C (en) * | 2001-08-08 | 2011-10-18 | Brown University Research Foundation | Methods for micronization of hydrophobic drugs |
| AU2002360549A1 (en) * | 2001-12-10 | 2003-06-23 | Spherics, Inc. | Methods and products useful in the formation and isolation of microparticles |
| EP1620387B1 (en) * | 2003-04-25 | 2010-05-19 | Dow Global Technologies Inc. | Aldehyde and alcohol compositions derived from seed oils |
| KR100547587B1 (ko) * | 2004-06-12 | 2006-01-31 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| CA2579766C (en) * | 2004-10-25 | 2013-12-17 | Dow Global Technologies Inc. | Polymer polyols and polymer dispersions made from vegetable oil-based hydroxyl-containing materials |
| CN101039977B (zh) * | 2004-10-25 | 2011-10-12 | 陶氏环球技术有限责任公司 | 由含羟甲基的脂肪酸或这种脂肪酸的烷基酯制成的聚氨酯 |
| RU2418813C2 (ru) * | 2004-10-25 | 2011-05-20 | Дау Глобал Текнолоджиз Инк. | Форполимеры, полученные из гидроксиметилсодержащих полиэфирполиолов на основе сложного эфира, полученных из жирных кислот |
| US7053253B1 (en) * | 2005-05-02 | 2006-05-30 | 3M Innovative Properties Company | Process for purifying hexafluoropropene dimers |
| DE602006016138D1 (de) * | 2005-09-15 | 2010-09-23 | Dow Global Technologies Inc | Verfahren zur monosulfonierung aromatischer phosphine und daraus entwickeltes zwitterionisches produkt |
| CN100526279C (zh) * | 2006-04-11 | 2009-08-12 | 中国科学院兰州化学物理研究所 | 连续制备正戊醛的工艺过程 |
| MY147009A (en) | 2006-05-15 | 2012-10-15 | Dow Global Technologies Inc | Hydroformylation process and product separation with improved recovery of rhodium |
| AU2007297828B2 (en) * | 2006-09-21 | 2013-06-27 | Dow Brasil Sudeste Industrial Ltda. | Viscoelastic foams having high air flow |
| EP1918247A1 (en) * | 2006-10-18 | 2008-05-07 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Hydrogen production from formic acid |
| EP2134822A2 (en) * | 2007-04-09 | 2009-12-23 | Dow Global Technologies Inc. | Capped polyester polyol lubricant composition |
| EP2150566B1 (en) * | 2007-04-27 | 2014-04-09 | Dow Global Technologies LLC | Low volatiles coatings, sealants and binders from renewable oils |
| EP2155796A1 (en) * | 2007-05-15 | 2010-02-24 | Dow Global Technologies Inc. | High resilience foams |
| WO2008156993A2 (en) * | 2007-06-13 | 2008-12-24 | Dow Global Technologies Inc. | Extraction process for aldehyde product separation and catalyst recovery |
| CN101802046B (zh) * | 2007-07-12 | 2014-06-18 | 陶氏环球技术有限责任公司 | 室温可固化聚合物及其前体 |
| WO2009009571A1 (en) * | 2007-07-12 | 2009-01-15 | Dow Global Technologies Inc. | Prepolymers and polymers for elastomers |
| WO2009017973A1 (en) * | 2007-08-01 | 2009-02-05 | Dow Global Technologies Inc. | Heat bonding polyurethane foams |
| US8394978B2 (en) * | 2008-01-15 | 2013-03-12 | Dow Global Technologies Llc | Sulfonated organophosphine compounds and use thereof in hydroformylation processes |
| US8466306B2 (en) * | 2008-01-15 | 2013-06-18 | Dow Global Technologies Llc | Sulfonated organophosphine compounds and use in hydroformylation processes |
| EP2231683B1 (en) * | 2008-01-15 | 2016-03-23 | Dow Global Technologies LLC | Sulfonated organophosphine compounds and use thereof in hydroformylation processes |
| EP2276786A2 (en) * | 2008-05-09 | 2011-01-26 | Dow Global Technologies Inc. | Natural oil based polyol blends |
| US20120123005A1 (en) | 2009-07-22 | 2012-05-17 | Dow Brasil Sudeste Industrial Ltda. | Natural oil based polyurethane foams |
| BR112012013415A2 (pt) | 2009-12-03 | 2016-03-22 | Dow Global Technologies Llc | processo para descolorir um poliol a base de óleo natural e poliol descolorado |
| JP2013513012A (ja) | 2009-12-08 | 2013-04-18 | ダウ グローバル テクノロジーズ エルエルシー | 天然油系ポリオール及びポリ（プロピレンオキシド）ポリオールを用いて製造される連続気泡フォームの調製プロセス |
| EP2516576B1 (en) | 2009-12-21 | 2018-05-16 | Dow Global Technologies LLC | Polyurethane-based sealant for insulated glass units |
| EP2545094A1 (en) | 2010-03-12 | 2013-01-16 | Dow Global Technologies LLC | Elastomer binding materials made with natural oil based polyols |
| US20130005900A1 (en) | 2010-03-12 | 2013-01-03 | Dow Global Technologies Llc | Gels and soft elastomers made with natural oil based polyols |
| EP2552990B1 (en) | 2010-03-31 | 2017-04-19 | Dow Global Technologies LLC | Polyurethane/polyurea spray elastomers |
| WO2011129940A1 (en) | 2010-04-14 | 2011-10-20 | Dow Global Technologies Llc | Polycarbonate polyols and polyurethanes made therefrom |
| US20130096251A1 (en) | 2010-06-22 | 2013-04-18 | Dow Global Technologies Llc | Curable silyl polymers |
| BR112012033611B1 (pt) | 2010-06-30 | 2020-11-10 | Dow Global Technologies Llc | composição compreendendo um polímero com terminação silano reticulável e método para produzir uma composição compreendendo um polímero com terminação silano reticulável |
| ITMI20101380A1 (it) | 2010-07-27 | 2012-01-28 | Dow Global Technologies Inc | Pannello composito poliuretanico a basso impatto ambientale |
| DK2638090T3 (da) | 2010-11-11 | 2015-05-04 | Dow Global Technologies Llc | Polyurethanbaseret tætningsmiddel til isoleret glas |
| KR20140043334A (ko) | 2011-03-31 | 2014-04-09 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리우레탄용 소수성 폴리에스테르 폴리카르보네이트 폴리올 |
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| EP4605366A1 (en) | 2022-12-08 | 2025-08-27 | Dow Global Technologies LLC | Process for preparing alkyl methacrylates |
| GB202307175D0 (en) | 2023-05-15 | 2023-06-28 | Johnson Matthey Davy Technologies Ltd | Process for hydrogenating a substrate |
| CN116606197B (zh) * | 2023-05-29 | 2025-05-06 | 国家能源集团宁夏煤业有限责任公司 | 费托油氢甲酰化反应制备醛的方法和产品 |
| GB202404300D0 (en) | 2024-03-26 | 2024-05-08 | Johnson Matthey Davy Technologies Ltd | Process for the production of 2-alkylalkanol |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US31812A (en) * | 1861-03-26 | Stump-extractor | ||
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| BE758502A (fr) * | 1969-11-06 | 1971-05-05 | Basf Ag | Preparation d'alcools et d'aldehydes |
| NL7106084A (enExample) * | 1970-05-06 | 1971-11-09 | ||
| US3968136A (en) * | 1974-07-12 | 1976-07-06 | Union Carbide Corporation | Catalytic process for polyhydric alcohols and derivatives |
| US4159999A (en) * | 1974-11-22 | 1979-07-03 | Celanese Corporation | Hydroformylation of olefins |
| US4148830A (en) * | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| US3984478A (en) * | 1975-05-27 | 1976-10-05 | Universal Oil Products Company | Hydroformylation process |
| US4248802A (en) | 1975-06-20 | 1981-02-03 | Rhone-Poulenc Industries | Catalytic hydroformylation of olefins |
| US4247486A (en) * | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| FR2351077A1 (fr) * | 1976-05-13 | 1977-12-09 | Celanese Corp | Procede perfectionne d'hydroformylation des olefines avec un catalyseur complexe au rhodium |
| US4162261A (en) * | 1976-09-29 | 1979-07-24 | Union Carbide Corporation | Novel solvents for the catalytic process for making polyhydric alcohols |
| ZA78146B (en) * | 1977-01-25 | 1978-12-27 | Union Carbide Corp | Improved hydroformylation process |
| US4211719A (en) * | 1978-02-13 | 1980-07-08 | Union Carbide Corporation | Catalytic process for polyhydric alcohols and derivatives |
| US4306084A (en) * | 1978-12-06 | 1981-12-15 | The University Of Texas | Alcohol and aldehyde production using ruthenium carbonyl catalysts |
| DE3022025A1 (de) * | 1979-06-18 | 1981-01-08 | Celanese Corp | Verfahren zur hydroformylierung von olefinen |
| US4329511A (en) * | 1979-06-18 | 1982-05-11 | Celanese Corporation | Hydroformylation process improved by choice of reaction solvent and control of product stripping parameters |
| US4283562A (en) * | 1979-10-26 | 1981-08-11 | Union Carbide Corporation | Hydroformylation process using stable rhodium catalyst |
| FR2478078A2 (fr) * | 1980-03-12 | 1981-09-18 | Rhone Poulenc Ind | Procede d'hydroformylation des olefines |
| US4302547A (en) * | 1980-06-30 | 1981-11-24 | Union Carbide Corporation | Novel solvents for the catalytic process for producing polyhydric alcohols |
| GB2085874B (en) * | 1980-09-04 | 1984-08-08 | Johnson Matthey Plc | Hydroformylation of olefins |
| DE3046355A1 (de) * | 1980-12-09 | 1982-07-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur hydroformylierung von olefinisch ungesaettigten verbindungen |
| US4400548A (en) * | 1981-08-17 | 1983-08-23 | Union Carbide Corporation | Hydroformylation process using bisphosphine monooxide ligands |
| JPS58157739A (ja) * | 1982-03-12 | 1983-09-19 | Kuraray Co Ltd | １，９−ノナンジア−ルの製造方法 |
| US4453022A (en) * | 1982-04-21 | 1984-06-05 | Union Carbide Corporation | Process for preparing nonionic surfactants-oxyalkylation with calcium and/or strontium catalysts |
| FR2532318B1 (fr) * | 1982-08-31 | 1985-06-14 | Rhone Poulenc Chim Base | Procede de preparation de triarylphosphines sulfonees |
| DE3234701A1 (de) * | 1982-09-18 | 1984-04-05 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3235029A1 (de) * | 1982-09-22 | 1984-03-22 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur rueckgewinnung von wasserloeslichen, rhodium enthaltenden hydroformylierungskatalysatoren |
| DE3235030A1 (de) * | 1982-09-22 | 1984-03-22 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von sulfonierten arylphosphinen |
| US4480138A (en) * | 1982-10-12 | 1984-10-30 | Celanese Corporation | Hydroformylation process |
| DE3245883A1 (de) * | 1982-12-11 | 1984-06-14 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur hydroformylierung von olefinen |
| FR2550202B1 (fr) * | 1983-08-03 | 1986-03-21 | Rhone Poulenc Rech | Procede de preparation de tri(m-sulfophenyl) phosphine |
| DE3341035A1 (de) * | 1983-11-12 | 1985-05-23 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3347406A1 (de) * | 1983-12-29 | 1985-07-11 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur abtrennung und wiedergewinnung von rhodium aus den produkten der oxosynthese |
| DE3412335A1 (de) * | 1984-04-03 | 1985-10-10 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| FR2561650B1 (fr) * | 1984-03-26 | 1987-10-23 | Rhone Poulenc Rech | Perfectionnement au procede de preparation de tri(m-sulfophenyl)phosphine par hydrolyse et dilution controlees du sulfonat |
| DE3411034A1 (de) * | 1984-03-26 | 1985-09-26 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur rueckgewinnung von rhodium aus reaktionsprodukten der oxosynthese |
| DE3413427A1 (de) * | 1984-04-10 | 1985-10-17 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3415968A1 (de) * | 1984-04-28 | 1985-10-31 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3420491A1 (de) * | 1984-06-01 | 1985-12-05 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3420493A1 (de) * | 1984-06-01 | 1985-12-05 | Ruhrchemie Ag, 4200 Oberhausen | Quartaere ammoniumsalze sulfonierter triarylphosphine |
| US4578523A (en) * | 1985-05-29 | 1986-03-25 | Ruhrchemie Aktiengesellschaft | Process for the preparation of aldehydes |
| DE3534314A1 (de) * | 1985-09-26 | 1987-04-02 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| US4633021A (en) * | 1985-11-29 | 1986-12-30 | National Distillers And Chemical Corporation | Olefin hydroformylation |
| US4716250A (en) * | 1986-07-10 | 1987-12-29 | Union Carbide Corporation | Hydroformylation using low volatile/organic soluble phosphine ligands |
-
1986
- 1986-11-18 US US06/932,002 patent/US4731486A/en not_active Expired - Lifetime
-
1987
- 1987-11-17 DE DE19873739064 patent/DE3739064A1/de active Granted
- 1987-11-17 MX MX009383A patent/MX166784B/es unknown
- 1987-11-17 RU SU874203758A patent/RU2002728C1/ru active
- 1987-11-17 DE DE8787116971T patent/DE3779725D1/de not_active Expired - Lifetime
- 1987-11-17 AT AT87116971T patent/ATE77075T1/de active
- 1987-11-17 AU AU81280/87A patent/AU611867B2/en not_active Ceased
- 1987-11-17 EP EP87116971A patent/EP0268268B1/en not_active Expired - Lifetime
- 1987-11-17 BE BE8701298A patent/BE1000619A5/fr not_active IP Right Cessation
- 1987-11-18 SE SE8704533A patent/SE8704533L/ not_active Application Discontinuation
- 1987-11-18 JP JP62289666A patent/JPH0667868B2/ja not_active Expired - Fee Related
- 1987-11-18 CN CN87101178A patent/CN1017145B/zh not_active Expired
- 1987-11-18 ES ES8703288A patent/ES2009221A6/es not_active Expired
- 1987-11-18 HU HU875125A patent/HU202177B/hu not_active IP Right Cessation
- 1987-11-18 NL NL8702752A patent/NL8702752A/nl not_active Application Discontinuation
- 1987-11-18 IT IT22675/87A patent/IT1223147B/it active
- 1987-11-18 DK DK605887A patent/DK605887A/da not_active Application Discontinuation
- 1987-11-18 AR AR87309326A patent/AR248390A1/es active
- 1987-11-18 BR BR8706223A patent/BR8706223A/pt not_active Application Discontinuation
- 1987-11-18 KR KR1019870012952A patent/KR920003556B1/ko not_active Expired
- 1987-11-18 YU YU2091/87A patent/YU45074B/xx unknown
- 1987-11-18 FR FR878715930A patent/FR2606771B1/fr not_active Expired
- 1987-11-18 IN IN834/MAS/87A patent/IN170369B/en unknown
- 1987-11-18 GB GB8727013A patent/GB2197867B/en not_active Expired - Lifetime
- 1987-11-18 PL PL1987268876A patent/PL153062B1/pl unknown
- 1987-11-18 NO NO874810A patent/NO166440C/no unknown
- 1987-11-18 FI FI875087A patent/FI90858C/fi not_active IP Right Cessation
- 1987-11-18 ZA ZA878638A patent/ZA878638B/xx unknown
- 1987-11-18 CA CA000552143A patent/CA1307296C/en not_active Expired - Lifetime
-
1989
- 1989-04-24 ES ES8901418A patent/ES2012719A6/es not_active Expired - Lifetime
- 1989-04-24 ES ES8901417A patent/ES2012718A6/es not_active Expired - Lifetime
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| RU2135456C1 (ru) * | 1994-01-14 | 1999-08-27 | Басф Аг | Способ получения н-бутиральдегида и/или н-бутанола |
| RU2296739C2 (ru) * | 2000-07-14 | 2007-04-10 | Оксено Олефинхеми Гмбх | Способ многоступенчатого гидроформилирования олефинов c6-c24 в альдегиды и/или спирты |
| RU2546110C2 (ru) * | 2009-12-22 | 2015-04-10 | Дау Текнолоджи Инвестментс Ллс | Регулирование соотношения альдегид нормального строения: альдегид изо-строения в процессе гидроформилирования со смешанным лигандом регулированием парциального давления синтез-газа |
| RU2561171C1 (ru) * | 2014-09-12 | 2015-08-27 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ непрерывного двухступенчатого гидроформилирования олефинов с3, с4 и технологическая установка для его осуществления |
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