RU2699368C2 - Способ гидроформилирования - Google Patents
Способ гидроформилирования Download PDFInfo
- Publication number
- RU2699368C2 RU2699368C2 RU2017121307A RU2017121307A RU2699368C2 RU 2699368 C2 RU2699368 C2 RU 2699368C2 RU 2017121307 A RU2017121307 A RU 2017121307A RU 2017121307 A RU2017121307 A RU 2017121307A RU 2699368 C2 RU2699368 C2 RU 2699368C2
- Authority
- RU
- Russia
- Prior art keywords
- evaporator
- stream
- catalyst
- kpa
- reaction
- Prior art date
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- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 90
- 239000003446 ligand Substances 0.000 claims abstract description 127
- 239000003054 catalyst Substances 0.000 claims abstract description 99
- 239000010948 rhodium Substances 0.000 claims abstract description 78
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 68
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 68
- 238000006243 chemical reaction Methods 0.000 claims abstract description 58
- 239000012530 fluid Substances 0.000 claims abstract description 36
- 150000008301 phosphite esters Chemical class 0.000 claims abstract description 35
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 150000001336 alkenes Chemical class 0.000 claims abstract description 32
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 135
- 239000000047 product Substances 0.000 claims description 57
- 230000008569 process Effects 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000006227 byproduct Substances 0.000 claims description 26
- 150000003624 transition metals Chemical class 0.000 claims description 19
- 229910052723 transition metal Inorganic materials 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 13
- 230000003134 recirculating effect Effects 0.000 claims description 7
- 230000000295 complement effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 12
- 239000000126 substance Substances 0.000 abstract description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 136
- 239000007789 gas Substances 0.000 description 111
- -1 C 5 aldehyde Chemical class 0.000 description 108
- 150000001299 aldehydes Chemical class 0.000 description 41
- 239000000243 solution Substances 0.000 description 35
- 229910052751 metal Inorganic materials 0.000 description 33
- 239000002184 metal Substances 0.000 description 33
- 239000001257 hydrogen Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 30
- 238000002474 experimental method Methods 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 238000000926 separation method Methods 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
- 239000004215 Carbon black (E152) Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000009423 ventilation Methods 0.000 description 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- 150000004696 coordination complex Chemical class 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000012263 liquid product Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000005840 aryl radicals Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000009616 inductively coupled plasma Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 241000183024 Populus tremula Species 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000008300 phosphoramidites Chemical class 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 3
- 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 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 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 239000012062 aqueous buffer Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 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 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003546 flue gas Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000013529 heat transfer fluid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229920001600 hydrophobic polymer Polymers 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- HAGKFWXVDSAFHB-UHFFFAOYSA-N pentacosanal Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC=O HAGKFWXVDSAFHB-UHFFFAOYSA-N 0.000 description 2
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical compound CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- PDVNOQOMGZLXSB-UHFFFAOYSA-N (4-sulfonylcyclohexa-1,5-dien-1-yl) bis(3,6,8-tritert-butylnaphthalen-2-yl) phosphite Chemical compound CC(C)(C)C1=CC2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2C=C1OP(OC=1C(=CC2=CC(=CC(=C2C=1)C(C)(C)C)C(C)(C)C)C(C)(C)C)OC1=CCC(=S(=O)=O)C=C1 PDVNOQOMGZLXSB-UHFFFAOYSA-N 0.000 description 1
- DTCCTIQRPGSLPT-ONEGZZNKSA-N (E)-2-pentenal Chemical compound CC\C=C\C=O DTCCTIQRPGSLPT-ONEGZZNKSA-N 0.000 description 1
- WUCQRXWCJPCWTQ-NSCUHMNNSA-N (e)-pent-3-enal Chemical compound C\C=C\CC=O WUCQRXWCJPCWTQ-NSCUHMNNSA-N 0.000 description 1
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- RRTJOAHJZQVSSE-UHFFFAOYSA-N 1,3,2-dioxaphosphepine Chemical compound C=1C=COPOC=1 RRTJOAHJZQVSSE-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- JRBDENXMNZQUIP-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylbutane-1,4-diol Chemical compound OCC(C)(CO)CCO JRBDENXMNZQUIP-UHFFFAOYSA-N 0.000 description 1
- ZKPFRIDJMMOODR-UHFFFAOYSA-N 2-Methyloctanal Chemical compound CCCCCCC(C)C=O ZKPFRIDJMMOODR-UHFFFAOYSA-N 0.000 description 1
- BRZMRZVKWQWYPJ-UHFFFAOYSA-N 2-hydroxy caproaldehyde Chemical compound CCCCC(O)C=O BRZMRZVKWQWYPJ-UHFFFAOYSA-N 0.000 description 1
- LBICMZLDYMBIGA-UHFFFAOYSA-N 2-methyldecanal Chemical compound CCCCCCCCC(C)C=O LBICMZLDYMBIGA-UHFFFAOYSA-N 0.000 description 1
- DHEKCFIOOSCJRW-UHFFFAOYSA-N 2-methylheptanal Chemical compound CCCCCC(C)C=O DHEKCFIOOSCJRW-UHFFFAOYSA-N 0.000 description 1
- MNXNDLQGVDOJQY-UHFFFAOYSA-N 2-methylnonanal Chemical compound CCCCCCCC(C)C=O MNXNDLQGVDOJQY-UHFFFAOYSA-N 0.000 description 1
- JNQRXMDVFIVLTO-UHFFFAOYSA-N 2-methyloctacosanal Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C=O JNQRXMDVFIVLTO-UHFFFAOYSA-N 0.000 description 1
- IQKPRZPVTQHVOY-UHFFFAOYSA-N 2-methylpentanedial Chemical compound O=CC(C)CCC=O IQKPRZPVTQHVOY-UHFFFAOYSA-N 0.000 description 1
- SVRCDLKKNASNPW-UHFFFAOYSA-N 2-methyltetracosanal Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(C)C=O SVRCDLKKNASNPW-UHFFFAOYSA-N 0.000 description 1
- AJLYPAZKAZMIJP-UHFFFAOYSA-N 2-methyltriacontanal Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C=O AJLYPAZKAZMIJP-UHFFFAOYSA-N 0.000 description 1
- MJHMCKKNRYKFGH-UHFFFAOYSA-N 2-methyltricosanal Chemical compound CCCCCCCCCCCCCCCCCCCCCC(C)C=O MJHMCKKNRYKFGH-UHFFFAOYSA-N 0.000 description 1
- BHCOGXLEVRDEIQ-UHFFFAOYSA-N 3-propylhexadecanal Chemical compound CCCCCCCCCCCCCC(CCC)CC=O BHCOGXLEVRDEIQ-UHFFFAOYSA-N 0.000 description 1
- KZGKBVMULRBWOD-UHFFFAOYSA-N 3-propylundecanal Chemical compound CCCCCCCCC(CCC)CC=O KZGKBVMULRBWOD-UHFFFAOYSA-N 0.000 description 1
- PKAUJJPTOIWMDM-UHFFFAOYSA-N 3h-dioxaphosphepine Chemical compound C=1C=CPOOC=1 PKAUJJPTOIWMDM-UHFFFAOYSA-N 0.000 description 1
- QUMSUJWRUHPEEJ-UHFFFAOYSA-N 4-Pentenal Chemical compound C=CCCC=O QUMSUJWRUHPEEJ-UHFFFAOYSA-N 0.000 description 1
- FPFTWHJPEMPAGE-UHFFFAOYSA-N 6-hydroxy caproaldehyde Chemical compound OCCCCCC=O FPFTWHJPEMPAGE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UDOBAAUJVYCEDK-UHFFFAOYSA-N CC(C)(C)C1=CC(C(C)(C)C)=C(C=C(C(C(C)(C)C)=C2)OP(C3=CC=CC=C3)(O)OC3=CC4=C(C(C)(C)C)C=C(C(C)(C)C)C=C4C=C3C(C)(C)C)C2=C1 Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(C=C(C(C(C)(C)C)=C2)OP(C3=CC=CC=C3)(O)OC3=CC4=C(C(C)(C)C)C=C(C(C)(C)C)C=C4C=C3C(C)(C)C)C2=C1 UDOBAAUJVYCEDK-UHFFFAOYSA-N 0.000 description 1
- YZMVHOCYEIPVPL-UHFFFAOYSA-N CC(C)(C)C1=CC(C(C)(C)C)=C(C=C(C(C(C)(C)C)=C2)OP(C3CCCCC3)(O)OC3=CC4=C(C(C)(C)C)C=C(C(C)(C)C)C=C4C=C3C(C)(C)C)C2=C1 Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(C=C(C(C(C)(C)C)=C2)OP(C3CCCCC3)(O)OC3=CC4=C(C(C)(C)C)C=C(C(C)(C)C)C=C4C=C3C(C)(C)C)C2=C1 YZMVHOCYEIPVPL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NRFHJUYXVZDBQQ-UHFFFAOYSA-N NP(O)O.OP(O)O Chemical class NP(O)O.OP(O)O NRFHJUYXVZDBQQ-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
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Images
Classifications
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
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- 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
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- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- 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
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- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
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- 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
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- 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
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- 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)
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| RU2845007C2 (ru) * | 2021-10-27 | 2025-08-12 | Наньцзян Инститьют Оф Микроинтэрфейс Текнолоджи Ко.,Лтд | Способ катализирования карбонилирования олефинов |
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| PL3374340T3 (pl) | 2015-11-10 | 2022-04-11 | Dow Technology Investments Llc | Sposób wytwarzania aldehydów |
| RU2751511C9 (ru) | 2016-02-11 | 2021-08-18 | Дау Текнолоджи Инвестментс Ллк | Способы превращения олефинов в спирты, простые эфиры или их комбинации |
| CN107469860B (zh) * | 2017-08-22 | 2020-05-19 | 中国海洋石油集团有限公司 | 一种提高铑/双亚膦酸酯催化剂稳定性的方法 |
| TWI793216B (zh) | 2017-12-07 | 2023-02-21 | 美商陶氏科技投資公司 | 氫甲醯化方法 |
| MY203235A (en) * | 2018-11-29 | 2024-06-19 | Dow Technology Investments Llc | Hydroformylation process |
| GB201907659D0 (en) | 2019-05-30 | 2019-07-17 | Johnson Matthey Davy Technologies Ltd | Process |
| WO2021247177A1 (en) | 2020-06-05 | 2021-12-09 | SCION Holdings LLC | Alcohols production |
| EP4161696A4 (en) * | 2020-06-05 | 2025-05-28 | Scion Holdings LLC | BRANCHED ALCOHOLS |
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| ES2974422T3 (es) * | 2020-07-30 | 2024-06-27 | Evonik Oxeno Gmbh & Co Kg | Procedimiento para la preparación de aldehídos y separación del sistema catalítico mediante separación por membrana |
| GB202012930D0 (en) * | 2020-08-19 | 2020-09-30 | Johnson Matthey Davy Technologies Ltd | Process for hydroformylation with removal of dissolved hydrogen |
| CN116261565A (zh) | 2020-10-13 | 2023-06-13 | 美国陶氏有机硅公司 | 具有醛官能团的有机硅化合物的制备 |
| CN112403401B (zh) * | 2020-11-06 | 2022-06-21 | 中国海洋石油集团有限公司 | 一种烯烃氢甲酰化制醛中醛和催化剂分离的装置和方法 |
| WO2022132372A1 (en) * | 2020-12-14 | 2022-06-23 | Dow Technology Investments Llc | Processes to improve catalytic metal accountability in hydroformylation processes |
| US12145904B2 (en) | 2020-12-17 | 2024-11-19 | SCION Holdings LLC | Branched products |
| CN118019747A (zh) | 2021-10-06 | 2024-05-10 | 陶氏环球技术有限责任公司 | 丙基亚胺官能化有机硅化合物和伯氨基丙基官能化有机硅化合物的制备 |
| KR20240074844A (ko) | 2021-10-06 | 2024-05-28 | 다우 글로벌 테크놀로지스 엘엘씨 | 프로필이민-작용성 유기규소 화합물 및 1차 아미노프로필-작용성 유기규소 화합물의 제조 |
| JP2024536162A (ja) | 2021-10-06 | 2024-10-04 | ダウ グローバル テクノロジーズ エルエルシー | イミン官能性有機ケイ素化合物及び一級アミノ官能性有機ケイ素化合物の調製 |
| WO2023086718A1 (en) | 2021-11-11 | 2023-05-19 | Dow Technology Investments Llc | Processes for recovering rhodium from hydroformylation processes |
| EP4437031A2 (en) | 2021-11-22 | 2024-10-02 | Dow Global Technologies LLC | Preparation of organosilicon compounds with carbinol functionality |
| CN118338965A (zh) | 2021-12-16 | 2024-07-12 | 陶氏技术投资有限责任公司 | 包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法 |
| EP4448170B1 (en) | 2021-12-16 | 2025-08-20 | Dow Technology Investments LLC | Compounds, transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes |
| EP4496833A1 (en) | 2022-03-21 | 2025-01-29 | Dow Global Technologies LLC | Preparation of organosilicon compounds with carboxy functionality |
| EP4508106A1 (en) | 2022-04-13 | 2025-02-19 | Dow Global Technologies LLC | Silicone - vinylester functional compounds and methods for their preparation and use in personal care compositions |
| KR20250003565A (ko) | 2022-04-13 | 2025-01-07 | 다우 실리콘즈 코포레이션 | 조성물, 우레탄 프리폴리머, 및 관련 방법 및 용도 |
| US20250145647A1 (en) | 2022-04-13 | 2025-05-08 | Dow Silicones Corporation | Preparation of organosilicon compounds with vinylester functionality |
| CN118843652A (zh) | 2022-04-13 | 2024-10-25 | 陶氏环球技术有限责任公司 | 制备聚醚官能有机硅化合物 |
| CN114773172B (zh) * | 2022-06-20 | 2022-10-18 | 中海油天津化工研究设计院有限公司 | 一种烯烃氢甲酰化制醛工艺优化方法 |
| GB202213997D0 (en) | 2022-09-26 | 2022-11-09 | Johnson Matthey Davy Technologies Ltd | Parallel zone hydroformylation reaction |
| WO2024123510A1 (en) | 2022-12-06 | 2024-06-13 | Dow Technology Investments Llc | Process of controlling heavies in a recycle catalyst stream |
| GB202303617D0 (en) | 2023-03-13 | 2023-04-26 | Johnson Matthey Davy Technologies Ltd | Method and apparatus for producing aldehyde |
| WO2025029369A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Process for improving rhodium/phosphite- based homogenous hydroformylation catalyst activity |
| WO2025029349A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Hydroformylation process |
| WO2025038266A1 (en) | 2023-08-14 | 2025-02-20 | Dow Global Technologies Llc | Cobalt catalyzed hydroformylation of vinyl-functional polyorganosiloxanes |
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| WO2025170887A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Gas distribution in gas-stripping hydroformylation reactor for oxo aldehydes |
| WO2025170886A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Purge for a gas-stripping hydroformylation reactor for oxo aldehydes |
| WO2025170891A1 (en) * | 2024-02-06 | 2025-08-14 | Eastman Chemical Company | Composition of matter for gas-stripping oxo aldehydes hydroformylation process |
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- 2015-11-18 BR BR112017011447-0A patent/BR112017011447B1/pt active IP Right Grant
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2847260C1 (ru) * | 2020-12-14 | 2025-10-02 | Дау Текнолоджи Инвестментс Ллк | Способы улучшения контролируемости металлического катализатора в процессах гидроформилирования |
| RU2845007C2 (ru) * | 2021-10-27 | 2025-08-12 | Наньцзян Инститьют Оф Микроинтэрфейс Текнолоджи Ко.,Лтд | Способ катализирования карбонилирования олефинов |
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| Publication number | Publication date |
|---|---|
| EP3230248B1 (en) | 2019-12-25 |
| JP2017537918A (ja) | 2017-12-21 |
| TW201620863A (zh) | 2016-06-16 |
| RU2017121307A3 (enExample) | 2019-02-01 |
| CN107001218A (zh) | 2017-08-01 |
| JP2021008477A (ja) | 2021-01-28 |
| BR112017011447B1 (pt) | 2020-12-15 |
| MX2017006792A (es) | 2017-09-08 |
| PL3230248T3 (pl) | 2020-05-18 |
| WO2016089602A1 (en) | 2016-06-09 |
| RU2017121307A (ru) | 2018-12-19 |
| CA2969527A1 (en) | 2016-06-09 |
| MX381950B (es) | 2025-03-13 |
| US20170355656A1 (en) | 2017-12-14 |
| KR102507703B1 (ko) | 2023-03-09 |
| CA2969527C (en) | 2023-08-22 |
| MY184826A (en) | 2021-04-24 |
| US10023516B2 (en) | 2018-07-17 |
| BR112017011447A2 (pt) | 2018-02-27 |
| KR20170093152A (ko) | 2017-08-14 |
| EP3230248A1 (en) | 2017-10-18 |
| TWI586644B (zh) | 2017-06-11 |
| JP7128622B2 (ja) | 2022-08-31 |
| CN107001218B (zh) | 2021-02-26 |
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