JP2003514877A - ハイドロホルミル化混合物からロジウム／フォスファイトリガンド複合体及び遊離のフォスファイトリガンド複合体を分離する方法 - Google Patents
ハイドロホルミル化混合物からロジウム／フォスファイトリガンド複合体及び遊離のフォスファイトリガンド複合体を分離する方法Info
- Publication number
- JP2003514877A JP2003514877A JP2001539595A JP2001539595A JP2003514877A JP 2003514877 A JP2003514877 A JP 2003514877A JP 2001539595 A JP2001539595 A JP 2001539595A JP 2001539595 A JP2001539595 A JP 2001539595A JP 2003514877 A JP2003514877 A JP 2003514877A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mixture
- alkyl
- hydroformylation
- phosphite ligand
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003446 ligand Substances 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 55
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 49
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 229910052703 rhodium Inorganic materials 0.000 title claims abstract description 39
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000010948 rhodium Substances 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 239000012528 membrane Substances 0.000 claims abstract description 64
- 238000009835 boiling Methods 0.000 claims abstract description 53
- 239000003085 diluting agent Substances 0.000 claims abstract description 27
- 229920005597 polymer membrane Polymers 0.000 claims abstract description 13
- -1 alkyl 3-pentenoate Chemical compound 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 46
- 238000000926 separation method Methods 0.000 claims description 38
- 229940070710 valerate Drugs 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims description 3
- 150000008301 phosphite esters Chemical class 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000003134 recirculating effect Effects 0.000 claims 1
- 238000010790 dilution Methods 0.000 abstract description 7
- 239000012895 dilution Substances 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 17
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 16
- 239000012466 permeate Substances 0.000 description 11
- FDNFXHCDOASWAY-UHFFFAOYSA-N methyl 6-oxohexanoate Chemical compound COC(=O)CCCCC=O FDNFXHCDOASWAY-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- 230000004907 flux Effects 0.000 description 9
- 239000012465 retentate Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 6
- KJALUUCEMMPKAC-ONEGZZNKSA-N methyl (e)-pent-3-enoate Chemical compound COC(=O)C\C=C\C KJALUUCEMMPKAC-ONEGZZNKSA-N 0.000 description 6
- SHCSFZHSNSGTOP-UHFFFAOYSA-N Methyl 4-pentenoate Chemical compound COC(=O)CCC=C SHCSFZHSNSGTOP-UHFFFAOYSA-N 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000001336 alkenes Chemical group 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- ISBHMJZRKAFTGE-ONEGZZNKSA-N (e)-pent-2-enenitrile Chemical compound CC\C=C\C#N ISBHMJZRKAFTGE-ONEGZZNKSA-N 0.000 description 2
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- BVOQAUOJSQUGLN-UHFFFAOYSA-N acetyl pentanoate Chemical compound CCCCC(=O)OC(C)=O BVOQAUOJSQUGLN-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- MBAHGFJTIVZLFB-SNAWJCMRSA-N methyl (e)-pent-2-enoate Chemical compound CC\C=C\C(=O)OC MBAHGFJTIVZLFB-SNAWJCMRSA-N 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- 241001503974 Adriana Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000004940 MPF-50 Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 101100121112 Oryza sativa subsp. indica 20ox2 gene Proteins 0.000 description 1
- 101100121113 Oryza sativa subsp. japonica GA20OX2 gene Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SJYROXINNJQCSO-UHFFFAOYSA-N cyclohexyl pent-3-enoate Chemical compound CC=CCC(=O)OC1CCCCC1 SJYROXINNJQCSO-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008380 degradant Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- GXOGLXKLKOVKEA-UHFFFAOYSA-N formyl pentanoate Chemical compound CCCCC(=O)OC=O GXOGLXKLKOVKEA-UHFFFAOYSA-N 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000013628 high molecular weight specie Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000013627 low molecular weight specie Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052698 phosphorus Chemical group 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000005406 washing Methods 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/027—Nanofiltration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/04—Feed pretreatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/147—Microfiltration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/16—Feed pretreatment
-
- 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
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4061—Regeneration or reactivation of catalysts containing metals involving membrane separation
-
- 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
- C07C45/786—Separation; Purification; Stabilisation; Use of additives by membrane separation process, e.g. pervaporation, perstraction, reverse osmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2311/00—Details relating to membrane separation process operations and control
- B01D2311/04—Specific process operations in the feed stream; Feed pretreatment
-
- 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
-
- 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
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Nanotechnology (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99203927A EP1103303A1 (en) | 1999-11-23 | 1999-11-23 | Process to separate a rhodium/phosphite ligand complex and free phosphite ligand complex from a hydroformylation mixture |
| EP99203927.1 | 1999-11-23 | ||
| PCT/EP2000/010699 WO2001037993A1 (en) | 1999-11-23 | 2000-10-27 | Process to separate a rhodium/phosphite ligand complex and free phosphite ligand complex from a hydroformylation mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003514877A true JP2003514877A (ja) | 2003-04-22 |
| JP2003514877A5 JP2003514877A5 (enExample) | 2007-12-20 |
Family
ID=8240899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001539595A Pending JP2003514877A (ja) | 1999-11-23 | 2000-10-27 | ハイドロホルミル化混合物からロジウム／フォスファイトリガンド複合体及び遊離のフォスファイトリガンド複合体を分離する方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20030018210A1 (enExample) |
| EP (2) | EP1103303A1 (enExample) |
| JP (1) | JP2003514877A (enExample) |
| KR (1) | KR100697916B1 (enExample) |
| CN (1) | CN1164365C (enExample) |
| AT (1) | ATE245483T1 (enExample) |
| AU (1) | AU1277601A (enExample) |
| CA (1) | CA2392195A1 (enExample) |
| DE (1) | DE60004088T2 (enExample) |
| TW (1) | TW527217B (enExample) |
| WO (1) | WO2001037993A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007509029A (ja) * | 2003-06-25 | 2007-04-12 | ビーエーエスエフ アクチェンゲゼルシャフト | 少なくとも２つの官能基を有する化合物の連続的製造方法 |
| JP2009524511A (ja) * | 2006-01-26 | 2009-07-02 | エボニック オクセノ ゲゼルシャフト ミット ベシュレンクテル ハフツング | テロメリゼーション混合物からの金属−錯体触媒の分離法 |
| JP2012522813A (ja) * | 2009-04-07 | 2012-09-27 | オクセア・ゲゼルシャフト・ミト・べシュレンクテル・ハフツング | 液状ヒドロホルミル化生産物の仕上げ処理法 |
| JP2015509491A (ja) * | 2012-02-23 | 2015-03-30 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | イソブテンのヒドロホルミル化のための、及び、生成物混合物の分離のための、方法及び装置 |
| WO2019017490A1 (ja) * | 2017-07-21 | 2019-01-24 | 宇部興産株式会社 | ペンテン酸エステル誘導体の製造方法 |
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| RU2337090C2 (ru) | 2002-08-31 | 2008-10-27 | Оксено Олефинхеми Гмбх | Способ гидроформилирования олефиновых соединений в присутствии циклических эфиров угольной кислоты |
| DE102005046250B4 (de) * | 2005-09-27 | 2020-10-08 | Evonik Operations Gmbh | Anlage zur Abtrennung von organischen Übergangsmetallkomplexkatalysatoren |
| DE102009001225A1 (de) | 2009-02-27 | 2010-09-02 | Evonik Oxeno Gmbh | Verfahren zur Anreicherung eines Homogenkatalysators aus einem Prozessstrom |
| DE102009001230A1 (de) * | 2009-02-27 | 2010-09-02 | Evonik Oxeno Gmbh | Verfahren zur Abtrennung und teilweiser Rückführung von Übergangsmetallen bzw. deren katalytisch wirksamen Komplexverbindungen aus Prozessströmen |
| JP2012525245A (ja) | 2009-04-29 | 2012-10-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 膜濾過による触媒の調整方法 |
| DE102012223572A1 (de) | 2012-12-18 | 2014-06-18 | Evonik Industries Ag | Steuerung der Viskosität von Reaktionslösungen in Hydroformylierungverfahren |
| RU2585285C1 (ru) * | 2015-04-20 | 2016-05-27 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ непрерывного гидроформилирования олефинов c2-c8 |
| WO2019094290A1 (en) | 2017-11-13 | 2019-05-16 | Dow Technology Investments Llc | Processes for recovery of rhodium from a hydroformylation process |
| CN112479841B (zh) * | 2020-11-26 | 2022-09-20 | 万华化学集团股份有限公司 | 一种丙烯氢甲酰化合成丁醛的工艺 |
| WO2024123510A1 (en) | 2022-12-06 | 2024-06-13 | Dow Technology Investments Llc | Process of controlling heavies in a recycle catalyst stream |
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| GB1312076A (en) * | 1970-05-15 | 1973-04-04 | Bp Chem Int Ltd | Hydroformylation process |
| EP0839794A1 (en) * | 1996-11-04 | 1998-05-06 | Dsm N.V. | Process for the continuous preparation of an alkyl 5-formylvalerate compound |
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- 1999-11-23 EP EP99203927A patent/EP1103303A1/en not_active Withdrawn
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- 2000-10-27 CA CA002392195A patent/CA2392195A1/en not_active Abandoned
- 2000-10-27 AT AT00974489T patent/ATE245483T1/de not_active IP Right Cessation
- 2000-10-27 JP JP2001539595A patent/JP2003514877A/ja active Pending
- 2000-10-27 CN CNB008185581A patent/CN1164365C/zh not_active Expired - Fee Related
- 2000-10-27 WO PCT/EP2000/010699 patent/WO2001037993A1/en not_active Ceased
- 2000-10-27 DE DE60004088T patent/DE60004088T2/de not_active Revoked
- 2000-10-27 KR KR1020027006531A patent/KR100697916B1/ko not_active Expired - Fee Related
- 2000-10-27 AU AU12776/01A patent/AU1277601A/en not_active Abandoned
- 2000-10-27 EP EP00974489A patent/EP1232008B1/en not_active Revoked
- 2000-10-30 TW TW089122838A patent/TW527217B/zh not_active IP Right Cessation
-
2002
- 2002-05-23 US US10/153,179 patent/US20030018210A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH10503425A (ja) * | 1995-05-01 | 1998-03-31 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー コーポレイション | 膜分離方法 |
| JPH1059890A (ja) * | 1996-05-15 | 1998-03-03 | Hoechst Ag | アルデヒドの製造方法 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007509029A (ja) * | 2003-06-25 | 2007-04-12 | ビーエーエスエフ アクチェンゲゼルシャフト | 少なくとも２つの官能基を有する化合物の連続的製造方法 |
| JP2009524511A (ja) * | 2006-01-26 | 2009-07-02 | エボニック オクセノ ゲゼルシャフト ミット ベシュレンクテル ハフツング | テロメリゼーション混合物からの金属−錯体触媒の分離法 |
| JP2012522813A (ja) * | 2009-04-07 | 2012-09-27 | オクセア・ゲゼルシャフト・ミト・べシュレンクテル・ハフツング | 液状ヒドロホルミル化生産物の仕上げ処理法 |
| KR101740296B1 (ko) * | 2009-04-07 | 2017-05-26 | 옥세아 게엠베하 | 액체 하이드로포밀화 생산물의 후처리 방법 |
| JP2015509491A (ja) * | 2012-02-23 | 2015-03-30 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | イソブテンのヒドロホルミル化のための、及び、生成物混合物の分離のための、方法及び装置 |
| WO2019017490A1 (ja) * | 2017-07-21 | 2019-01-24 | 宇部興産株式会社 | ペンテン酸エステル誘導体の製造方法 |
| JPWO2019017490A1 (ja) * | 2017-07-21 | 2020-05-28 | 宇部興産株式会社 | ペンテン酸エステル誘導体の製造方法 |
| JP7215421B2 (ja) | 2017-07-21 | 2023-01-31 | Ｕｂｅ株式会社 | ペンテン酸エステル誘導体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU1277601A (en) | 2001-06-04 |
| DE60004088D1 (de) | 2003-08-28 |
| DE60004088T2 (de) | 2004-04-22 |
| US20030018210A1 (en) | 2003-01-23 |
| KR20020052214A (ko) | 2002-07-02 |
| KR100697916B1 (ko) | 2007-03-20 |
| EP1232008B1 (en) | 2003-07-23 |
| WO2001037993A1 (en) | 2001-05-31 |
| CN1424939A (zh) | 2003-06-18 |
| ATE245483T1 (de) | 2003-08-15 |
| EP1103303A1 (en) | 2001-05-30 |
| EP1232008A1 (en) | 2002-08-21 |
| CA2392195A1 (en) | 2001-05-31 |
| CN1164365C (zh) | 2004-09-01 |
| TW527217B (en) | 2003-04-11 |
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