JPS6311337B2 - - Google Patents
Info
- Publication number
- JPS6311337B2 JPS6311337B2 JP58108003A JP10800383A JPS6311337B2 JP S6311337 B2 JPS6311337 B2 JP S6311337B2 JP 58108003 A JP58108003 A JP 58108003A JP 10800383 A JP10800383 A JP 10800383A JP S6311337 B2 JPS6311337 B2 JP S6311337B2
- Authority
- JP
- Japan
- Prior art keywords
- aldehyde
- hydrogen
- mixture
- liquid
- organophosphorus
- 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.)
- Expired
Links
- 150000001299 aldehydes Chemical class 0.000 claims description 141
- 239000000203 mixture Substances 0.000 claims description 65
- 239000007788 liquid Substances 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 239000007789 gas Substances 0.000 claims description 34
- 239000000356 contaminant Substances 0.000 claims description 31
- 230000008016 vaporization Effects 0.000 claims description 26
- 238000005984 hydrogenation reaction Methods 0.000 claims description 21
- 239000006200 vaporizer Substances 0.000 claims description 21
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical group CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000009834 vaporization Methods 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000047 product Substances 0.000 description 33
- 238000004821 distillation Methods 0.000 description 26
- 238000007037 hydroformylation reaction Methods 0.000 description 16
- 238000000746 purification Methods 0.000 description 13
- 239000003446 ligand Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 229910052703 rhodium Inorganic materials 0.000 description 9
- 239000010948 rhodium Substances 0.000 description 9
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 9
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000005882 aldol condensation reaction Methods 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- -1 aldehyde compounds Chemical class 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- GBDSVWZDEWJBAM-UHFFFAOYSA-N 5-methylhept-1-en-3-one Chemical compound CCC(C)CC(=O)C=C GBDSVWZDEWJBAM-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- MBLXROIYHWIVRL-UHFFFAOYSA-N 3-methylideneheptan-4-one Chemical compound CCCC(=O)C(=C)CC MBLXROIYHWIVRL-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- 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
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- C07C47/58—Vanillin
-
- 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
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38997982A | 1982-06-18 | 1982-06-18 | |
| US389979 | 1982-06-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS597127A JPS597127A (ja) | 1984-01-14 |
| JPS6311337B2 true JPS6311337B2 (en, 2012) | 1988-03-14 |
Family
ID=23540549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58108003A Granted JPS597127A (ja) | 1982-06-18 | 1983-06-17 | 粗アルデヒド製品の精製 |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0097891B1 (en, 2012) |
| JP (1) | JPS597127A (en, 2012) |
| KR (1) | KR870000769B1 (en, 2012) |
| AU (1) | AU565848B2 (en, 2012) |
| BR (1) | BR8303184A (en, 2012) |
| CA (1) | CA1202326A (en, 2012) |
| DE (1) | DE3361169D1 (en, 2012) |
| ES (1) | ES8504100A1 (en, 2012) |
| IN (1) | IN159791B (en, 2012) |
| MX (1) | MX162489A (en, 2012) |
| PL (2) | PL141508B1 (en, 2012) |
| SU (1) | SU1526581A3 (en, 2012) |
| YU (1) | YU43314B (en, 2012) |
| ZA (1) | ZA834469B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03102455U (en, 2012) * | 1990-02-06 | 1991-10-24 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1259331A (en) * | 1984-03-30 | 1989-09-12 | Gregory J. Dembowski | Process for recovery of phosphorus ligand from vaporized aldehyde |
| US5227544A (en) * | 1991-02-15 | 1993-07-13 | Basf Corporation | Process for the production of 2-ethylhexanol |
| US6350819B1 (en) | 2000-10-27 | 2002-02-26 | Union Carbide Chemicals & Plastics Technology Corporation | Dendritic macromolecules for metal-ligand catalyzed processes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3501537A (en) * | 1964-04-01 | 1970-03-17 | Eastman Kodak Co | Process for separating high-boilers of the oxo process |
| US4247486A (en) * | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| CA1137519A (en) * | 1978-08-29 | 1982-12-14 | Chao-Chyan Pai | Heterogeneous vapor phase process for the catalytic hydrogenation of aldehydes to alcohols |
| DE2912230B1 (de) * | 1979-03-28 | 1980-10-09 | Union Carbide Corp | Verfahren zur Rueckgewinnung und Reaktivierung gebrauchter Rhodium- und Phosphin-enthaltender Katalysatoren aus Reaktionsprodukten der Rhodium-katalysierten Oxosynthese |
| JPS55151521A (en) * | 1979-05-15 | 1980-11-26 | Toyo Soda Mfg Co Ltd | Preparation of alcohol |
-
1983
- 1983-05-27 CA CA000429075A patent/CA1202326A/en not_active Expired
- 1983-06-16 BR BR8303184A patent/BR8303184A/pt not_active IP Right Cessation
- 1983-06-16 DE DE8383105942T patent/DE3361169D1/de not_active Expired
- 1983-06-16 EP EP83105942A patent/EP0097891B1/en not_active Expired
- 1983-06-17 ZA ZA834469A patent/ZA834469B/xx unknown
- 1983-06-17 PL PL1983242566A patent/PL141508B1/pl unknown
- 1983-06-17 IN IN763/CAL/83A patent/IN159791B/en unknown
- 1983-06-17 ES ES523361A patent/ES8504100A1/es not_active Expired
- 1983-06-17 YU YU1344/83A patent/YU43314B/xx unknown
- 1983-06-17 MX MX197706A patent/MX162489A/es unknown
- 1983-06-17 KR KR1019830002722A patent/KR870000769B1/ko not_active Expired
- 1983-06-17 SU SU833610811A patent/SU1526581A3/ru active
- 1983-06-17 PL PL1983261304A patent/PL145612B1/pl unknown
- 1983-06-17 JP JP58108003A patent/JPS597127A/ja active Granted
- 1983-06-17 AU AU15886/83A patent/AU565848B2/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03102455U (en, 2012) * | 1990-02-06 | 1991-10-24 |
Also Published As
| Publication number | Publication date |
|---|---|
| IN159791B (en, 2012) | 1987-06-06 |
| ES523361A0 (es) | 1985-04-01 |
| AU565848B2 (en) | 1987-10-01 |
| KR870000769B1 (ko) | 1987-04-15 |
| EP0097891B1 (en) | 1985-11-06 |
| ES8504100A1 (es) | 1985-04-01 |
| AU1588683A (en) | 1983-12-22 |
| CA1202326A (en) | 1986-03-25 |
| ZA834469B (en) | 1984-03-28 |
| MX162489A (es) | 1991-05-13 |
| JPS597127A (ja) | 1984-01-14 |
| EP0097891A1 (en) | 1984-01-11 |
| KR840005065A (ko) | 1984-11-03 |
| PL242566A1 (en) | 1984-07-02 |
| PL145612B1 (en) | 1988-10-31 |
| YU134483A (en) | 1986-02-28 |
| PL141508B1 (en) | 1987-07-31 |
| BR8303184A (pt) | 1984-01-31 |
| SU1526581A3 (ru) | 1989-11-30 |
| YU43314B (en) | 1989-06-30 |
| DE3361169D1 (en) | 1985-12-12 |
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