CS214833B2 - Method of making the aldehyds - Google Patents
Method of making the aldehyds Download PDFInfo
- Publication number
- CS214833B2 CS214833B2 CS804829A CS482980A CS214833B2 CS 214833 B2 CS214833 B2 CS 214833B2 CS 804829 A CS804829 A CS 804829A CS 482980 A CS482980 A CS 482980A CS 214833 B2 CS214833 B2 CS 214833B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- catalyst
- gas
- hydroformylation
- catalyst solution
- products
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000007789 gas Substances 0.000 claims abstract description 68
- 239000003054 catalyst Substances 0.000 claims abstract description 66
- 150000001336 alkenes Chemical class 0.000 claims abstract description 26
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 16
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003003 phosphines Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims description 33
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 14
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 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 12
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000012263 liquid product Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- FQSDTIQFGVAWNS-UHFFFAOYSA-N rhodium;(triphenyl-$l^{5}-phosphanylidene)methanone Chemical class [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C=O)C1=CC=CC=C1 FQSDTIQFGVAWNS-UHFFFAOYSA-N 0.000 abstract 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000001294 propane Substances 0.000 description 25
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- 229910052703 rhodium Inorganic materials 0.000 description 19
- 239000010948 rhodium Substances 0.000 description 19
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 18
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 13
- 239000001273 butane Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 10
- -1 hydridocarbonyl-bis (trisubstituted phosphine) rhodium Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792928314 DE2928314A1 (de) | 1979-07-13 | 1979-07-13 | Verfahren zur herstellung von aldehyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214833B2 true CS214833B2 (en) | 1982-06-25 |
Family
ID=6075619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS804829A CS214833B2 (en) | 1979-07-13 | 1980-07-07 | Method of making the aldehyds |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4299990A (it) |
| JP (1) | JPS5827777B2 (it) |
| AT (1) | AT372673B (it) |
| AU (1) | AU538102B2 (it) |
| BE (1) | BE884207A (it) |
| BR (1) | BR8004316A (it) |
| CA (1) | CA1118451A (it) |
| CS (1) | CS214833B2 (it) |
| DE (1) | DE2928314A1 (it) |
| ES (1) | ES8104982A1 (it) |
| FR (1) | FR2460909A1 (it) |
| GB (1) | GB2055367B (it) |
| HU (1) | HU184309B (it) |
| IT (1) | IT1145350B (it) |
| NL (1) | NL8003758A (it) |
| PL (1) | PL126648B1 (it) |
| SE (1) | SE447242B (it) |
| YU (1) | YU40601B (it) |
| ZA (1) | ZA804107B (it) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443638A (en) * | 1981-04-03 | 1984-04-17 | Conoco, Inc. | Preparation of alcohols from internal olefins |
| DE3114147A1 (de) * | 1981-04-08 | 1982-10-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von aldehyden |
| US4528404A (en) * | 1983-03-16 | 1985-07-09 | Exxon Research And Engineering Co. | High temperature hydroformylation in the presence of triarylphosphine rhodium carbonyl hydride complex catalyst systems |
| US4654445A (en) * | 1984-11-26 | 1987-03-31 | Mitsui Toatsu Chemicals Incorporated | Preparation process of 2-chloropropionaldehyde |
| DE3546123A1 (de) * | 1985-12-24 | 1987-06-25 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| JPH0612992B2 (ja) * | 1986-02-26 | 1994-02-23 | 日清製粉株式会社 | 固定化プロテア−ゼの製法 |
| JP2862509B2 (ja) * | 1996-05-28 | 1999-03-03 | 東洋電化工業株式会社 | リパーゼ固定化用担体及び固定化リパーゼ |
| DE10031519A1 (de) * | 2000-06-28 | 2002-01-10 | Basf Ag | Verfahren zur Hydroformylierung von Olefinen mit 2 bis 8 Kohlenstoffatomen, I |
| DE10031518A1 (de) * | 2000-06-28 | 2002-01-10 | Basf Ag | Verfahren zur Herstellung von Hydroformylierungsprodukten des Propylens und von Acrylsäure und/oder Acrolein |
| DE10031517A1 (de) * | 2000-06-28 | 2002-01-10 | Basf Ag | Verfahren zur Herstellung von Hydroformylierungspordukten von Olefinen mit 2 bis 8 Kohlenstoffatomen |
| US7868201B2 (en) * | 2005-07-01 | 2011-01-11 | Exxonmobil Research And Engineering Company | Process and catalyst for oxidation of hydrocarbons |
| US8822734B2 (en) * | 2011-03-04 | 2014-09-02 | The University Of Kansas | Single solvent gas expanded hydroformylation process |
| EP3414220B1 (en) * | 2016-02-11 | 2021-10-13 | Dow Technology Investments LLC | Processes for converting olefins to alcohols, ethers, or combinations thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754724A (fr) | 1969-08-12 | 1971-01-18 | Progil | Procede d'hydroformylation des olefines et catalyseurs utilisesa cet effet |
| US4060557A (en) * | 1973-06-04 | 1977-11-29 | Texaco Inc. | Hydroformylation |
| JPS5115007A (en) * | 1974-07-24 | 1976-02-06 | Shinmazusawa Kogyo Kk | Shakenyosuino fuhaiboshihoho |
| US4201728A (en) * | 1977-08-19 | 1980-05-06 | Celanese Corporation | Hydroformylation catalyst and process |
| US4230641A (en) * | 1977-11-21 | 1980-10-28 | Air Products And Chemicals, Inc. | Hydroformylation of olefins |
| US4215077A (en) * | 1978-02-09 | 1980-07-29 | Kuraray Co., Ltd. | Hydroformylation of olefins |
-
1979
- 1979-07-13 DE DE19792928314 patent/DE2928314A1/de not_active Withdrawn
-
1980
- 1980-06-27 NL NL8003758A patent/NL8003758A/nl not_active Application Discontinuation
- 1980-06-30 US US06/164,386 patent/US4299990A/en not_active Expired - Lifetime
- 1980-07-02 YU YU1727/80A patent/YU40601B/xx unknown
- 1980-07-03 GB GB8021874A patent/GB2055367B/en not_active Expired
- 1980-07-03 ES ES493071A patent/ES8104982A1/es not_active Expired
- 1980-07-04 SE SE8004960A patent/SE447242B/sv not_active IP Right Cessation
- 1980-07-04 FR FR8014981A patent/FR2460909A1/fr active Granted
- 1980-07-04 AT AT0349780A patent/AT372673B/de not_active IP Right Cessation
- 1980-07-07 PL PL1980225528A patent/PL126648B1/pl unknown
- 1980-07-07 BE BE0/201320A patent/BE884207A/fr unknown
- 1980-07-07 CS CS804829A patent/CS214833B2/cs unknown
- 1980-07-07 HU HU801691A patent/HU184309B/hu not_active IP Right Cessation
- 1980-07-07 JP JP55091813A patent/JPS5827777B2/ja not_active Expired
- 1980-07-08 ZA ZA00804107A patent/ZA804107B/xx unknown
- 1980-07-09 CA CA000355753A patent/CA1118451A/en not_active Expired
- 1980-07-11 BR BR8004316A patent/BR8004316A/pt unknown
- 1980-07-11 AU AU60355/80A patent/AU538102B2/en not_active Ceased
- 1980-07-11 IT IT49234/80A patent/IT1145350B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| AU6035580A (en) | 1981-01-15 |
| PL225528A1 (it) | 1981-06-05 |
| SE8004960L (sv) | 1981-01-14 |
| JPS5615231A (en) | 1981-02-14 |
| HU184309B (en) | 1984-08-28 |
| SE447242B (sv) | 1986-11-03 |
| GB2055367B (en) | 1983-09-21 |
| FR2460909A1 (fr) | 1981-01-30 |
| JPS5827777B2 (ja) | 1983-06-11 |
| BR8004316A (pt) | 1981-01-27 |
| AU538102B2 (en) | 1984-07-26 |
| BE884207A (fr) | 1981-01-07 |
| ATA349780A (de) | 1983-03-15 |
| PL126648B1 (en) | 1983-08-31 |
| NL8003758A (nl) | 1981-01-15 |
| ES493071A0 (es) | 1981-05-16 |
| CA1118451A (en) | 1982-02-16 |
| DE2928314A1 (de) | 1981-02-12 |
| YU40601B (en) | 1986-02-28 |
| ES8104982A1 (es) | 1981-05-16 |
| FR2460909B1 (it) | 1984-03-30 |
| AT372673B (de) | 1983-11-10 |
| YU172780A (en) | 1983-09-30 |
| ZA804107B (en) | 1981-07-29 |
| GB2055367A (en) | 1981-03-04 |
| IT8049234A0 (it) | 1980-07-11 |
| US4299990A (en) | 1981-11-10 |
| IT1145350B (it) | 1986-11-05 |
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