JPS6120341B2 - - Google Patents

Info

Publication number: JPS6120341B2
Authority: JP; Japan
Prior art keywords: oxo; gas; carbon; hydrogen; catalyst
Prior art date: 1977-09-09
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

Application number

JP52107867A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5441293A (en

Inventor

Masaru Ichikawa

Hiroo Kido

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sagami Chemical Research Institute

Original Assignee

Sagami Chemical Research Institute

Priority date (The priority date 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 date listed.)

1977-09-09

Filing date

1977-09-09

Publication date

1986-05-21

1977-09-09 Application filed by Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute

1977-09-09 Priority to JP10786777A priority Critical patent/JPS5441293A/ja

1979-04-02 Publication of JPS5441293A publication Critical patent/JPS5441293A/ja

1986-05-21 Publication of JPS6120341B2 publication Critical patent/JPS6120341B2/ja

Status Granted legal-status Critical Current

Links

OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 53
239000010948 rhodium Substances 0.000 claims description 38
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
239000003054 catalyst Substances 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 25
229910052703 rhodium Inorganic materials 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 9
239000012298 atmosphere Substances 0.000 claims description 8
229910017052 cobalt Inorganic materials 0.000 claims description 7
239000010941 cobalt Substances 0.000 claims description 7
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 3
239000007809 chemical reaction catalyst Substances 0.000 claims description 2
239000007789 gas Substances 0.000 description 35
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
229910052739 hydrogen Inorganic materials 0.000 description 22
239000001257 hydrogen Substances 0.000 description 21
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 16
229910002091 carbon monoxide Inorganic materials 0.000 description 16
150000001299 aldehydes Chemical class 0.000 description 15
230000000694 effects Effects 0.000 description 15
229910052751 metal Inorganic materials 0.000 description 14
239000002184 metal Substances 0.000 description 14
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 10
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 10
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
239000005977 Ethylene Substances 0.000 description 8
239000001307 helium Substances 0.000 description 8
229910052734 helium Inorganic materials 0.000 description 8
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 8
239000012071 phase Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000008188 pellet Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
238000005292 vacuum distillation Methods 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
150000001336 alkenes Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
-1 cobalt carbonyl compounds Chemical class 0.000 description 5
239000011521 glass Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000012263 liquid product Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
238000004445 quantitative analysis Methods 0.000 description 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000011324 bead Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
238000011068 loading method Methods 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229920001002 functional polymer Polymers 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
238000001308 synthesis method Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
229920000049 Carbon (fiber) Polymers 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
229920002535 Polyethylene Glycol 1500 Polymers 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005210 alkyl ammonium group Chemical group 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
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000004917 carbon fiber Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
SUCYXRASDBOYGB-UHFFFAOYSA-N cobalt rhodium Chemical compound [Co].[Rh] SUCYXRASDBOYGB-UHFFFAOYSA-N 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1

Classifications

- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP10786777A 1977-09-09 1977-09-09 Oxo reaction catalyst and production thereof Granted JPS5441293A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP10786777A JPS5441293A (en)	1977-09-09	1977-09-09	Oxo reaction catalyst and production thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP10786777A JPS5441293A (en)	1977-09-09	1977-09-09	Oxo reaction catalyst and production thereof

Publications (2)

Publication Number	Publication Date
JPS5441293A JPS5441293A (en)	1979-04-02
JPS6120341B2 true JPS6120341B2 (2)	1986-05-21

Family

ID=14470079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10786777A Granted JPS5441293A (en)	1977-09-09	1977-09-09	Oxo reaction catalyst and production thereof

Country Status (1)

Country	Link
JP (1)	JPS5441293A (2)

1977
- 1977-09-09 JP JP10786777A patent/JPS5441293A/ja active Granted

Also Published As

Publication number	Publication date
JPS5441293A (en)	1979-04-02

Publication	Publication Date	Title
Arai et al.	1982	Hydroformylation and hydrogenation of olefins over rhodium zeolite catalyst
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Arai	1978	Hydroformylation, hydrogenation, and isomerization of olefins over polymer-immobilized rhodium complexes
Wang et al.	2023	Influence of phosphite ligands concentration on 1-butene hydroformylation over Rh-supported porous organic polymer catalysts
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