CS270208B2 - Method of aldehydes production by means of olefins' hydroformylation - Google Patents

Method of aldehydes production by means of olefins' hydroformylation Download PDF

Info

Publication number: CS270208B2
Authority: CS; Czechoslovakia
Prior art keywords: reactor; hydroformylation; primary; rhodium; hydrogen
Prior art date: 1985-01-11

Application number

CS86264A

Other languages

Czech (cs)

English (en)

Other versions

CS26486A2 (en

Inventor

Donlad L Ing Bunning

Michael A Ing Blessing

Original Assignee

Union Carbide Corp

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.)

1985-01-11

Filing date

1986-01-13

Publication date

1990-06-13

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24774467&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CS270208(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1986-01-13 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1989-10-13 Publication of CS26486A2 publication Critical patent/CS26486A2/cs

1990-06-13 Publication of CS270208B2 publication Critical patent/CS270208B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 154
238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 88
150000001336 alkenes Chemical class 0.000 title claims abstract description 71
150000001299 aldehydes Chemical class 0.000 title description 72
238000004519 manufacturing process Methods 0.000 title description 9
230000008569 process Effects 0.000 claims abstract description 146
239000007788 liquid Substances 0.000 claims abstract description 56
239000003054 catalyst Substances 0.000 claims description 90
239000007789 gas Substances 0.000 claims description 86
239000000047 product Substances 0.000 claims description 58
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 55
238000006243 chemical reaction Methods 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 45
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 42
238000004064 recycling Methods 0.000 claims description 42
229910052703 rhodium Inorganic materials 0.000 claims description 42
239000010948 rhodium Substances 0.000 claims description 42
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 42
229910002091 carbon monoxide Inorganic materials 0.000 claims description 41
239000003446 ligand Substances 0.000 claims description 41
239000006227 byproduct Substances 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
238000009835 boiling Methods 0.000 claims description 21
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 17
229910052698 phosphorus Inorganic materials 0.000 claims description 17
239000011574 phosphorus Substances 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 14
238000009833 condensation Methods 0.000 claims description 13
230000005494 condensation Effects 0.000 claims description 13
FSHNFAOXXJLGJE-UHFFFAOYSA-N [Rh].[P] Chemical compound [Rh].[P] FSHNFAOXXJLGJE-UHFFFAOYSA-N 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
239000007859 condensation product Substances 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
238000011084 recovery Methods 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 5
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims 1
239000000376 reactant Substances 0.000 abstract description 8
230000006872 improvement Effects 0.000 abstract description 4
235000019256 formaldehyde Nutrition 0.000 abstract description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 39
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 34
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 34
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 26
230000015572 biosynthetic process Effects 0.000 description 25
238000003786 synthesis reaction Methods 0.000 description 23
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 19
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
239000012429 reaction media Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000002474 experimental method Methods 0.000 description 7
238000010926 purge Methods 0.000 description 7
239000007858 starting material Substances 0.000 description 7
239000000463 material Substances 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
239000001294 propane Substances 0.000 description 6
-1 rhodium-phosphorus compound Chemical class 0.000 description 6
239000013638 trimer Substances 0.000 description 6
230000000052 comparative effect Effects 0.000 description 5
238000004821 distillation Methods 0.000 description 5
238000002955 isolation Methods 0.000 description 5
238000000746 purification Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
238000000926 separation method Methods 0.000 description 5
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
238000010586 diagram Methods 0.000 description 4
230000009467 reduction Effects 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000002912 waste gas Substances 0.000 description 4
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000007809 chemical reaction catalyst Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000008859 change Effects 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
238000010924 continuous production Methods 0.000 description 2
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
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 2
238000005201 scrubbing Methods 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
238000012360 testing method Methods 0.000 description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
241000680714 Rhodine Species 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
238000005094 computer simulation Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000007701 flash-distillation Methods 0.000 description 1
239000003546 flue gas Substances 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
239000000446 fuel Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
238000011027 product recovery Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- 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)
Catalysts (AREA)
Saccharide Compounds (AREA)
Other Investigation Or Analysis Of Materials By Electrical Means (AREA)

CS86264A 1985-01-11 1986-01-13 Method of aldehydes production by means of olefins' hydroformylation CS270208B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/690,912 US4593127A (en)	1985-01-11	1985-01-11	Hydroformylation process

Publications (2)

Publication Number	Publication Date
CS26486A2 CS26486A2 (en)	1989-10-13
CS270208B2 true CS270208B2 (en)	1990-06-13

Family

ID=24774467

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS86264A CS270208B2 (en)	1985-01-11	1986-01-13	Method of aldehydes production by means of olefins' hydroformylation

Country Status (16)

Country	Link
US (1)	US4593127A (de)
EP (1)	EP0188246B2 (de)
JP (1)	JPS61218546A (de)
KR (1)	KR900008107B1 (de)
CN (1)	CN1008089B (de)
AT (1)	ATE73752T1 (de)
AU (1)	AU594034B2 (de)
CA (1)	CA1258871A (de)
CS (1)	CS270208B2 (de)
DE (1)	DE3684335D1 (de)
DK (1)	DK11486A (de)
ES (1)	ES8701710A1 (de)
FI (1)	FI88915C (de)
IN (1)	IN166934B (de)
YU (1)	YU46163B (de)
ZA (1)	ZA86222B (de)

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US4247486A (en) *	1977-03-11	1981-01-27	Union Carbide Corporation	Cyclic hydroformylation process
WO1980001689A1 (en) *	1979-02-12	1980-08-21	Exxon Research Engineering Co	Phosphine and phosphonium compound and catalyst and their use in hydrocarbon conversion processes
US4298541A (en) *	1979-02-12	1981-11-03	Exxon Research & Engineering Co.	Trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes and their use as homogeneous catalysts
DE2965158D1 (en) *	1979-03-21	1983-05-11	Davy Mckee London	Hydroformylation process
DE2965157D1 (en) *	1979-03-21	1983-05-11	Davy Mckee London	Process for the production of aldehydes by hydroformylation of alkenes
US4267383A (en) *	1979-05-04	1981-05-12	Celanese Corporation	Hydrocarbonylation
US4283562A (en) *	1979-10-26	1981-08-11	Union Carbide Corporation	Hydroformylation process using stable rhodium catalyst
DE3102281C2 (de) *	1980-02-02	1982-12-23	Basf Ag, 6700 Ludwigshafen	Verfahren zur Hydroformylierung von Propylen
JPS5828857A (ja) *	1981-08-12	1983-02-19	Toshiba Corp	半導体装置
US4400548A (en) *	1981-08-17	1983-08-23	Union Carbide Corporation	Hydroformylation process using bisphosphine monooxide ligands
EP0096986B1 (de) *	1982-06-11	1987-04-22	DAVY McKEE (LONDON) LIMITED	Hydroformylierungsverfahren
DE3372361D1 (en) *	1982-06-11	1987-08-13	Davy Mckee London	Hydroformylation process
ATE16475T1 (de) *	1982-06-11	1985-11-15	Davy Mckee London	Hydroformylierungsverfahren.
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1985
- 1985-01-11 US US06/690,912 patent/US4593127A/en not_active Expired - Lifetime
1986
- 1986-01-09 CA CA000499305A patent/CA1258871A/en not_active Expired
- 1986-01-10 AU AU52229/86A patent/AU594034B2/en not_active Ceased
- 1986-01-10 AT AT86100278T patent/ATE73752T1/de not_active IP Right Cessation
- 1986-01-10 CN CN86101063A patent/CN1008089B/zh not_active Expired
- 1986-01-10 EP EP86100278A patent/EP0188246B2/de not_active Expired - Lifetime
- 1986-01-10 FI FI860125A patent/FI88915C/fi not_active IP Right Cessation
- 1986-01-10 YU YU2686A patent/YU46163B/sh unknown
- 1986-01-10 ZA ZA86222A patent/ZA86222B/xx unknown
- 1986-01-10 KR KR1019860000159A patent/KR900008107B1/ko not_active Expired
- 1986-01-10 ES ES550785A patent/ES8701710A1/es not_active Expired
- 1986-01-10 DK DK11486A patent/DK11486A/da not_active Application Discontinuation
- 1986-01-10 DE DE8686100278T patent/DE3684335D1/de not_active Expired - Lifetime
- 1986-01-11 JP JP61004098A patent/JPS61218546A/ja active Pending
- 1986-01-13 CS CS86264A patent/CS270208B2/cs unknown
- 1986-01-22 IN IN39/MAS/86A patent/IN166934B/en unknown

Also Published As

Publication number	Publication date
DK11486A (da)	1986-07-12
JPS61218546A (ja)	1986-09-29
YU2686A (en)	1988-02-29
EP0188246B2 (de)	1996-04-17
FI88915C (fi)	1993-07-26
AU5222986A (en)	1986-07-17
CA1258871A (en)	1989-08-29
ZA86222B (en)	1986-08-27
EP0188246B1 (de)	1992-03-18
YU46163B (sh)	1993-05-28
ES550785A0 (es)	1986-12-01
IN166934B (de)	1990-08-11
ATE73752T1 (de)	1992-04-15
DK11486D0 (da)	1986-01-10
EP0188246A3 (en)	1987-05-27
ES8701710A1 (es)	1986-12-01
CN1008089B (zh)	1990-05-23
DE3684335D1 (en)	1992-04-23
AU594034B2 (en)	1990-03-01
KR860005772A (ko)	1986-08-13
CN86101063A (zh)	1986-08-20
EP0188246A2 (de)	1986-07-23
CS26486A2 (en)	1989-10-13
KR900008107B1 (ko)	1990-10-31
FI860125A0 (fi)	1986-01-10
FI860125L (fi)	1986-07-12
FI88915B (fi)	1993-04-15
US4593127A (en)	1986-06-03

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