DD283371A5 - Verfahren zur trennung von in kleinen gehalten in einer reaktionsmischung anwesendem butyraldehyd - Google Patents

Verfahren zur trennung von in kleinen gehalten in einer reaktionsmischung anwesendem butyraldehyd Download PDF

Info

Publication number: DD283371A5
Authority: DD; German Democratic Republic
Prior art keywords: hydroformylation; residue; reaction mixture; butyraldehyde; rhodium
Prior art date: 1987-10-27

Application number

DD88321105A

Other languages

German (de)

English (en)

Inventor

Keith A Laird

Original Assignee

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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.)

1987-10-27

Filing date

1988-10-26

Publication date

1990-10-10

1988-10-26 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1990-10-10 Publication of DD283371A5 publication Critical patent/DD283371A5/de

Links

ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 title claims abstract description 48
238000000034 method Methods 0.000 title claims abstract description 27
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 title claims abstract description 19
239000011541 reaction mixture Substances 0.000 title claims abstract 9
238000007037 hydroformylation reaction Methods 0.000 claims abstract description 53
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 37
229910052703 rhodium Inorganic materials 0.000 claims abstract description 36
239000010948 rhodium Substances 0.000 claims abstract description 36
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
238000004821 distillation Methods 0.000 claims abstract description 22
239000007788 liquid Substances 0.000 claims abstract description 20
239000003054 catalyst Substances 0.000 claims abstract description 15
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
239000006227 byproduct Substances 0.000 claims abstract description 11
239000012429 reaction media Substances 0.000 claims abstract description 11
238000000926 separation method Methods 0.000 claims abstract description 10
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 8
238000009835 boiling Methods 0.000 claims description 28
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 3
150000001336 alkenes Chemical class 0.000 abstract description 6
239000011261 inert gas Substances 0.000 abstract description 3
150000001299 aldehydes Chemical class 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 20
239000007789 gas Substances 0.000 description 19
239000000047 product Substances 0.000 description 13
239000003446 ligand Substances 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 6
239000007810 chemical reaction solvent Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000011084 recovery Methods 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
229910002091 carbon monoxide Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000003595 mist Substances 0.000 description 4
238000004064 recycling Methods 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
150000003003 phosphines Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
PYLMCYQHBRSDND-UHFFFAOYSA-N 2-ethyl-2-hexenal Chemical compound CCCC=C(CC)C=O PYLMCYQHBRSDND-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
206010000210 abortion Diseases 0.000 description 2
231100000176 abortion Toxicity 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000002360 explosive Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
229920001515 polyalkylene glycol Polymers 0.000 description 2
238000011027 product recovery Methods 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000002679 ablation Methods 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
238000000137 annealing Methods 0.000 description 1
238000000998 batch distillation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
238000007664 blowing Methods 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
-1 butyraldehyde Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000007701 flash-distillation Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000003958 fumigation Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012827 research and development Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002699 waste material Substances 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
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/06—Reactor-distillation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Inorganic Compounds Of Heavy Metals (AREA)

DD88321105A 1987-10-27 1988-10-26 Verfahren zur trennung von in kleinen gehalten in einer reaktionsmischung anwesendem butyraldehyd DD283371A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/114,171 US4871879A (en)	1987-10-27	1987-10-27	Rhodium recovery from hydroformylation reaction product

Publications (1)

Publication Number	Publication Date
DD283371A5 true DD283371A5 (de)	1990-10-10

Family

ID=22353737

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88321105A DD283371A5 (de)	1987-10-27	1988-10-26	Verfahren zur trennung von in kleinen gehalten in einer reaktionsmischung anwesendem butyraldehyd

Country Status (10)

Country	Link
US (1)	US4871879A (fr)
EP (1)	EP0314434A1 (fr)
JP (1)	JP2602707B2 (fr)
CN (1)	CN1019192B (fr)
AU (1)	AU618288B2 (fr)
BR (1)	BR8805512A (fr)
CA (1)	CA1301190C (fr)
DD (1)	DD283371A5 (fr)
MX (1)	MX167056B (fr)
SU (1)	SU1676441A3 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5030774A (en) *	1986-10-03	1991-07-09	Exxon Research And Engineering Co.	Process for the hydroformylation of sulfur-containing thermally cracked petroleum residue and novel products thereof
US5001274A (en) *	1989-06-23	1991-03-19	Union Carbide Chemicals And Plastics Company Inc.	Hydroformylation process
DE4135049A1 (de) *	1991-10-24	1993-05-06	Hoechst Ag, 6230 Frankfurt, De	Verfahren zur rueckgewinnung von rhodium aus den reaktionsprodukten der oxosynthese
US5865957A (en) *	1994-12-01	1999-02-02	Mitsubishi Chemical Company	Method for producing butyraldehydes
US6599348B2 (en)	2001-06-01	2003-07-29	Celanese International Corporation	Methods for reducing entrainment of solids and liquids
US7667079B2 (en) *	2005-04-21	2010-02-23	Oxea Corporation	Processes for recovery of a triarylphosphine from a group VIII metal catalyst complex mixture
RU2310644C1 (ru) *	2006-05-23	2007-11-20	Александр Петрович Хворов	Способ выделения н-масляного альдегида
CN102826972B (zh) *	2011-06-17	2015-05-13	中国石油化工股份有限公司	一种烯烃氢甲酰化反应制备醛的方法
CN116059674B (zh) *	2023-02-09	2026-01-09	迈瑞尔实验设备（上海）有限公司	一种高碳链烯烃氢甲酰化反应和分离的组合系统

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1833717A (en) *	1927-01-13	1931-11-24	Heat Treating Company	Purification and concentration of liquids
US4188363A (en) *	1976-08-19	1980-02-12	Bayer Aktiengesellschaft	Recovery of rhodium complex catalysts homogeneously dissolved in organic media
JPS6054939B2 (ja) *	1977-08-04	1985-12-03	住友化学工業株式会社	粗製アクリル酸の精製方法
DE2915830A1 (de) *	1979-04-19	1980-10-23	Basf Ag	Gewinnung von toluylendiisocyanat und/oder hoehersiedenden loesungsmitteln im wirbelbett aus destillationsrueckstaenden der toluylendiisocanat-herstellung
US4258215A (en) *	1979-08-29	1981-03-24	Eastman Kodak Company	Hydroformylation process
DE3114147A1 (de) *	1981-04-08	1982-10-28	Basf Ag, 6700 Ludwigshafen	Verfahren zur gewinnung von aldehyden
US4593127A (en) *	1985-01-11	1986-06-03	Union Carbide Corporation	Hydroformylation process
US4613701A (en) *	1985-09-19	1986-09-23	Celanese Corporation	Recovery of rhodium from hydroformylation reaction product

1987
- 1987-10-27 US US07/114,171 patent/US4871879A/en not_active Expired - Lifetime
1988
- 1988-10-21 AU AU24104/88A patent/AU618288B2/en not_active Ceased
- 1988-10-24 CA CA000581094A patent/CA1301190C/fr not_active Expired - Lifetime
- 1988-10-24 MX MX013540A patent/MX167056B/es unknown
- 1988-10-25 EP EP88310020A patent/EP0314434A1/fr not_active Withdrawn
- 1988-10-25 BR BR8805512A patent/BR8805512A/pt unknown
- 1988-10-26 DD DD88321105A patent/DD283371A5/de not_active IP Right Cessation
- 1988-10-26 SU SU884356763A patent/SU1676441A3/ru active
- 1988-10-26 CN CN88107369A patent/CN1019192B/zh not_active Expired
- 1988-10-27 JP JP63269633A patent/JP2602707B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1033794A (zh)	1989-07-12
JP2602707B2 (ja)	1997-04-23
CA1301190C (fr)	1992-05-19
US4871879A (en)	1989-10-03
MX167056B (es)	1993-03-01
JPH01148713A (ja)	1989-06-12
AU618288B2 (en)	1991-12-19
EP0314434A1 (fr)	1989-05-03
CN1019192B (zh)	1992-11-25
SU1676441A3 (ru)	1991-09-07
BR8805512A (pt)	1989-07-04
AU2410488A (en)	1989-04-27

Legal Events

Date	Code	Title	Description
1997-08-28	ENJ	Ceased due to non-payment of renewal fee

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DE3035468C2 (fr)	1988-07-28
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DD283371A5 (de)	1990-10-10	Verfahren zur trennung von in kleinen gehalten in einer reaktionsmischung anwesendem butyraldehyd
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