SE444312B - Sett for kontinuerlig framstellning av aldehyder genom omsettning av olefiner med kolmonoxid och vete i nervaro av rodiumkatalysatorer - Google Patents

Sett for kontinuerlig framstellning av aldehyder genom omsettning av olefiner med kolmonoxid och vete i nervaro av rodiumkatalysatorer

Info

Publication number: SE444312B
Authority: SE; Sweden
Prior art keywords: rhodium; catalyst; carbon monoxide; sulfur; product
Prior art date: 1977-08-20

Application number

SE7808651A

Other languages

English (en)

Swedish (sv)

Other versions

SE7808651L (sv

Inventor

L Bexten

H-D Hahn

B Cornils

H Tummes

Original Assignee

Ruhrchemie Ag

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.)

1977-08-20

Filing date

1978-08-15

Publication date

1986-04-07

1978-08-15 Application filed by Ruhrchemie Ag filed Critical Ruhrchemie Ag

1979-02-21 Publication of SE7808651L publication Critical patent/SE7808651L/xx

1986-04-07 Publication of SE444312B publication Critical patent/SE444312B/sv

Links

UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims description 7
229910002091 carbon monoxide Inorganic materials 0.000 title claims description 7
150000001299 aldehydes Chemical class 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 2
239000010948 rhodium Substances 0.000 claims description 39
229910052703 rhodium Inorganic materials 0.000 claims description 38
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 35
239000003054 catalyst Substances 0.000 claims description 33
230000015572 biosynthetic process Effects 0.000 claims description 21
238000003786 synthesis reaction Methods 0.000 claims description 21
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 17
239000011593 sulfur Substances 0.000 claims description 17
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 12
238000009835 boiling Methods 0.000 claims description 10
238000004821 distillation Methods 0.000 claims description 10
150000001336 alkenes Chemical class 0.000 claims description 9
239000007795 chemical reaction product Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
150000003284 rhodium compounds Chemical class 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
238000010924 continuous production Methods 0.000 claims 1
239000007789 gas Substances 0.000 description 16
239000000047 product Substances 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000003921 oil Substances 0.000 description 5
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
238000007664 blowing Methods 0.000 description 4
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
238000007037 hydroformylation reaction Methods 0.000 description 4
239000012263 liquid product Substances 0.000 description 4
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000007701 flash-distillation Methods 0.000 description 3
GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
-1 compounds which Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003464 sulfur compounds Chemical class 0.000 description 2
230000007306 turnover Effects 0.000 description 2
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000007038 hydrochlorination reaction Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
238000003260 vortexing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax 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

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)

SE7808651A 1977-08-20 1978-08-15 Sett for kontinuerlig framstellning av aldehyder genom omsettning av olefiner med kolmonoxid och vete i nervaro av rodiumkatalysatorer SE444312B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2737633A DE2737633C2 (de)	1977-08-20	1977-08-20	Verfahren zur Herstellung von Aldehyden

Publications (2)

Publication Number	Publication Date
SE7808651L SE7808651L (sv)	1979-02-21
SE444312B true SE444312B (sv)	1986-04-07

Family

ID=6016912

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7808651A SE444312B (sv)	1977-08-20	1978-08-15	Sett for kontinuerlig framstellning av aldehyder genom omsettning av olefiner med kolmonoxid och vete i nervaro av rodiumkatalysatorer

Country Status (17)

Country	Link
US (1)	US4222966A (fr)
JP (1)	JPS5811931B2 (fr)
AT (1)	AT356640B (fr)
AU (1)	AU518880B2 (fr)
BE (1)	BE869767A (fr)
BR (1)	BR7805273A (fr)
CA (1)	CA1081258A (fr)
DE (1)	DE2737633C2 (fr)
ES (1)	ES472518A1 (fr)
FR (1)	FR2400497A1 (fr)
GB (1)	GB2002768B (fr)
HU (1)	HU179757B (fr)
IT (1)	IT1106884B (fr)
NL (1)	NL172051C (fr)
PL (1)	PL118118B1 (fr)
SE (1)	SE444312B (fr)
SU (1)	SU1017166A3 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4374278A (en) *	1980-02-28	1983-02-15	Union Carbide Corporation	Hydroformylation catalyst reactivation
US4324695A (en) *	1980-11-17	1982-04-13	National Distillers & Chemical Corp.	Catalyst compositions of transition metal carbonyl complexes intercalcated with lamellar materials
DE3114147A1 (de) *	1981-04-08	1982-10-28	Basf Ag, 6700 Ludwigshafen	Verfahren zur gewinnung von aldehyden
US5082977A (en) *	1990-02-15	1992-01-21	University Of Akron	Aldehydes by olefin hydroformylation
DE102012014395B3 (de)	2012-07-13	2013-08-22	Oxea Gmbh	Isononylamine ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE102012013968A1 (de)	2012-07-13	2014-04-03	Oxea Gmbh	Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1430719A (fr) *	1965-04-16	1966-03-04	Eastman Kodak Co	Perfectionnements au procédé d'hydroformylation
DE1945574B2 (de) *	1968-09-14	1975-01-23	Mitsubishi Chemical Industries, Ltd., Tokio	Verfahren zur Rückgewinnung eines Rhodiumkatalysators aus einem Oxo-Reaktionsprodukt
GB1326013A (en) *	1969-07-14	1973-08-08	Johnson Matthey Co Ltd	Catalytic hydroformylation process
US3994978A (en) *	1972-08-13	1976-11-30	Mobil Oil Corporation	Hydroformylation of olefins
DE2245565B1 (de) *	1972-09-16	1974-04-04	Ruhrchemie Ag, 4200 Oberhausen	Verfahren zur abtrennung von kobalt aus den primaerprodukten der oxosynthese und dessen wiedereinsatz in der synthesestufe
DE2406323C3 (de) *	1974-02-09	1979-07-12	Ruhrchemie Ag, 4200 Oberhausen	Kontinuierliches Verfahren zur Herstellung sauerstoffhaltiger Verbindungen durch Oxo-Synthese unter Einsatz des zurückgewonnenen Rhodiumkatalysators
JPS5822453B2 (ja) *	1974-07-15	1983-05-09	三菱化学株式会社	ブチルアルデヒドの製造方法
US4248802A (en) *	1975-06-20	1981-02-03	Rhone-Poulenc Industries	Catalytic hydroformylation of olefins

1977
- 1977-08-20 DE DE2737633A patent/DE2737633C2/de not_active Expired
- 1977-09-28 NL NLAANVRAGE7710612,A patent/NL172051C/xx not_active IP Right Cessation
1978
- 1978-08-10 AT AT581578A patent/AT356640B/de not_active IP Right Cessation
- 1978-08-11 FR FR7823686A patent/FR2400497A1/fr active Granted
- 1978-08-11 ES ES472518A patent/ES472518A1/es not_active Expired
- 1978-08-14 PL PL1978209050A patent/PL118118B1/pl unknown
- 1978-08-14 HU HU78RU167A patent/HU179757B/hu not_active IP Right Cessation
- 1978-08-15 SU SU782648754A patent/SU1017166A3/ru active
- 1978-08-15 JP JP53098735A patent/JPS5811931B2/ja not_active Expired
- 1978-08-15 SE SE7808651A patent/SE444312B/sv not_active IP Right Cessation
- 1978-08-16 BR BR7805273A patent/BR7805273A/pt unknown
- 1978-08-16 BE BE189908A patent/BE869767A/fr not_active IP Right Cessation
- 1978-08-17 CA CA309,517A patent/CA1081258A/fr not_active Expired
- 1978-08-17 US US05/934,668 patent/US4222966A/en not_active Expired - Lifetime
- 1978-08-17 AU AU39010/78A patent/AU518880B2/en not_active Expired
- 1978-08-18 GB GB7833835A patent/GB2002768B/en not_active Expired
- 1978-08-18 IT IT7850777A patent/IT1106884B/it active

Also Published As

Publication number	Publication date
AT356640B (de)	1980-05-12
FR2400497A1 (fr)	1979-03-16
JPS5436210A (en)	1979-03-16
HU179757B (en)	1982-12-28
SE7808651L (sv)	1979-02-21
NL172051C (nl)	1983-07-01
SU1017166A3 (ru)	1983-05-07
PL209050A1 (pl)	1979-05-07
DE2737633C2 (de)	1979-09-27
ATA581578A (de)	1979-10-15
US4222966A (en)	1980-09-16
AU518880B2 (en)	1981-10-22
BR7805273A (pt)	1979-04-10
JPS5811931B2 (ja)	1983-03-05
PL118118B1 (en)	1981-09-30
NL7710612A (nl)	1979-02-22
AU3901078A (en)	1980-02-21
GB2002768A (en)	1979-02-28
BE869767A (fr)	1979-02-16
DE2737633B1 (de)	1979-02-08
ES472518A1 (es)	1979-03-16
IT7850777A0 (it)	1978-08-18
CA1081258A (fr)	1980-07-08
NL172051B (nl)	1983-02-01
FR2400497B1 (fr)	1983-09-16
IT1106884B (it)	1985-11-18
GB2002768B (en)	1982-03-24

Legal Events

Date

Code

Title

Description

1995-01-31

NUG

Patent has lapsed

Ref document number: 7808651-9

Effective date: 19920306

Format of ref document f/p: F

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SE444312B (sv)	1986-04-07	Sett for kontinuerlig framstellning av aldehyder genom omsettning av olefiner med kolmonoxid och vete i nervaro av rodiumkatalysatorer
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US3083231A (en)	1963-03-26	Production of mercaptans