CH629738A5 - Process for preparing undecenals - Google Patents
Process for preparing undecenals Download PDFInfo
- Publication number
- CH629738A5 CH629738A5 CH664577A CH664577A CH629738A5 CH 629738 A5 CH629738 A5 CH 629738A5 CH 664577 A CH664577 A CH 664577A CH 664577 A CH664577 A CH 664577A CH 629738 A5 CH629738 A5 CH 629738A5
- Authority
- CH
- Switzerland
- Prior art keywords
- catalyst
- compound
- formula
- decadiene
- rhodium
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 12
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000007037 hydroformylation reaction Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 4
- 239000004913 cyclooctene Substances 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- 150000003284 rhodium compounds Chemical class 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 claims description 2
- PANBRUWVURLWGY-UHFFFAOYSA-N 2-undecenal Chemical compound CCCCCCCCC=CC=O PANBRUWVURLWGY-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- SMOJNZMNQIIIPK-UHFFFAOYSA-N silylphosphane Chemical compound P[SiH3] SMOJNZMNQIIIPK-UHFFFAOYSA-N 0.000 claims description 2
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 239000012437 perfumed product Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 238000007323 disproportionation reaction Methods 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- VNYQFJIEUNEILL-UHFFFAOYSA-N 2-methyldec-9-enal Chemical compound O=CC(C)CCCCCCC=C VNYQFJIEUNEILL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
- C07C6/06—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond at a cyclic carbon-to-carbon double bond
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)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Description
Aufgabe der Erfindung war es daher, ein Verfahren zur Herstellung von Undecenalen zur Verfügung zu stellen, bei dem von leichten verfügbaren Ausgangsverbindungen ausgegangen wird. The object of the invention was therefore to provide a process for the preparation of undecenals, which is based on readily available starting compounds.
Gegenstand der Erfindung ist somit ein Verfahren zur Herstellung von Undecenalen der Formeln I oder II The invention thus relates to a process for the preparation of undecenals of the formulas I or II
CH2 = CH(CH2)8CHO CH2 = CH(CH2)6CHCH3 CH2 = CH (CH2) 8CHO CH2 = CH (CH2) 6CHCH3
i i
CHO CHO
(I) (II) (I) (II)
das dadurch gekennzeichnet ist, dass man 1,9-Decadien in Gegenwart einer Rhodiumverbindung als Katalysator hy-droformyliert. which is characterized in that 1,9-decadiene is hydroformylated in the presence of a rhodium compound as catalyst.
Das im erfindungsgemässen Verfahren als Ausgangsverbindung verwendete 1,9-Decadien enthält man zweckmässig durch Umsetzen von Cycloocten mit Äthylen in Gegenwart eines Olefin-Disproportionierungskatalysators. Jeder her-5 kömmliche Olefin-Disproportionierungskatalysator ist für diese Reaktion geeignet, z. B. die Katalysatoren, die in «Ca-talyst Reviews», Band 3 (1969) Seiten 37 bis 60 beschrieben sind. Bevorzugte Katalysatoren sind solche, in denen sich ein Übergangsmetalloxid, z.B. Rheniumoxid, auf einem Träger, io wie y-Aluminiumoxid, befindet, insbesondere 10 bis 70 Gewichtsprozent Re207 auf y-Aluminiumoxid, das eine geringe Menge, z.B. bis zu 5 Gewichtsprozent, einer Alkalimetallverbindung enthält (vgl. Schweizer Patentschrift Nr. 609 313). The 1,9-decadiene used as the starting compound in the process according to the invention is expediently obtained by reacting cyclooctene with ethylene in the presence of an olefin disproportionation catalyst. Any conventional olefin disproportionation catalyst is suitable for this reaction, e.g. B. the catalysts, which are described in «Catalyst Reviews», Volume 3 (1969) pages 37 to 60. Preferred catalysts are those in which a transition metal oxide, e.g. Rhenium oxide, on a support, such as y-aluminum oxide, is in particular 10 to 70% by weight of Re207 on y-aluminum oxide, which contains a small amount, e.g. contains up to 5 percent by weight of an alkali metal compound (cf. Swiss Patent No. 609 313).
i5 Die Disproportionierung kann man bei 25 bis 200 °C, vorzugsweise 50 bis 100 °C, und einem Druck von 1- bis 100 bar in einem flüssigen organischen Verdünnungsmittel, z.B. einem Alkan mit 6 bis 14 Kohlenstoffatomen, wie Heptan, und/oder in Gegenwart von gasförmigen Verdünnungsmit-20 teln durchführen. Diese Reaktion kann kontinuierlich oder diskontinuierlich durchgeführt werden. i5 The disproportionation can be carried out at 25 to 200 ° C, preferably 50 to 100 ° C, and a pressure of 1 to 100 bar in a liquid organic diluent, e.g. an alkane with 6 to 14 carbon atoms, such as heptane, and / or in the presence of gaseous diluents. This reaction can be carried out continuously or batchwise.
Bei der Hydroformylierung des 1,9-Decadiens werden praktisch äquimolare Mengen von Kohlenmonoxid und Wasserstoff in Gegenwart einer Rhodiumverbindung als Ka-2s talysator zu Monoaldehyden umgesetzt. Als Katalysator ist ein Rhodiumcarbonyl-Derivat bevorzugt, insbesondere eine Verbindung, die zusätzlich zu einer oder mehreren Car-bonylgruppen einen oder mehrere Phosphor enthaltende Liganden enthält. Der Katalysator kann homogen sein, z.B. 30 eine Verbindung der Formel XRh(CO)[P(C6H5)3]3, in der X ein Wasserstoff- oder Halogenatom ist, oder heterogen sein, z. B. kann man den homogenen Katalysator mit einem Phosphinosilan, wie einer Verbindung der Formel (C2H50)3SiCH2CH2P(C6Hs)2, und einem Kieselsäure ent-35 haltenden Träger umsetzen. In the hydroformylation of 1,9-decadiene, practically equimolar amounts of carbon monoxide and hydrogen are converted into monoaldehydes in the presence of a rhodium compound as a Ka-2s catalyst. A rhodium carbonyl derivative is preferred as the catalyst, in particular a compound which, in addition to one or more carbonyl groups, contains one or more ligands containing phosphorus. The catalyst can be homogeneous, e.g. 30 is a compound of the formula XRh (CO) [P (C6H5) 3] 3, in which X is a hydrogen or halogen atom, or be heterogeneous, e.g. For example, the homogeneous catalyst can be reacted with a phosphinosilane, such as a compound of the formula (C2H50) 3SiCH2CH2P (C6Hs) 2, and a support containing silica.
Die erfindungsgemässe Hydroformylierung erfolgt vorzugsweise bei 50 bis 200 °C bei einem Druck bis zu 200 bar. The hydroformylation according to the invention is preferably carried out at 50 to 200 ° C. at a pressure of up to 200 bar.
Die Verwendung eines heterogenen Katalysators gestattet die Durchführung der Hydroformylierung unter kon-40 tinuierlichen Fliessbedingungen. Unter diesen Bedingungen zeigt die Reaktion eine unerwartet hohe Selektivität zu den Monoaldehyden der Formeln I und II, selbst dann, wenn man einen Uberschuss an Kohlenmonoxid und Wasserstoff verwendet. The use of a heterogeneous catalyst allows the hydroformylation to be carried out under continuous flow conditions. Under these conditions, the reaction shows an unexpectedly high selectivity for the monoaldehydes of the formulas I and II, even when using an excess of carbon monoxide and hydrogen.
45 Das Undecenal der Formel II, nämlich 2-Methyldec-9-enal, ist neu. Das Beispiel erläutert die Erfindung. 45 The undecenal of formula II, namely 2-methyldec-9-enal, is new. The example explains the invention.
Ausführungsbeispiel Embodiment
(a) Disproportionierung von Cycloocten so Der Katalysator enthält 14 Gewichtsprozent Re207,1,3 Gewichtsprozent Kaliumionen und 84,7 Gewichtsprozent y -Aluminiumoxid. Das Cycloocten wird mit einer Geschwindigkeit von 0,75 g je g Katalysator je Stunde über den Katalysator geleitet, zusammen mit Äthylen mit einer Geschwin-55 digkeit von 1,7 g je g Katalysator je Stunde. Der Gesamtdruck der Reaktionsteilnehmer beträgt 70 bar, die Temperatur 20 °C. Unter diesen Bedingungen erhält man eine Cyc-loocten-Umwandlung von 97% (Gas-Flüssigchromatographie). Die Selektivität zu dem benötigten 1,9-Decadien be-60 trägt 52,6%. Das Produkt wird durch Destillation isoliert, Kp. 112 bis 113°C/18662Pa. (a) Disproportionation of cyclooctene so The catalyst contains 14 percent by weight of Re207.1.3 percent by weight of potassium ions and 84.7 percent by weight of y-aluminum oxide. The cyclooctene is passed over the catalyst at a rate of 0.75 g per g of catalyst per hour, together with ethylene at a rate of 1.7 g per g of catalyst per hour. The total pressure of the reactants is 70 bar, the temperature 20 ° C. Under these conditions, a Cyc-loocten conversion of 97% is obtained (gas-liquid chromatography). The selectivity to the required 1,9-decadiene be-60 is 52.6%. The product is isolated by distillation, bp 112 to 113 ° C / 18662Pa.
(b) Hydroformylierung von 1,9-Decadien (b) Hydroformylation of 1,9-decadiene
Der Katalysator ist heterogen, hergestellt durch Umset-65 zen von Siliciumdioxid mit einem vorgebildeten Komplex von The catalyst is heterogeneous, made by reacting silicon dioxide with a preformed complex of
(C2HsO)3SiCH2CH2P(C6H5)2 und RhCl(CO)[P(C6H5)3]3. Die Hydroformylierung wird im Fliessverfahren mit einer (C2HsO) 3SiCH2CH2P (C6H5) 2 and RhCl (CO) [P (C6H5) 3] 3. The hydroformylation is carried out in the flow process with a
3 3rd
629 738 629 738
Lösung von 1,9-Decadien in n-Heptan in einem Gewichtsverhältnis von 1:1 durchgeführt. Solution of 1,9-decadiene in n-heptane in a weight ratio of 1: 1 performed.
Die anderen Reaktionsbedingungen sind: Dien-Fliessgeschwindigkeit: 4,0 g/g Katalysator/Stunde Molverhältnis von Wasserstoff:Kohlenmonooxid:Dien: 2,5:2,5:1 The other reaction conditions are: diene flow rate: 4.0 g / g catalyst / hour molar ratio of hydrogen: carbon monoxide: diene: 2.5: 2.5: 1
Temperatur: 80 °C Druck: 40 bar Temperature: 80 ° C pressure: 40 bar
Unter diesen Bedingungen erhält man eine Dien-Um-wandlung von 30%. Das Produkt besteht hauptsächlich (80%) aus den beiden Monoaldehyden A und B im Verhältnis von 6:4, die durch Destillation getrennt werden können. Under these conditions, a diene conversion of 30% is obtained. The product consists mainly (80%) of the two mono aldehydes A and B in a ratio of 6: 4, which can be separated by distillation.
A: Undec-10-enal, Kp. 105 bis 107°C/2666 Pa B: 2-Methyldec-9-enal, Kp. 100 bis 101 °C/2666 Pa Das NMR-Spektrum des Monoaldehyds B wird in deu-teriertem Chloroform bei 60 MHz gemessen und mit einem s Tetramethylsilan-Standard verglichen (Werte in ppm). A: Undec-10-enal, bp. 105 to 107 ° C / 2666 Pa B: 2-methyldec-9-enal, bp. 100 to 101 ° C / 2666 Pa The NMR spectrum of the monoaldehyde B is under-interpreted Chloroform measured at 60 MHz and compared with a s tetramethylsilane standard (values in ppm).
NMR: § = 9,50 (Dublett, CHO); 5,8 bis 6,1 Multiple«, -CH = CH2); 2,30 (Multiple«, CH3-CH-CO); 2,04 (Multiple«, =CH-CH2); 1,33 (Multiple«,-(CH2)6-); 1,08 (Dublett, CH-CH3). NMR: § = 9.50 (doublet, CHO); 5.8 to 6.1 multiple «, -CH = CH2); 2.30 (multiple, CH3-CH-CO); 2.04 (multiple, = CH-CH2); 1.33 (multiple «, - (CH2) 6-); 1.08 (doublet, CH-CH3).
10 10th
Der Geruch dieser Verbindung ist dem Geruch des bekannten Isomeren A sehr ähnlich. The smell of this compound is very similar to the smell of the known isomer A.
s s
Claims (8)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2279776A GB1555551A (en) | 1976-06-02 | 1976-06-02 | Preparation of aldehydes |
Publications (1)
Publication Number | Publication Date |
---|---|
CH629738A5 true CH629738A5 (en) | 1982-05-14 |
Family
ID=10185214
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH664577A CH629738A5 (en) | 1976-06-02 | 1977-05-31 | Process for preparing undecenals |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS52148011A (en) |
CH (1) | CH629738A5 (en) |
DE (1) | DE2724484A1 (en) |
FR (1) | FR2361325A1 (en) |
GB (1) | GB1555551A (en) |
NL (1) | NL7705927A (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2833538C2 (en) * | 1978-07-31 | 1984-09-20 | Ruhrchemie Ag, 4200 Oberhausen | Process for the preparation of α-methyl branched aldehydes |
DE2929340A1 (en) * | 1979-07-20 | 1981-02-12 | Haarmann & Reimer Gmbh | 3-METHYL ALDEHYDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A FRAGRANCE |
DE3628664A1 (en) * | 1986-08-23 | 1988-03-03 | Degussa | METHOD FOR PRODUCING 1,12-DODECANDEIAEUR II |
GB2195117B (en) * | 1986-09-16 | 1990-10-31 | Agency Ind Science Techn | Process for direct carbonylation of hydrocarbons |
GB8923433D0 (en) * | 1989-10-18 | 1989-12-06 | Shell Int Research | Novel compounds |
US6756411B2 (en) | 1995-06-29 | 2004-06-29 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
-
1976
- 1976-06-02 GB GB2279776A patent/GB1555551A/en not_active Expired
-
1977
- 1977-05-31 CH CH664577A patent/CH629738A5/en not_active IP Right Cessation
- 1977-05-31 FR FR7716480A patent/FR2361325A1/en active Granted
- 1977-05-31 JP JP6287777A patent/JPS52148011A/en active Granted
- 1977-05-31 NL NL7705927A patent/NL7705927A/en active Search and Examination
- 1977-05-31 DE DE19772724484 patent/DE2724484A1/en active Granted
Also Published As
Publication number | Publication date |
---|---|
FR2361325B1 (en) | 1981-01-09 |
DE2724484C2 (en) | 1987-09-03 |
FR2361325A1 (en) | 1978-03-10 |
DE2724484A1 (en) | 1977-12-22 |
JPS52148011A (en) | 1977-12-08 |
NL7705927A (en) | 1977-12-06 |
GB1555551A (en) | 1979-11-14 |
JPS6120528B2 (en) | 1986-05-22 |
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