ES2298577T3 - Procedimiento para la hidrogenacion continua de citronelal para dar citronelol. - Google Patents
Procedimiento para la hidrogenacion continua de citronelal para dar citronelol. Download PDFInfo
- Publication number
- ES2298577T3 ES2298577T3 ES03763837T ES03763837T ES2298577T3 ES 2298577 T3 ES2298577 T3 ES 2298577T3 ES 03763837 T ES03763837 T ES 03763837T ES 03763837 T ES03763837 T ES 03763837T ES 2298577 T3 ES2298577 T3 ES 2298577T3
- Authority
- ES
- Spain
- Prior art keywords
- catalyst
- catalyst particles
- citronelal
- carbon
- procedure
- Prior art date
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- 239000002245 particle Substances 0.000 claims abstract description 30
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000007791 liquid phase Substances 0.000 claims abstract description 20
- 239000007789 gas Substances 0.000 claims abstract description 14
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims abstract description 11
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000000484 citronellol Nutrition 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 4
- 239000012071 phase Substances 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 7
- 238000012856 packing Methods 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 abstract 4
- 229930003633 citronellal Natural products 0.000 abstract 2
- 235000000983 citronellal Nutrition 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 241000060340 Citronella Species 0.000 description 1
- 235000018791 Cymbopogon nardus Nutrition 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- PWGQHOJABIQOOS-UHFFFAOYSA-N copper;dioxido(dioxo)chromium Chemical compound [Cu+2].[O-][Cr]([O-])(=O)=O PWGQHOJABIQOOS-UHFFFAOYSA-N 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- -1 graphite Chemical compound 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10231942A DE10231942A1 (de) | 2002-07-15 | 2002-07-15 | Verfahren zur kontinuierlichen Hydrierung von Citronellal zu Citronellol |
| DE10231942 | 2002-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2298577T3 true ES2298577T3 (es) | 2008-05-16 |
Family
ID=29796364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03763837T Expired - Lifetime ES2298577T3 (es) | 2002-07-15 | 2003-07-14 | Procedimiento para la hidrogenacion continua de citronelal para dar citronelol. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7005554B2 (enExample) |
| EP (1) | EP1523464B1 (enExample) |
| JP (1) | JP2005538078A (enExample) |
| CN (1) | CN1281564C (enExample) |
| AT (1) | ATE384034T1 (enExample) |
| AU (1) | AU2003254347A1 (enExample) |
| CA (1) | CA2492261C (enExample) |
| DE (2) | DE10231942A1 (enExample) |
| ES (1) | ES2298577T3 (enExample) |
| WO (1) | WO2004007411A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6018928B2 (ja) * | 2012-03-02 | 2016-11-02 | 国立大学法人大阪大学 | 選択的水素化方法、その方法に使用する触媒 |
| JP6233032B2 (ja) * | 2013-06-05 | 2017-11-22 | デクセリアルズ株式会社 | 光学活性化合物の製造方法 |
| CN111148779B (zh) * | 2017-07-31 | 2023-12-01 | P2科学公司 | 聚醚衍生物、用途及其制备方法 |
| US11152279B2 (en) | 2018-03-26 | 2021-10-19 | Raytheon Company | Monolithic microwave integrated circuit (MMIC) cooling structure |
| WO2020048991A1 (de) * | 2018-09-05 | 2020-03-12 | Basf Se | Reaktor zur durchführung einer gas/flüssig-zweiphasigen hochdruckreaktion mit einem schäumenden medium |
| EP4341380A4 (en) | 2021-05-17 | 2025-06-04 | P2 Science, Inc. | TERPENE ALCOHOL FATTY ACID ESTERS |
| US12215120B1 (en) | 2021-05-17 | 2025-02-04 | P2 Science, Inc. | Terpene O-glycosides |
| EP4549622A1 (en) | 2023-10-31 | 2025-05-07 | Basf Se | Hydrogenation of carbonyl compounds using hydrogen with low deuterium content |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3346650A (en) * | 1965-03-22 | 1967-10-10 | Glidden Co | Preparation of citronellol |
| US4029709A (en) * | 1976-02-17 | 1977-06-14 | Rhodia, Inc. | Process for the hydrogenation of citral to citronellal and of citronellal to citronellol using chromium-promoted Raney nickel catalyst |
| DE19611976A1 (de) * | 1996-03-26 | 1997-10-02 | Basf Ag | Verfahren und Reaktor zur Durchführung von Stoffumwandlungen mit in Flüssigkeiten suspendierten Katalysatoren |
| DE10160141A1 (de) | 2001-12-07 | 2003-06-18 | Basf Ag | Verfahren zur selektiven Flüssiphasenhydrierung von alpha,beta-ungesättigren Carbonylverbindungen zu ungesättigten Alkoholen in Gegenwart eines Pt/ZnO-Katalysators |
-
2002
- 2002-07-15 DE DE10231942A patent/DE10231942A1/de not_active Withdrawn
-
2003
- 2003-07-14 WO PCT/EP2003/007599 patent/WO2004007411A1/de not_active Ceased
- 2003-07-14 EP EP03763837A patent/EP1523464B1/de not_active Expired - Lifetime
- 2003-07-14 DE DE50309035T patent/DE50309035D1/de not_active Expired - Lifetime
- 2003-07-14 JP JP2004520615A patent/JP2005538078A/ja active Pending
- 2003-07-14 US US10/519,686 patent/US7005554B2/en not_active Expired - Lifetime
- 2003-07-14 AU AU2003254347A patent/AU2003254347A1/en not_active Abandoned
- 2003-07-14 CA CA2492261A patent/CA2492261C/en not_active Expired - Lifetime
- 2003-07-14 ES ES03763837T patent/ES2298577T3/es not_active Expired - Lifetime
- 2003-07-14 AT AT03763837T patent/ATE384034T1/de not_active IP Right Cessation
- 2003-07-14 CN CN03817019.1A patent/CN1281564C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005538078A (ja) | 2005-12-15 |
| DE50309035D1 (de) | 2008-03-06 |
| ATE384034T1 (de) | 2008-02-15 |
| CA2492261A1 (en) | 2004-01-22 |
| US7005554B2 (en) | 2006-02-28 |
| EP1523464B1 (de) | 2008-01-16 |
| US20050256347A1 (en) | 2005-11-17 |
| DE10231942A1 (de) | 2004-01-29 |
| WO2004007411A1 (de) | 2004-01-22 |
| CN1668559A (zh) | 2005-09-14 |
| CN1281564C (zh) | 2006-10-25 |
| CA2492261C (en) | 2010-09-28 |
| EP1523464A1 (de) | 2005-04-20 |
| AU2003254347A1 (en) | 2004-02-02 |
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