CA1082737A - Preparation de citral - Google Patents
Preparation de citralInfo
- Publication number
- CA1082737A CA1082737A CA268,595A CA268595A CA1082737A CA 1082737 A CA1082737 A CA 1082737A CA 268595 A CA268595 A CA 268595A CA 1082737 A CA1082737 A CA 1082737A
- Authority
- CA
- Canada
- Prior art keywords
- citral
- dehydrolinalol
- cocatalyst
- catalyst
- isomerization
- 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
Links
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 title claims abstract description 25
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 229940043350 citral Drugs 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 19
- 238000004821 distillation Methods 0.000 claims description 11
- -1 vanadium ester Chemical class 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 4
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical group [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003682 vanadium compounds Chemical class 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000001371 (5E)-3,5-dimethylocta-1,5,7-trien-3-ol Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZJIQIJIQBTVTDY-SREVYHEPSA-N dehydrolinalool Chemical compound CC(=C)\C=C/CC(C)(O)C=C ZJIQIJIQBTVTDY-SREVYHEPSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000004819 silanols Chemical class 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- CFYUBZHJDXXXQE-UHFFFAOYSA-N 2-ethylcyclohexan-1-ol Chemical compound CCC1CCCCC1O CFYUBZHJDXXXQE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052721 tungsten Inorganic materials 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
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 |
|---|---|---|---|
| FR7539784A FR2335483A1 (fr) | 1975-12-19 | 1975-12-19 | Preparation de citral |
| FR75/39784 | 1975-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082737A true CA1082737A (fr) | 1980-07-29 |
Family
ID=9164188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA268,595A Expired CA1082737A (fr) | 1975-12-19 | 1976-12-17 | Preparation de citral |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4463196A (enExample) |
| JP (1) | JPS5953889B2 (enExample) |
| BE (1) | BE849541A (enExample) |
| CA (1) | CA1082737A (enExample) |
| CH (1) | CH598171A5 (enExample) |
| DE (1) | DE2657335C3 (enExample) |
| FR (1) | FR2335483A1 (enExample) |
| GB (1) | GB1499610A (enExample) |
| IT (1) | IT1065799B (enExample) |
| NL (1) | NL187682C (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1409323A (en) * | 1972-11-02 | 1975-10-08 | Roche Products Ltd | Process for the manufacture of oxo compounds |
| DE2926562A1 (de) * | 1979-06-30 | 1981-01-22 | Basf Ag | Verfahren zur herstellung von citral |
| US5093538A (en) * | 1989-06-09 | 1992-03-03 | Union Camp Corporation | Processes for the conversion of myrcene to citral |
| US5094720A (en) * | 1990-10-18 | 1992-03-10 | Union Camp Corporation | Process for the distillative purification of citral |
| SG72861A1 (en) * | 1997-09-30 | 2000-05-23 | Kuraray Co | Process for producing 7-octen-1-al |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524866A (en) * | 1947-11-14 | 1950-10-10 | Publicker Ind Inc | Conversion of acetylenic alcohols in the vapor phase |
| US2524865A (en) * | 1947-11-14 | 1950-10-10 | Publicker Ind Inc | Vapor phase conversion of 1-alkynols |
| US2853520A (en) * | 1953-11-05 | 1958-09-23 | Univ Ohio State Res Found | Conversion of ethynyl compounds to acetyl compounds |
| US3920751A (en) * | 1967-11-28 | 1975-11-18 | Rhone Poulenc Sa | Process for the preparation of ethylenic carbonyl compounds |
| FR96548E (fr) * | 1968-12-17 | 1972-10-20 | Rhone Poulenc Sa | Procédé de préparation de composés carbonyles α-éthyléniques. |
| CH577360A5 (enExample) * | 1973-02-08 | 1976-07-15 | Muellheim Ag Utilis | |
| US3994936A (en) * | 1973-10-29 | 1976-11-30 | Hoffmann-La Roche Inc. | Catalytic rearrangement |
-
1975
- 1975-12-19 FR FR7539784A patent/FR2335483A1/fr active Granted
-
1976
- 1976-12-17 BE BE173383A patent/BE849541A/xx not_active IP Right Cessation
- 1976-12-17 JP JP51150995A patent/JPS5953889B2/ja not_active Expired
- 1976-12-17 NL NLAANVRAGE7614062,A patent/NL187682C/xx not_active IP Right Cessation
- 1976-12-17 CH CH1595576A patent/CH598171A5/xx not_active IP Right Cessation
- 1976-12-17 DE DE2657335A patent/DE2657335C3/de not_active Expired
- 1976-12-17 GB GB52832/76A patent/GB1499610A/en not_active Expired
- 1976-12-17 IT IT30562/76A patent/IT1065799B/it active
- 1976-12-17 CA CA268,595A patent/CA1082737A/fr not_active Expired
-
1980
- 1980-05-08 US US06/147,740 patent/US4463196A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2335483B1 (enExample) | 1978-06-23 |
| DE2657335C3 (de) | 1979-08-30 |
| NL187682B (nl) | 1991-07-16 |
| GB1499610A (en) | 1978-02-01 |
| US4463196A (en) | 1984-07-31 |
| BE849541A (fr) | 1977-06-17 |
| IT1065799B (it) | 1985-03-04 |
| JPS5953889B2 (ja) | 1984-12-27 |
| NL187682C (nl) | 1991-12-16 |
| JPS5277006A (en) | 1977-06-29 |
| NL7614062A (nl) | 1977-06-21 |
| CH598171A5 (enExample) | 1978-04-28 |
| DE2657335B2 (de) | 1978-12-21 |
| DE2657335A1 (de) | 1977-06-30 |
| FR2335483A1 (fr) | 1977-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |