CA1305726C - Procede de preparation du citral - Google Patents
Procede de preparation du citralInfo
- Publication number
- CA1305726C CA1305726C CA000596507A CA596507A CA1305726C CA 1305726 C CA1305726 C CA 1305726C CA 000596507 A CA000596507 A CA 000596507A CA 596507 A CA596507 A CA 596507A CA 1305726 C CA1305726 C CA 1305726C
- Authority
- CA
- Canada
- Prior art keywords
- lithium
- cracking
- halide
- carried out
- prenatal
- 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 14
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229940043350 citral Drugs 0.000 title claims abstract description 8
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 13
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims abstract description 9
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 9
- -1 lithium halide Chemical class 0.000 claims abstract description 9
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 11
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 11
- 238000005336 cracking Methods 0.000 claims description 11
- 238000006359 acetalization reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 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
- C07C45/51—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
- C07C45/515—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 an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8806524A FR2631337B1 (fr) | 1988-05-16 | 1988-05-16 | Procede de preparation du citral |
| FR8806524 | 1988-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1305726C true CA1305726C (fr) | 1992-07-28 |
Family
ID=9366324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000596507A Expired - Lifetime CA1305726C (fr) | 1988-05-16 | 1989-04-12 | Procede de preparation du citral |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4933500A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0344043B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH0217145A (cg-RX-API-DMAC7.html) |
| KR (1) | KR900017975A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE73754T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1305726C (cg-RX-API-DMAC7.html) |
| DE (1) | DE68901002D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2030284T3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2631337B1 (cg-RX-API-DMAC7.html) |
| GR (1) | GR3004087T3 (cg-RX-API-DMAC7.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2656604B1 (fr) * | 1990-01-03 | 1992-03-20 | Rhone Poulenc Sante | Procede de preparation du citral. |
| US5094720A (en) * | 1990-10-18 | 1992-03-10 | Union Camp Corporation | Process for the distillative purification of citral |
| US6278016B1 (en) | 1999-12-09 | 2001-08-21 | Loyola University Of Chicago | Methods for conversion of isoprene to prenyl alcohol and related compounds |
| JP4784913B2 (ja) * | 2004-10-29 | 2011-10-05 | 独立行政法人産業技術総合研究所 | シトラールの合成反応法とその装置 |
| WO2008037693A1 (de) * | 2006-09-26 | 2008-04-03 | Basf Se | Kontinuierliches verfahren zur herstellung von citral |
| CN103787852B (zh) * | 2014-01-23 | 2015-06-10 | 万华化学集团股份有限公司 | 一种柠檬醛的制备方法 |
| CN111018682A (zh) * | 2019-12-17 | 2020-04-17 | 南通天泽化工有限公司 | 一种柠檬醛的制备方法 |
| CN112058313B (zh) * | 2020-09-30 | 2023-06-16 | 山东新和成药业有限公司 | 一种复合催化剂、其制备方法及其在柠檬醛合成中的应用 |
| CN112299962B (zh) * | 2020-10-19 | 2022-04-12 | 山东新和成药业有限公司 | 一种3-甲基-2-丁烯-1-醛二异戊烯基缩醛的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2157035C3 (de) * | 1971-11-17 | 1974-07-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung höhermolekularer alpha-beta-ungesättigter Aldehyde |
| CH597126A5 (cg-RX-API-DMAC7.html) * | 1973-03-12 | 1978-03-31 | Hoffmann La Roche | |
| US3978092A (en) * | 1973-05-14 | 1976-08-31 | Teijin Limited | Process for the preparation of unsaturated carbonyl compounds |
| US3943166A (en) * | 1973-06-21 | 1976-03-09 | General Electric Company | Separation of an isomeric mixture of acetoxy-aldehydes by catalytic decomposition of an aldehyde to acetic acid and methacrolein |
| DE2926562A1 (de) * | 1979-06-30 | 1981-01-22 | Basf Ag | Verfahren zur herstellung von citral |
| JPS5695142A (en) * | 1979-12-28 | 1981-08-01 | T Hasegawa Co Ltd | Preparation of aliphatic aldehyde |
| JPS6122038A (ja) * | 1984-07-06 | 1986-01-30 | Kuraray Co Ltd | 不飽和アセタ−ルの製法 |
| US4551560A (en) * | 1984-11-09 | 1985-11-05 | The Halcon Sd Group, Inc. | Thermally-induced hydrolysis of acetal |
| US4562296A (en) * | 1984-11-13 | 1985-12-31 | Ethyl Corporation | Production of aldehydes and ketones |
-
1988
- 1988-05-16 FR FR8806524A patent/FR2631337B1/fr not_active Expired - Lifetime
-
1989
- 1989-04-12 CA CA000596507A patent/CA1305726C/fr not_active Expired - Lifetime
- 1989-05-12 DE DE8989401334T patent/DE68901002D1/de not_active Expired - Fee Related
- 1989-05-12 EP EP89401334A patent/EP0344043B1/fr not_active Expired - Lifetime
- 1989-05-12 AT AT89401334T patent/ATE73754T1/de not_active IP Right Cessation
- 1989-05-12 ES ES198989401334T patent/ES2030284T3/es not_active Expired - Lifetime
- 1989-05-15 JP JP1118832A patent/JPH0217145A/ja active Pending
- 1989-05-15 US US07/351,833 patent/US4933500A/en not_active Expired - Fee Related
- 1989-05-15 KR KR1019890006477A patent/KR900017975A/ko not_active Ceased
-
1992
- 1992-03-19 GR GR910401087T patent/GR3004087T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE68901002D1 (de) | 1992-04-23 |
| ES2030284T3 (es) | 1992-10-16 |
| FR2631337A1 (fr) | 1989-11-17 |
| EP0344043B1 (fr) | 1992-03-18 |
| US4933500A (en) | 1990-06-12 |
| JPH0217145A (ja) | 1990-01-22 |
| FR2631337B1 (fr) | 1990-07-27 |
| GR3004087T3 (cg-RX-API-DMAC7.html) | 1993-03-31 |
| ATE73754T1 (de) | 1992-04-15 |
| EP0344043A1 (fr) | 1989-11-29 |
| KR900017975A (ko) | 1990-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |