JPWO2020099461A5 - - Google Patents
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- Publication number
- JPWO2020099461A5 JPWO2020099461A5 JP2021525580A JP2021525580A JPWO2020099461A5 JP WO2020099461 A5 JPWO2020099461 A5 JP WO2020099461A5 JP 2021525580 A JP2021525580 A JP 2021525580A JP 2021525580 A JP2021525580 A JP 2021525580A JP WO2020099461 A5 JPWO2020099461 A5 JP WO2020099461A5
- Authority
- JP
- Japan
- Prior art keywords
- aqueous mixture
- reaction vessel
- feed
- reactor
- hydroxide
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 claims description 268
- 238000000034 method Methods 0.000 claims description 184
- 238000006243 chemical reaction Methods 0.000 claims description 161
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 130
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 110
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 claims description 95
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 87
- 238000002156 mixing Methods 0.000 claims description 81
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 80
- 229940043350 citral Drugs 0.000 claims description 71
- 239000007858 starting material Substances 0.000 claims description 64
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 claims description 62
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 238000011144 upstream manufacturing Methods 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 23
- 230000035484 reaction time Effects 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 8
- 238000004891 communication Methods 0.000 claims description 7
- 230000003247 decreasing effect Effects 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
- 230000008569 process Effects 0.000 description 88
- 229910000000 metal hydroxide Inorganic materials 0.000 description 57
- 150000004692 metal hydroxides Chemical class 0.000 description 57
- 239000007864 aqueous solution Substances 0.000 description 23
- 239000007791 liquid phase Substances 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 18
- 238000012856 packing Methods 0.000 description 14
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 10
- -1 e.g. Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 241000134874 Geraniales Species 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- CUEGEJLBVIFULZ-DHZHZOJOSA-N (5E)-4-hydroxy-6,10-dimethylundeca-5,9-dien-2-one Chemical compound CC(C)=CCC\C(C)=C\C(O)CC(C)=O CUEGEJLBVIFULZ-DHZHZOJOSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CUEGEJLBVIFULZ-FLIBITNWSA-N (5Z)-4-hydroxy-6,10-dimethylundeca-5,9-dien-2-one Chemical compound CC(C)=CCC\C(C)=C/C(O)CC(C)=O CUEGEJLBVIFULZ-FLIBITNWSA-N 0.000 description 2
- RBGLEUBCAJNCTR-UHFFFAOYSA-N 6,10-dimethylundecan-2-one Chemical compound CC(C)CCCC(C)CCCC(C)=O RBGLEUBCAJNCTR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019440 Mg(OH) Inorganic materials 0.000 description 2
- 229910003514 Sr(OH) Inorganic materials 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009529 body temperature measurement Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 235000015872 dietary supplement Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005204 segregation Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JXJIQCXXJGRKRJ-CQJQESKGSA-N (3e,5z)-6,10-dimethylundeca-3,5,9-trien-2-one Chemical compound CC(C)=CCC\C(C)=C/C=C/C(C)=O JXJIQCXXJGRKRJ-CQJQESKGSA-N 0.000 description 1
- JXJIQCXXJGRKRJ-ZQNGMKBSSA-N (3z,5e)-6,10-dimethylundeca-3,5,9-trien-2-one Chemical compound CC(C)=CCC\C(C)=C\C=C/C(C)=O JXJIQCXXJGRKRJ-ZQNGMKBSSA-N 0.000 description 1
- JXJIQCXXJGRKRJ-LQBUGXQISA-N (3z,5z)-6,10-dimethylundeca-3,5,9-trien-2-one Chemical compound CC(C)=CCC\C(C)=C/C=C\C(C)=O JXJIQCXXJGRKRJ-LQBUGXQISA-N 0.000 description 1
- BTCJFWDPNBNPJE-YRNVUSSQSA-N (6E)-4-hydroxy-6,10-dimethylundeca-6,9-dien-2-one Chemical compound OC(CC(C)=O)C\C(=C\CC=C(C)C)\C BTCJFWDPNBNPJE-YRNVUSSQSA-N 0.000 description 1
- BTCJFWDPNBNPJE-XFFZJAGNSA-N (6Z)-4-hydroxy-6,10-dimethylundeca-6,9-dien-2-one Chemical compound OC(CC(C)=O)C\C(=C/CC=C(C)C)\C BTCJFWDPNBNPJE-XFFZJAGNSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FEWIGMWODIRUJM-UHFFFAOYSA-N 4-hexen-3-one Chemical compound CCC(=O)C=CC FEWIGMWODIRUJM-UHFFFAOYSA-N 0.000 description 1
- CUEGEJLBVIFULZ-UHFFFAOYSA-N 4-hydroxy-6,10-dimethylundeca-5,9-dien-2-one Chemical compound CC(C)=CCCC(C)=CC(O)CC(C)=O CUEGEJLBVIFULZ-UHFFFAOYSA-N 0.000 description 1
- BTCJFWDPNBNPJE-UHFFFAOYSA-N 4-hydroxy-6,10-dimethylundeca-6,9-dien-2-one Chemical compound OC(CC(C)=O)CC(=CCC=C(C)C)C BTCJFWDPNBNPJE-UHFFFAOYSA-N 0.000 description 1
- 238000005705 Cannizzaro reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18206006.1 | 2018-11-13 | ||
| EP18206006 | 2018-11-13 | ||
| PCT/EP2019/081125 WO2020099461A1 (en) | 2018-11-13 | 2019-11-13 | Apparatus for and process of making pseudoionone and hydroxy pseudoionone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2022507150A JP2022507150A (ja) | 2022-01-18 |
| JPWO2020099461A5 true JPWO2020099461A5 (de) | 2024-04-26 |
Family
ID=64564548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021525580A Pending JP2022507150A (ja) | 2018-11-13 | 2019-11-13 | プソイドイオノン及びヒドロキシプソイドイオノンを製造するための装置及び方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20240116019A1 (de) |
| EP (1) | EP3880638B1 (de) |
| JP (1) | JP2022507150A (de) |
| KR (1) | KR20210092237A (de) |
| CN (2) | CN118847021A (de) |
| CA (1) | CA3118525A1 (de) |
| ES (1) | ES2936631T3 (de) |
| WO (1) | WO2020099461A1 (de) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6704541A (de) | 1967-03-30 | 1968-10-01 | ||
| US3840601A (en) * | 1972-02-07 | 1974-10-08 | Rhodia | Process for preparation of methyl ionones |
| DE3114071A1 (de) * | 1981-04-08 | 1982-10-28 | Basf Ag, 6700 Ludwigshafen | Verbessertes verfahren zur herstellung mehrfach ungesaettigter ketone |
| US4874900A (en) * | 1987-06-16 | 1989-10-17 | Union Camp Corporation | Preparation of pseudoionones |
| IL134687A (en) * | 1998-07-08 | 2005-05-17 | Montell Technology Company Bv | Process and apparatus for gas-phase polymerisation |
| WO2003029175A1 (en) * | 2001-09-28 | 2003-04-10 | Dsm Ip Assets B.V. | Ethynylation process |
| CN1310863C (zh) * | 2002-11-07 | 2007-04-18 | 巴斯福股份公司 | 假紫罗酮和紫罗酮的连续制备方法 |
| DE10359026A1 (de) * | 2003-12-15 | 2005-07-21 | Basf Ag | Verfahren zur Herstellung von Tetrahydrogeranylaceton |
| US9073027B2 (en) * | 2010-09-09 | 2015-07-07 | Basell Poliolefine Italia S.R.L. | Process and apparatus for the gas-phase polymerization of olefins |
| MY169083A (en) * | 2012-11-30 | 2019-02-14 | Basf Se | Method for the catalytic aldol condensation of aldehydes |
| CN103566862B (zh) * | 2013-11-01 | 2015-10-07 | 太原理工大学 | 一种强剪切力化学反应器 |
| WO2018007165A1 (en) * | 2016-07-06 | 2018-01-11 | Ineos Europe Ag | Polymerisation process |
| PT3826763T (pt) * | 2018-07-24 | 2023-12-15 | Noram Eng And Constructors Ltd | Reactor e método de nitração |
-
2019
- 2019-11-13 CA CA3118525A patent/CA3118525A1/en active Pending
- 2019-11-13 CN CN202410867731.XA patent/CN118847021A/zh active Pending
- 2019-11-13 KR KR1020217017120A patent/KR20210092237A/ko unknown
- 2019-11-13 WO PCT/EP2019/081125 patent/WO2020099461A1/en unknown
- 2019-11-13 US US17/293,503 patent/US20240116019A1/en active Pending
- 2019-11-13 EP EP19801346.8A patent/EP3880638B1/de active Active
- 2019-11-13 ES ES19801346T patent/ES2936631T3/es active Active
- 2019-11-13 CN CN201980082278.9A patent/CN113166018B/zh active Active
- 2019-11-13 JP JP2021525580A patent/JP2022507150A/ja active Pending
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