JP2019524661A5 - - Google Patents
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- Publication number
- JP2019524661A5 JP2019524661A5 JP2018566851A JP2018566851A JP2019524661A5 JP 2019524661 A5 JP2019524661 A5 JP 2019524661A5 JP 2018566851 A JP2018566851 A JP 2018566851A JP 2018566851 A JP2018566851 A JP 2018566851A JP 2019524661 A5 JP2019524661 A5 JP 2019524661A5
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- peroxide
- quench
- flow
- peroxide mixture
- 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.)
- Granted
Links
- 150000002978 peroxides Chemical class 0.000 claims description 161
- 238000010791 quenching Methods 0.000 claims description 149
- 239000000203 mixture Substances 0.000 claims description 100
- 239000000243 solution Substances 0.000 claims description 95
- 238000000034 method Methods 0.000 claims description 72
- 239000003153 chemical reaction reagent Substances 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 35
- 239000007924 injection Substances 0.000 claims description 35
- 239000007788 liquid Substances 0.000 claims description 35
- 230000000171 quenching effect Effects 0.000 claims description 33
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 17
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 13
- 238000005949 ozonolysis reaction Methods 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 239000010408 film Substances 0.000 claims description 10
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 claims description 10
- 238000004448 titration Methods 0.000 claims description 9
- 239000012159 carrier gas Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000007599 discharging Methods 0.000 claims description 6
- -1 fatty acid ester Chemical class 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 150000003505 terpenes Chemical class 0.000 claims description 6
- 235000007586 terpenes Nutrition 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000008158 vegetable oil Substances 0.000 claims description 6
- 239000002826 coolant Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000011552 falling film Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims 10
- 239000007789 gas Substances 0.000 claims 6
- 230000001804 emulsifying effect Effects 0.000 claims 2
- 239000002420 orchard Substances 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 7
- 229950006389 thiodiglycol Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 229910000541 Marine grade stainless Inorganic materials 0.000 description 3
- 229910000990 Ni alloy Inorganic materials 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 230000003134 recirculating effect Effects 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662352926P | 2016-06-21 | 2016-06-21 | |
| US62/352,926 | 2016-06-21 | ||
| US201762504487P | 2017-05-10 | 2017-05-10 | |
| US62/504,487 | 2017-05-10 | ||
| PCT/US2017/038577 WO2017223220A1 (en) | 2016-06-21 | 2017-06-21 | Flow-through reactors for the continuous quenching of peroxide mixtures and methods comprising the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019524661A JP2019524661A (ja) | 2019-09-05 |
| JP2019524661A5 true JP2019524661A5 (enExample) | 2020-02-20 |
| JP7028457B2 JP7028457B2 (ja) | 2022-03-02 |
Family
ID=60783379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018566851A Active JP7028457B2 (ja) | 2016-06-21 | 2017-06-21 | 過酸化物混合物の連続クエンチのためのフロースルー反応器およびそれを含む方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10668446B2 (enExample) |
| EP (1) | EP3472124A4 (enExample) |
| JP (1) | JP7028457B2 (enExample) |
| CA (1) | CA3026192A1 (enExample) |
| WO (1) | WO2017223220A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9682914B2 (en) | 2014-01-13 | 2017-06-20 | P2 Science, Inc. | Terpene-derived acids and esters and methods for preparing and using same |
| US10071944B2 (en) | 2014-06-20 | 2018-09-11 | P2 Science, Inc. | Film ozonolysis in a tubular or multitubular reactor |
| WO2017223220A1 (en) | 2016-06-21 | 2017-12-28 | P2 Science, Inc. | Flow-through reactors for the continuous quenching of peroxide mixtures and methods comprising the same |
| EP3512631B1 (en) | 2016-09-16 | 2022-03-23 | P2 Science, Inc. | Uses of vanadium to oxidize aldehydes and ozonides |
| JP7546296B2 (ja) | 2018-10-19 | 2024-09-06 | ピー２・サイエンス・インコーポレイテッド | オゾニドの不均化クエンチの新規方法 |
| CN113578244A (zh) * | 2021-08-09 | 2021-11-02 | 聊城鲁西甲胺化工有限公司 | 一种列管式反应装置及其应用 |
| EP4605368A1 (en) | 2022-11-22 | 2025-08-27 | P2 Science, Inc. | New method for the ozonolytic synthesis of high melting dicarboxylic acids and oxo-acids |
| WO2024167957A1 (en) * | 2023-02-06 | 2024-08-15 | P2 Science, Inc. | New method for ozonolysis and reductive quenching of ozonides |
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|---|---|---|---|---|
| US2404666A (en) * | 1944-11-08 | 1946-07-23 | Thompson Prod Inc | Shock absorbing device |
| US2813113A (en) | 1953-05-07 | 1957-11-12 | Emery Industries Inc | Method of making azelaic acid |
| US3023244A (en) | 1959-04-02 | 1962-02-27 | Givaudan Corp | Process for making pinonic aldehyde |
| CH493451A (de) | 1967-09-15 | 1970-07-15 | Givaudan & Cie Sa | Verfahren zur Herstellung von Terpenderivaten |
| GB1555333A (en) | 1975-05-29 | 1979-11-07 | Bush Boake Allen Ltd | Perfumery compositions comprising hydroxy- or alkoxy-substituted c9 alkanals alkanols and esters |
| IT1100096B (it) | 1978-11-10 | 1985-09-28 | Snia Viscosa | Procedimento per la preparazione di acidi alfa,omega-dicarbossilici |
| US4296258A (en) * | 1979-01-26 | 1981-10-20 | Firmenich Sa | Process for the preparation of macrocyclic ketones |
| IT1166068B (it) | 1979-02-23 | 1987-04-29 | Ballestra Chim | Procedimento perfezionato per la solfonazione a film in un reattore multitubolare a reattore multitubolare atto a realizare detto procedimento |
| US4491537A (en) | 1983-07-08 | 1985-01-01 | International Flavors & Fragrances Inc. | Tertiary hydroxyl carboxaldehydes and organoleptic use thereof |
| DE3722566A1 (de) | 1987-07-08 | 1989-01-19 | Henkel Kgaa | Verfahren zur kontinuierlichen ozonisierung von ungesaettigten organischen verbindungen |
| EP0555472B1 (en) | 1991-08-06 | 1995-11-29 | Lion Corporation | Process for ozonizing unsaturated fatty acid or lower alkyl ester thereof and oxidative decomposition of the resulting ozonide |
| JP3271785B2 (ja) | 1992-02-20 | 2002-04-08 | 長谷川香料株式会社 | ８−ヒドロキシ−８−メチルノナナールを含有する香料組成物 |
| US5650536A (en) * | 1992-12-17 | 1997-07-22 | Exxon Chemical Patents Inc. | Continuous process for production of functionalized olefins |
| DK0707566T3 (da) | 1993-07-09 | 2000-09-04 | Theramex | Hidtil ukendte strukturelle analoger til vitamin D |
| US5543565A (en) | 1995-01-20 | 1996-08-06 | Henkel Corporation | Method for forming two terminal carboxylic acid groups from an ozonide |
| DE19532886A1 (de) | 1995-09-06 | 1997-03-13 | Haarmann & Reimer Gmbh | Offenkettige olefinisch ungesättigte Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Riechstoffe |
| US6287431B1 (en) | 1997-03-21 | 2001-09-11 | Lynntech International, Ltd. | Integrated ozone generator system |
| CN1268107A (zh) | 1997-06-27 | 2000-09-27 | 普罗格特-甘布尔公司 | 直链缩醛和缩酮香料前体 |
| DE19741645A1 (de) | 1997-09-22 | 1999-03-25 | Bayer Ag | Verfahren und Vorrichtung zur Oxidation organischer Verbindungen in flüssiger Phase unter Verwendung peroxidischer Oxidationsmittel |
| EP1095700A1 (de) | 1999-10-29 | 2001-05-02 | Dr. Frische GmbH | Verfahren zur Durchführung einer Mehrphasenreaktion nach dem Gegenstromprinzip einer flüssigen und gasförmigen Phase und Vorrichtung zur Durchführung des Verfahrens |
| DE10010770C5 (de) | 2000-03-04 | 2007-02-22 | Celanese Chemicals Europe Gmbh | Nichtkatalytisches Verfahren zur Herstellung geradkettiger aliphatischer Carbonsäuren aus Aldehyden |
| DE10010771C1 (de) | 2000-03-04 | 2001-05-03 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung aliphatischer Carbonsäuren aus Aldehyden |
| DE60109058T2 (de) | 2000-12-12 | 2006-03-02 | Lynntech International, Ltd., College Station | Elektrochemische vorrichtung mit ausfahrbarer elektrode |
| AT500421A1 (de) | 2000-12-14 | 2005-12-15 | Dsm Fine Chem Austria Gmbh | Verbessertes verfahren zur reinigung von ketonen, erhalten aus den korrespondierenden terpenen durch ozonolyse und reduktion |
| WO2003011802A1 (de) | 2001-07-09 | 2003-02-13 | Symrise Gmbh & Co. Kg | ISO-β-BISABOLOL ALS DUFT-UND AROMASTOFF |
| KR101142653B1 (ko) | 2004-02-09 | 2012-05-10 | 미츠비시 레이온 가부시키가이샤 | α,β-불포화 카복실산의 제조방법 |
| KR100843594B1 (ko) | 2005-09-07 | 2008-07-03 | 주식회사 엘지화학 | 액상 산화 반응을 이용한 알데히드 화합물로부터의유기산의 제조 방법 |
| EP1969131A1 (en) | 2005-12-15 | 2008-09-17 | Isobionics B.V. | Process for the preparation of delta lactones |
| DE102005060816B3 (de) | 2005-12-21 | 2007-03-29 | Rudolf Aigner | Verfahren zur Sulfonierung bzw. Sulfatierung von sulfonierbaren bzw. sulfatierbaren organischen Substanzen |
| DE102006021438A1 (de) | 2006-05-09 | 2007-11-15 | Cognis Ip Management Gmbh | Verfahren zur Ozonolyse von ungesättigten Verbindungen |
| WO2008145683A1 (en) | 2007-06-01 | 2008-12-04 | Dsm Fine Chemicals Austria Nfg Gmbh & Co Kg | Tube bundle falling film microreactor for performing gas liquid reactions |
| US7829342B2 (en) | 2007-10-03 | 2010-11-09 | The Board Of Trustees Of The Universiy Of Illinois | Selective aliphatic C-H oxidation |
| US8425784B2 (en) | 2007-11-05 | 2013-04-23 | University Of Kansas | Ozonolysis reactions in liquid CO2 and CO2-expanded solvents |
| EP2399897B1 (en) | 2009-02-17 | 2015-08-12 | Utsunomiya University | Method for producing oxygen-containing compound |
| EP2404666A1 (fr) * | 2010-07-09 | 2012-01-11 | Rhodia Opérations | Module de transformation continue d'au moins un produit fluide, unité et procédé associés. |
| CN102653531B (zh) | 2011-03-04 | 2014-08-13 | 上海爱普植物科技有限公司 | 一种马索亚内酯的合成方法 |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8912350B2 (en) | 2011-06-23 | 2014-12-16 | The Procter & Gamble Company | Perfume systems |
| US8840705B2 (en) | 2011-07-07 | 2014-09-23 | Linde Aktiengesellschaft | Methods for the ozonolysis of organic compounds |
| DE102011083285A1 (de) | 2011-09-23 | 2013-03-28 | Evonik Degussa Gmbh | Ozonolyse von ungesättigten Fettsäuren und Derivaten davon |
| WO2013053102A1 (en) | 2011-10-11 | 2013-04-18 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2014015290A1 (en) * | 2012-07-19 | 2014-01-23 | P2 Science, Inc. | Ozonolysis operations for generation of reduced and/or oxidized product streams |
| CN102795987A (zh) | 2012-08-09 | 2012-11-28 | 西安近代化学研究所 | 3，3，3-三氟丙酸的制备方法 |
| US9586883B2 (en) | 2013-04-19 | 2017-03-07 | California Institute Of Technology | Aldehyde-selective wacker-type oxidation of unbiased alkenes |
| AP2016009125A0 (en) | 2013-09-16 | 2016-04-30 | Emergent Virology Llc | Deoxynojirimycin derivatives and methods of their using |
| US9682914B2 (en) | 2014-01-13 | 2017-06-20 | P2 Science, Inc. | Terpene-derived acids and esters and methods for preparing and using same |
| WO2015126936A1 (en) | 2014-02-19 | 2015-08-27 | P2 Science, Inc. | Substituted delta-lactones and methods of preparing same |
| US10071941B2 (en) | 2014-06-10 | 2018-09-11 | P2 Science, Inc. | Terpene-derived compounds and methods for preparing and using same |
| US10071944B2 (en) | 2014-06-20 | 2018-09-11 | P2 Science, Inc. | Film ozonolysis in a tubular or multitubular reactor |
| US20170247314A1 (en) | 2014-08-06 | 2017-08-31 | P2 Science, Inc. | Fragrances from the esters of fatty acids |
| GB201421855D0 (en) | 2014-12-09 | 2015-01-21 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2017223220A1 (en) | 2016-06-21 | 2017-12-28 | P2 Science, Inc. | Flow-through reactors for the continuous quenching of peroxide mixtures and methods comprising the same |
| EP3512631B1 (en) | 2016-09-16 | 2022-03-23 | P2 Science, Inc. | Uses of vanadium to oxidize aldehydes and ozonides |
-
2017
- 2017-06-21 WO PCT/US2017/038577 patent/WO2017223220A1/en not_active Ceased
- 2017-06-21 EP EP17816151.9A patent/EP3472124A4/en not_active Ceased
- 2017-06-21 JP JP2018566851A patent/JP7028457B2/ja active Active
- 2017-06-21 US US16/081,819 patent/US10668446B2/en active Active
- 2017-06-21 CA CA3026192A patent/CA3026192A1/en active Pending
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