DE2713863C2 - - Google Patents
Info
- Publication number
- DE2713863C2 DE2713863C2 DE19772713863 DE2713863A DE2713863C2 DE 2713863 C2 DE2713863 C2 DE 2713863C2 DE 19772713863 DE19772713863 DE 19772713863 DE 2713863 A DE2713863 A DE 2713863A DE 2713863 C2 DE2713863 C2 DE 2713863C2
- Authority
- DE
- Germany
- Prior art keywords
- ozone
- reactors
- reactor
- feed mixture
- ozonized
- 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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 238000006385 ozonation reaction Methods 0.000 claims description 26
- 239000000376 reactant Substances 0.000 claims description 16
- 230000003068 static effect Effects 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 9
- -1 ester hydroperoxides Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 7
- 238000012856 packing Methods 0.000 claims description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 4
- 235000020778 linoleic acid Nutrition 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 3
- 239000007789 gas Substances 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000000047 product Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 9
- 238000007248 oxidative elimination reaction Methods 0.000 description 8
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000003776 cleavage reaction Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000005643 Pelargonic acid Substances 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 238000003915 air pollution Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/245—Stationary reactors without moving elements inside placed in series
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/242—Tubular reactors in series
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00094—Jackets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00121—Controlling the temperature by direct heating or cooling
- B01J2219/00128—Controlling the temperature by direct heating or cooling by evaporation of reactants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772713863 DE2713863A1 (de) | 1977-03-29 | 1977-03-29 | Verfahren und vorrichtung zum kontinuierlichen ozonisieren |
| NL7802549A NL7802549A (nl) | 1977-03-29 | 1978-03-08 | Werkwijze en inrichting voor het continu ozoniseren. |
| BE186302A BE865357A (fr) | 1977-03-29 | 1978-03-28 | Procede et dispositif d'ozonisation en continu |
| US05/966,948 US4185025A (en) | 1977-03-29 | 1978-12-06 | Continuous process for ozonizing unsaturated compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772713863 DE2713863A1 (de) | 1977-03-29 | 1977-03-29 | Verfahren und vorrichtung zum kontinuierlichen ozonisieren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2713863A1 DE2713863A1 (de) | 1978-10-12 |
| DE2713863C2 true DE2713863C2 (enrdf_load_stackoverflow) | 1989-06-01 |
Family
ID=6005006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772713863 Granted DE2713863A1 (de) | 1977-03-29 | 1977-03-29 | Verfahren und vorrichtung zum kontinuierlichen ozonisieren |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE865357A (enrdf_load_stackoverflow) |
| DE (1) | DE2713863A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7802549A (enrdf_load_stackoverflow) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2754366A1 (de) * | 1977-12-07 | 1979-06-13 | Henkel Kgaa | Vorrichtung zum kontinuierlichen ozonisieren |
| DE2942279C2 (de) * | 1979-10-19 | 1986-01-09 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Reinigung des bei der Umsetzung von Olefinen mit Ozon in carbonsaurem Medium die Ozonolysestufe verlassenden Gasstromes |
| DE3005514A1 (de) * | 1980-02-14 | 1981-10-01 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur kontinuierlichen ozonolyse von olefinen |
| DE3722566A1 (de) * | 1987-07-08 | 1989-01-19 | Henkel Kgaa | Verfahren zur kontinuierlichen ozonisierung von ungesaettigten organischen verbindungen |
| DE69115053T2 (de) * | 1991-08-06 | 1996-06-27 | Lion Corp | Verfahren zur ozonisierung ungesättigter fettsäuren oder deren niedriger alkylester und zum oxidativen abbau der resultierenden ozonide. |
| JP2000219886A (ja) | 1999-02-01 | 2000-08-08 | Masatoshi Matsumura | 植物油（バージン油）又は植物性廃油のディーゼルエンジン用燃料化精製方法及び装置 |
| AT500489A1 (de) * | 2001-03-09 | 2006-01-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von mono- oder biscarbonyl- oder hydroxylverbindungen |
| CN102657927A (zh) * | 2012-05-18 | 2012-09-12 | 西安费斯达自动化工程有限公司 | 一种臭氧对亚油酸的处理方法 |
| US12312557B2 (en) | 2020-08-17 | 2025-05-27 | Poet Research, Inc. | Methods of making antimicrobial compositions and/or virucidal disinfectant compositions from vegetable oil, and related antimicrobial compositions and/or virucidal disinfectant compositions and uses |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2813113A (en) * | 1953-05-07 | 1957-11-12 | Emery Industries Inc | Method of making azelaic acid |
| US2865937A (en) * | 1956-03-06 | 1958-12-23 | Welsbach Corp | Processes for the production of dibasic and monobasic acids |
-
1977
- 1977-03-29 DE DE19772713863 patent/DE2713863A1/de active Granted
-
1978
- 1978-03-08 NL NL7802549A patent/NL7802549A/xx not_active Application Discontinuation
- 1978-03-28 BE BE186302A patent/BE865357A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7802549A (nl) | 1978-10-03 |
| BE865357A (fr) | 1978-09-28 |
| DE2713863A1 (de) | 1978-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07D323/02 |
|
| 8125 | Change of the main classification |
Ipc: C07C179/087 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |