DE1095284B - Verfahren zur Herstellung von í¸-Thiazolinen - Google Patents
Verfahren zur Herstellung von í¸-ThiazolinenInfo
- Publication number
- DE1095284B DE1095284B DEV10477A DEV0010477A DE1095284B DE 1095284 B DE1095284 B DE 1095284B DE V10477 A DEV10477 A DE V10477A DE V0010477 A DEV0010477 A DE V0010477A DE 1095284 B DE1095284 B DE 1095284B
- Authority
- DE
- Germany
- Prior art keywords
- ammonia
- thiazolines
- mixture
- general formula
- reaction
- 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
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical class C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical class N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- TWOGJUHCCNLYPC-UHFFFAOYSA-N 2-Mercapto-3-pentanone Chemical compound CCC(=O)C(C)S TWOGJUHCCNLYPC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- VINFWNLYQUNBOU-UHFFFAOYSA-N 1-sulfanylbutan-2-one Chemical compound CCC(=O)CS VINFWNLYQUNBOU-UHFFFAOYSA-N 0.000 description 2
- XLMPYCGSRHSSSX-UHFFFAOYSA-N 3-Mercapto-2-butanone Chemical compound CC(S)C(C)=O XLMPYCGSRHSSSX-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003549 thiazolines Chemical class 0.000 description 2
- SOFPIAMTOZWXKT-UHFFFAOYSA-N 2h-1,2,4-triazine-3-thione Chemical compound SC1=NC=CN=N1 SOFPIAMTOZWXKT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- KAOHYMHKNXJUFY-HYXAFXHYSA-N ethyl (z)-2-aminobut-2-enoate Chemical compound CCOC(=O)C(\N)=C\C KAOHYMHKNXJUFY-HYXAFXHYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- -1 oxo compound Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/16—Sulfur-containing compounds
- C23F11/165—Heterocyclic compounds containing sulfur as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE547299D BE547299A (en:Method) | 1955-11-30 | ||
| DEV10477A DE1095284B (de) | 1955-11-30 | 1956-04-14 | Verfahren zur Herstellung von í¸-Thiazolinen |
| CH345344D CH345344A (de) | 1955-11-30 | 1956-04-20 | Verfahren zur Herstellung von 3,4-Thiazolinen |
| GB12692/56A GB824113A (en) | 1955-11-30 | 1956-04-25 | Process for producing í¸-3,4-thiazolines |
| US615025A US2879273A (en) | 1955-11-30 | 1956-10-10 | Process for the manufacture of delta-3, 4-thiazolines |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE345344X | 1955-11-30 | ||
| DEV10477A DE1095284B (de) | 1955-11-30 | 1956-04-14 | Verfahren zur Herstellung von í¸-Thiazolinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1095284B true DE1095284B (de) | 1960-12-22 |
Family
ID=25827940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEV10477A Pending DE1095284B (de) | 1955-11-30 | 1956-04-14 | Verfahren zur Herstellung von í¸-Thiazolinen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2879273A (en:Method) |
| BE (1) | BE547299A (en:Method) |
| CH (1) | CH345344A (en:Method) |
| DE (1) | DE1095284B (en:Method) |
| GB (1) | GB824113A (en:Method) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617248A (en) * | 1969-03-19 | 1971-11-02 | Allied Chem | Selective weed control with herbicidal diphenyl-n-(chlorophenoxy-acetyl)-thiazone imines |
| DE2254701C3 (de) * | 1972-11-09 | 1978-12-07 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von in 2- und 5-Stellung substituierten Thiazolinen-(3) |
| US4040987A (en) * | 1976-10-07 | 1977-08-09 | International Flavors & Fragrances Inc. | 2-Alkyl-substituted-4,5-dimethyl thiazoline perfume and cologne compositions |
| US4256776A (en) * | 1979-03-05 | 1981-03-17 | International Flavors & Fragrances Inc. | Flavoring with certain 2-alkyl-4,5-dialkyl-Δ3 -thiazolines |
| US4263332A (en) * | 1979-03-05 | 1981-04-21 | International Flavors & Fragrances Inc. | Use of 2(2'-methylthiopropyl)-4,5-dimethyl-Δ3 -thiazoline to augment or enhance the aroma or taste of mashed potato flavor or mashed potato flavored foodstuffs |
| US4255583A (en) * | 1979-03-05 | 1981-03-10 | International Flavors & Fragrances Inc. | 2-Alkylthioalkyl-4,5-dialkyl-Δ3 -thiazolines |
| US4243688A (en) * | 1979-12-05 | 1981-01-06 | International Flavors & Fragrances Inc. | Flavoring with 2-substituted-4,5-dimethyl-Δ3 -thiazolines |
| US4326876A (en) * | 1980-01-28 | 1982-04-27 | Chevron Research Company | 2-Aminosubstituted-5-methylene-thiazole and 3-aminosubstituted-1 methylene-2,4-thiazaspiro[5.4]decane herbicides |
| US20110052775A1 (en) * | 2009-09-01 | 2011-03-03 | Agyemang David O | Use of Thiazoline Compounds in Flavor Applications |
| US20120244089A1 (en) * | 2009-09-01 | 2012-09-27 | Agyemang David O | Use of thiazole compound in flavor applications |
-
0
- BE BE547299D patent/BE547299A/xx unknown
-
1956
- 1956-04-14 DE DEV10477A patent/DE1095284B/de active Pending
- 1956-04-20 CH CH345344D patent/CH345344A/de unknown
- 1956-04-25 GB GB12692/56A patent/GB824113A/en not_active Expired
- 1956-10-10 US US615025A patent/US2879273A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CH345344A (de) | 1960-03-31 |
| GB824113A (en) | 1959-11-25 |
| US2879273A (en) | 1959-03-24 |
| BE547299A (en:Method) |
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