CH495942A - Verfahren zur Herstellung von antimikrobiell und antimykotisch wirksamen 2-Aminoalkanen und deren Säureadditionssalzen - Google Patents
Verfahren zur Herstellung von antimikrobiell und antimykotisch wirksamen 2-Aminoalkanen und deren SäureadditionssalzenInfo
- Publication number
- CH495942A CH495942A CH309268A CH309268A CH495942A CH 495942 A CH495942 A CH 495942A CH 309268 A CH309268 A CH 309268A CH 309268 A CH309268 A CH 309268A CH 495942 A CH495942 A CH 495942A
- Authority
- CH
- Switzerland
- Prior art keywords
- catalyst
- reductive amination
- general formula
- methanol
- hydrogen
- Prior art date
Links
- -1 2-amino alkanes Chemical class 0.000 title claims abstract description 10
- 230000000845 anti-microbial effect Effects 0.000 title abstract description 4
- 229940121375 antifungal agent Drugs 0.000 title abstract description 3
- 230000000843 anti-fungal effect Effects 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 238000006268 reductive amination reaction Methods 0.000 claims abstract description 7
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 5
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FVUCJMMROXQUQR-UHFFFAOYSA-N hexadecan-2-amine Chemical compound CCCCCCCCCCCCCCC(C)N FVUCJMMROXQUQR-UHFFFAOYSA-N 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- TVTCXPXLRKTHAU-UHFFFAOYSA-N Heptadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(C)=O TVTCXPXLRKTHAU-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- VXUXKOBYNVVANW-UHFFFAOYSA-N dodecan-2-amine Chemical compound CCCCCCCCCCC(C)N VXUXKOBYNVVANW-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- XDEJSVFPGICHRQ-UHFFFAOYSA-N heptadecan-2-amine Chemical compound CCCCCCCCCCCCCCCC(C)N XDEJSVFPGICHRQ-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- BGEHHAVMRVXCGR-UHFFFAOYSA-N methylundecylketone Natural products CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- PYLMYKPRPCABPR-UHFFFAOYSA-N pentadecan-2-amine Chemical compound CCCCCCCCCCCCCC(C)N PYLMYKPRPCABPR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- RRLSSXNOPYHNQL-UHFFFAOYSA-N tetradecan-2-amine Chemical compound CCCCCCCCCCCCC(C)N RRLSSXNOPYHNQL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- WCLHZVGJULAEJH-UHFFFAOYSA-N tridecan-2-amine Chemical compound CCCCCCCCCCCC(C)N WCLHZVGJULAEJH-UHFFFAOYSA-N 0.000 description 1
- CYIFVRUOHKNECG-UHFFFAOYSA-N tridecan-2-one Chemical compound CCCCCCCCCCCC(C)=O CYIFVRUOHKNECG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS163567 | 1967-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH495942A true CH495942A (de) | 1970-09-15 |
Family
ID=5351180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH309268A CH495942A (de) | 1967-03-06 | 1968-03-01 | Verfahren zur Herstellung von antimikrobiell und antimykotisch wirksamen 2-Aminoalkanen und deren Säureadditionssalzen |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT280975B (en。) |
| BE (1) | BE711541A (en。) |
| CA (1) | CA921828A (en。) |
| CH (1) | CH495942A (en。) |
| DE (1) | DE1668970C3 (en。) |
| DK (1) | DK138738B (en。) |
| FI (1) | FI49495C (en。) |
| FR (1) | FR1555349A (en。) |
| GB (1) | GB1182562A (en。) |
| NL (1) | NL6803193A (en。) |
| YU (1) | YU32290B (en。) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976697A (en) | 1974-10-29 | 1976-08-24 | Texaco Inc. | Preparation of tertiary amines |
| GB1593194A (en) * | 1976-10-27 | 1981-07-15 | Ciba Geigy Ag | Method of controoling coccidial diseases |
-
1968
- 1968-03-01 CH CH309268A patent/CH495942A/de not_active IP Right Cessation
- 1968-03-01 BE BE711541D patent/BE711541A/xx unknown
- 1968-03-04 DE DE1968S0114406 patent/DE1668970C3/de not_active Expired
- 1968-03-04 GB GB1030668A patent/GB1182562A/en not_active Expired
- 1968-03-05 YU YU50968A patent/YU32290B/xx unknown
- 1968-03-05 AT AT215168A patent/AT280975B/de not_active IP Right Cessation
- 1968-03-06 FR FR1555349D patent/FR1555349A/fr not_active Expired
- 1968-03-06 DK DK92168A patent/DK138738B/da unknown
- 1968-03-06 NL NL6803193A patent/NL6803193A/xx unknown
- 1968-03-06 CA CA014113A patent/CA921828A/en not_active Expired
- 1968-03-06 FI FI60968A patent/FI49495C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1182562A (en) | 1970-02-25 |
| FR1555349A (en。) | 1969-01-24 |
| DE1668970C3 (de) | 1979-03-22 |
| NL6803193A (en。) | 1968-09-09 |
| AT280975B (de) | 1970-05-11 |
| CA921828A (en) | 1973-02-27 |
| FI49495B (en。) | 1975-04-01 |
| DK138738B (da) | 1978-10-23 |
| DK138738C (en。) | 1979-03-26 |
| FI49495C (fi) | 1975-07-10 |
| DE1668970B2 (de) | 1978-07-13 |
| YU32290B (en) | 1974-08-31 |
| BE711541A (en。) | 1968-07-15 |
| YU50968A (en) | 1974-02-28 |
| DE1668970A1 (de) | 1972-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |