DE1670548A1 - Verfahren zur Herstellung von N-Acyloxazolidinen - Google Patents
Verfahren zur Herstellung von N-AcyloxazolidinenInfo
- Publication number
- DE1670548A1 DE1670548A1 DE19671670548 DE1670548A DE1670548A1 DE 1670548 A1 DE1670548 A1 DE 1670548A1 DE 19671670548 DE19671670548 DE 19671670548 DE 1670548 A DE1670548 A DE 1670548A DE 1670548 A1 DE1670548 A1 DE 1670548A1
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- acid
- hydroxyethyl
- aliphatic
- water
- 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 4
- 238000002360 preparation method Methods 0.000 title description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 150000002917 oxazolidines Chemical class 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 230000002779 inactivation Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- 229920002866 paraformaldehyde Polymers 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- -1 cyclohexane mono- Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RSVUWERPAVTSKU-UHFFFAOYSA-N 1,3-oxazolidin-2-yl(phenyl)methanone Chemical class C1(=CC=CC=C1)C(=O)C1OCCN1 RSVUWERPAVTSKU-UHFFFAOYSA-N 0.000 description 1
- DLEDLGUCQNINRT-UHFFFAOYSA-N 1-(1,3-oxazolidin-3-yl)decan-1-one Chemical compound C(CCCCCCCCC)(=O)N1COCC1 DLEDLGUCQNINRT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LMVSBYPDMNAXPF-UHFFFAOYSA-N N-(decanoyl)ethanolamine Chemical compound CCCCCCCCCC(=O)NCCO LMVSBYPDMNAXPF-UHFFFAOYSA-N 0.000 description 1
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 1
- GSILMNFJLONLCJ-UHFFFAOYSA-N N-(octanoyl)ethanolamine Chemical compound CCCCCCCC(=O)NCCO GSILMNFJLONLCJ-UHFFFAOYSA-N 0.000 description 1
- JHIXEZNTXMFXEK-UHFFFAOYSA-N N-(tetradecanoyl)ethanolamine Chemical compound CCCCCCCCCCCCCC(=O)NCCO JHIXEZNTXMFXEK-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ZZISDKBMXAZCIP-UHFFFAOYSA-N n-(2-hydroxyethyl)cyclohexanecarboxamide Chemical compound OCCNC(=O)C1CCCCC1 ZZISDKBMXAZCIP-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0052196 | 1967-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670548A1 true DE1670548A1 (de) | 1971-02-11 |
Family
ID=7053983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671670548 Pending DE1670548A1 (de) | 1967-02-04 | 1967-02-04 | Verfahren zur Herstellung von N-Acyloxazolidinen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE710255A (enrdf_load_stackoverflow) |
| CH (1) | CH487176A (enrdf_load_stackoverflow) |
| DE (1) | DE1670548A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1574701A (enrdf_load_stackoverflow) |
| GB (1) | GB1148704A (enrdf_load_stackoverflow) |
| LU (1) | LU55020A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6715493A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1014563A (en) * | 1972-10-13 | 1977-07-26 | Stauffer Chemical Company | Substituted oxazolidines and thiazolidines |
-
1967
- 1967-02-04 DE DE19671670548 patent/DE1670548A1/de active Pending
- 1967-11-15 NL NL6715493A patent/NL6715493A/xx unknown
- 1967-11-20 CH CH1621267A patent/CH487176A/de not_active IP Right Cessation
- 1967-12-05 LU LU55020D patent/LU55020A1/xx unknown
-
1968
- 1968-01-30 GB GB481568A patent/GB1148704A/en not_active Expired
- 1968-02-02 FR FR1574701D patent/FR1574701A/fr not_active Expired
- 1968-02-02 BE BE710255D patent/BE710255A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH487176A (de) | 1970-03-15 |
| LU55020A1 (enrdf_load_stackoverflow) | 1968-02-27 |
| FR1574701A (enrdf_load_stackoverflow) | 1969-07-18 |
| GB1148704A (en) | 1969-04-16 |
| BE710255A (enrdf_load_stackoverflow) | 1968-06-17 |
| NL6715493A (enrdf_load_stackoverflow) | 1968-08-05 |
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