DE2547654C2 - Herstellung von 2-Amino-1-alkoholen und 3-Oxalin-Derivate - Google Patents
Herstellung von 2-Amino-1-alkoholen und 3-Oxalin-DerivateInfo
- Publication number
- DE2547654C2 DE2547654C2 DE2547654A DE2547654A DE2547654C2 DE 2547654 C2 DE2547654 C2 DE 2547654C2 DE 2547654 A DE2547654 A DE 2547654A DE 2547654 A DE2547654 A DE 2547654A DE 2547654 C2 DE2547654 C2 DE 2547654C2
- Authority
- DE
- Germany
- Prior art keywords
- ammonia
- amino
- reactor
- alcohols
- compound
- 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
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 48
- 229910021529 ammonia Inorganic materials 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000005576 amination reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- DDPRYTUJYNYJKV-UHFFFAOYSA-N 1,4-diethylpiperazine Chemical compound CCN1CCN(CC)CC1 DDPRYTUJYNYJKV-UHFFFAOYSA-N 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002918 oxazolines Chemical class 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910000428 cobalt oxide Inorganic materials 0.000 description 2
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 2
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- 241001473877 Biserrula isolate Species 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940072185 drug for treatment of tuberculosis Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229960000285 ethambutol Drugs 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Chemical class 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2547654A DE2547654C2 (de) | 1975-10-24 | 1975-10-24 | Herstellung von 2-Amino-1-alkoholen und 3-Oxalin-Derivate |
| IT27005/76A IT1068266B (it) | 1975-10-24 | 1976-09-08 | Preparazione di 2 amino i alcooli |
| IL50634A IL50634A (en) | 1975-10-24 | 1976-10-07 | Preparation of aliphatic 2-amino-1-alcohols, and oxazoline intermediates therefor |
| FR7631584A FR2328701A1 (fr) | 1975-10-24 | 1976-10-20 | Preparation de 2-amino-1-alcools |
| CH1331276A CH622489A5 (en) | 1975-10-24 | 1976-10-21 | Process for the preparation of 2-amino-1-alcohols |
| GB43919/76A GB1554176A (en) | 1975-10-24 | 1976-10-22 | Manufacture of aliphatic 2-amino-1-alcohols |
| BE171735A BE847568A (fr) | 1975-10-24 | 1976-10-22 | Preparation de 2-amino-1-alcools, |
| JP51127410A JPS6013020B2 (ja) | 1975-10-24 | 1976-10-25 | ２―アミノー１―アルコールの製法 |
| US05/807,925 US4105669A (en) | 1975-10-24 | 1977-06-20 | Manufacture of 2-amino-1-alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2547654A DE2547654C2 (de) | 1975-10-24 | 1975-10-24 | Herstellung von 2-Amino-1-alkoholen und 3-Oxalin-Derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2547654A1 DE2547654A1 (de) | 1977-04-28 |
| DE2547654C2 true DE2547654C2 (de) | 1982-09-09 |
Family
ID=5960008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2547654A Expired DE2547654C2 (de) | 1975-10-24 | 1975-10-24 | Herstellung von 2-Amino-1-alkoholen und 3-Oxalin-Derivate |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS6013020B2 (https=) |
| BE (1) | BE847568A (https=) |
| CH (1) | CH622489A5 (https=) |
| DE (1) | DE2547654C2 (https=) |
| FR (1) | FR2328701A1 (https=) |
| GB (1) | GB1554176A (https=) |
| IL (1) | IL50634A (https=) |
| IT (1) | IT1068266B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3609978A1 (de) * | 1986-03-25 | 1987-10-01 | Merck Patent Gmbh | Verfahren zur herstellung von hydroxyaminen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3516028A1 (de) * | 1985-05-04 | 1986-11-06 | Hüls AG, 4370 Marl | Di-(tert.-butanol)-amin und verfahren zu seiner herstellung durch hydrierung von 2(1-hydroxy-1-methyl-ethyl)-5,5-dimethyl-1,3-oxazolin |
| US7619118B2 (en) | 2006-06-07 | 2009-11-17 | The Procter & Gamble Company | Process for the conversion of glycerol to propylene glycol and amino alcohols |
| MX2008015685A (es) * | 2006-06-07 | 2009-01-12 | Procter & Gamble | Procesos para convertir glicerol en aminoalcoholes. |
| US7619119B2 (en) | 2006-06-07 | 2009-11-17 | The Procter & Gamble Company | Processes for converting glycerol to amino alcohols |
| WO2016038632A1 (en) * | 2014-09-12 | 2016-03-17 | Council Of Scientific And Industrial Research | A one pot process for synthesis of oxazoline and imidazole compounds from glycerol |
-
1975
- 1975-10-24 DE DE2547654A patent/DE2547654C2/de not_active Expired
-
1976
- 1976-09-08 IT IT27005/76A patent/IT1068266B/it active
- 1976-10-07 IL IL50634A patent/IL50634A/xx unknown
- 1976-10-20 FR FR7631584A patent/FR2328701A1/fr active Granted
- 1976-10-21 CH CH1331276A patent/CH622489A5/de not_active IP Right Cessation
- 1976-10-22 BE BE171735A patent/BE847568A/xx not_active IP Right Cessation
- 1976-10-22 GB GB43919/76A patent/GB1554176A/en not_active Expired
- 1976-10-25 JP JP51127410A patent/JPS6013020B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3609978A1 (de) * | 1986-03-25 | 1987-10-01 | Merck Patent Gmbh | Verfahren zur herstellung von hydroxyaminen |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1068266B (it) | 1985-03-21 |
| JPS5253807A (en) | 1977-04-30 |
| GB1554176A (en) | 1979-10-17 |
| FR2328701B1 (https=) | 1980-03-14 |
| DE2547654A1 (de) | 1977-04-28 |
| IL50634A0 (en) | 1976-12-31 |
| JPS6013020B2 (ja) | 1985-04-04 |
| FR2328701A1 (fr) | 1977-05-20 |
| BE847568A (fr) | 1977-04-22 |
| CH622489A5 (en) | 1981-04-15 |
| IL50634A (en) | 1979-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OB | Request for examination as to novelty | ||
| OC | Search report available | ||
| OD | Request for examination | ||
| 8126 | Change of the secondary classification |
Ipc: C07D263/14 |
|
| D2 | Grant after examination |