AT403297B - Verfahren zur selektiven abtrennung von morpholin - Google Patents
Verfahren zur selektiven abtrennung von morpholin Download PDFInfo
- Publication number
- AT403297B AT403297B AT140395A AT140395A AT403297B AT 403297 B AT403297 B AT 403297B AT 140395 A AT140395 A AT 140395A AT 140395 A AT140395 A AT 140395A AT 403297 B AT403297 B AT 403297B
- Authority
- AT
- Austria
- Prior art keywords
- methylmorpholine
- morpholine
- nmmo
- cation exchanger
- oxide
- Prior art date
Links
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims description 80
- 238000000034 method Methods 0.000 title claims description 64
- 238000000926 separation method Methods 0.000 title claims description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 99
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 claims description 57
- 150000001412 amines Chemical class 0.000 claims description 36
- 150000001768 cations Chemical class 0.000 claims description 31
- ZKXDGKXYMTYWTB-UHFFFAOYSA-N N-nitrosomorpholine Chemical compound O=NN1CCOCC1 ZKXDGKXYMTYWTB-UHFFFAOYSA-N 0.000 claims description 28
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007857 degradation product Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 150000004005 nitrosamines Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000012465 retentate Substances 0.000 description 3
- 238000001223 reverse osmosis Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229920000875 Dissolving pulp Polymers 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- -1 are combined Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physical Water Treatments (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT140395A AT403297B (de) | 1995-08-18 | 1995-08-18 | Verfahren zur selektiven abtrennung von morpholin |
| CN96191128A CN1071750C (zh) | 1995-08-18 | 1996-08-16 | 选择性分离吗啉的方法 |
| EP96926960A EP0783497A1 (fr) | 1995-08-18 | 1996-08-16 | Procede pour la separation selective de morpholine |
| CA 2202153 CA2202153A1 (fr) | 1995-08-18 | 1996-08-16 | Procede pour la separation selective de morpholine |
| JP9508733A JPH10508318A (ja) | 1995-08-18 | 1996-08-16 | モルホリンの選択的な分離方法 |
| AU66954/96A AU700207B2 (en) | 1995-08-18 | 1996-08-16 | Process for selective separation of morpholine |
| PCT/AT1996/000146 WO1997007108A1 (fr) | 1995-08-18 | 1996-08-16 | Procede pour la separation selective de morpholine |
| BR9606585A BR9606585A (pt) | 1995-08-18 | 1996-08-16 | Processo para a separação seletiva de morfolina |
| NO19971753A NO310572B1 (no) | 1995-08-18 | 1997-04-17 | Fremgangsmåte for selektiv fraskillelse av morfolin ved hjelp av en regenererbar kationebytter |
| US08/843,850 US6113799A (en) | 1995-08-18 | 1997-04-17 | Process for selective separation of morpholine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT140395A AT403297B (de) | 1995-08-18 | 1995-08-18 | Verfahren zur selektiven abtrennung von morpholin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA140395A ATA140395A (de) | 1997-05-15 |
| AT403297B true AT403297B (de) | 1997-12-29 |
Family
ID=3513141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT140395A AT403297B (de) | 1995-08-18 | 1995-08-18 | Verfahren zur selektiven abtrennung von morpholin |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0783497A1 (fr) |
| JP (1) | JPH10508318A (fr) |
| CN (1) | CN1071750C (fr) |
| AT (1) | AT403297B (fr) |
| AU (1) | AU700207B2 (fr) |
| BR (1) | BR9606585A (fr) |
| CA (1) | CA2202153A1 (fr) |
| NO (1) | NO310572B1 (fr) |
| WO (1) | WO1997007108A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19842556C2 (de) * | 1998-09-17 | 2003-02-06 | Alceru Schwarza Gmbh | Verfahren zur Herstellung von cellulosischen Formkörpern |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111801319A (zh) * | 2018-03-15 | 2020-10-20 | 巴斯夫欧洲公司 | 从包含甲氧基乙醇和吗啉的混合物中移除甲氧基乙醇的方法 |
| CN110563669A (zh) * | 2019-10-09 | 2019-12-13 | 四川鸿鹏新材料有限公司 | 一种提高吗啉纯度的方法及装置 |
| CN112480035A (zh) * | 2020-10-28 | 2021-03-12 | 华茂伟业绿色科技股份有限公司 | N-甲基吗啉及其纯化方法、氧化甲基吗啉及其制备方法 |
| CN114539186A (zh) * | 2021-07-02 | 2022-05-27 | 华茂伟业绿色科技股份有限公司 | Nmmo的纯化方法、系统及得到的nmmo水合物晶体 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD259863A1 (de) * | 1987-04-06 | 1988-09-07 | Schwarza Chemiefaser | Verfahren zur herstellung waessriger, reiner n-methylmorpholin-n-oxid-loesungen |
| EP0402347A1 (fr) * | 1989-06-08 | 1990-12-12 | Lenzing Aktiengesellschaft | Procédé pour l'élimination d'amines |
| DD254199B5 (de) * | 1986-12-04 | 1994-01-05 | Thueringische Faser Ag Schwarz | Verfahren zur reinigung waessriger n-methylmorpholin-n-oxyd-loesungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD274435B5 (de) * | 1988-08-02 | 1996-10-31 | Thueringisches Inst Textil | Verfahren zur Rueckgewinnung von N-Methylmorpholin-N-Oxid |
| AT392915B (de) * | 1990-03-28 | 1991-07-10 | Chemiefaser Lenzing Ag | Verfahren zum abtrennen von wasser aus einer verduennten waesserigen loesung von n-methylmorpholin-n-oxid, n-methylmorpholin und/oder morpholin |
-
1995
- 1995-08-18 AT AT140395A patent/AT403297B/de not_active IP Right Cessation
-
1996
- 1996-08-16 WO PCT/AT1996/000146 patent/WO1997007108A1/fr not_active Ceased
- 1996-08-16 JP JP9508733A patent/JPH10508318A/ja not_active Ceased
- 1996-08-16 CA CA 2202153 patent/CA2202153A1/fr not_active Abandoned
- 1996-08-16 CN CN96191128A patent/CN1071750C/zh not_active Expired - Fee Related
- 1996-08-16 AU AU66954/96A patent/AU700207B2/en not_active Ceased
- 1996-08-16 EP EP96926960A patent/EP0783497A1/fr not_active Ceased
- 1996-08-16 BR BR9606585A patent/BR9606585A/pt not_active Application Discontinuation
-
1997
- 1997-04-17 NO NO19971753A patent/NO310572B1/no not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD254199B5 (de) * | 1986-12-04 | 1994-01-05 | Thueringische Faser Ag Schwarz | Verfahren zur reinigung waessriger n-methylmorpholin-n-oxyd-loesungen |
| DD259863A1 (de) * | 1987-04-06 | 1988-09-07 | Schwarza Chemiefaser | Verfahren zur herstellung waessriger, reiner n-methylmorpholin-n-oxid-loesungen |
| EP0402347A1 (fr) * | 1989-06-08 | 1990-12-12 | Lenzing Aktiengesellschaft | Procédé pour l'élimination d'amines |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19842556C2 (de) * | 1998-09-17 | 2003-02-06 | Alceru Schwarza Gmbh | Verfahren zur Herstellung von cellulosischen Formkörpern |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9606585A (pt) | 1997-10-28 |
| CA2202153A1 (fr) | 1997-02-27 |
| NO971753D0 (no) | 1997-04-17 |
| CN1071750C (zh) | 2001-09-26 |
| AU700207B2 (en) | 1998-12-24 |
| EP0783497A1 (fr) | 1997-07-16 |
| NO971753L (no) | 1997-04-17 |
| NO310572B1 (no) | 2001-07-23 |
| CN1165514A (zh) | 1997-11-19 |
| WO1997007108A1 (fr) | 1997-02-27 |
| ATA140395A (de) | 1997-05-15 |
| JPH10508318A (ja) | 1998-08-18 |
| AU6695496A (en) | 1997-03-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties | ||
| ELJ | Ceased due to non-payment of the annual fee |