DK168436B1 - Fremgangsmåde til fremstilling af hydroxyalkylerede aminer via fremstilling af oxazolidiner ved alkoxylering af iminer - Google Patents
Fremgangsmåde til fremstilling af hydroxyalkylerede aminer via fremstilling af oxazolidiner ved alkoxylering af iminer Download PDFInfo
- Publication number
- DK168436B1 DK168436B1 DK380086A DK380086A DK168436B1 DK 168436 B1 DK168436 B1 DK 168436B1 DK 380086 A DK380086 A DK 380086A DK 380086 A DK380086 A DK 380086A DK 168436 B1 DK168436 B1 DK 168436B1
- Authority
- DK
- Denmark
- Prior art keywords
- group
- oxazolidine
- formula
- carbon atoms
- amine
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000002466 imines Chemical class 0.000 title description 23
- 150000002917 oxazolidines Chemical class 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- -1 N-substituted mono-oxazolidine Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 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 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000004821 distillation Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000003760 tallow Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([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])[H] 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- 239000002262 Schiff base Substances 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- DMTMVPJQAJZQAQ-KTKRTIGZSA-N 3-[(z)-octadec-9-enyl]-1,3-oxazolidine Chemical compound CCCCCCCC\C=C/CCCCCCCCN1CCOC1 DMTMVPJQAJZQAQ-KTKRTIGZSA-N 0.000 description 2
- KHJZYXVCTXVEDS-UHFFFAOYSA-N 3-dodecyl-2-ethyl-2,5-dimethyl-1,3-oxazolidine Chemical compound CCCCCCCCCCCCN1CC(C)OC1(C)CC KHJZYXVCTXVEDS-UHFFFAOYSA-N 0.000 description 2
- RDRURTGSFBSIKX-UHFFFAOYSA-N 3-ethyl-1,3-oxazolidine Chemical compound CCN1CCOC1 RDRURTGSFBSIKX-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- QZOMSYGNYBDMCH-UHFFFAOYSA-N 1-(dodecylamino)propan-2-ol Chemical compound CCCCCCCCCCCCNCC(C)O QZOMSYGNYBDMCH-UHFFFAOYSA-N 0.000 description 1
- CLOHYXDBRAWKGF-SEYXRHQNSA-N 2-methyl-2-(3-methylbutyl)-3-[(z)-octadec-9-enyl]-1,3-oxazolidine Chemical compound CCCCCCCC\C=C/CCCCCCCCN1CCOC1(C)CCC(C)C CLOHYXDBRAWKGF-SEYXRHQNSA-N 0.000 description 1
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YPTGWXTUMCREDZ-UHFFFAOYSA-N n-dodecylbutan-2-imine Chemical compound CCCCCCCCCCCCN=C(C)CC YPTGWXTUMCREDZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003553 thiiranes Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/765,053 US4677208A (en) | 1985-08-12 | 1985-08-12 | Manufacture of oxazolidines by the alkoxylation of imines |
| US76505385 | 1985-08-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK380086D0 DK380086D0 (da) | 1986-08-08 |
| DK380086A DK380086A (da) | 1987-02-13 |
| DK168436B1 true DK168436B1 (da) | 1994-03-28 |
Family
ID=25072516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK380086A DK168436B1 (da) | 1985-08-12 | 1986-08-08 | Fremgangsmåde til fremstilling af hydroxyalkylerede aminer via fremstilling af oxazolidiner ved alkoxylering af iminer |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4677208A (fr) |
| EP (1) | EP0212742B1 (fr) |
| AT (1) | ATE62681T1 (fr) |
| CA (1) | CA1286678C (fr) |
| DE (1) | DE3678769D1 (fr) |
| DK (1) | DK168436B1 (fr) |
| ES (1) | ES2000856A6 (fr) |
| NO (1) | NO164018C (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000212172A (ja) * | 1999-01-26 | 2000-08-02 | Daicel Chem Ind Ltd | １，３―オキサゾリジン誘導体の製造法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3743626A (en) * | 1968-10-18 | 1973-07-03 | Rohm & Haas | Hydrocurable oxazolidine-isocyanate compositions |
| US3897362A (en) * | 1969-10-02 | 1975-07-29 | David Ross Mccoy | Stabilized surfactants and their preparation |
| US3912691A (en) * | 1973-12-14 | 1975-10-14 | Rohm & Haas | Hydrocurable compositions of hydroxy (polyalkylenecarbonyloxy)-alkyleneoxazolidine and an isocyanate |
-
1985
- 1985-08-12 US US06/765,053 patent/US4677208A/en not_active Expired - Lifetime
-
1986
- 1986-08-06 DE DE8686201378T patent/DE3678769D1/de not_active Expired - Lifetime
- 1986-08-06 AT AT86201378T patent/ATE62681T1/de not_active IP Right Cessation
- 1986-08-06 EP EP86201378A patent/EP0212742B1/fr not_active Expired - Lifetime
- 1986-08-08 DK DK380086A patent/DK168436B1/da not_active IP Right Cessation
- 1986-08-11 NO NO863227A patent/NO164018C/no unknown
- 1986-08-11 ES ES8600990A patent/ES2000856A6/es not_active Expired
- 1986-08-12 CA CA000515805A patent/CA1286678C/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3678769D1 (de) | 1991-05-23 |
| US4677208A (en) | 1987-06-30 |
| EP0212742B1 (fr) | 1991-04-17 |
| DK380086D0 (da) | 1986-08-08 |
| EP0212742A1 (fr) | 1987-03-04 |
| ATE62681T1 (de) | 1991-05-15 |
| NO863227L (no) | 1987-02-13 |
| DK380086A (da) | 1987-02-13 |
| NO164018C (no) | 1990-08-22 |
| ES2000856A6 (es) | 1988-03-16 |
| NO164018B (no) | 1990-05-14 |
| CA1286678C (fr) | 1991-07-23 |
| NO863227D0 (no) | 1986-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |