CA2084335A1 - Method of producing storage stable 1-di-(c1- to c3-) alkylamino-2,3-propanediols - Google Patents
Method of producing storage stable 1-di-(c1- to c3-) alkylamino-2,3-propanediolsInfo
- Publication number
- CA2084335A1 CA2084335A1 CA 2084335 CA2084335A CA2084335A1 CA 2084335 A1 CA2084335 A1 CA 2084335A1 CA 2084335 CA2084335 CA 2084335 CA 2084335 A CA2084335 A CA 2084335A CA 2084335 A1 CA2084335 A1 CA 2084335A1
- Authority
- CA
- Canada
- Prior art keywords
- glycidol
- amine
- propanediols
- alkylamino
- reaction
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 3
- QCMHUGYTOGXZIW-UHFFFAOYSA-N 3-(dimethylamino)propane-1,2-diol Chemical compound CN(C)CC(O)CO QCMHUGYTOGXZIW-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001412 amines Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- ZGCHLAJIRWDGFE-UHFFFAOYSA-N 1-aminopropane-1,1-diol Chemical compound CCC(N)(O)O ZGCHLAJIRWDGFE-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- RJUGWLIJYSWLRS-UHFFFAOYSA-N 1-amino-2,2-dimethylpropane-1,1-diol Chemical compound CC(C(O)(O)N)(C)C RJUGWLIJYSWLRS-UHFFFAOYSA-N 0.000 description 5
- 125000005265 dialkylamine group Chemical group 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914141349 DE4141349C1 (enrdf_load_stackoverflow) | 1991-12-14 | 1991-12-14 | |
| DEP4141349.0 | 1991-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2084335A1 true CA2084335A1 (en) | 1993-06-15 |
Family
ID=6447109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2084335 Abandoned CA2084335A1 (en) | 1991-12-14 | 1992-12-02 | Method of producing storage stable 1-di-(c1- to c3-) alkylamino-2,3-propanediols |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0547402A3 (enrdf_load_stackoverflow) |
| JP (1) | JPH05255208A (enrdf_load_stackoverflow) |
| CA (1) | CA2084335A1 (enrdf_load_stackoverflow) |
| DE (1) | DE4141349C1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6284930B1 (en) | 1999-07-30 | 2001-09-04 | E.I. Du Pont De Nemours And Company | Process for the preparation of 3-hydroxypropanal |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3014098C2 (de) * | 1980-04-12 | 1984-08-30 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von 1-Amino-propandiol-(2,3) |
-
1991
- 1991-12-14 DE DE19914141349 patent/DE4141349C1/de not_active Expired - Fee Related
-
1992
- 1992-11-23 EP EP19920119879 patent/EP0547402A3/de not_active Withdrawn
- 1992-12-02 CA CA 2084335 patent/CA2084335A1/en not_active Abandoned
- 1992-12-11 JP JP33155892A patent/JPH05255208A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0547402A3 (en) | 1993-09-08 |
| DE4141349C1 (enrdf_load_stackoverflow) | 1993-06-03 |
| EP0547402A2 (de) | 1993-06-23 |
| JPH05255208A (ja) | 1993-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |