SE447990B - Forfarande for rening av n,n-dialkylaminoetanoler - Google Patents
Forfarande for rening av n,n-dialkylaminoetanolerInfo
- Publication number
- SE447990B SE447990B SE8007424A SE8007424A SE447990B SE 447990 B SE447990 B SE 447990B SE 8007424 A SE8007424 A SE 8007424A SE 8007424 A SE8007424 A SE 8007424A SE 447990 B SE447990 B SE 447990B
- Authority
- SE
- Sweden
- Prior art keywords
- hydrochlorate
- ppm
- dimethylaminoethanol
- vinyloxy
- ethanol
- Prior art date
Links
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 9
- 238000000746 purification Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 8
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 6
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 235000021317 phosphate Nutrition 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- 229950005228 bromoform Drugs 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- GATVIKZLVQHOMN-UHFFFAOYSA-N Chlorodibromomethane Chemical compound ClC(Br)Br GATVIKZLVQHOMN-UHFFFAOYSA-N 0.000 claims description 2
- BLHVJAAEHMLMOI-UHFFFAOYSA-N N,N-dimethylethanolamine phosphate Chemical compound CN(C)CCOP(O)(O)=O BLHVJAAEHMLMOI-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- 229940073608 benzyl chloride Drugs 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims 1
- 150000001649 bromium compounds Chemical class 0.000 claims 1
- 150000001721 carbon Chemical class 0.000 claims 1
- JOHCVVJGGSABQY-UHFFFAOYSA-N carbon tetraiodide Chemical compound IC(I)(I)I JOHCVVJGGSABQY-UHFFFAOYSA-N 0.000 claims 1
- 150000004694 iodide salts Chemical class 0.000 claims 1
- 150000003891 oxalate salts Chemical class 0.000 claims 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
- 229940067157 phenylhydrazine Drugs 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 claims 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical class OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 46
- 238000004821 distillation Methods 0.000 description 17
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 238000011282 treatment Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 229960002887 deanol Drugs 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- -1 ethyl 2-vinyloxyacrylate Chemical compound 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- NFEQKIOTZVZZFF-UHFFFAOYSA-N 1-(diethylamino)ethyl dihydrogen phosphate Chemical compound CCN(CC)C(C)OP(O)(O)=O NFEQKIOTZVZZFF-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MROYOSVOQDJQDE-UHFFFAOYSA-N ClO.C(C)N(CC)C(C)O Chemical compound ClO.C(C)N(CC)C(C)O MROYOSVOQDJQDE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GWTIOWQZLVIYEH-UHFFFAOYSA-N [NH3+]CCO.[NH3+]CCO.[NH3+]CCO.[O-]P([O-])([O-])=O Chemical compound [NH3+]CCO.[NH3+]CCO.[NH3+]CCO.[O-]P([O-])([O-])=O GWTIOWQZLVIYEH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NAMLQZOPLCRCAQ-UHFFFAOYSA-N bromomethylbenzene;hydrochloride Chemical class Cl.BrCC1=CC=CC=C1 NAMLQZOPLCRCAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 238000004383 yellowing 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
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7926988A FR2468579A1 (fr) | 1979-10-31 | 1979-10-31 | Procede de purification des n,n,dialkylaminoethanols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8007424L SE8007424L (sv) | 1981-05-01 |
| SE447990B true SE447990B (sv) | 1987-01-12 |
Family
ID=9231222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8007424A SE447990B (sv) | 1979-10-31 | 1980-10-22 | Forfarande for rening av n,n-dialkylaminoetanoler |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE885795A (cg-RX-API-DMAC10.html) |
| DE (1) | DE3040732C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2468579A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB2061939B (cg-RX-API-DMAC10.html) |
| SE (1) | SE447990B (cg-RX-API-DMAC10.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5424482A (en) * | 1991-08-08 | 1995-06-13 | Elf Atochem N.A., Inc. | Process for preparing color-stable tertiary butyldiethanolamine |
| EP2651861B1 (de) | 2010-12-17 | 2015-02-25 | Basf Se | Verfahren zur herstellung eines n,n-dialkyl-ethanolamins mit hoher farbstabilität |
| US8791302B2 (en) | 2010-12-17 | 2014-07-29 | Basf Se | Process for preparing an N,N-dialky-ethanolamine having high color stability |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3151166A (en) * | 1960-09-12 | 1964-09-29 | Jefferson Chem Co Inc | Method for preparing color stable ethanolamines |
| US3131132A (en) * | 1962-06-06 | 1964-04-28 | Jefferson Chem Co Inc | Purification of dimethylaminoethanol by acid treatment and distillation |
| US3686279A (en) * | 1964-07-09 | 1972-08-22 | Giffin D Jones | 2-methylene-3-butenyl sulfonium salts useful as monomers |
| US3567779A (en) * | 1967-11-20 | 1971-03-02 | Jefferson Chem Co Inc | Color stabilized dimethylethanolamine |
| JPS51146406A (en) * | 1975-06-11 | 1976-12-16 | Sanyo Chem Ind Ltd | Purification of aminoalcohols |
-
1979
- 1979-10-31 FR FR7926988A patent/FR2468579A1/fr active Granted
-
1980
- 1980-10-20 BE BE0/202529A patent/BE885795A/fr not_active IP Right Cessation
- 1980-10-22 SE SE8007424A patent/SE447990B/sv not_active IP Right Cessation
- 1980-10-27 GB GB8034558A patent/GB2061939B/en not_active Expired
- 1980-10-29 DE DE19803040732 patent/DE3040732C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2468579A1 (fr) | 1981-05-08 |
| DE3040732A1 (de) | 1981-05-27 |
| FR2468579B1 (cg-RX-API-DMAC10.html) | 1984-02-10 |
| GB2061939B (en) | 1984-05-02 |
| SE8007424L (sv) | 1981-05-01 |
| BE885795A (fr) | 1981-04-21 |
| GB2061939A (en) | 1981-05-20 |
| DE3040732C2 (de) | 1986-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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