CA2566465C - Method for the production of long-chained quaternary ammonium oxalates and ammonium hydrogen oxalates - Google Patents
Method for the production of long-chained quaternary ammonium oxalates and ammonium hydrogen oxalates Download PDFInfo
- Publication number
- CA2566465C CA2566465C CA2566465A CA2566465A CA2566465C CA 2566465 C CA2566465 C CA 2566465C CA 2566465 A CA2566465 A CA 2566465A CA 2566465 A CA2566465 A CA 2566465A CA 2566465 C CA2566465 C CA 2566465C
- Authority
- CA
- Canada
- Prior art keywords
- oxalic acid
- formula
- reaction
- amine
- quaternary ammonium
- 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 - Fee Related
Links
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- AJGPQPPJQDDCDA-UHFFFAOYSA-N azanium;hydron;oxalate Chemical class N.OC(=O)C(O)=O AJGPQPPJQDDCDA-UHFFFAOYSA-N 0.000 title description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 73
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 22
- 239000013067 intermediate product Substances 0.000 claims abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 22
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000006260 foam Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 238000005349 anion exchange Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- IASNHTVFXYNISW-UHFFFAOYSA-M 2-hydroxy-2-oxoacetate;trimethyl(tetradecyl)azanium Chemical compound OC(=O)C([O-])=O.CCCCCCCCCCCCCC[N+](C)(C)C IASNHTVFXYNISW-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- XNYQOAOGCKKCNI-UHFFFAOYSA-L oxalate;trimethyl(tetradecyl)azanium Chemical compound [O-]C(=O)C([O-])=O.CCCCCCCCCCCCCC[N+](C)(C)C.CCCCCCCCCCCCCC[N+](C)(C)C XNYQOAOGCKKCNI-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023417.5 | 2004-05-12 | ||
| DE102004023417A DE102004023417A1 (de) | 2004-05-12 | 2004-05-12 | Verfahren zur Herstellung von langkettigen quaternären Ammonium-oxalaten und -hydrogenoxalaten |
| PCT/EP2005/004535 WO2005113480A1 (de) | 2004-05-12 | 2005-04-28 | Verfahren zur herstellung von langkettigen quaternären ammonium-oxalaten und -hydrogenoxalaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2566465A1 CA2566465A1 (en) | 2005-12-01 |
| CA2566465C true CA2566465C (en) | 2013-05-14 |
Family
ID=34968368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2566465A Expired - Fee Related CA2566465C (en) | 2004-05-12 | 2005-04-28 | Method for the production of long-chained quaternary ammonium oxalates and ammonium hydrogen oxalates |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20070191605A1 (enExample) |
| EP (1) | EP1747188B1 (enExample) |
| JP (1) | JP4884375B2 (enExample) |
| CA (1) | CA2566465C (enExample) |
| DE (1) | DE102004023417A1 (enExample) |
| ES (1) | ES2543837T3 (enExample) |
| PT (1) | PT1747188E (enExample) |
| WO (1) | WO2005113480A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8137647B2 (en) * | 2006-12-28 | 2012-03-20 | E. I. Du Pont De Nemours And Company | Processes for producing titanium dioxide |
| US9677020B2 (en) | 2014-06-25 | 2017-06-13 | Afton Chemical Corporation | Hydrocarbyl soluble quaternary ammonium carboxylates and fuel compositions containing them |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1207517B (it) * | 1985-12-19 | 1989-05-25 | Enichem Sintesi | Inibitori di corrosione sottosforzo di acciai inossidabili. |
| US4786429A (en) * | 1986-06-20 | 1988-11-22 | Mitsubishi Petrochemical Co., Ltd. | Electrolyte for aluminum electrolytic capacitor |
| JPH0819060B2 (ja) * | 1987-05-13 | 1996-02-28 | 三菱化学株式会社 | 四級アンモニウム有機酸塩の製造方法 |
| US4892944A (en) * | 1987-05-13 | 1990-01-09 | Mitsubishi Petrochemical Co., Ltd. | Process for producing quaternary salts |
| DE3816328A1 (de) * | 1988-05-13 | 1989-11-23 | Hoechst Ag | Verfahren zur herstellung von quaternaeren ammoniumsalzen langkettiger aliphatischer carbonsaeuren und verwendung dieser ammoniumsalze |
| US6293973B1 (en) * | 1996-10-11 | 2001-09-25 | Nalco Chemical Company | Method of controlling oxalate precipitation in bayer process liquor |
| JP2919419B2 (ja) * | 1997-02-07 | 1999-07-12 | 三菱化学株式会社 | 電解液用の電解質 |
| DE19813338A1 (de) * | 1998-03-26 | 1999-09-30 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Hydroxybenzoesäureestern von Oxoalkoholen |
| DE10031236A1 (de) * | 2000-06-27 | 2002-01-10 | Qiagen Gmbh | Verwendung von Carbonsäuren und anderen Additiven in Kombination mit kationischen Verbindungen zur Stabilisierung von Nukleinsäuren in biologischen Materialien |
-
2004
- 2004-05-12 DE DE102004023417A patent/DE102004023417A1/de not_active Ceased
-
2005
- 2005-04-28 PT PT57448169T patent/PT1747188E/pt unknown
- 2005-04-28 ES ES05744816.9T patent/ES2543837T3/es not_active Expired - Lifetime
- 2005-04-28 EP EP05744816.9A patent/EP1747188B1/de not_active Expired - Lifetime
- 2005-04-28 CA CA2566465A patent/CA2566465C/en not_active Expired - Fee Related
- 2005-04-28 WO PCT/EP2005/004535 patent/WO2005113480A1/de not_active Ceased
- 2005-04-28 JP JP2007511963A patent/JP4884375B2/ja not_active Expired - Fee Related
- 2005-04-28 US US11/596,172 patent/US20070191605A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| PT1747188E (pt) | 2015-10-06 |
| JP4884375B2 (ja) | 2012-02-29 |
| DE102004023417A1 (de) | 2005-12-08 |
| WO2005113480A1 (de) | 2005-12-01 |
| EP1747188B1 (de) | 2015-07-08 |
| EP1747188A1 (de) | 2007-01-31 |
| US20070191605A1 (en) | 2007-08-16 |
| CA2566465A1 (en) | 2005-12-01 |
| JP2007537174A (ja) | 2007-12-20 |
| ES2543837T3 (es) | 2015-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180430 |