DE102004023417A1 - Verfahren zur Herstellung von langkettigen quaternären Ammonium-oxalaten und -hydrogenoxalaten - Google Patents
Verfahren zur Herstellung von langkettigen quaternären Ammonium-oxalaten und -hydrogenoxalaten Download PDFInfo
- Publication number
- DE102004023417A1 DE102004023417A1 DE102004023417A DE102004023417A DE102004023417A1 DE 102004023417 A1 DE102004023417 A1 DE 102004023417A1 DE 102004023417 A DE102004023417 A DE 102004023417A DE 102004023417 A DE102004023417 A DE 102004023417A DE 102004023417 A1 DE102004023417 A1 DE 102004023417A1
- Authority
- DE
- Germany
- Prior art keywords
- oxalic acid
- formula
- reaction
- amine
- dimethyl carbonate
- 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.)
- Ceased
Links
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 81
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 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 26
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 24
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000010409 thin film Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000006260 foam Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 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
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- -1 quaternary ammonium halides Chemical class 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000005349 anion exchange Methods 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 238000004821 distillation 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
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 3
- 230000001681 protective effect Effects 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
- 239000012467 final product 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
- 238000006386 neutralization reaction 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 230000009286 beneficial effect Effects 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
- 239000003990 capacitor Substances 0.000 description 1
- 150000007942 carboxylates 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
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003792 electrolyte 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
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001879 gelation 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
- 239000013067 intermediate product 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
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000005700 microbiome Species 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
- 238000000926 separation method Methods 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
- 238000004448 titration Methods 0.000 description 1
- GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000005303 weighing 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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023417A DE102004023417A1 (de) | 2004-05-12 | 2004-05-12 | Verfahren zur Herstellung von langkettigen quaternären Ammonium-oxalaten und -hydrogenoxalaten |
| PT57448169T PT1747188E (pt) | 2004-05-12 | 2005-04-28 | Processo para a produção de oxalatos de amónio e hidrogeno-oxalatos de amónio quaternários de cadeia longa |
| CA2566465A CA2566465C (en) | 2004-05-12 | 2005-04-28 | Method for the production of long-chained quaternary ammonium oxalates and ammonium hydrogen oxalates |
| ES05744816.9T ES2543837T3 (es) | 2004-05-12 | 2005-04-28 | Procedimiento para la preparación de oxalatos e hidrógeno-oxalatos de amonio cuaternarios de cadenas largas |
| PCT/EP2005/004535 WO2005113480A1 (de) | 2004-05-12 | 2005-04-28 | Verfahren zur herstellung von langkettigen quaternären ammonium-oxalaten und -hydrogenoxalaten |
| JP2007511963A JP4884375B2 (ja) | 2004-05-12 | 2005-04-28 | 長鎖の第四級シュウ酸アンモニウムおよびシュウ酸水素アンモニウムの製造方法 |
| US11/596,172 US20070191605A1 (en) | 2004-05-12 | 2005-04-28 | Method for the production of ling-chained quaternary ammonium oxalates and ammonium hydrogenoxalates |
| EP05744816.9A EP1747188B1 (de) | 2004-05-12 | 2005-04-28 | Verfahren zur herstellung von langkettigen quaternären ammonium-oxalaten und -hydrogenoxalaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004023417A DE102004023417A1 (de) | 2004-05-12 | 2004-05-12 | Verfahren zur Herstellung von langkettigen quaternären Ammonium-oxalaten und -hydrogenoxalaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004023417A1 true DE102004023417A1 (de) | 2005-12-08 |
Family
ID=34968368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004023417A Ceased DE102004023417A1 (de) | 2004-05-12 | 2004-05-12 | Verfahren zur Herstellung von langkettigen quaternären Ammonium-oxalaten und -hydrogenoxalaten |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20070191605A1 (https=) |
| EP (1) | EP1747188B1 (https=) |
| JP (1) | JP4884375B2 (https=) |
| CA (1) | CA2566465C (https=) |
| DE (1) | DE102004023417A1 (https=) |
| ES (1) | ES2543837T3 (https=) |
| PT (1) | PT1747188E (https=) |
| WO (1) | WO2005113480A1 (https=) |
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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0291074A2 (en) * | 1987-05-13 | 1988-11-17 | Mitsubishi Petrochemical Co., Ltd. | Process for producing quaternary salts |
| EP0345475A1 (de) * | 1988-05-13 | 1989-12-13 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von quaternären Ammoniumsalzen langkettiger aliphatischer Carbonsäuren |
Family Cites Families (7)
| 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 |
| 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 CA CA2566465A patent/CA2566465C/en not_active Expired - Fee Related
- 2005-04-28 ES ES05744816.9T patent/ES2543837T3/es not_active Expired - Lifetime
- 2005-04-28 US US11/596,172 patent/US20070191605A1/en not_active Abandoned
- 2005-04-28 JP JP2007511963A patent/JP4884375B2/ja not_active Expired - Fee Related
- 2005-04-28 WO PCT/EP2005/004535 patent/WO2005113480A1/de not_active Ceased
- 2005-04-28 PT PT57448169T patent/PT1747188E/pt unknown
- 2005-04-28 EP EP05744816.9A patent/EP1747188B1/de not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0291074A2 (en) * | 1987-05-13 | 1988-11-17 | Mitsubishi Petrochemical Co., Ltd. | Process for producing quaternary salts |
| EP0345475A1 (de) * | 1988-05-13 | 1989-12-13 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von quaternären Ammoniumsalzen langkettiger aliphatischer Carbonsäuren |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007537174A (ja) | 2007-12-20 |
| EP1747188B1 (de) | 2015-07-08 |
| CA2566465A1 (en) | 2005-12-01 |
| US20070191605A1 (en) | 2007-08-16 |
| ES2543837T3 (es) | 2015-08-24 |
| JP4884375B2 (ja) | 2012-02-29 |
| PT1747188E (pt) | 2015-10-06 |
| CA2566465C (en) | 2013-05-14 |
| EP1747188A1 (de) | 2007-01-31 |
| WO2005113480A1 (de) | 2005-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH, 65929 FRANKF |
|
| 8131 | Rejection |