CA2453391A1 - In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates - Google Patents
In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates Download PDFInfo
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- CA2453391A1 CA2453391A1 CA002453391A CA2453391A CA2453391A1 CA 2453391 A1 CA2453391 A1 CA 2453391A1 CA 002453391 A CA002453391 A CA 002453391A CA 2453391 A CA2453391 A CA 2453391A CA 2453391 A1 CA2453391 A1 CA 2453391A1
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- alkyl
- quaternary ammonium
- carbonate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/20—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of quaternary ammonium compounds
Abstract
Applicant has discovered an in situ method of preparing quaternary ammonium methocarbonate salts and quaternary ammonium alkylcarbonate salts in high yield from tertiary amines, methanol, and at least one of a cyclic carbonate , an aliphatic polyester (such as a polycarbonate), or an ester (such as a carbonate ester), and their subsequent conversion to quaternary ammonium bicarbonates, quaternary ammonium carbonates or both in a one-pot reaction. According to one embodiment of the invention, the method includes reacting a n amine and methanol with at least one of a cyclic carbonate and an aliphatic polyester to yield a quaternary ammonium methocarbonate. This method does no t produce or require the handling of corrosive quaternary ammonium hydroxides. Another embodiment is a method of preparing quaternary ammonium alkylcarbona te salts by reacting tertiary amines, methanol, and an ester. The quaternary ammonium methocarbonate or alkylcarbonate can be converted to the corresponding bicarbonate, carbonate, or mixture thereof by methods know in the art.
Claims (52)
1. A method of preparing a quaternary ammonium methocarbonate having the formula wherein R1 and R2 are independently C1-C30 alkyl and R3 is a C8-C30 alkyl, the method comprising reacting (a) an amine having the formula NR1R2R3;
(b) (i) a cyclic carbonate having the formula wherein R4 is hydrogen or C1-C4 alkyl and n is an integer from 1 to 10, (ii) an aliphatic polyester having the formula wherein R5, R6, R7, and R8 are independently hydrogen or C1-C10 alkyl and m is an integer from 1 to 1200, or (iii) a mixture thereof; and (c) methanol to form the methocarbonate.
(b) (i) a cyclic carbonate having the formula wherein R4 is hydrogen or C1-C4 alkyl and n is an integer from 1 to 10, (ii) an aliphatic polyester having the formula wherein R5, R6, R7, and R8 are independently hydrogen or C1-C10 alkyl and m is an integer from 1 to 1200, or (iii) a mixture thereof; and (c) methanol to form the methocarbonate.
2. The method of claim 1, wherein R1 and R2 are independently C1-C20 alkyl and R3 is a C8-C20 alkyl.
3. The method of claim 1, wherein R1 and R2 are independently C1-C16 alkyl and R3 is a C8-C16 alkyl.
4. The method of claim 3, wherein R1 is methyl.
5. The method of claim 1, wherein R2 is C1-C20 alkyl.
6. The method of claim 5, wherein R2 is methyl.
7. The method of claim 5, wherein R2 is C8-C12 alkyl.
8. The method of claim 7, wherein R2 is C10 alkyl.
9. The method of claim 1, wherein R3 is C8-C20 alkyl.
10. The method of claim 9, wherein R3 is C8-C12 alkyl.
11. The method of claim 10, wherein R3 is C10 alkyl.
12. The method of claim 1, wherein R1 is methyl and R2 and R3 are independently C8-C12 alkyl.
13. The method of claim 12, wherein R2 and R3 are C10 alkyl.
14. The method of claim 1, wherein R1 and R2 are methyl and R3 is C8-C20 alkyl.
15. The method of claim 1, wherein the amine is selected from the group consisting of didecylmethylamine, dodecyldimethylamine, dioctylmethylamine, octadecyldimethylamine, dioctadecylmethylamine, trioctylamine, and any combination of any of the foregoing.
16. The method of claim 1, wherein R4 is hydrogen or methyl.
17. The method of claim 16, wherein the cyclic carbonate is ethylene carbonate.
18. The method of claim 16, wherein the cyclic carbonate is propylene carbonate.
19. The method of claim 1, wherein R5, R6, R7, and R8 are independently hydrogen or C1-C4 alkyl.
20. The method of claim 19, wherein R5, R6, R7, and R8 are independently hydrogen or methyl.
21. The method of claim 1, wherein R5 is methyl and R6, R7, and R8 are hydrogen.
22. The method of claim 1, wherein m ranges from 1 to 100.
23. The method of claim 1, wherein the molar ratio of amine to component (b) ranges from about 1:1 to about 1:10.
24. The method of claim 23, wherein the molar ratio of amine to component (b) ranges from about 1:2 to about 1:3.
25. The method of claim 1, wherein the molar ratio of amine to methanol ranges from about 1:2 to about 1:20.
26. The method of claim 1, wherein the reaction step is performed at from about 120 to about 160° C.
27. The method of claim 26, wherein the reaction step is performed at from about 120 to about 150° C.
28. The method of claim 27, wherein the reaction step is performed at from about 120 to about 140 ° C.
29. The method of claim 1, further comprising the step of recovering the dimethyl carbonate.
30. The method of claim 1, wherein the reaction step comprises reacting (a)the amine;
(b) (i) the cyclic carbonate, (ii) the aliphatic polyester, or (iii) a mixture thereof;
(c) methanol; and (d) dimethylcarbonate.
(b) (i) the cyclic carbonate, (ii) the aliphatic polyester, or (iii) a mixture thereof;
(c) methanol; and (d) dimethylcarbonate.
31. The method of claim 30, wherein the molar ratio of amine to dimethylcarbonate ranges from about 2:1 to about 1:3.
32. A method of preparing didecyldimethyl ammonium methocarbonate comprising reacting (a) didecylmethylamine;
(b) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof; and (c) methanol to form didecyldimethyl ammonium methocarbonate.
(b) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof; and (c) methanol to form didecyldimethyl ammonium methocarbonate.
33. The method of claim 32, wherein the reaction step comprises reacting (a) didecylmethylamine;
(b) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof;
(c) methanol; and (d) dimethylcarbonate.
(b) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof;
(c) methanol; and (d) dimethylcarbonate.
34. The method of claim 32, wherein the cyclic carbonate is propylene carbonate.
35. A method of preparing a quaternary ammonium bicarbonate having the formula wherein R1, R2, and R3 are independently C1-C30 alkyl, the method comprising (a) preparing a quaternary ammonium methocarbonate by the method of claim 1; and (b) converting the quaternary ammonium methocarbonate to the quaternary ammonium bicarbonate.
36. A method of preparing didecyldimethyl ammonium bicarbonate comprising (a) reacting (i) didecylmethylamine, (ii) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof, and (iii) methanol to form didecyldimethyl ammonium methocarbonate; and (b) converting the didecyldimethyl ammonium methocarbonate to didecyldimethyl ammonium bicarbonate.
37. The method of claim 36, wherein step (a) comprises reacting (i) didecylmethylamine, (ii) a cyclic carbonate selected from the group consisting of ethylene carbonate, propylene carbonate, and mixtures thereof, (iii) methanol, and (iv) dimethylcarbonate to form didecyldimethyl ammonium methocarbonate.
38. A method of preparing a mixture of quaternary ammonium bicarbonate and quaternary ammoinium carbonate wherein the quaternary ammonium cation has the formula N+(CH3)R1R2R3 and R1, R2, and R3 are independently C1-C30 alkyl, the method comprising (a) preparing a quaternary ammonium methocarbonate by the method of claim 1; and (b) converting the quaternary ammonium methocarbonate to a mixture of quaternary ammonium bicarbonate and quaternary ammonium carbonate.
39. A method of preparing a quaternary ammonium alkylcarbonate having the formula wherein R1 is methyl, R2 and R~ are independently C10-C20 alkyl, and R9 is a C1-C10 alkyl, the method comprising reacting (a) an amine having the formula NR1R2R~;
(b) an ester having the formula wherein R10 is a C1-C10 alkyl; and (c) methanol to form the quaternary ammonium alkylcarbonate.
(b) an ester having the formula wherein R10 is a C1-C10 alkyl; and (c) methanol to form the quaternary ammonium alkylcarbonate.
40. The method of claim 39, wherein R1 is methyl and R2 and R3 are independently C10 alkyl.
41. The method of claim 39, wherein the amine is selected from the group consisting of didecylmethylamine, dodecyldimethylamine, dioctadecylmethylamine,and any combination of any of the foregoing.
42. The method of claim 39, wherein the molar ratio of amine to ester ranges from about 1:1 to about 1:10.
43. The method of claim 42, wherein the molar ratio of amine to ester ranges from about 1:2 to about 1.3.
44. The method of claim 39, wherein the molar ratio of amine to methanol ranges from about 1:2 to about 1:20.
45. The method of claim 39, wherein the reaction step is performed at from about 120 to about 160° C.
46. The method of claim 45, wherein the reaction step is performed at from about 120 to about 150° C.
47. The method of claim 46, wherein the reaction step is performed at from about 120 to about 140° C.
48. The method of claim 39, further comprising the step of recovering alkanol having the formula R~O~.
49. The method of claim 37, wherein the reaction step comprises reacting (a) the amine;
(b) the ester;
(c) methanol; and (d) alkyl methyl carbonate having the formula CH~OC(O)OR~.
(b) the ester;
(c) methanol; and (d) alkyl methyl carbonate having the formula CH~OC(O)OR~.
50. The method of preparing quaternary ammonium bicarbonate having the formula wherein R1 is methyl, R2 and R~ are independently C10-C20 alkyl, the method comprising (a) preparing a quaternary ammonium alkylcarbonate by the method of claim 39;
and (b) converting the quaternary ammonium alkylcarbonate to the quaternary ammonium bicarbonate.
and (b) converting the quaternary ammonium alkylcarbonate to the quaternary ammonium bicarbonate.
51. A method of preparing a quaternary ammonium methocarbonate having the formula wherein R1 and R2 are independently C1-C30 alkyl and R3 is a C8-C30 alkyl, the method comprising reacting (a) an amine having the formula NR1R2R3;
(b) (i) a cyclic carbonate having the formula wherein R4 is hydrogen or C1-C4 alkyl and n is an integer from 1 to 10, (ii) a polycarbonate, (iii) a carbonate ester, or (iv) a mixture thereof; and (c) methanol to form the methocarbonate.
(b) (i) a cyclic carbonate having the formula wherein R4 is hydrogen or C1-C4 alkyl and n is an integer from 1 to 10, (ii) a polycarbonate, (iii) a carbonate ester, or (iv) a mixture thereof; and (c) methanol to form the methocarbonate.
52. The method of claim 51, wherein the carbonate ester has the formula wherein R9 is -CH3 and R10 is a C1-C10 alkyl.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30397101P | 2001-07-09 | 2001-07-09 | |
| US60/303,971 | 2001-07-09 | ||
| PCT/US2002/021236 WO2003006419A1 (en) | 2001-07-09 | 2002-07-02 | In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2453391A1 true CA2453391A1 (en) | 2003-01-23 |
| CA2453391C CA2453391C (en) | 2011-05-03 |
Family
ID=23174485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2453391A Expired - Fee Related CA2453391C (en) | 2001-07-09 | 2002-07-02 | In situ process for preparing quaternary ammonium bicarbonates and quaternary ammonium carbonates |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6784307B2 (en) |
| EP (1) | EP1406856B1 (en) |
| JP (1) | JP4326327B2 (en) |
| KR (1) | KR100886984B1 (en) |
| CN (1) | CN100396660C (en) |
| AT (1) | ATE466833T1 (en) |
| AU (1) | AU2002316559B2 (en) |
| BR (1) | BR0211229B1 (en) |
| CA (1) | CA2453391C (en) |
| DE (1) | DE60236286D1 (en) |
| ES (1) | ES2345141T3 (en) |
| HU (1) | HU230546B1 (en) |
| MX (1) | MX244518B (en) |
| NO (1) | NO333584B1 (en) |
| NZ (1) | NZ530911A (en) |
| PL (1) | PL205566B1 (en) |
| RU (1) | RU2299193C2 (en) |
| TW (1) | TWI242546B (en) |
| UA (1) | UA76478C2 (en) |
| WO (1) | WO2003006419A1 (en) |
| ZA (1) | ZA200400698B (en) |
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| US20050003978A1 (en) * | 2003-05-28 | 2005-01-06 | Lonza Inc. | Quaternary ammonium carbonates and bicarbonates as anticorrosive agents |
| US20070260089A1 (en) * | 2004-03-26 | 2007-11-08 | Albemarle Corporation | Method for the Synthesis of Quaternary Ammonium Compounds and Compositions Thereof |
| US20070255074A1 (en) * | 2004-03-26 | 2007-11-01 | Sauer Joe D | Method for Exchanging Anions of Tetraalkylammonium Salts |
| MY148568A (en) | 2004-12-09 | 2013-04-30 | Lonza Ag | Quaternary ammonium salts as a conversion coating or coating enhancement |
| US20070167407A1 (en) * | 2005-12-20 | 2007-07-19 | Albemarle Corporation | Quaternary ammonium borate compositions and substrate preservative solutions containing them |
| US20070259781A1 (en) * | 2006-05-08 | 2007-11-08 | Sinha Rabindra K | Chemical formulations for removal of hazardous pollutants from combustion gases |
| US20080287331A1 (en) * | 2007-05-18 | 2008-11-20 | Hai-Hui Lin | Low voc cleaning composition for cleaning printing blankets and ink rollers |
| EP2374836A1 (en) | 2010-04-07 | 2011-10-12 | Nuplex Resins B.V. | Crosslinkable composition crosslinkable with a latent base catalyst. |
| CN101992055B (en) * | 2010-11-03 | 2013-09-11 | 天津大学 | Method and device of continuously synthesizing tetramethyl ammonium carbonate by multi-reactors in series |
| SI2764037T1 (en) * | 2011-10-07 | 2017-08-31 | Allnex Netherlands B.V. | A crosslinkable composition cross-linkable by real michael addition reaction and resins for use in said composition |
| WO2013050574A1 (en) | 2011-10-07 | 2013-04-11 | Nuplex Resins B.V. | A crosslinkable composition comprising a latent base catalyst and latent base catalyst compositions |
| CN103111324B (en) * | 2013-01-25 | 2014-12-17 | 中南大学 | Application of bromine or iodine-containing haloid and method for synthesizing methyl three-long-chain aliphatic group quaternary ammonium salt derivative |
| CN105324426B (en) | 2013-04-08 | 2018-07-03 | 欧尼克斯荷兰有限公司 | It is reacted by true Michael's addition (RMA) and crosslinkable composition |
| KR102299906B1 (en) | 2013-08-28 | 2021-09-09 | 존슨 맛쎄이 퍼블릭 리미티드 컴파니 | Method of making a templating agent |
| JP6281280B2 (en) * | 2013-12-19 | 2018-02-21 | 東ソー株式会社 | Allophanate / isocyanurate-forming catalyst, polyisocyanate composition using the catalyst, method for producing the composition, and two-component coating composition using the composition |
| US9677020B2 (en) | 2014-06-25 | 2017-06-13 | Afton Chemical Corporation | Hydrocarbyl soluble quaternary ammonium carboxylates and fuel compositions containing them |
| AU2016250030C1 (en) | 2015-04-17 | 2021-06-24 | Allnex Netherlands B.V. | A method for curing a RMA crosslinkable resin coating, RMA crosslinkable compositions and resins for use therein |
| EP3283556B1 (en) | 2015-04-17 | 2021-03-10 | Allnex Netherlands B.V. | Floor coating compositions |
| CA2983148C (en) | 2015-04-17 | 2023-05-09 | Allnex Netherlands B.V. | Process for the manufacture of a crosslinkable composition |
| US10759962B2 (en) | 2015-04-17 | 2020-09-01 | Allnex Netherlands B.V. | Method for applying RMA crosslinkable coating on modified epoxy primer coating |
| CN104926668B (en) * | 2015-05-21 | 2018-02-27 | 北京盖雅环境科技有限公司 | A kind of preparation method of tri-long-chain alkyl ammonium bicarbonate and carbonate |
| IT201600130571A1 (en) | 2016-12-23 | 2018-06-23 | Lamberti Spa | INHIBITORS OF GAS HYDRATES |
| IT201600130556A1 (en) | 2016-12-23 | 2018-06-23 | Lamberti Spa | INHIBITORS OF GAS HYDRATES |
| CN107281994B (en) * | 2017-05-16 | 2019-08-27 | 天津大学 | Circulation shell and tube reactor series connection tubular reactor prepares the device and method of tetramethyl ammonium hydrogen carbonate |
| US11673976B2 (en) | 2017-12-11 | 2023-06-13 | Swimc Llc | Method for making water-dispersible and water-dispersed polymers |
| CN108440306B (en) * | 2018-05-24 | 2023-11-03 | 柏川新材料科技(宁波)有限公司 | Green production equipment and method of tetramethyl ammonium carbonate |
| KR102215414B1 (en) | 2020-07-07 | 2021-02-15 | 김상원 | Hue circle |
| CN114570307A (en) * | 2022-03-18 | 2022-06-03 | 西安吉利电子新材料股份有限公司 | Preparation system and method for directly producing electronic-grade tetramethylammonium hydroxide from dimethyl carbonate |
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-
2002
- 2002-02-07 UA UA2004010608A patent/UA76478C2/en unknown
- 2002-07-02 WO PCT/US2002/021236 patent/WO2003006419A1/en active IP Right Grant
- 2002-07-02 NZ NZ530911A patent/NZ530911A/en not_active IP Right Cessation
- 2002-07-02 ES ES02746871T patent/ES2345141T3/en not_active Expired - Lifetime
- 2002-07-02 AT AT02746871T patent/ATE466833T1/en active
- 2002-07-02 AU AU2002316559A patent/AU2002316559B2/en not_active Ceased
- 2002-07-02 JP JP2003512192A patent/JP4326327B2/en not_active Expired - Fee Related
- 2002-07-02 EP EP02746871A patent/EP1406856B1/en not_active Expired - Lifetime
- 2002-07-02 BR BRPI0211229-9A patent/BR0211229B1/en not_active IP Right Cessation
- 2002-07-02 RU RU2004104323/04A patent/RU2299193C2/en not_active IP Right Cessation
- 2002-07-02 US US10/188,692 patent/US6784307B2/en not_active Expired - Lifetime
- 2002-07-02 CA CA2453391A patent/CA2453391C/en not_active Expired - Fee Related
- 2002-07-02 MX MXPA04000353 patent/MX244518B/en active IP Right Grant
- 2002-07-02 CN CNB02802303XA patent/CN100396660C/en not_active Expired - Fee Related
- 2002-07-02 HU HU0401230A patent/HU230546B1/en not_active IP Right Cessation
- 2002-07-02 DE DE60236286T patent/DE60236286D1/en not_active Expired - Lifetime
- 2002-07-02 PL PL367612A patent/PL205566B1/en unknown
- 2002-07-05 TW TW091114946A patent/TWI242546B/en not_active IP Right Cessation
-
2003
- 2003-07-02 KR KR1020047000405A patent/KR100886984B1/en not_active IP Right Cessation
-
2004
- 2004-01-08 NO NO20040069A patent/NO333584B1/en not_active IP Right Cessation
- 2004-01-28 ZA ZA200400698A patent/ZA200400698B/en unknown
- 2004-02-10 US US10/776,368 patent/US6989459B2/en not_active Expired - Lifetime
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20190702 |