Transition metal-catalyzed processes for the preparation of N-allyl compounds and use thereof
US-9499557-B2 · Nov 22, 2016 · US
Method of making a templating agent
US9365490B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9365490-B2 |
| Application number | US-201414227222-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 27, 2014 |
| Priority date | Mar 27, 2013 |
| Publication date | Jun 14, 2016 |
| Grant date | Jun 14, 2016 |
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Abstract
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A method for preparing 1-adamantyltrimethylammonium hydroxide is disclosed. The method comprises reacting 1-adamantyldimethylamine with dimethyl carbonate to produce 1-adamantyltrimethylammonium methylcarbonate, which is then reacted with calcium hydroxide or magnesium hydroxide in the presence of water to produce 1-adamantyltrimethylammonium hydroxide.
First claim
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We claim: 1. A method for preparing 1-adamantyltrimethylammonium hydroxide, comprising: (a) reacting the 1-adamantyldimethylamine with dimethyl carbonate to produce 1-adamantyltrimethylammonium methylcarbonate, wherein the molar ratio of dimethylcarbonate:1-adamantyldimethylamine is in the range of 3 to 5; and (b) reacting the 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide or magnesium hydroxide in the presence of a water to produce 1-adamantyltrimethylammonium hydroxide. 2. The method of claim 1 wherein the molar ratio of calcium hydroxide or magnesium hydroxide:1-adamantyltrimethylammonium methylcarbonate is in the range of 1.05 to 1.75. 3. The method of claim 1 wherein the reaction of 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide or magnesium hydroxide in the presence of water is performed at reflux. 4. The method of claim 1 wherein the reaction of 1-adamantyldimethylamine with dimethyl carbonate is performed at a temperature in the range of 120-160° C. 5. The method of claim 1 wherein the 1-adamantyltrimethylammonium methylcarbonate is reacted with calcium hydroxide. 6. A method for preparing 1-adamantyltrimethylammonium hydroxide, comprising: (a) producing 1-adamantyldimethylamine by reacting 1-adamantylamine hydrochloride, formaldehyde, formic acid, and an inorganic base to produce 1-adamantyldimethylamine, wherein the molar ratio of formaldehyde:1-adamantylamine hydrochloride is in the range of 2.1 to 2.4 and the molar ratio of formic acid:1-adamantylamine hydrochloride is in the range of 2.3 to 2.7; (b) reacting the 1-adamantyldimethylamine with dimethyl carbonate to produce 1-adamantyltrimethylammonium methylcarbonate, wherein the molar ratio of dimethyl carbonate:1-adamantyldimethylamine is in the range of 3 to 5; and (c) reacting the 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide or magnesium hydroxide in the presence of a water to produce 1-adamantyltrimethylammonium hydroxide. 7. The method of claim 6 wherein the inorganic base is a hydroxide, a carbonate or a bicarbonate of a Group I metal. 8. The method of claim 6 wherein the inorganic base is sodium hydroxide. 9. The method of claim 6 wherein the reaction of 1-adamantylamine hydrochloride, formaldehyde, formic acid, and the inorganic base is performed by mixing 1-adamantylamine hydrochloride and formic acid, followed by the addition of the inorganic base, and then adding the formaldehyde. 10. The method of claim 6 wherein the 1-adamantyltrimethylammonium methylcarbonate is reacted with calcium hydroxide. 11. The method of claim 6 wherein the molar ratio of calcium hydroxide or magnesium hydroxide:1-adamantyltrimethylammonium methylcarbonate is in the range of 1.05 to 1.75. 12. The method of claim 6 wherein the reaction of 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide or magnesium hydroxide in the presence of water is performed at reflux. 13. The method of claim 6 wherein the reaction of 1-adamantyldimethylamine with dimethyl carbonate is performed at a temperature in the range of 120-160° C. 14. The method of claim 6 wherein the 1-adamantyltrimethylammonium methylcarbonate is reacted with calcium hydroxide.
Assignees
Inventors
Classifications
- C07C209/00Primary
Preparation of compounds containing amino groups bound to a carbon skeleton · CPC title
Quaternary ammonium compounds · CPC title
- C07C209/68Primary
from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title
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Frequently asked questions
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- What does patent US9365490B2 cover?
- A method for preparing 1-adamantyltrimethylammonium hydroxide is disclosed. The method comprises reacting 1-adamantyldimethylamine with dimethyl carbonate to produce 1-adamantyltrimethylammonium methylcarbonate, which is then reacted with calcium hydroxide or magnesium hydroxide in the presence of water to produce 1-adamantyltrimethylammonium hydroxide.
- Who is the assignee on this patent?
- Johnson Matthey Plc
- What technology area does this patent fall under?
- Primary CPC classification C07C209/00. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Jun 14 2016 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).