Method for producing adamantane

Patent metadata

Field	Value
Publication number	US-9714202-B2
Application number	US-201414546667-A
Country	US
Kind code	B2
Filing date	Nov 18, 2014
Priority date	Jun 3, 2014
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

A method for producing adamantane includes the steps of preparing a catalytic composition including an acidic ionic liquid and a co-catalyst and subjecting a tetrahydrodicyclopentadiene-containing component to isomerization in the presence of the catalytic composition to form adamantane. The acidic ionic liquid includes aluminum chloride and a quaternary onium compound selected from the group consisting of a quaternary ammonium halide, a quaternary phosphonium halide, and a combination thereof. The co-catalyst is an oxygen-containing reagent.

First claim

What is claimed is:

1. A method for producing adamantane, comprising the steps of:
preparing a catalytic composition including an acidic ionic liquid and a co-catalyst, wherein the acidic ionic liquid includes aluminum chloride and a quaternary onium compound selected from the group consisting of a quaternary ammonium halide, a quaternary phosphonium halide, and a combination thereof, and wherein the co-catalyst is selected from the group consisting of water and an aqueous solution of 1-50 wt. % hydrogen peroxide; and
subjecting a tetrahydrodicyclopentadiene-containing component to isomerization in the presence of the catalytic composition to form adamantane.

2. The method according to claim 1 , wherein the tetrahydrodicyclopentadiene-containing component includes a tetrahydrodicyclopentadiene compound selected from the group consisting of exo-tetrahydrodicyclopentadiene, endo-tetrahydrodicyclopentadiene, and a combination thereof.

3. The method according to claim 1 , wherein the quaternary ammonium halide is selected from the group consisting of ammonium halide, pyridinium halide, imidazolium halide, pyrrolium halide, pyridinium halide, pyrimidinium halide, pyrazinium halide, pyridazinium halide, alkyl-substituted ammonium halide, alkyl-substituted pyridinium halide, alkyl-substituted imidazolium halide, alkyl-substituted pyrrolium halide, alkyl-substituted pyrimidinium halide, alkyl-substituted pyrazinium halide, alkyl-substituted pyridazinium halide, and combinations thereof.

4. The method according claim 3 , wherein each of said alkyl-substituted ammonium halide, said alkyl-substituted pyridinium halide, said alkyl-substituted imidazolium halide, said alkyl-substituted pyrrolium halide, said alkyl-substituted pyrimidinium halide, said alkyl-substituted pyrazinium halide, and said alkyl-substituted pyridazinium halide contains an alkyl substituent having a carbon number ranging from 1 to 18.

5. The method according to claim 1 , wherein the quaternary phosphonium halide is tetraalkylphosphonium halide.

6. The method according to claim 1 , wherein a molar ratio of aluminum chloride to the acidic ionic liquid ranges from 0.5 to 0.9.

7. The method according to claim 2 , wherein the tetrahydrodicyciopeniadiene compound is endo-tetrahydrodicyclopentadiene, the tetrahydrodicyclopentadiene-containing component further including a solvent for dissolving endo-tetrahydrodicyclopentadiene, the solvent included in the tetrahydrodicyclopentadiene-containing component being used in an amount greater than 0 wt % and up to 50 wt % based on 100 wt % of the tetrahydrodicyclopentadiene-containing component.

8. The method according to claim 7 , wherein the solvent included in the tetrahydrodicyclopentadiene-containing component is selected from the group consisting of a C 5 -C 18 n-alkane, a C 5 -C 18 iso-alkane, a C 5 -C 18 neo-alkane, a C 5 -C 18 cycloalkane, a C 1 -C 6 halogen-containing hydrocarbon, and combinations thereof.

9. The method according to claim 1 , wherein the isomerization is conducted at a temperature ranging from 25 to 150° C.

Assignees

• Cpc Corp Taiwan

Inventors

• Huang Ming-Yu
• Lin Jann-Chen
• Wang Yih-Ping
• Wu Jung-Chung

Classifications

• C07C2531/02

  containing organic compounds or metal hydrides · CPC title

• B01J31/0209

  Esters of carboxylic or carbonic acids · CPC title

• B01J31/0202

  Alcohols or phenols · CPC title

• C07C2531/04

  containing carboxylic acids or their salts · CPC title

• B01J31/08

  Ion-exchange resins · CPC title