# US 11,027,270 B1 · Method of performing coupling reactions

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- Number: US 11,027,270 B1
- Document ID: US11027270B1
- Status: Granted
- Kind: B1
- Application number: 17/146,542
- Filed: 2021-01-12
- Granted: 2021-06-08
- Earliest claimed: 2021-01-12
- Assignees: King Abdulaziz University
- Applicants: King Abdulaziz University
- Inventors: Mohamed Mokhtar Mohamed Mostafa; Ghalia Saeed Alzhrani; Elham Shafik Aazam; Tamer Said Sayed Saleh
- Web page: https://patentgrep.com/patent/US11027270B1

## CPC

- B01J 37/031: {Precipitation}
- B01J 23/755: Nickel
- B01J 29/084: {Y-type faujasite}
- B01J 35/19: {Catalysts containing parts with different compositions}
- B01J 37/0215: {Coating}
- C07C 2/84: catalytic
- C07C 15/50: polycyclic non-condensed
- C07C 41/30: by increasing the number of carbon atoms, e.g. by oligomerisation
- C07C 2523/755: Nickel
- C07C 2529/14: Iron group metals or copper
- Y02P 20/50: Improvements relating to the production of bulk chemicals
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A method of preparing an amalgamated transition metal layered double hydroxide (LDH)@Y-zeolite hybrid catalyst is provided. The method includes combining a transition metal with aluminum nitrate and precipitating using an alkali under ultrasound irradiation and an inert atmosphere to form a transition metal-containing LDH catalyst. A Y-zeolite is pretreated by an ion exchange process utilizing ammonia prior to calcination at temperature (250-1000° C.) under an inert atmosphere to form an H—Y-zeolite. Followed by refluxing the transition metal-containing LDH catalyst together with the H—Y-zeolite at 50° C. for a predetermined time to form a precipitate. The precipitate is filtering and washing with distilled water to obtain the amalgamated transitional metal LDH@Y-zeolite hybrid catalyst. The disclosure also relates to a method for performing a terminal alkyne dehydrogenation coupling reaction involving a synergetic effect of a bill mill and an amalgamated transition metal layered double hydroxide (LDH)@Y-zeolite hybrid catalyst.

## Claims

### Claim 1

A method for performing a terminal alkyne dehydrogenation coupling reaction, the method comprising:
combining a transitional metal LDH@Y-zeolite hybrid catalyst, to a terminal alkyne, and pyrrolidine to form a mixture;
transferring a portion of the mixture into a ball mill;
performing a mechanochemical agitation of the portion of the mixture in the ball mill for a first predetermined time to form a reaction mixture;
oxidizing the reaction mixture for a second predetermined time;
filtering the oxidized reaction mixture to obtain a filtrate;
concentrating the filtrate in a vacuum under reduced pressure; and
purifying the concentrated filtrate using chromatography to obtain a purified end product of the terminal alkyne dehydrogenation coupling reaction.

### Claim 2 (depends on 1)

The method of claim 1, further comprising filtering the oxidized reaction mixture using ethyl acetate.

### Claim 3 (depends on 1)

The method of claim 1, wherein a yield of the purified end product is more than or equal to 80%.

### Claim 4 (depends on 1)

The method of claim 1, wherein the reaction is a solvent-free reaction.

### Claim 5 (depends on 1)

The method of claim 1, further comprising using the transitional metal LDH@Y-zeolite hybrid catalyst for at least 4 cycles.

### Claim 6 (depends on 1)

The method of claim 1, further comprising, oxidizing the reaction mixture using an oxidant, wherein the oxidant is air.

### Claim 7 (depends on 1)

The method of claim 1, wherein the coupling reaction is completed in less than or equal to 60 minutes.

### Claim 8 (depends on 1)

The method of claim 1, further comprising sonicating the reaction mixture for less than or equal to 5 minutes.

### Claim 9 (depends on 1)

The method of claim 1, wherein the coupling reaction is a homocoupling reaction.

### Claim 10 (depends on 9)

The method of claim 9, wherein the homocoupling reaction is a Glaser homocoupling.

### Claim 11 (depends on 1)

The method of claim 1, where the coupling reaction is a cross-coupling reaction.

### Claim 12 (depends on 1)

The method of claim 1, wherein the transitional metal LDH@Y-zeolite hybrid catalyst is a NiLDH@YZ hybrid catalyst.

### Claim 13 (depends on 12)

The method of claim 12, wherein the NiLDH@YZ hybrid catalyst is a 0.5NiLDH@0.5YZ hybrid catalyst.