# US 2024/0189802 A1 · Spirocyclic compound containing catalyst for use in catalyzing reaction of epoxide compound and carbon dioxide

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2024/0189802 A1
- Document ID: US20240189802A1
- Status: Published application
- Kind: A1
- Application number: 18/044,219
- Filed: 2022-10-28
- Published: 2024-06-13
- Earliest claimed: 2022-10-21
- Assignees: Shenzhen Capchem Technology Co., Ltd.
- Applicants: Shenzhen Capchem Technology Co., Ltd.
- Inventors: Zhongtian ZHENG; Tianqian HE; Yuanyuan KANG; Qiyou HUANG
- Web page: https://patentgrep.com/patent/US20240189802A1

## CPC

- B01J 27/24: Nitrogen compounds
- B01J 31/0239: {Quaternary ammonium compounds}
- B01J 31/0268: {Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous}
- C07D 317/26: Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
- C07D 317/36: Alkylene carbonates; Substituted alkylene carbonates
- B01J 2231/341: 1,2-additions, e.g. aldol or Knoevenagel condensations
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure provides a use of a catalyst for catalyzing a reaction of an epoxide compound and carbon dioxide, the catalyst includes a spirocyclic compound including at least one compound of formula (1): where X is selected from nitrogen, or phosphorus; Y is selected from halogens; A and B are independently selected from materials having formulae (a) to (d). Compared with catalysts with a non-spirocyclic structure or Lewis acid metal catalysts, the catalyst including the spirocyclic compound having the structural shown in formula 1 has the advantages of better catalytic effect, more stable performance and longer service life when catalyzing the reaction of the epoxy compounds and carbon dioxide. The present catalyst has both high efficiency and safety, and thus has broad application prospects.

## Claims

### Claim 1

A method for preparing a cyclic carbonate by using a catalyst for catalyzing a reaction of an epoxide compound and carbon dioxide, wherein the catalyst comprises a spirocyclic compound comprising at least one compound of formula (1):
where X is selected from nitrogen, or phosphorus; Y is selected from halogens; A and B are independently selected from the following formulae with a sign * representing a bonding position:
Ra1-Ra8, Rb1-Rb10, Rc1-Rc12, and Rd1-Rd14 are independently selected from H, or a C1-C5 alkyl group,
wherein the method comprises:
dissolving the catalyst in a cyclic carbonate to obtain a mixed solution, and
adding the epoxide compound to the mixed solution, and introducing carbon dioxide to adjust a pressure of a reaction system to allow the epoxide compound to react with carbon dioxide to generate the cyclic carbonate.

### Claim 2 (depends on 1)

The method of claim 1, wherein Y is selected from Cl, Br, or I.

### Claim 3 (depends on 1)

The method of claim 1, wherein at least one of A and B is selected from formula (a).

### Claim 4 (depends on 1)

The method of claim 1, wherein the spirocyclic compound comprises at least one selected from a group consisting of 5-azoniaspiro[4.6]undecane chloride; 5 -azoniaspiro[4.6]undecane bromide; 5-azoniaspiro[4.6]undecane iodide; 5-azoniaspiro[4.4]nonane chloride; 5-azoniaspiro[4.4]nonane bromide; 5-azoniaspiro[4.4]nonane iodide; 5-phosphaspiro[4.5]decane chloride; 5-phosphaspiro[4.5]decane bromide; 5-phosphaspiro[4.5]decane iodide; 8,8-dimethyl-5-azoniaspiro[4.5]decane chloride; 8,8-dimethyl-5-azoniaspiro[4.5]decane bromide; 8,8-dimethyl-5-azoniaspiro[4.5]decane iodide; 7,9-dimethyl-5-phosphaspiro[4.5]decane chloride; 7,9-dimethyl-5-phosphaspiro[4.5]decane bromide; 7,9-dimethyl-5-phosphaspiro[4.5]decane iodide; 2-butyl-5-phosphaspiro[4.4]nonane chloride; 2-butyl-5-phosphaspiro[4.4]nonane bromide; 2-butyl-5-phosphaspiro[4.4]nonane iodide; 1,6-dimethyl-5-azoniaspiro[4.6]undecane chloride; 1,6-dimethyl-5-azoniaspiro[4.6]undecane bromide; 1,6-dimethyl-5-azoniaspiro[4.6]undecane iodide; 5-azoniaspiro[4.5]decane bromide; and 6-azoniaspiro[5.5]undecane bromide.

### Claim 5 (depends on 1)

The method of claim 1, wherein the catalyst further comprises at least one of water or alcohol, water is present in the catalyst in a concentration of 2000 ppm or less, the alcohol is present in the catalyst in a concentration of 2000 ppm or less.

### Claim 6 (depends on 5)

The method of claim 5, wherein the alcohol is selected from at least one of methanol, ethanol, propanol, isopropanol or n-butanol.

### Claim 7 (depends on 1)

The method of claim 1, wherein the epoxide compound is selected from at least one of ethylene oxide or propylene oxide.

### Claim 8

(canceled)

### Claim 9 (depends on 1)

The method of claim 1, wherein a mass percent concentration of the spirocyclic compound in the mixed solution is in the range from 0.5 to 10%.

### Claim 10 (depends on 1)

The method of claim 1, wherein a temperature of the reaction system is in a range from 100 to 200° C.

### Claim 11 (depends on 9)

The method of claim 9, wherein the mass percent concentration of the spirocyclic compound in the mixed solution is in the range from 1 to 5%.

### Claim 12 (depends on 1)

The method of claim 1, wherein the pressure of the reaction system is in a range from 0.5 to 10 MPa.

### Claim 13 (depends on 12)

The method of claim 12, wherein the pressure of the reaction system is in a range from 1 to 5 MPa.

### Claim 14 (depends on 1)

The method of claim 1, wherein a reaction time is in a range from 0.3 h to 20 h.

### Claim 15 (depends on 14)

The method of claim 14, wherein the reaction time is in a range from 0.5 h to 15 h.

### Claim 16 (depends on 1)

The method of claim 1, wherein an initial concentration of the epoxide compound in the mixed solution is in a range of 1 to 15 wt %.