# US 10,479,799 B2 · Solid catalyst for dehydration of mannitol, and method for producing 2, 5-sorbitan and/or isomannide using this catalyst

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- Number: US 10,479,799 B2
- Document ID: US10479799B2
- Status: Granted
- Kind: B2
- Application number: 16/322,351
- Filed: 2017-07-20
- Published: 2019-06-06
- Granted: 2019-11-19
- Earliest claimed: 2016-08-29
- Assignees: National University Corporation Hokkaido University; Clariant Catalysts (Japan) K.K.
- Applicants: National University Corporation Hokkaido University; Clariant Catalysts (Japan) K.K.
- Inventors: Atsushi Fukuoka; Hirokazu Kobayashi; Xin Chen
- Web page: https://patentgrep.com/patent/US10479799B2

## CPC

- C07D 493/04: Ortho-condensed systems
- B01J 29/08: of the faujasite type, e.g. type X or Y
- B01J 29/082: {X-type faujasite}
- B01J 29/084: {Y-type faujasite}
- B01J 29/70: of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J 29/7007: {Zeolite Beta}
- C07B 61/00: Other general methods
- B01J 2523/00: Constitutive chemical elements of heterogeneous catalysts
- Y02P 20/584: Recycling of catalysts
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Provided is a solid acid catalyst which enables the production of isomannide and/or 2,5-sorbitan from mannitol with high yield and high safety at low cost. The mannitol may be derived from a cellulose and/or a hemicellulose. The solid acid catalyst for dehydration contains an acid type β-zeolite and/or a Y type zeolite.

## Claims

### Claim 1

A solid, dehydration catalyst for producing 2,5-sorbitan and/or isomannide from mannitol comprising an H-type β zeolite and/or a Y-type zeolite.

### Claim 2 (depends on 1)

The solid, dehydration catalyst according to claim 1 consisting essentially of the H-type β-zeolite.

### Claim 3 (depends on 1)

The solid, dehydration catalyst according to claim 1 consisting essentially of the Y-type zeolite.

### Claim 4 (depends on 1)

The solid, dehydration catalyst according to claim 1, wherein the H-type β-zeolite and/or Y-type zeolite has a Si/Al atomic composition ratio of 10 to 300.

### Claim 5 (depends on 4)

The solid, dehydration catalyst according to claim 4, wherein the Si/Al atomic composition ratio of the H-type β-zeolite and/or Y-type zeolite is 25 to 150.

### Claim 6 (depends on 5)

The solid, dehydration catalyst according to claim 5, wherein the Si/Al atomic composition ratio of the H-type β-zeolite and/or Y-type zeolite is 40 to 100.

### Claim 7 (depends on 1)

A process for producing 2,5-sorbitan and/or isomannide from mannitol, comprising the steps of:
(a) adding the solid, dehydration catalyst according to claim 1 to mannitol to obtain a reaction mixture, and
(b) heating the reaction mixture obtained in step (a) to a temperature of 110° C. to 170° C. at ambient pressure or under reduced pressure.

### Claim 8 (depends on 7)

The process according to claim 7, wherein the amount of the solid, dehydration catalyst is 5 to 50% by weight, based on 100% by weight of the mannitol.

### Claim 9 (depends on 7)

The process according to claim 7, wherein the solid, dehydration catalyst consists essentially of the H-type β zeolite, and wherein the process further comprises producing isomannide.

### Claim 10 (depends on 7)

The process according to claim 7, wherein the process further comprises producing isomannide by 1,4-mannitan.

### Claim 11 (depends on 7)

The process according to claim 7, wherein the solid, dehydration catalyst consists essentially of the Y-type zeolite, and wherein the process further comprises producing 2,5-sorbitan.

### Claim 12

A process for selectively producing isomannide from mannitol or 2,5-sorbitan from mannitol comprising catalytically dehydrating mannitol by use of any of the compositions selected from the group consisting of an H-type β zeolite, a Y-type zeolite or a mixture thereof.