# US 8,785,666 B1 · Method for preparation of anhydrosugar ethers

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- Number: US 8,785,666 B1
- Document ID: US8785666B1
- Status: Granted
- Kind: B1
- Application number: 14/262,836
- Filed: 2014-04-28
- Granted: 2014-07-22
- Earliest claimed: 2014-04-28
- Assignees: Archer Daniels Midland Company
- Applicants: Stephen Howard; Alexandra Sanborn
- Inventors: Stephen Howard; Alexandra Sanborn
- Web page: https://patentgrep.com/patent/US8785666B1

## CPC

- C07D 493/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A method for alkylation of an anhydrosugar compound in which a dialkyl carbonate is reacted with an anhydrosugar compound in the presence of a solid phase basic catalyst. Typical anhydrosugars are isosorbide.

## Claims

### Claim 1

A method for alkylation of a 1,4:3,6-dianhydrohexitol comprising the steps of reacting a dialkyl carbonate with a starting 1,4:3,6-dianhydrohexitol selected from the group consisting of sorbitol, mannitol, iditol, and mixtures thereof, in the presence of a solid phase basic zeolite catalyst to form a product mixture comprising at least one of a monoalkyl- or dialkyl-ether of the 1,4:3,6-dianhydrohexitol.

### Claim 2 (depends on 1)

The method of claim 1, wherein the alkyl component of the dialkyl carbonate comprises an alkyl group having 1 to 10 carbon atoms.

### Claim 3 (depends on 2)

The method of claim 2, wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, butyl and combinations of any thereof.

### Claim 4 (depends on 3)

The method of claim 3, wherein the alkyl group is methyl.

### Claim 5 (depends on 1)

The method of claim 1 wherein the zeolite catalyst is a zeolite having ammonium groups.

### Claim 6 (depends on 1)

The method of claim 1 wherein the reaction is carried out at a temperature below 240° C.

### Claim 7 (depends on 5)

The method of claim 5 wherein the reaction is carried out at a temperature below 240° C.

### Claim 8 (depends on 1)

The method of claim 1 wherein the reaction is carried out at a temperature below 240° C. and the reaction time is 2 hours or less.

### Claim 9 (depends on 5)

The method of claim 5 wherein the reaction is carried out at a temperature below 240° C. and the reaction time is 2 hours or less.

### Claim 10 (depends on 1)

The method of claim 1, wherein the product mixture contains unreacted 1,4:3,6-dianhydrohexitol, and the product mixture is recycled to the solid phase basic zeolite catalyst in the presence of the dialkyl carbonate.

### Claim 11 (depends on 10)

The method of claim 10, wherein recycling the unreacted starting 1,4:3,6-dianhydrohexitol results in a reduced amount of unreacted 1,4:3,6-dianhydrohexitol and an increased amount of the monoalkyl- or dialkyl-ether.