IP Library Granted Patent US 8,398,728
Granted Patent B2
US 8,398,728 · App. 12/742,282 · Granted Mar 19, 2013

Process for making a composition comprising at least two different dialkyl ethers

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Quick Facts
Patent No.
US 8,398,728
App. No.
12/742,282
Granted
Mar 19, 2013
Kind
B2
Abstract

The present invention further contemplates a process for making a dialkyl ether composition comprising two or more ethers of the formula R 1 —O—R 2 . The present invention further contemplates a process for making a dialkyl ether composition starting from a first reaction product comprising 1-butanol. The invention further contemplates a dialkyl ether composition comprising two or more ethers of the formula R 1 —O—R 2 , where each R 1 and R 2 can independently be any carbon chain length, saturated or unsaturated; branched or straight-chain, of between C 2 and C 10 ; specifically between C 4 and C 10 ; more specifically between C 4 and C 6 ; more specifically C 6 ; more specifically 0 4 . The present invention further contemplates a process where a first reaction product comprising 1-butanol is used to produce a dialkyl ether composition where each R 1 and R 2 can independently be any carbon chain length, saturated or unsaturated; branched or straight-chain, of between C 2 and C 10 ; specifically between C 4 and C 10 ; more specifically between C 4 and C 6 ; more specifically C 6 ; more specifically C 4 .

Claims (20)

1. A process for making a dialkyl ether composition comprising two or more ethers of the formula R 1 —O—R 2 , wherein each R 1 and R 2 is independently C 2 - C 10 straight-chain or branched alkyl groups, comprising:

a) contacting a reactant comprising ethanol with a base catalyst to make a first reaction product comprising 1-butanol and water, and optionally comprising unreacted ethanol;

b) optionally removing a substantial portion of the water from said first reaction product;

c) optionally removing a substantial portion of the unreacted ethanol from said first reaction product;

d) contacting the product of either step (a), step (b), step (c), or steps (b) and (c), optionally in the presence of a solvent, with at least one acid catalyst at a temperature of about 100° C. to about 250° C. and a pressure 4.8 MPa to produce a second reaction product comprising two or more ethers of the formula R 1 —O—R 2 ; and

e) recovering said dialkyl ether composition from said second reaction product, wherein the selectivity to the ethers is at least about 74%.

2. The process of claim 1 , wherein each R 1 and R 2 is independently C 4 - C 10 straight-chain or branched alkyl.

3. The process of claim 1 , wherein the acidic catalyst is a homogenous catalyst.

4. The process of claim 1 , wherein the acidic catalyst is a heterogeneous catalyst.

5. A process for making a dialkyl ether composition comprising two or more ethers of the formula R 3 —O—R 4 , wherein each R 3 and R 4 is independently C 1 - C 10 straight-chain or branched alkyl groups, comprising:

a) contacting a reactant comprising ethanol and methanol with a base catalyst to make a first reaction product comprising at least one C 3 - C 10 straight-chain or branched alkyl alcohol and water, and optionally comprising unreacted reactant;

b) optionally removing a substantial portion of the water from said first reaction product;

c) optionally removing a substantial portion of the unreacted reactant from said first reaction product;

d) contacting the product of either step (a), step (b), step (c), or steps (b) and (c), optionally in the presence of a solvent, with at least one acid catalyst at a temperature of about 100° C. to about 250° C. and a pressure 4.8 MPa to produce a second reaction product comprising two or more ethers of the formula R 3 —O—R 4 ; and

e) recovering said dialkyl ether composition from said second reaction product, wherein the selectivity to the ethers is at least about 74%.

6. The process of claim 5 , wherein each R 1 and R 2 is independently C 4 - C 6 straight-chain or branched alkyl.

7. The process of claim 5 , wherein each R 1 and R 2 is independently C 6 chain or branched alkyl.

8. The process of claim 5 , wherein each R 1 and R 2 is independently C 4 straight-chain or branched alkyl.

9. The process of claim 5 , wherein the acidic catalyst is a homogenous catalyst.

10. The process of claim 5 , wherein the acidic catalyst is a heterogeneous catalyst.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2022
From: DUPONT US HOLDING, LLC
To: VIRIDIS CHEMICAL, LLC
Reel/Frame 058897/0129 →
CORRECTIVE ASSIGNMENT TO CORRECT THE DESIGNATION OF ASSIGNEE AS A DELAWARE CORPORATION TO A DELAWARE LIMITED LIABILITY COMPANY PREVIOUSLY RECORDED ON REEL 049880 FRAME 0001. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 28, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT US HOLDING, LLC
Reel/Frame 051502/0610 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT US HOLDING, LLC
Reel/Frame 049880/0001 →