Method for producing alkylene glycol diethers

A technology of alkylene glycol diether and alkyl, which is applied in the field of preparing chain alkylene glycol diether, and can solve problems such as difficult sales

Inactive Publication Date: 2008-09-10
CLARIANT PROD DEUT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In both processes, however, 10 to 15% of triglyme is formed, which can only be sold with difficulty due to its high boiling point of 275° C.

Method used

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  • Method for producing alkylene glycol diethers
  • Method for producing alkylene glycol diethers
  • Method for producing alkylene glycol diethers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 4

[0070] Example 4: HBF 4 / H 2 SO 4 catalytic

[0071] Similar to Comparative Example 1, 200 mg (2.28 mmol) of fluoroboric acid, 231 mg (2.28 mmol) of sulfuric acid and 157 g (3.41 mol) of dimethyl ether were initially charged in a 1-liter steel autoclave, and heated at 55° C. and 15 bar, 15.0 g (0.34 mol) of ethylene oxide were added. After an after-reaction time of 50 minutes and draining of the dimethyl ether, 30.7 g of residue were isolated. This residue has the following composition:

[0072] 59.9% Ethylene glycol dimethyl ether

[0073] 2.1% 1,4-dioxane

[0074] 6.8% Ethylene glycol monomethyl ether

[0075] 17.8% diglyme

[0076] 3.0% Diethylene glycol monomethyl ether

[0077] 4.3% Triglyme

[0078] 0.7% triethylene glycol monomethyl ether

[0079] 1.2% Tetraglyme

[0080] 0.3% Pentaethylene glycol dimethyl ether

[0081] 3.9% Unknown

Embodiment 5

[0082] Example 5: HBF 4 / H 3 PO 4 catalytic

[0083] Similar to Comparative Example 1, 200 mg (2.28 mmol) of fluoroboric acid, 223 mg (2.28 mmol) of phosphoric acid and 157 g (3.41 mol) of dimethyl ether were initially charged in a 1 liter steel autoclave, and heated at 55° C. and 15 bar, 15.0 g (0.34 mol) of ethylene oxide were added. After an after-reaction time of 50 minutes and draining of the dimethyl ether, 23.8 g of residue were isolated. This residue has the following composition:

[0084] 60.1% Ethylene glycol dimethyl ether

[0085] 1.7% 1,4-dioxane

[0086] 5.0% Ethylene glycol monomethyl ether

[0087] 16.9% diglyme

[0088] 4.6% Diethylene glycol monomethyl ether

[0089] 3.8% Triglyme

[0090] 1.6% triethylene glycol monomethyl ether

[0091] 0.9% Tetraglyme

[0092] 1.4% tetraethylene glycol monomethyl ether

[0093] 0.1% Pentaethylene glycol dimethyl ether

[0094] 3.9% Unknown

Embodiment 6

[0095] Example 6: HBF 4 / HNO 3 catalytic

[0096] Similar to Comparative Example 1, 200 mg (2.28 mmol) of fluoroboric acid, 288 mg (2.96 mmol) of nitric acid and 157 g (3.41 mol) of dimethyl ether were initially charged in a 1 liter steel autoclave, and heated at 55° C. and 15 bar, 15.0 g (0.34 mol) of ethylene oxide were added. After an after-reaction time of 50 minutes and draining of the dimethyl ether, 29.7 g of residue were isolated. This residue has the following composition:

[0097] 59.8% Ethylene glycol dimethyl ether

[0098] 1.8% 1,4-dioxane

[0099] 3.0% Ethylene glycol monomethyl ether

[0100] 16.3% diglyme

[0101] 4.3% Diethylene glycol monomethyl ether

[0102] 3.8% Triglyme

[0103] 1.9% triethylene glycol monomethyl ether

[0104] 3.2% tetraglyme

[0105] 1.1% tetraethylene glycol monomethyl ether

[0106] 0.3% Pentaethylene glycol dimethyl ether

[0107] 4.5% Unknown

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PUM

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Abstract

The invention relates to a method for producing alkylene glycol diethers by reacting a linear or cyclic ether with an alkylene oxide in the presence of a Lewis acid. The method is characterized in that the Lewis acid is a mixture of 1 part by weight of HBF4 and / or BF3 and 0.1 to 10 parts by weight of H2SO4, HNO3 and / or H3PO4. The new catalyst system allows to reduce undesired by-products such as e.g. dioxan or dimethyltriethylene glycol, and to increase the quantity of valuable substances such as dimethyl glycol and dimethyl diglycol.

Description

technical field [0001] The present invention relates to a process for the preparation of chain-like alkylene glycol diethers by means of a novel catalyst system. Background technique [0002] Alkylene glycol diethers have long been used as polar inert solvents. For their preparation, indirect processes are used or described industrially, such as the Williamson ether synthesis (K. Weissermel, H.J. Arpe, "Industrielle Organische Chemie", 1998, p. 179) or diethylene glycol ether formal hydrogenation (DE-A-24 34 057), but also direct methods, e.g. in Lewis acids such as BF 3 (US-4 146 736, DE-A-2 741 676 and DE-A-2 640 505 together with DE-A-3 128 962) or SnCl 4 (DE-A-3 025 434) is used to insert alkylene oxides into chain ethers. [0003] The technical advantage of the direct process lies not only in the simplification of the preparation process, but also in the absence of by-products, such as large amounts of sodium chloride or sodium sulfate in the Williamson synthesis, or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/02C07C43/10C07C43/11
CPCC07C41/02C07C43/10C07C43/11
Inventor G·奥伯伦德费尔纳A·斯内尔
Owner CLARIANT PROD DEUT GMBH
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