Process and assembly for producing alkylene oxides and glycol ethers

Patent metadata

Field	Value
Publication number	US-9273019-B2
Application number	US-201514806498-A
Country	US
Kind code	B2
Filing date	Jul 22, 2015
Priority date	Jul 14, 2010
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

Abstract

There is provided a process for manipulating the amount of alkyl alcohol in a product stream, e.g., such as an alkylene oxide product stream. More particularly, and in contrast to conventional processes wherein substantially all of the alkyl alcohol must be separated and desirably recycled, in the present process, a greater amount of alkyl alcohol may be allowed to remain in a partially refined alkylene oxide product stream. The residual alkyl alcohol is subsequently substantially entirely reacted to form a downstream product, e.g., a glycol ether, which is more easily separated from the alkylene oxide product stream. Indeed, the amount of alkyl alcohol in the partially refined alkylene oxide product stream can be selected based upon the output of glycol ethers, if desired.

First claim

The invention claimed is:

1. A process for manipulating the amount of an alkyl alcohol in a mixture comprising from about 5 to about 15 weight percent alkylene oxide, about 50 to about 85 weight percent alcohol and about 10 to about 25 weight percent water, comprising:
Introducing the mixture into a distillation column to produce a refined stream comprising from about 70 to about 95 weight percent alkylene oxide, about 1 to about 30 weight percent alkyl alcohol and about 0.1 to about 4.9 weight percent water; and
Reacting the refined stream with a catalyst comprising a metal-ligand complex, an acid, a base, a metal alkoxide, or a combination of any number of these to reduce the alkyl alcohol content in a resulting reacted stream to less than 1 wt %.

2. The process of claim 1 , further comprising introducing the reacted stream into a second distillation column to provide a substantially pure stream of alkylene oxide and a stream of glycol ethers.

3. The process of claim 1 , wherein the alkylene oxide comprises ethylene oxide, propylene oxide, butylene oxide, pentylene oxide, hexylene oxide, and combinations thereof.

4. The process of claim 1 , wherein the alcohol comprises methanol, ethanol, propanol, butanol, pentanol, hexanol, 2-ethylhexyl alcohol, and combinations thereof.

5. The process of claim 1 , wherein the metal ligand complex comprises a monomer defined by the formula:

wherein R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 , X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are, independently of one another, selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, hydrocarbyl, hydroxyl, alkoxyl, amino, nitro, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, silyl, ether, thioether, sulfonyl, selenoether, ketone, aldehyde, and ester;
or wherein two or more of R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 , X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 together form a ring selected from the group consisting of a carbocyclic ring and a heterocyclic ring, said ring having from 4 to 10 atoms in the ring;
wherein R 5 group is selected from the group consisting of a carbon-carbon bond, a methylene group, an ethylene group, an amine, an oxygen atom, and a sulfur atom;
wherein M t+ is a Group 2-15 metal capable of complexing with a ligand to affect catalysis, wherein t is an integer between 2 and 4;
wherein group A is selected from the group consisting of neutral group, bound anionic group, unbound anionic group, and combinations thereof, wherein s is the number of A groups associated with the metal and is an integer between 0 and 2.

6. The process of claim 5 , wherein A is carboxylate, sulfonate, halide, alkoxide, phenoxide, hexafluorophosphate, tetrafluoroborate, hexafluoroantimonate or bis(trialkylsilyl)amide.

7. The process of claim 5 , wherein one or more of R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 , X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are capable of providing a complementary interaction with a second monomer to form a component selected from the group consisting of oligomer, polymer, and copolymer.

8. The process of claim 1 , wherein the acid comprises one or more metal triflates, metal tosylates, tris-perfluoronated aryl borons, p-toluenesulfonic acid, phosphoric acid, sulfuric acid, acidic ion exchange resin, acidic alumina, zeolites, acid modified silicas, aluminas, or silica-aluminas, metal oxides and sulfides, mounted acids on silica, quartz sand, alumina or diatomaceous earth, mixed oxides, metal salts, heat treated charcoal, or combinations thereof.

9. The process of claim 1 , wherein the base comprises one or more metal hydroxides, metal carbonates, metal oxides, imidazoles, amines, pyridines, metal alkoxides, basic ion-exchange resins, basic alumina, alkali ion-exchanged zeolites, hydrotalcites, chrysotile, sepiolite, KF supported on alumina, lanthanide imide, nitride on zeolite, or combinations thereof.

Assignees

• Dow Global Technologies Llc

Inventors

• Arrowood Tina L
• Flick Derrick W
• Ackford John F

Classifications

• C07D301/32 Primary

  Separation; Purification · CPC title

• C07D301/36

  Use of additives, e.g. for stabilisation · CPC title

• B01J19/245

  placed in series · CPC title

• A61K31/336

  having three-membered rings, e.g. oxirane, fumagillin · CPC title

• C07D301/12

  with hydrogen peroxide or inorganic peroxides or peracids · CPC title