Process for preparing vinyl acetate with inhibited by-product formation

Patent metadata

Field	Value
Publication number	US-9561997-B2
Application number	US-201415101764-A
Country	US
Kind code	B2
Filing date	Dec 2, 2014
Priority date	Dec 6, 2013
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

The invention provides a process for preparing vinyl acetate in a heterogeneously catalyzed, continuous gas phase process by reacting ethylene with acetic acid and oxygen and subsequently working up the product gas stream, with inhibition of the polymerization of vinyl acetate during the workup of the product gas mixture by addition of one or more N-oxyl compounds which contain at least one N-oxyl radical group —N—O. as inhibitors which comprises adding the N-oxyl compound as a 50 to 85% by weight strength aqueous solution.

First claim

The invention claimed is:

1. A process for preparing vinyl acetate in a heterogeneously catalyzed, continuous gas phase process by reacting ethylene with acetic acid and oxygen and subsequently working up the product gas stream, with inhibition of the polymerization of vinyl acetate during the workup of the product gas mixture by addition of one or more N-oxyl compounds which contain at least one N-oxyl radical group —N—O. as inhibitors which comprises adding the N-oxyl compound as a 50 to 85% by weight strength aqueous solution, wherein the aqueous solution of the N-oxyl compound that is used is the aqueous solution obtained in the synthesis of the N-oxyl compound.

2. The process as claimed in claim 1 , wherein N-oxyl compounds added are those from the group of secondary amines in which the N-oxyl group is part of a saturated or unsaturated six-membered ring, and in which each of the C atoms adjacent to the N-oxyl group bears two C1- to C4-alkyl groups.

3. The process as claimed in claim 1 , wherein the N-oxyl compound added comprises 2,2,6,6-tetramethylpiperidinyloxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl, 4-oxo-2,2,6,6-tetramethylpiperidinyloxyl and/or 4-ethanoyloxy-2,2,6,6-tetramethylpiperidinyloxyl.

4. The process as claimed in claim 1 , wherein the N-oxyl compounds are used in a water/vinyl acetate mixture.

5. The process as claimed in claim 1 , wherein 50 to 500 ppm of N-oxyl compound are added per tonne of vinyl acetate in the product gas stream.

6. The process as claimed in claim 1 , wherein the N-oxyl compound is added at one point or distributed over two or more points in the plant for working up the product gas stream.

7. The process as claimed in claim 5 , wherein the N-oxyl compound is added
to the condensate from a preliminary dewatering column and/or
to a gas stream from the preliminary dewatering column and/or
to a return stream to the preliminary dewatering column and/or
to a bottom product from a cycle gas scrubber and/or
to a top product of an azeotrope column and/or
to a return stream into the azeotrope column and/or
to the inlet into a wastewater column and/or
to a return stream into an ethyl acetate column and/or
to a top product of a dewatering column and/or
to a side draw of the dewatering column and/or
to a return stream into the dewatering column and/or
to a top product of a pure vinyl acetate column.

Assignees

• Wacker Chemie Ag

Inventors

• Dafinger Willibald
• Eckert Marc

Classifications

• C07C67/62

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

• C07C67/04 Primary

  by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds · CPC title

• C07C69/15

  Vinyl acetate · CPC title

• C07C67/05 Primary

  with oxidation · CPC title