Production process of polyphenylene ether

Details Production process of polyphenylene ether Production process of polyphenylene ether

2001-06-19

2003-02-18

Truong, Duc (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From phenol, phenol ether, or inorganic phenolate

C528S217000, C528S490000, C528S492000, C528S482000, C502S165000

Reexamination Certificate

active

06521735

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to a production process of a polyphenylene ether improved by highly efficient preparation of a catalyst.
BACKGROUND OF THE INVENTION
As a polymerization catalyst employed upon production of a polyphenylene ether by oxidative polymerization of a phenol compound, a number of proposals have been made on the combined use of a copper compound and an amine since being proposed by JP-B-36-18692 (The term “JP-B” used herein means an “examined Japanese patent publication”). These proposals differ in, for example, the kind of the copper compound employed, the kind of a halide which works in cooperation therewith, or the kind of the amine employed whether it is a primary amine, secondary amine or tertiary amine, or whether it is a monoamine, diamine or polyamine.
In U.S. Pat. Nos. 3,306,875, 3,344,116 and 3,432,466 which is not a recent patent example, proposed is a process using a catalyst system composed of a copper compound and a tetraalkyl type diamine such as N,N,N′,N′-tetramethyl-1,4-butanediamine, while in JP-B-52-17075 or JP-B-52-17076, proposed is the combination of a copper compound, a tetraalkyl type diamine and an iodine compound.
In U.S. Pat. Nos. 4,028,341 and 4,092,294, proposed is a process using a combination of a copper compound, a bromine compound, a diamine compound such as N,N′-di-t-butylethylenediamine and a tertiary amine compound such as n-butyldimethylamine, or using a combination of a copper compound, a bromine compound, the above-described diamine and tertiary amine compounds and a secondary monoamine such as N-di-n-butylamine. Moreover, U.S. Pat. No. 4,788,277 discloses a production process in the presence of a highly active catalyst having improved water resistance which is composed of a copper compound; a secondary aliphatic amine or a secondary aliphatic amine and an aniline having a special structure; N,N,N′,N′-tetramethyl-1,3-diamino-(substituted or unsubstituted)-propane; and a bromine or chlorine compound.
In particular, the catalyst system as described in U.S. Pat. No. 4,092,294 has the merit of a relatively good activity in the batch-wise polymerization process, which however does not apply to the continuous production process. An improved process, in the continuous production, using the catalyst as described in the above-described patent publication is disclosed in U.S. Pat. No. 4,477,650 but it requires a special reaction vessel during the latter half of polymerization.
The above-described catalysts which permit oxidative polymerization of a phenol compound, thereby producing a polyphenylene ether, are usually composed of not a single component but various compounds. Such a catalyst system is accompanied with a serious problem that no attention has so far been paid on the preparation technique of such a complex catalyst. For example, in a batch-wise system polymerizer, such a catalyst system induces variations in activity among batches, which is undesirable from the viewpoint of production of a polyphenylene ether having stable quality. In the continuous production, these variations in activity are less than that in the batch-wise production, but undesirable scale (scale deposits) happens to appear in a reactor for a long period of time. Deposition of scale is fatal to the production of a polyphenylene ether, which is presumed to be a reason why batch-wise production is most prevalent now as a production process of a polyphenylene ether.
SUMMARY OF THE INVENTION
The present invention has been made to solve the above-described problems in the background arts.
Accordingly, an object of the present invention is to provide a production process of a polyphenylene ether which has improved productivity and is efficient in catalyst preparation.
Other objects and effects of the present invention will become apparent from the following description.
The present inventors carried out an extensive investigation on the means for overcoming the above-described problem of the conventional batch-wise polymerization process. As a result, it was surprisingly found that the performance of a catalyst largely depends on its preparation process, leading to the completion of the invention.
That is, the above-described objects of the present invention have been achieved by providing the following production processes of a polyphenylene ether.
1) A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas,
wherein said catalyst comprises a copper compound, a bromine compound, a diamine compound represented by the following formula (1):
 (wherein R
1
, R
2
, R
3
and R
4
each independently represents hydrogen or a C
1-6
linear or branched alkyl group, with the proviso that all of them do not represent hydrogen simultaneously, and R
5
represents a linear or methyl-branched C
2-5
alkylene group), a tertiary monoamine compound and a secondary monoamine compound, and
wherein said process comprises the steps of:
preparing a catalyst component (P1) (hereinafter which may be called simply “component (P1)”) in a container which is under a substantially oxygen-free inert atmosphere by mixing the copper compound and the bromine compound to obtain a mixture and then mixing the mixture with the secondary monoamine compound in an amount of at least 2 times the molar amount of the copper atom;
separately preparing a catalyst component (P2) (hereinafter which may be called simply “component (P2)”) by mixing the diamine compound of formula (1) and the tertiary monoamine compound together with a solvent in an oxidative polymerization vessel;
adding a predetermined amount of the catalyst component (P1) to the polymerization vessel containing the catalyst component (P2), and mixing the catalyst components (P1) and (P2); and
initiating oxidative polymerization.
2) The process according to item 1) above, wherein the catalyst component (P2) is prepared in an inert atmosphere.
3) The process according to item 1) above, wherein the catalyst component (P1) is prepared and stored at a temperature of from 10° C. to 100° C.
4) The process according to any one of items 1) to 3) above, further comprising adding a tertiary monoamine to the catalyst component (P1) in a substantially oxygen-free inert atmosphere.
5) The process according to any one of items 1) to 4) above, further comprising adding a tetraalkylammonium salt to the catalyst component (P2).
6) The process according to any one of items 1) to 5) above, wherein the copper compound is cuprous oxide, and the bromine compound is hydrogen bromide or an aqueous solution thereof.
7) The process according to any one of items 1) to 6) above, wherein the initiation of the oxidative polymerization is effected by gradually adding the phenol compound to the polymerization vessel containing the mixed catalyst components (P1) and (P2) while feeding thereto an oxygen-containing gas.
8) The process according to any one of items 1) to 6) above, wherein the initiation of the oxidative polymerization is effected by adding a portion of the phenol compound to the polymerization vessel containing the catalyst component (P2); adding a predetermined amount of the catalyst component (P1) to the resulting mixture and mixing; and gradually adding the remaining portion of the phenol compound to the polymerization vessel while feeding thereto an oxygen-containing gas.
9) The process according to any one of items 1) to 6) above, wherein the initiation of the oxidative polymerization is effected by adding the phenol compound to the polymerization vessel containing the mixed catalyst components (P1) and (P2) and then feeding thereto an oxygen-containing gas.
10) The process according to any one of items 1) to 6) above, wherein the initiation of the oxidative polymerization is effected by adding the phenol compound to the polymerization vessel containing the catalyst component (P2); adding a predetermined amount of the catalyst component (P1) to the resulting mixture and mixing; and then feeding thereto an oxygen-c

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