Economical purification of bisphenol A

Details Economical purification of bisphenol A Economical purification of bisphenol A

2003-09-29

2004-10-19

Shippen, Michael L. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

Reexamination Certificate

active

06806394

ABSTRACT:

FIELD OF THE INVENTION
P, P Bisphenol A (BPA) is a commercially significant compound used to manufacture polycarbonates and epoxy resins. The polycarbonate application in particular demands high purity BPA due to stringent requirements for optical clarity and color in the finished application. Accordingly those skilled in the art continually strive to improve the product quality of bisphenol A in economically efficient process schemes. This invention concerns a new process scheme to purify bisphenol A via adduct crystallization.
BACKGROUND OF THE INVENTION
To understand this invention it is first necessary to understand the prior art for BPA, which includes U.S. Pat. No. 4,950,805 (Iimuro, et al.) and U.S. Pat. No. 5,345,000 (Moriya et al.), which patents are incorporated herein by reference.
BPA is formed by the condensation of two moles of phenol with one mole of acetone under acidic conditions. The reaction may take place in the presence of a strong homogenous acid, such as hydrochloric acid, sulfur acid, or toluene sulfonic acid, or in the presence of a heterogeneous acid catalyst, such as a sulfonated ion exchange resin. The reaction may take place in the absence or presence of a thiol promoter, such as a mercaptan, which may be homogeneous in the reaction mixture or fixed to a heterogeneous catalyst A stoichiometric excess of phenol is employed to improve selectivity to the highly desired p,p′-BPA isomer. The crude reaction effluent stream thus contains not only unconsumed phenol, p,p′-BPA and water byproduct from the condensation reaction, but also contains undesirable BPA isomers and impurities, such as the o,p-BPA isomer, trisphenols, codimers, spiroindanes, and colored impurities as well as unreacted acetone, homogeneous acid catalysts, and thiol promoters. Those skilled in the art of producing BPA, recognize that regardless of the method of reacting acetone and phenol to produce BPA, it is necessary to purify the crude reaction effluent stream to obtain a BPA product that is useful for the manufacture of polycarbonates and other engineering thermoplastics.
A conventional practice in the purification of bisphenol A can be generically described by reference to FIG.
1
.
Acetone feed to reaction (
1
) is either makeup acetone (
21
) or a combination of makeup acetone and unreacted recycle acetone (
23
) recovered from the downstream distillation system (
2
). Phenol feed to the reaction consists of distilled phenol (
22
) from the downstream distillation section (
2
) or phenol recycle (
24
) produced as the liquid separation or wash product from the downstream solid/liquid separation (
4
), and typically contains a large quantity of impurities and BPA, or a combination of these two streams. Stream (
22
) may in some cases be combined with the acetone recycle stream
23
. The reaction system effluent (
25
) is sent to a distillation system (
2
), which recovers unreacted acetone (
23
), phenol (
22
) and waste streams, such as the wastewater of condensation (
40
). These lighter fractions are separated from the reactor effluent stream to form a concentrated BPA stream (
26
), which still contains a large quantity of phenol.
In the adduct crystallization technology that is widely practiced, for example in U.S. Pat. No. 4,927,978, U.S. Pat. No. 4,950,805 and U.S. Pat. No. 5,345,000, sufficient cooling of the concentrated BPA and phenol stream produces a crystalline adduct which comprises one molecule of phenol and one molecule of the desired p,p′-BPA isomer. This crystallization is a relatively efficient way to purify p,p′-BPA from the other isomers and impurities contained in the stream. The crystallization, depending on purity requirements and economic considerations, can be conducted in a selected number of multiple stages, with each stage producing a much higher purity adduct crystal. Each crystallization stage may consist of a single crystallizer or a multitude of crystallizers in series. The preferred number of crystallizers per stage is between 1 and 3. The number of crystallization stages may be any number greater than or equal to two. For illustration purposes in
FIG. 1
, three stages of crystallization (
3
,
5
and
7
) are indicated. The effluent (
27
) from the first crystallization stage (
3
) is sent to a solid-liquid separation device (
4
). These devices can use hardware well known to those skilled in the art, such as filters or centrifuges. A key feature in all of these systems is to first separate the bulk of the liquid to produce a solids crystal cake and a mother liquor (filtrate/centrate) stream, and then to wash the cake to remove impurities. Phenol is typically used to effect this wash, and the ultimate product quality is strongly determined by the purity of the washing agent. Phenol is a useful washing agent to the extent that it does not introduce new impurities into the BPA-phenol adduct crystal.
The solid-liquid separation devices (
4
,
6
and
8
) produce an adduct stream (respectively
35
,
36
,
37
) and one or more liquid streams containing some mixture of spent wash and/or filtrate/centrate (e.g.,
28
,
33
,
34
,
54
,
53
). For the purposes of adduct dissolution, crystal recovery, and for the enhancement of crystallization and material flow, those skilled in the art will typically recycle some or all of each of the mother liquor and wash effluent streams from one separation stage back to the preceding crystallization stage (e.g.,
33
,
34
).
The adduct produced from each stage may be placed in a phenol solution again and recrystallized to afford additional purification. The final adduct (
37
) is sent to the BPA finishing apparatus (
9
), wherein a liquid state phenol is vaporized in some fashion away from BPA to produce a high purity molten BPA product (
51
). The clean phenol (
38
) so produced can be combined with the makeup phenol to the plant (
50
) to provide a solvent (
52
) for washing the solid adduct crystals produced in, at least, the last solid-liquid separation (
8
).
It is known to those skilled in the art that an efficient means to produce a high purity product through multi-stage crystallization is to send the cleanest wash liquid to the final stage, and in turn send some combination of filtrate/centrate or spent wash from each stage as wash (
53
,
54
) to the immediate upstream stage. Such a scheme effectively minimizes the phenol requirements for the overall crystallization wash system, and uses the cleanest phenol where it is most necessary, i.e., in the final stage. This wash scheme is usually referred to as a counter-current wash flow.
The total liquid (
28
) recovered from the first stage solid/liquid separation (
4
), a combination of mother liquor and wash effluent, is recirculated to the condensation reactor system (
1
). Optionally a stream (
29
), consisting of all or a portion of the recycle liquid (
28
), may be sent to a recovery system (
10
) which rearranges unwanted heavy byproducts contained in the recycle liquid to useful precursors of BPA or to BPA itself A waste stream (
32
) is removed, and the improved stream (
30
) is returned to the recycle liquid. Some of the recycle liquid (
31
) may bypass the recovery system (
10
). The combined streams (
30
) and (
31
) are used as a reactor feed stream (
24
).
SUMMARY OF THE INVENTION
By contrast, in the present invention, as illustrated in
FIG. 2
, the washing scheme is changed in order to provide an even higher purity product, and to accomplish this beneficial result without compromising the yields of raw materials to product. In addition, other process modifications shown in FIG.
2
and described below cooperate synergistically with the modified wash scheme to achieve unexpectedly enhanced results.
In accordance with the present invention, it has now been found that an extremely high quality BPA product can be produced by co-feeding a clean or substantially clean phenol stream to every stage of washing. This type of washing is herein referred to as a cross-flow wash system. While generally counter-current wash flow maxim

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