DE2059714C - Process for the production of Diphenyl sulfone 4 4 dicarboxylic acid esters - Google Patents

Description

While in the removal of the isomeric Bcisniel 5

Diphenylsilfondicarboxylic acid esters by digesting 4 "P-

with ketones or aromatic hydrocarbons 200 g of diphenyl sulfone ^^ '- dicarboxylic acid dimethyl

is advantageous with as low-boiling products as possible, with a purity of 97.6 percent by weight,

works, it is advisable to recrystallize from xylene. 186 g fell

to use higher-acidic ketones or aromatics, 93% diphenyl sulfone ^^ '- dicarboxylic acid dimethyl

ilamil man / u a cheap solvent: ester 45 ester with a purity of 99.94 percent by weight.

Ratio comes without being under increased pressure for the same EITck was cr / iclt when one

work / u have to. At 140 Γ are /.B. 150 g place of xylene butanone used.

Oiphenylsiilfoii ^^ '- dicarnonsäurcdimclhylestcr in _Ri . . ,,

1 liter of aromatic hydrocarbon soluble. ncispiei η

These conditions can be achieved without pressure with xylene

sicrbar. . -.11 ^ percent by weight Diph <"iylsulfon-4,4'-dicarbon-

Uc 1 s pie I siiurcdimclhyleMcr by benzene treatment

f-in hui the purification of 4,4'-Dimulhyldiphcnyl- wonncnc esters / with a purity of 97 l "» was

sulfone isomer recrystallized from xylene as a by-product. A 99.9 ^{3 fell} , Oiger

guimdi was oxidized and esterified with methanol. 55 Diphenylsulfon ^^ '- dicarbonsüurcdimethylcslcr with

Liiiil tfiisfrnklomelriidier analysis showed that diphe- a bulge of 2% by weight. .

nylsulfondiearbniisiitiredimelhylestergemiseli 27 Oe- _H.

wielihprti / enl Diphenylsuiron-4,4'-di «: arbon«.

melhylesicr. Process for the production of diphenylsulfone

100 μ of the l ^: .s (e ^ emisehes were mixed with 4 (K) ml of hen-β «4,4'-di-carbonic acid on their oemischcti

/ Oil 15 minutes. 'Cooked in the UüeklluH. Dithei did not join isomeric compounds and with esters

not a complete solution. Subsequently, a sufficiently oxidized waste product was used, since *

20C iih ^ ekiihli, tihiiltriert and with wenin benzene characterized by that mim this

if necessary. Ls were 21.1 kg of Fillerriiekstantl , the Ocmisclic with the 1 to 2 () fnchcn amount of one

According to the friiklometrisclte Aaalys "97.1 Clcwithls- H Ketone »or öromntischen hydrocarbon

Percent Diplteifylsilfon ^^ '- dicirhonic acid dimethyl tempering between 10 and 50 "C washes

contained ester. l) 's home, about HO "/" in the isomeric or in the common solvents around.

The 4,4'-compound present could be crystallized by,

Claims (1)

1 2 In addition to the large-scale and extremely pure solvent treatment with a purity of recoverable terephthalic acid can be isolated lately 97 percent by weight,
also binuclear dicarboxylic acids on the synthetic more and more interest in the stolf area. Example 2 In the synthesis of the diphenyl sulfone-M'-dicar- 5 lüüg isomer mixture, as in Example I, were In the preparation of the bonsai acid, the mixture is mixed with 200 ml of acetone at 20.degree. C. and then added initial product a mixture of dimethyldiphenyl 15 minutes filtered off. The remaining filter sulfones, in which the desired 4,4'-dimethyl residue was mixed with a further 100 ml of acetone diphenyl sulfone predominates. There are ways to stir, suck off after 15 minutes and with little the 4,4'-dimethyldiphenyl sulfone was washed from the isomeric acetone. It fell 20.4 g insoluble in acetone to isolate mixture, but this process is with liches, with a content of 97.4 percent by weight the simultaneous loss of considerable amounts of diphenyl sulfone ^^ '-dicarboxylic acid dimelhyl ester. 4,4'-Dimethyldiphenylsulfon connected, the so the higher the purity, the greater it is. Example .i In the. Diphenylsulfondicarboxylic acids are i5 The procedure was as in Example 1, but dependent on the valuable 4,4'-compound were instead of the methyl the isobutyl ester cin- largely impossible to set from the isomer mixture. With a single Beiizol treatment to win. the diphenylsulfone-M'-dicarboxylic acid diiso- It has now been found that it is advantageous to use butyl ester at a content of 27 percent by weight if the isomer separation is only reduced to 96.8 percent by weight ^{for the acid ao in the isomer mixture} esters or in the dimethyl stage. -14 diphenylsulfone only carries out a preliminary separation, Example 4 without striving for the purity required later, 100 g of dimethyl diphenylsulfonedicarboxylate which you then in the ester stage in a simple manner with 66.5 percent by weight of the 4,4'-compound can achieve. In addition to the isomeric Diphenylsulfon- ³ 5 den with 400 ml of benzene for 15 minutes under reflux dicarboxylic acid esters, the mixture can still be methyl-boiled. Then it was cooled to room temperature, Diphenylsulfonmonocarbonsäurccster, which is filtered and the filter residue with about 50 ml of ben- incomplete oxidation present in the mixture -'- «I washed, may be included. There were 68.2 g of filter residue with 95.1 weight For the production of diphenyl sulfone ^^ '- dicarbon- 3 "percent Diphcnylsulfon ^' - dicarboxylic acid dimethyl- acid esters from their mixtures with isomeric Vcr- ^cslcr . That means more than 95Vt. the one in the starting binuunm.11 and the 4,4'-compound not sufficiently present with esters was through According to the invention, the starting product is ^{treated in this way by} solvent treatment to a purity lead, one brought dicsc mixtures with 1 to 95.1 percent by weight. 20 times the amount of a ketone or aromatic 35 Ras filtrate was concentrated to dryness. Included Hydrocarbon at temperatures between 10 ⁿ ' ^cIcn - ""' ß isomeric Diphcnylsulfondicarbonsäure- and 50 C washes or from the mentioned solution dimethyl chloride with only 7.0 percent by weight of the medium recrystallized. "4,4 'connection.