Bisphenol S.

Structural formula
General
Surname	Bisphenol S.
other names	Bis (4-hydroxyphenyl) sulfone 4,4'-sulfonyldiphenol 4,4-dihydroxydiphenyl sulfone
Molecular formula	C 12 H 10 O 4 S
Brief description	white, odorless solid
External identifiers / databases
CAS number 80-09-1 EC number 201-250-5 ECHA InfoCard 100.001.137 PubChem 6626 Wikidata Q418379
properties
Molar mass	250.28 g mol −1
Physical state	firmly
density	0.5-0.6 g · cm −3
Melting point	245-250 ° C
solubility	poor in water (1.1 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	4556 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bisphenol S ( BPS ) is a chemical compound from the bisphenol group in which the central methylene group is replaced by a sulfonyl group .

presentation

Bisphenol S is composed of two equivalents of phenol and one equivalent of sulfuric acid shown .

${\displaystyle \mathrm {2\ (C_{6}H_{5}OH)+\ H_{2}SO_{4}\longrightarrow (C_{6}H_{4}OH)_{2}SO_{2}+2\ H_{2}O} }$

In addition to 4,4'-sulfonyldiphenol, 4,2'-sulfonyldiphenol is also formed as a by-product

There are also reactions with other sulfonating agents in e.g. B. chlorotoluenes described.

use

Bisphenol S is used in polymer reactions (for example in the manufacture of polycarbonates ). It is also used as a component of epoxy resins and as an anti-corrosive and electroplating auxiliary material and as an intermediate product for the production of flame retardants , thermal printing paper and more. A current study showed that bisphenol S could be detected in 3% of the thermal papers examined. The mean value of the bisphenol-S content was 10 mg / g thermal paper (range = 8.3–12.6 mg / g).

In the EU market, the share of thermal papers based on BPS increased from 21% to 39% between 2018 and 2019. In Switzerland, the use of thermal papers with BPS - with the exception of special applications (self-adhesive labels, medical and laboratory areas, etc.) - is prohibited from mid-December 2020.

toxicology

Endocrine effect

In an in vitro test on a human cell line is the production of 17 β -estradiol by bisphenol A and bisphenol F , but not induced by bisphenol S. In the same in-vitro-test system, the testosterone release is measured for both bisphenol A and bisphenol S: 100 μ M bisphenol S result in 67% reduction of testosterone release in the cell line. In zebrafish , a reduction of reproduction was found. Bisphenol S was included in the SIN list ("Substitute It Now!") By the NGO ChemSec because of its endocrine properties .

Health hazards

Bisphenol S was included by the EU in 2012 in accordance with Regulation (EC) No. 1907/2006 (REACH) in the context of substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of bisphenol S were concerns about high (aggregated) tonnage and the dangers arising from a possible assignment to the group of CMR substances and as a potential endocrine disruptor . The re-evaluation has been running since 2014 and is carried out by Belgium . In order to be able to reach a final assessment, further information was requested.

Individual evidence

1. ↑ ^{a b c d} Entry on 4,4′-sulfonyldiphenol in the GESTIS substance database of the IFA , accessed on May 9, 2017(JavaScript required) .
2. ↑ ^{a b} Entry on 4,4′-sulfonyldiphenol at ChemBlink , accessed on February 25, 2011.
3. ↑ Data sheet 4,4′-sulfonyldiphenol from Sigma-Aldrich , accessed on February 25, 2011 ( PDF ).
4. ↑ METHOD OF PREPARATION OF 4,4′-DIHYDROXYDIPHENYLSULPHONE (Freepatentsonline) .
5. ↑ Polyarylene ether sulfone blends (Freepatentsonline) .
6. ↑ chemconserve.com: Bisphenol S (Technical Information) ( Memento from November 4, 2013 in the Internet Archive ) (PDF; 76 kB).
7. ^ ^{A b} D. M. Goldinger, AL Demierre, O. Zoller, H. Rupp, H. Reinhard, R. Magnin, TW Becker, M. Bourqui-Pittet: Endocrine activity of alternatives to BPA found in thermal paper in Switzerland. In: Regulatory Toxicology and Pharmacology 71, 2015, pp. 453-462, doi : 10.1016 / j.yrtph.2015.01.002 . PMID 25579646 .
8. ↑ European Chemicals Agency (ed.): The use of bisphenol A and its alternatives in thermal paper in the EU during 2014–2022 . 2020, ISBN 978-92-9481-591-0 , doi : 10.2823 / 592282 .
9. ↑ Coronavirus: Federal Council decides temporary relief in the environmental area. Federal Council / DETEC / FOEN, June 5, 2020, accessed on June 24, 2020 . 
10. ↑ Effects of Bisphenol S Exposure on Endocrine Functions and Reproduction of Zebrafish , Environmental Science & Technology , doi : 10.1021 / es400329t .
11. ↑ ChemSec: Bisphenol S , February 2018.
12. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 4,4'-sulfonyldiphenol , accessed on March 26, 2019.