CAS 80-08-0 4,4′-Diaminodiphenylsulfone

Introduction

CAS:80-08-0,

80-08-0 – Names and Identifiers

Name	4-Aminophenyl sulfone
Synonyms	DDS EPORAL Dapsone 4,4′-DDS
CAS	80-08-0
EINECS	201-248-4
InChI	InChI=1/C12H10O2S.C7H6N2O5/c13-15(14,;/h1-10H;2-3,10H,1H3
InChIKey	MQJKPEGWNLWLTK-UHFFFAOYSA-N

80-08-0 – Physico-chemical Properties

Molecular Formula	C12H12N2O2S
Molar Mass	248.3
Density	1.2701 (rough estimate)
Melting Point	175-177°C(lit.)
Boling Point	511.7±35.0 °C(Predicted)
Water Solubility	<0.1 g/100 mL at 20 ºC
Solubility	0.38g/l
Vapor Presure	0.004Pa at 25℃
Appearance	Crystalline Powder
Color	White to beige
Merck	14,2822
BRN	788055
pKa	pKb 13.0(at 25℃)
PH	5.5-7.5 (H2O, 20℃)(saturated aqueous solution)
Storage Condition	2-8°C
Stability	Stable. Combustible. Incompatible with strong oxidizing agents.
Refractive Index	1.5950 (estimate)
Physical and Chemical Properties	Melting point 173-178°C water-soluble <0.1g/100 mL at 20°C
Use	The drug of choice for the treatment of leprosy, can also be combined with other anti-leprosy drugs

80-08-0 – Risk and Safety

Hazard Symbols	Xn – Harmful
Risk Codes	22 – Harmful if swallowed
Safety Description	22 – Do not breathe dust.
UN IDs	3249
WGK Germany	1
RTECS	BY8925000
TSCA	Yes
HS Code	29309070
Hazard Class	6.1(b)
Packing Group	III
Toxicity	LD50 orally in Rabbit: 1000 mg/kg LD50 dermal Rabbit > 4000 mg/kg

80-08-0 – Reference Information

LogP	0.97 at 25℃
(IARC) carcinogen classification	3 (Vol. 24, Sup 7) 1987
Overview	4-4 ‘-diaminodiphenyl sulfone is a widely used chemical entity, it is used both as a hardener in the curing of epoxy resins and as a therapeutic agent for the treatment of bacterial infections in humans or animals, and has been approved as an antibiotic by the Food and Drug Administration since 1963. With regard to its use in human medicine, dapsone is in fact an effective antibiotic for the initial treatment of leprosy and subsequently also as an inhibitor of dermatitis herpetiformis.
Application	4,4 ‘-diaminodiphenyl sulfone is an important aryl sulfone compound refined by high temperature and high pressure through ammoniation reaction. It is mainly used in the synthesis of polysulfone amide resin and other polymer synthetic materials, synthesis of a variety of acid azo dyes and disperse dyes. Can be used as epoxy resin curing agent and electrical insulation materials, textile equipment, can also be used as a catalyst, can also be used in the pharmaceutical industry for the treatment of leprosy and dermatitis herpetiformis, AIDS, etc.
preparation process	will melt 4,4 ‘-dichlorodiphenyl sulfone is pumped into the pipeline reactor at a flow rate of 140g/h via a high pressure pump, at the same time, the mixture of ammonia water and cuprous chloride with a mass fraction of 25% is also injected into the pipeline reactor together through a high-pressure pump at a flow rate of 800g/h (wherein the flow rate of cuprous chloride is 5.6g/h), the continuous aminolysis reaction is carried out at a pressure of 14Mpa and a temperature of 220 ℃, and the residence time of the reaction material in the high-pressure pipe is 20 minutes. The product is analyzed by liquid chromatography after being discharged under reduced pressure through a pressure reducing valve, the ammonolysis product contains 0.1% of 4,4’-dichlorodiphenyl sulfone, and the output is sent to the recovery unit to distill the excess ammonia and separate the crude 4,4 ‘-diaminodiphenyl sulfone; the crude product is dissolved in hydrochloric acid with a mass fraction of 10% at 30 ℃, decolorized with activated carbon, filtered, cooled to below 10 ℃, and adjusted to Ph 2-10% with sodium carbonate solution with a mass fraction of 2.5, centrifugal filtration, then washed with water until neutral, and dried to obtain finished product, purity of 99.5% 4,4’-diaminodiphenyl sulfone product (liquid chromatography analysis), the total yield of 97.1% (4,4 ‘-dichlorobis Phenyl sulfone meter).
Use	for the synthesis of polysulfonamide resin and other polymers, anti-leprosy drugs. used as medicine, polymer material intermediates for the treatment of leprosy drug of choice, can also be combined with other anti-leprosy drugs for the treatment of various types of leprosy. It is industrially used as a curing agent for epoxy resins. used as gas chromatography stationary liquid, organic synthesis intermediate and epoxy resin curing agent
production method	add 4,4 ‘-dichlorodiphenyl sulfone, ketone powder, methylene chloride and ammonia water into the autoclave, heat with stirring, under the pressure of 170~202 ℃ and 3MPA, the reaction was carried out for 14h, then the temperature was lowered to 60 ℃, filtered, washed with water and dried to obtain the crude product 4,4’-diaminodiphenyl sulfone. According to the purpose of the product, the crude product is refined. For example, the crude product can be dissolved in 10% hydrochloric acid, decolorized with activated carbon, filtered, cooled to below 10 ℃, adjusted to Ph 2~2.5 with sodium carbonate solution, and centrifuged and filtered, after washing with water until neutral, the product is obtained by drying. The yield was more than 78%. (1) with p-nitrochlorobenzene and p-aminobenzene sulfonic acid as raw materials (2) with p-nitrochlorobenzene as raw materials (3) with p-chlorobenzene sulfonyl chloride and chlorobenzene as raw materials

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