41481-66-7

Usage

Uses

Used in Imaging Systems:
Bis(3-allyl-4-hydroxyphenyl)sulfone is used as a component in the preparation of microcapsules for light-thermal sensitive imaging systems. Its light-thermal sensitivity allows for the development of advanced imaging techniques that can be utilized in various fields, such as medical diagnostics and research.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to its chemical properties and synthesis process, Bis(3-allyl-4-hydroxyphenyl)sulfone may also have potential applications in the pharmaceutical industry. It could be used as a starting material or intermediate in the development of new drugs or drug delivery systems, particularly those that require light-thermal sensitive properties for targeted drug release or imaging purposes.

Synthetic route

4,4'-sulfonediphenol (80-09-1) + allyl tosylate (4873-09-0) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With tetrabutyl-ammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 8h; Large scale;	98.5%
With potassium carbonate In N,N-dimethyl-formamide	30.4 parts (92.1%)

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With α-alanine-N-diacetic acid at 198 - 200℃; for 7h; Temperature; Inert atmosphere;	96.2%
With 1,10-Phenanthroline; ethylenediaminetetraacetic acid; sodium hydroxide In paraffin oil at 203 - 207℃; for 7h; Inert atmosphere;	93.7%
With iron(III) chloride In 1,2-dichloro-ethane at 60℃; for 15h; Reagent/catalyst; Solvent; Temperature;	93.9%

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With sodium carbonate; sodium hydroxide In water at 95 - 100℃; for 5h; Solvent; Reagent/catalyst; Temperature; Autoclave; Large scale;	84.4%

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 4-allyloxy-4'-hydroxydiphenyl-sulfone

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium carbonate; sodium hydroxide In water; paraffin oil; kerosene at 95 - 100℃; for 5h; Autoclave; Large scale;	A 73.9% B 10.2%

4,4'-sulfonediphenol (80-09-1) + allyl tosylate (4873-09-0) + 3-chloroprop-1-ene (107-05-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 4-allyloxy-4'-hydroxydiphenyl-sulfone

Conditions	Yield
Stage #1: 4,4'-sulfonediphenol; allyl tosylate With tetrabutyl-ammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 8h; Large scale; Stage #2: 3-chloroprop-1-ene In N,N-dimethyl-formamide at 200 - 220℃; for 6h; Large scale;	A 35.3% B 8.6%

4,4'-sulfonediphenol (80-09-1) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH, Me4NBr / toluene; H2O / 15 h / 49.9 - 59.9 °C 2: 85 percent / various solvent(s) / 30 h / 207.9 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 1.2: Reflux; Inert atmosphere 2.1: 4 h / 220 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 80 °C / Inert atmosphere 2: 1,2-dichloro-benzene / 8 h / 190 °C / Inert atmosphere View Scheme

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → 3-allyl-4,4'-dihydroxydiphenyl sulfone + 3-allyl-4'-allyloxy-4-hydroxydiphenyl sulfone (737795-84-5) + 5-(3-allyl-4-hydroxyphenylsulfonyl)-1-oxa-2-methylindane + 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With dmap at 160 - 280℃; for 0.0833333 - 0.333333h; Product distribution / selectivity; Microwave irradiation;
With 1,10-Phenanthroline; ascorbic acid In 1,2,3-trichlorobenzene at 210℃; for 7h; Product distribution / selectivity;
With 1,10-Phenanthroline; ascorbic acid at 160 - 280℃; for 0.266667h; Product distribution / selectivity; Microwave irradiation;

48%-caustic soda + 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

Conditions	Yield
With 1,2,3-trichlorobenzene In water	14.0 parts (93.3%)

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 3-dibutylamino-6-methyl-7-anilinofluoran → C35H36N2O3*C18H18O4S

Conditions	Yield
In hexane; acetone at 5℃; for 336h;	41.7%

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C18H16O4S(2-)*2Na(1+)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C32H42O8S5 (1636900-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 1.2: Reflux; Inert atmosphere 2.1: 2,2'-azobis(isobutyronitrile) / tetrahydrofuran / 16.5 h / 20 - 65 °C / Inert atmosphere View Scheme

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C24H34O4S5 (1636900-15-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 1.2: Reflux; Inert atmosphere 2.1: 2,2'-azobis(isobutyronitrile) / tetrahydrofuran / 16.5 h / 20 - 65 °C / Inert atmosphere 3.1: hydrogenchloride; water / tetrahydrofuran; methanol / 24 h / 60 °C / Inert atmosphere View Scheme

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + allyl bromide (106-95-6) → 4,4’-sulfonylbis(2-allyl-1-(allyloxy)benzene) (122438-87-3)

Conditions	Yield
Stage #1: 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux; Stage #2: allyl bromide In acetone Reflux; Inert atmosphere;	47.5 g

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C24H34O4SSi2

Conditions	Yield
In 1,4-dioxane for 2h;	6.5 g

di-tert-butyl dicarbonate (24424-99-5) + 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C28H34O8S

Conditions	Yield
In 1,4-dioxane for 4h;	6.5 g

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) → C36H58O12S3Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / isopropyl alcohol; water / 3 h / 60 °C / Inert atmosphere 2: 2,2-dimethoxy-2-phenylacetophenone / 24 h / 20 °C / Inert atmosphere; Darkness View Scheme

3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7) + epichlorohydrin (106-89-8) → C24H26O6S

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 60℃; for 3h; Inert atmosphere;

Upstream product

• 41481-63-4 4,4’-sulfonylbis((allyloxy)benzene) 
• 80-09-1 4,4'-sulfonediphenol 
• 4873-09-0 allyl tosylate 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 1636900-13-4 C₃₂H₄₂O₈S₅ 
• 1636900-15-6 C₂₄H₃₄O₄S₅ 
• 122438-87-3 4,4’-sulfonylbis(2-allyl-1-(allyloxy)benzene) 

Relevant academic research and scientific papers

Synthesis method of thermosensitive color developing agent 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol

The invention provides a synthesis method of a thermosensitive color developing agent 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol, which comprises the following step: directly heating and rearranging 4, 4'-diallyl diphenyl sulfone in an organic solvent under the action of a catalyst to obtain the 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol. In the process of preparing 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol, a Lewis acid catalyst is used, so that a high-temperature reaction at 200 DEG C or above can be avoided, safety accidents are greatly reduced, energy is saved, consumption is reduced, andequipment investment is greatly reduced. The catalysts zinc chloride, aluminum trichloride, ferric trichloride and titanium tetrachloride used in the preparation process of the 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol are low in cost and convenient to post-treat. In the process of preparing the 4, 4'-sulfonyl bis [2-(2-propenyl)] phenol, the use of a high-boiling-point solvent and heat conduction oil can be avoided, and the production cost is greatly reduced.

Synthetic method of thermosensitive color developing agent 4,4'- sulfonyl bis [2-(2-propenyl)] phenol

The invention discloses a synthetic method of a thermosensitive color developing agent 4,4'- sulfonyl bis [2-(2-propenyl)] phenol; 4, 4, 4'- diallyl diphenyl sulfone is directly heated and reacted ina solvent under the action of a chelating agent to prepare the 4, 4'- sulfonyl bis [2-(2-propenyl)] phenol; and the method is simple and convenient to operate, low in cost, less in three wastes, greenand environment-friendly, and has a good industrial application prospect. According to the synthetic method of the thermosensitive color developing agent 4,4'- sulfonyl bis [2-(2-propenyl)] phenol, the yield is 92.5-96.2%, and the purity is 97.5-98%, optimally, the yield is 95-96.2%; and the chelating agent used in the method is environment-friendly glycine diacetic acid, and is low in cost and biodegradable.

PROCESS FOR PRODUCING ALLYL-SUBSTITUTED BISPHENOL COMPOUND

The present invention relates to a process for producing an allyl-substituted bisphenol compound including a step of subjecting a diallyl etherified bisphenol compound represented by the following general formula (I) to a thermal rearrangement reaction in the presence of a specific phosphine compound [in the formula, A represents a single bond, —SO2—, —S—, —O—, a divalent group represented by the following formula (i-1), or a divalent group represented by —CY1Y2—(Y1 and Y2 each independently represent hydrogen, a linear, branched, or cyclic alkyl group having 6 or less carbon atoms, a phenyl group, or an aralkyl group having 7 or 8 carbon atoms), B1 and B2 each independently represent a linear, branched, or cyclic alkyl group having 6 or less carbon atoms, an allyl group, a phenyl group, or an aralkyl group having 7 or 8 carbon atoms, and n1 and n2 each independently represent an integer from 0 to 2,

Bisphenol-based epoxy compound using thiol-ene reaction and method for preparing the same, and composite of organic-inorganic materials comprising a cured product thereof and method for preparing the composite

The present invention relates to a bisphenol-based epoxy compound having an alkoxysilylalkyl-S-alkyl group and a method for preparing the same, a composite of organic-inorganic materials comprising the cured product and a method for preparing the composite. The novel bisphenol-based epoxy compound can provide a composite which shows improved thermal resistance and thermal expansion properties and has excellent hardness when being used for manufacturing high-integration and high-performance electronic components such as a next-generation semiconductor substrate and PCB.COPYRIGHT KIPO 2017

METHOD OF CONSISTENTLY PRODUCING DIALLYLBISPHENOLS

The purpose of the present invention is to provide a method of consistently producing high-quality diallylbisphenols with high yields from bisphenols. This method involves steps (1) through (3) below, and enables the consistent production of diallylbisphenols from bisphenols. (1) A step for reacting allyl halides and bisphenols or alkali metal salts thereof in a cellosolve solvent in the presence or absence of basic alkali metal salts, (2) a step for separating inorganic salt by-products from a reaction solution obtained in step (1), and (3) a step for heating and subjecting to a rearrangement reaction the reaction solution obtained in step (2).

METHOD FOR PRODUCING 3,3'-DIALLYL-4,4'-DIHYDROXYDIPHENYL SULFONE

PROBLEM TO BE SOLVED: To provide a method for producing 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone in high purity and high yield, the sulfone having, as a heat-sensitive recording material, little background fogging after color recording and being a developer having excellent heat resistance. SOLUTION: Provided is a method for producing 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone by an intramolecular rearrangement reaction of 4,4'-diallyloxydiphenyl sulfone by heating to 200°C or higher in the presence of a catalytic amount of a heterocyclic compound and an amine compound. COPYRIGHT: (C)2015,JPOandINPIT

Investigations of thiol-modified phenol derivatives for the use in thiol-ene photopolymerizations

Thiol-ene photopolymerizations gain a growing interest in academic research. Coatings and dental restoratives are interesting applications for thiol-ene photopolymerizations due to their unique features. In most studies the relative flexible and hydrophilic ester derivative, namely pentaerythritoltetra(3-mercaptopropionate) (PETMP), is investigated as the thiol component. Thus, in the present study we are encouraged to investigate the performance of more hydrophobic ester-free thiol-modified bis-and trisphenol derivatives in thiol-ene photopolymerizations. For this, six different thiol-modified bis-and trisphenol derivatives exhibiting four to six thiol groups are synthesized via the radical addition of thioacetic acid to suitable allyl-modified precursors and subsequent hydrolysis. Compared to PETMP better flexural strength and modulus of elasticity are achievable in thiol-ene photopolymerizations employing 1,3,5-triallyl-1,3,5-triazine-2,4,6-trione (TATATO) as the ene derivative. Especially, after storage in water, the flexural strength and modulus of elasticity is twice as high compared to the PETMP reference system.

COLOR DEVELOPING COMPOSITION CONTAINING MOLECULAR COMPOUND, AND RECORDING MATERIAL

Provided is a color-developing composition containing a molecular compound which has as a component compound a compound represented by formula (I) [wherein Y represents a C1-C12 hydrocarbon group which is chained or branched and saturated or unsaturated, or a C1-C8 hydrocarbon group which is chained or branched, saturated or unsaturated and has an ether or thioether bond; R1, R2, R3 and R4 each independently represent a C1-C6 alkyl group or C2-C6 alkenyl group; n, p, q and r each represents any integer of 0 to 4; and m represents any integer of 0 to 2]. Also provided is a recording material with a sufficient color-forming sensitivity, superior storage stability, and especially with an extremely little background fogging in a heat resistance test.

METHOD FOR PRODUCING 3,3';-DIALLYL-4,4';-DIHYDROXYDIPHENYLSULFONE

The present invention is characterized by subjecting 4,4'-diallyloxydiphenyl sulfone to a rearrangement reaction under microwave irradiation, preferably in molten state, to produce objective 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone efficiently in a short time, in high yield and in high purity. Further preferably, by carrying out said reaction in substantially oxygen-free atmosphere in the presence of at least one compound selected from a group consisting of an antioxidant, an organic basic compound and a chelate compound, the above-described object can be attained in more preferable manner.

Novel diepoxide derivatives of diallyl phenolics

The present invention relates to the preparation of ethers and esters of diallylphenols and the epoxidation of the diallyl moiety to provide bis-epoxide ether and ester intermediates useful in the preparation of epoxy resins.