41481-63-4

Basic information

• Product Name: 1-Prop-2-enoxy-4-(4-prop-2-enoxyphenyl)sulfonyl-benzene
• Synonyms: 1,1'-sulfonylbis[4-(2-propenyl)oxy-benzene];1-prop-2-enoxy-4-(4-prop-2-enoxyphenyl)sulfonyl-benzene;BIS(4-ALLYLOXYPHENYL)SULFONE;1,1'-PHENYLSULFONYL-4,4'-DIENEPROPYL ETHER;1,1'-Phenylsulfonyl-4,4'-Dienepropyl(2)Ether;Bis-[4-(2propenyloxy)-phenyl]-sulfone;Bis(p-allyloxyphenyl) sulfone;Sulfonylbis(4,1-phenylene)bis(allyl ether)
• CAS NO: 41481-63-4
• Molecular Formula: C₁₈H₁₈O₄S
• Molecular Weight: 330.4
• EINECS: 1533716-785-6
• Product Categories: Industrial/Fine Chemicals;Aromatics
• Mol File: 41481-63-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 141-142 °C(Solv: ethanol (64-17-5))
• Boiling Point: 500.7 °C at 760 mmHg
• Flash Point: 256.6 °C
• Appearance: /
• Density: 1.172 g/cm³
• Vapor Pressure: 1.15E-09mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-Prop-2-enoxy-4-(4-prop-2-enoxyphenyl)sulfonyl-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Prop-2-enoxy-4-(4-prop-2-enoxyphenyl)sulfonyl-benzene(41481-63-4)
• EPA Substance Registry System: 1-Prop-2-enoxy-4-(4-prop-2-enoxyphenyl)sulfonyl-benzene(41481-63-4)

Safety Data

• Hazardous Substances Data: 41481-63-4(Hazardous Substances Data)

Usage

Uses

1,1'-Sulfonylbis[4-(prop-2-en-1-yloxy)benzene is a useful research chemical.

Chemical Properties

White crystalline powder

Preparation

The preparation of 1,1'-Sulfonylbis[4-(prop-2-en-1-yloxy)benzene is as follows:2400g water, 216g caustic soda lye of 48% strength, 600g 4,4'-dihydroxydiphenyl sulfone and 204g Allyl chloride were mixed and the reaction was carried out at 55-60°C and autogenously generated pressure of 0.8-1. Okg/cm2?for 8 hours. 204g caustic soda lye of 48% strength was added in the reaction mixture, and maintained for 1 hour at 80°C thereafter filtered at 80°C to remove 4,4'-diallyloxydiphenyl sulfone. Further, the filtrate solution was treated with 5g activated carbon and 5g sequestering agent at 85- 90°C. The pH of filtrated solution was adjusted to 8.9 with 20% sulfuric acid and cooled to 35°C. The precipitate was separated by filtration and slurred in water. The pH was adjusted to 4.94 with 20% sulfuric acid and the precipitate was separated by filtration, and washed with water and dried to obtain 615g the product 4-allyloxy 4'-hydroxydiphenyl sulfone of 96% purity. The yield was 93.5% with respect to 4,4'-dihydroxydiphenyl sulfone. The wet cake of 4,4'-diallyloxydiphenyl sulfone was slurred in 100g of 5%w/v aqueous solution of sodium hydroxide and refluxed for 1 hour, then cooled to 80°C. The precipitate was filtered, washed with water and dried to obtain 45g of 4,4'-diallyloxy diphenyl sulfone of 91.9% purity. The yield was 6% with respect to 4,4'-dihydroxydiphenyl sulfone. pH of the mother liquor obtained after separation of 4-allyloxy 4'-hydroxydiphenyl sulfone, was adjusted to 4.5 with 20% sulfuric acid. The precipitate was separated by filtration, washed with water and dried to obtain 33g of 4,4'-dihydroxydiphenyl sulfone of 87.9% purity. The conversion of 4,4'-dihydroxydiphenyl sulfone was 94.50%.; 595g of 4-allyloxy 4'-hydroxydiphenyl sulfone of 96% purity was dissolved in 230g of 48% strength caustic soda lye and 1000g water, treated with 5g activated carbon and 5g sequestering agent at 85-90°C. The slurry was filtered and pH of the filtrate was adjusted to 8.95 with 20% sulfuric acid and then cooled to 35°C. The precipitate was separated by filtration, slurried in water and the pH was adjusted to 5.0 with 20% sulfuric acid. The slurry was filtrated and the precipitate was washed with water and dried to obtain 563g of 4- allyloxy 4'-hydroxydiphenyl sulfone of 99.273% purity.

InChI:InChI=1/C18H18O4S/c1-3-13-21-15-5-9-17(10-6-15)23(19,20)18-11-7-16(8-12-18)22-14-4-2/h3-12H,1-2,13-14H2

Synthetic route

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4)

Conditions	Yield
With potassium iodide; sodium hydroxide In methanol at 35 - 65℃; for 5h; Reagent/catalyst; Solvent;	98%
Stage #1: 4,4'-sulfonediphenol With sodium hydroxide for 0.166667h; Stage #2: 3-chloroprop-1-ene at 60 - 100℃; for 5h; Inert atmosphere; Sealed tube;	93%
With sodium hydroxide In methanol at 45℃;
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 8h; Concentration; Temperature; Time;	612 g
Stage #1: 4,4'-sulfonediphenol With sodium hydroxide In water; toluene at 80℃; for 8h; Stage #2: 3-chloroprop-1-ene at 75℃; for 8h;

propene (187737-37-7) + 4,4'-sulfonediphenol (80-09-1) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4)

Conditions	Yield
Stage #1: 4,4'-sulfonediphenol With chlorine; sodium hydroxide for 0.166667h; Stage #2: propene at 60 - 100℃; for 5h; Inert atmosphere; Sealed tube;	96%

4,4'-sulfonediphenol (80-09-1) + allyl bromide (106-95-6) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4)

Conditions	Yield
Stage #1: 4,4'-sulfonediphenol With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux; Stage #2: allyl bromide In acetone Reflux; Inert atmosphere;	94%
With sodium hydroxide; tetramethylammonium bromide In water; toluene at 49.9 - 59.9℃; for 15h;
In methanol; water; toluene	30.5 parts (91.2%)
With potassium carbonate In acetone at 80℃; Inert atmosphere;

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) + 4-allyloxy-4'-hydroxydiphenyl-sulfone

Conditions	Yield
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 8h; Concentration; Temperature; Time;	A n/a B 93.5%
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 4h; Concentration; Temperature; Time;	A 73.98% B 25.32%

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → tetrabromobisphenol-S-bis-(2,3-dibromopropyl ether)

Conditions	Yield
With tetrabutylammomium bromide; bromine In chloroform; water at 15 - 35℃; for 2h; Solvent; Temperature;	98%

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’-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%)

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → 4,4’-sulfonylbis(2-allyl-1-(allyloxy)benzene) (122438-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4 h / 220 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 2.2: Reflux; Inert atmosphere View Scheme

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → C32H42O8S5 (1636900-13-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 4 h / 220 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 2.2: Reflux; Inert atmosphere 3.1: 2,2'-azobis(isobutyronitrile) / tetrahydrofuran / 16.5 h / 20 - 65 °C / Inert atmosphere View Scheme

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → C24H34O4S5 (1636900-15-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 4 h / 220 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Reflux 2.2: Reflux; Inert atmosphere 3.1: 2,2'-azobis(isobutyronitrile) / tetrahydrofuran / 16.5 h / 20 - 65 °C / Inert atmosphere 4.1: hydrogenchloride; water / tetrahydrofuran; methanol / 24 h / 60 °C / Inert atmosphere View Scheme

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → C24H26O6S

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,2-dichloro-benzene / 8 h / 190 °C / Inert atmosphere 2: sodium hydroxide / isopropyl alcohol; water / 3 h / 60 °C / Inert atmosphere View Scheme

4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) → C36H58O12S3Si2

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,2-dichloro-benzene / 8 h / 190 °C / Inert atmosphere 2: sodium hydroxide / isopropyl alcohol; water / 3 h / 60 °C / Inert atmosphere 3: 2,2-dimethoxy-2-phenylacetophenone / 24 h / 20 °C / Inert atmosphere; Darkness View Scheme

Upstream product

• 80-09-1 4,4'-sulfonediphenol 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 187737-37-7 propene 

Downstream Products

• 41481-66-7 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone 
• 737795-84-5 3-allyl-4-hydroxy-4'-allyloxydiphenyl sulfone 
• 122438-87-3 4,4’-sulfonylbis(2-allyl-1-(allyloxy)benzene) 
• 1636900-13-4 C₃₂H₄₂O₈S₅ 
• 1636900-15-6 C₂₄H₃₄O₄S₅ 
• 42757-55-1 tetrabromobisphenol-S-bis-(2,3-dibromopropyl ether) 

Relevant articles and documents

Preparation method of tetrabromobisphenol S bis(2,3-dibromopropyl ether) flame retardant

The invention provides a preparation method of a tetrabromobisphenol S bis(2,3-dibromopropyl ether) flame retardant. Bisphenol S used as a raw material and chloropropene undergo a substitution reaction to obtain a bisphenol S diallyl ether intermediate, and the bisphenol S diallyl ether and liquid bromine undergo addition and substitution reactions to obtain tetrabromobisphenol S bis(2,3-dibromopropyl ether). One-time bromination is adopted to introduce all eight bromine atoms into an aromatic ring and a side chain at the same time, so that the process route is shortened, the operation is simple, the safety is high, and the production cost is low. A solvent can be recycled in the process of preparing the bisphenol S diallyl ether intermediate, and the output of three wastes is greatly reduced, so the pollution to the environment is reduced, and the production cost is saved. The tetrabromobisphenol S bis(2,3-dibromopropyl ether) flame retardant prepared in the invention has high productpurity and improved application quality.

Process for synthesizing diallyl phenol ether compound through azeotropic dehydration

The invention discloses a process for synthesizing a diallyl phenol ether compound by azeotropic dehydration, which comprises the following steps: (1) dissolving a bisphenol compound in an organic solvent, and adding an inorganic base or an aqueous solution of the inorganic base to react to generate phenolate; and (2) vacuumizing the mixture obtained by the reaction in the step (1) or adding a water-carrying agent for dehydration, adding an allyl compound after dehydration is finished, and reacting to obtain the diallyl phenol ether compound. The invention provides a method for preparing a bisphenol compound into an intermediate product phenate and then reacting the intermediate product phenate with a propenyl compound to generate a diallyl phenol ether compound product, which comprises the following steps: adding a water-carrying agent or vacuumizing to remove water in a reaction system; according to the method, the problem of raw material waste caused by hydrolysis of propylene compounds can be effectively avoided, the reaction yield and purity are improved, aftertreatment is simple, and economic benefits are improved.

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.