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80-05-7 Usage

Uses

Different sources of media describe the Uses of 80-05-7 differently. You can refer to the following data:
1. A high-production-volume chemical used in manufacture of epoxy-phenolic resins (protective linings for food and beverage cans); monomer for polycarbonate resins (used in food contact materials such as returnable beverage bottles, infant feeding bottles, plates, and mugs); antioxidant in PVC plastics; inhibitor of end polymerization in PVC plastics
2. Bisphenol A (BPA) is used as the constitutional monomer or the monomeric building block of polycarbonate plastics, either by trans-esterification with diphenyl carbonate or via the interfacial process with a monohydroxylic phenol. Together with epichlorohydrin, BPA is also used as a major component of epoxy resins. Bisphenol A-polycarbonate plastics are in turn used in the manufacture of plastic food containers such as reusable water bottles, while epoxy resins are used as inner linings of tin cans. In addition, BPA is also used as an additive in other plastics and polymers, particularly as an antioxidant or stabilizer in polyvinyl chloride, printer ink, and in some other products.
3. A monomer used for policarbonate and epoxy resins; exhibits estrogenic activity. BPA is also used as a building block in polycarbonate bottles and in the epoxy-resin liners of metal cans.
4. Bisphenol A is used with epichlorhydrin for the synthesis of epoxy resins bisphenol-A type. It leads to bisphenol-A diglycidyl ether, which is the monomer of bisphenol-A based epoxy resins.

Description

Reports of bisphenol- A sensitization, particularly in workers at epoxy resin plants, are controversial. Bisphenol-A was also reported as an allergen in fiberglass, semisynthetic waxes, footwear and dental materials.

Chemical Properties

Bisphenol A is a white or tan crystals or flakes with a mild phenolic odor and a very low vapor pressure (ECB, 2003). It is mildly soluble in water. It is not considered to be an explosive in the conventional sense but can pose a hazard as a finely powdered material in air (ECB, 2003). It is not considered to be a chemical oxidizer.

History

Bisphenol A (BPA) was first synthesized in 1891, but it was not used widely until applications in the plastics industry were identified in the 1950s (University of Minnesota, 2008). While the most prominent use of BPA is in the manufacture of polycarbonate plastic and epoxy resins, it is also used in the production and processing of polyvinyl chloride (PVC) and modified polyamide and in the manufacture of carbonless and thermal paper, wood filler, adhesives, printing inks, surface coatings, polyurethane, brake fluid, resin-based dental composites and sealants, flame retardants, paints, and tires (ECB, 2003; EFSA, 2006).

Preparation

The formation of bisphenol A is thought to proceed as follows:Although the reaction theoretically requires the molar ratio of reactants to be 2: 1, an improved yield of bisphenol A is obtained if additional phenol is present; the optimum molar ratio is 4: 1. In a typical process, the phenol and acetone are mixed and warmed to 50°C. Hydrogen chloride (catalyst) is passed into the mixture for about 8 hours, during which period the temperature is kept below 70°C to suppress the formation of isomeric products. Bisphenol A precipitates and is filtered off and washed with toluene to remove unreacted phenol (which is recovered). The product is then recrystallized from aqueous ethanol. Since epoxy resins are oflow molecular weight and because colour is not normally particularly important, the purity of bisphenol A used in resin production is not critical. Material with a p,p'-isomer content of 95-98% is usually satisfactory; the principal impurities in such material are o,p'- and o,o'-isomers.

Definition

ChEBI: A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2287, 1949 DOI: 10.1021/ja01175a004

General Description

White to light brown flakes or powder. Has a weak medicine odor. Sinks in water.

Air & Water Reactions

The finely powdered resin is a significant dust explosion hazard. Insoluble in water.

Reactivity Profile

Bisphenol A is incompatible with strong oxidizers. Bisphenol A is also incompatible with strong bases, acid chlorides and acid anhydrides.

Hazard

Poison; moderately toxic; teratogen; irritant.

Health Hazard

Dusts irritating to upper respiratory passages; may cause sneezing.

Fire Hazard

Bisphenol A is combustible. Bisphenol A may form explosive dust clouds. Static electricity can cause its dust to explode.

Flammability and Explosibility

Notclassified

Contact allergens

Bisphenol A is used with epichlorhydrin for the synthesis of epoxy resins bisphenol-A type, for unsaturated polyester and polycarbonate resins, and epoxy di(meth)acrylates. In epoxy resins, it leads to bisphenol-A diglycidyl ether, which is the monomer of bisphenol-A-based epoxy resins. Reports of bisphenol-A sensitization are rare and concern workers at epoxy resin plants, after contact with fiber glass, semi-synthetic waxes, footwear, and dental materials. It is also a possible sensitizer in vinyl gloves.

Potential Exposure

Workers engaged in the manufacture of epoxy, polysulfone, polycarbonate and certain polyester resins. It is also used in flame retardants, rubber chemicals, and as a fungicide. Bisphenol A (BP A), an environmental estrogen, is found in a wide variety of products, including polycarbonate bottles food and drink containers. According to 2008 research conducted at University of Cincinnati, when it comes to BPA, it’s not whether polycarbonate bottles are new or old but the liquid’s temperature that has the greatest impact on how much BPA is released. When exposed to boiling hot water, BPA was released 55 times more rapidly than exposure to cold water.

Environmental Fate

Bisphenol A can be released into the environment during the production, processing, and use of BPA-containing materials, although levels in environmental samples are generally very low or undetectable (ECB, 2003). This is because BPA has low volatility and a short half-life in the atmosphere, is rapidly biodegraded in water, and is not expected to be stable, mobile, or bioavailable from soils (ECB, 2003; Cousins et al., 2002). Most environmental releases of BPA are during the manufacture of BPA-containing products when residual BPA in wastewater is released from treatment plants into receiving streams (Cousins et al., 2002). BPA's half-life in soil and water is in the order of 4.5 days while in air it is <1 day (Cousins et al., 2002). It has a low bioconcentration factor and is rapidly metabolized in fish, with a half-life of <1 day (Cousins et al., 2002).

Purification Methods

Crystallise bisphenol from acetic acid/water (1:1). It is used for making polycarbonate bottles and leaches out slowly on heating. It is a known “estrogenic chemical” shown to disrupt chemical signaling in the complex network of glands, hormones and cell receptors which make up the endocrine system. It causes low sperm count and damages the ecosystem by the feminisation of fish, reptiles and birds. [cf Chapter 1, p 3, Beilstein 6 IV 6717.]

Toxicity evaluation

Bisphenol-A is a chemical substance with known oestrogenic action that is used in the manufacture of a wide range of products. The low-dose in utero exposure to bisphenol-A of experimental animals caused striking morphological changes in the vagina of postpubertal offspring. In addition, the oestrogen receptor alpha was not expressed during oestrus in the vagina of female offspring exposed to bisphenol-A and the altered vaginal morphology is attributed to the down regulation of oestrogen receptor alpha (Schonfelder et at., 2002). Another experiment on mice after intrauterine exposure to bisphenol-A showed differences in the rate of ductal migration into the stroma at 1 month of age and a significant increase in the percentage of ducts, terminal ducts, terminal end buds, and alveolar buds at 6 months of age. The changes in histoarchitecture, coupled with an increased presence of secretory product within alveoli, resemble those of early pregnancy. This suggests a disruption of the hypothalamic-pituitary-ovarian axis and/or mis-expression of developmental genes. It was concluded that the altered relationship in DNA synthesis between the epithelium and stroma and the increase in terminal ducts and terminal end buds are noteworthy, because these changes are associated with carcinogenesis in both rodents and humans (Markey et at., 2001).

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid chlorides and acid anhydrides.

Check Digit Verification of cas no

The CAS Registry Mumber 80-05-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 80-05:
(4*8)+(3*0)+(2*0)+(1*5)=37
37 % 10 = 7
So 80-05-7 is a valid CAS Registry Number.

80-05-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A10324)  Bisphenol A, 97+%   

  • 80-05-7

  • 250g

  • 197.0CNY

  • Detail
  • Alfa Aesar

  • (A10324)  Bisphenol A, 97+%   

  • 80-05-7

  • 1000g

  • 410.0CNY

  • Detail
  • Alfa Aesar

  • (A10324)  Bisphenol A, 97+%   

  • 80-05-7

  • 5000g

  • 1162.0CNY

  • Detail
  • Sigma-Aldrich

  • (42088)  Bisphenol A  certified reference material, TraceCERT®

  • 80-05-7

  • 42088-100MG

  • 1,075.23CNY

  • Detail
  • Supelco

  • (442840)  4,4′-Isopropylidenediphenol  analytical standard

  • 80-05-7

  • 000000000000442840

  • 449.28CNY

  • Detail
  • Aldrich

  • (133027)  Bisphenol A  97%

  • 80-05-7

  • 133027-500G

  • 308.88CNY

  • Detail
  • Aldrich

  • (133027)  Bisphenol A  97%

  • 80-05-7

  • 133027-2KG

  • 1,063.53CNY

  • Detail
  • Aldrich

  • (239658)  Bisphenol A  ≥99%

  • 80-05-7

  • 239658-50G

  • 834.21CNY

  • Detail
  • Aldrich

  • (239658)  Bisphenol A  ≥99%

  • 80-05-7

  • 239658-250G

  • 2,786.94CNY

  • Detail

80-05-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name bisphenol A

1.2 Other means of identification

Product number -
Other names Bisphenol A

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adhesives and sealant chemicals,CBI,Flame retardants,Intermediates,Paint additives and coating additives not described by other categories
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:80-05-7 SDS

80-05-7Synthetic route

Tetrabromobisphenol A
79-94-7

Tetrabromobisphenol A

Conditions
ConditionsYield
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 116h; Autoclave;95%
With hydrogen; triethylamine In ethanol; water at 120℃; under 22502.3 Torr; for 116h; Autoclave;95%
With cadmium selenide; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Irradiation; Sealed tube;87%
With sodium sulfite In water at 130℃; for 12h; Sealed tube; Microwave irradiation; Green chemistry;80%
acetone
67-64-1

acetone

phenol
108-95-2

phenol

Conditions
ConditionsYield
With silica supported perchloric acid In neat (no solvent) for 3.75h; Heating; Green chemistry;88%
With magnetic mesoporous silica supported azacrown ether hexafluorophosphate ionic liquid In water at 50℃; for 5h; Temperature; Green chemistry;86%
sulfonic-acid-form cation-exchange resin (DIAION "SK104H") modified with hydrolyzed 2-pyridylethyl thioacetate at 70℃; for 2h; Product distribution / selectivity; Inert atmosphere; Cooling;58%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1-butanethiol
109-79-5

1-butanethiol

phenol
108-95-2

phenol

Conditions
ConditionsYield
In chlorobenzene; acetone83%
Benzhydrylamine
91-00-9

Benzhydrylamine

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

N,N'-dibenzhydryl-urea
6744-64-5

N,N'-dibenzhydryl-urea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 81%
cyclohexylamine
108-91-8

cyclohexylamine

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 81%
C33H36O4
192867-23-5

C33H36O4

phenol
108-95-2

phenol

Conditions
ConditionsYield
With hydrogenchloride at 40℃; for 48h;80%
1-aminodecane
2016-57-1

1-aminodecane

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

N,N'-Di-n-decylurea
1943-09-5

N,N'-Di-n-decylurea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 78%
4-[1-(4-bromo-phenyl)-1-methyl-ethyl]-phenol

4-[1-(4-bromo-phenyl)-1-methyl-ethyl]-phenol

Conditions
ConditionsYield
With iron(III) chloride; potassium phosphate; tetrabutylammomium bromide; N,N`-dimethylethylenediamine In water at 180℃; under 5250.53 Torr; for 20h;76%
2,2'-[isopropylidenebis(1,4-phenyleneoxy)]diacetic acid
3539-42-2

2,2'-[isopropylidenebis(1,4-phenyleneoxy)]diacetic acid

Conditions
ConditionsYield
Stage #1: 2,2'-[isopropylidenebis(1,4-phenyleneoxy)]diacetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating;
Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.;
72%
ammonia
7664-41-7

ammonia

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

urea
57-13-6

urea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 68%
acetone
67-64-1

acetone

phenol
108-95-2

phenol

A

BPA
80-05-7

BPA

B

4-methyl-pent-3-en-2-one
141-79-7

4-methyl-pent-3-en-2-one

C

2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol
837-08-1

2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol

Conditions
ConditionsYield
beta zeolite acidic form at 120℃; under 760.051 Torr; for 12h;A 63.2%
B 0.01%
C 11.43%
benzylamine
100-46-9

benzylamine

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

1,3-dibenzylurea
1466-67-7

1,3-dibenzylurea

Conditions
ConditionsYield
In water; isopropyl alcohol at 80℃; for 12h; Solvent; Temperature; Green chemistry;A 62%
B 58%
4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

N,N'-bis[(4-methoxyphenyl)methyl]urea
93731-94-3

N,N'-bis[(4-methoxyphenyl)methyl]urea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 62%
3-METHOXYBENZYLAMINE
5071-96-5

3-METHOXYBENZYLAMINE

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

1,3-bis(3-methoxybenzyl)urea
57498-59-6

1,3-bis(3-methoxybenzyl)urea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 60%
4,4'-(1-methyl-ethane-1,1-diyl)-bis-aniline
2479-47-2

4,4'-(1-methyl-ethane-1,1-diyl)-bis-aniline

Conditions
ConditionsYield
With uranyl nitrate hydrate; water; trifluoroacetic acid In nitromethane for 48h; Irradiation; Inert atmosphere;60%
para-fluorobenzylamine
140-75-0

para-fluorobenzylamine

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

1,3-bis(4-fluorobenzyl)urea
930045-10-6

1,3-bis(4-fluorobenzyl)urea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 52%
acetone
67-64-1

acetone

phenol
108-95-2

phenol

A

BPA
80-05-7

BPA

B

2,2-bis(2-hydroxyphenyl)-propane
7559-72-0

2,2-bis(2-hydroxyphenyl)-propane

C

2-(2-hydroxyphenyl)-2,4,4-trimethylchroman
5026-12-0

2-(2-hydroxyphenyl)-2,4,4-trimethylchroman

D

4'-hydroxy-2,4,4-trimethylflavan
63661-69-8

4'-hydroxy-2,4,4-trimethylflavan

E

2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol
837-08-1

2-[1-(4-hydroxyphenyl)-1-methylethyl]-phenol

Conditions
ConditionsYield
With aluminium(III) phenoxide at 140 - 160℃; for 1h; Product distribution; oth. temperature, oth. ratio of reactants, solvents;A 8.1%
B 1.5%
C 7%
D 21.6%
E 50.3%
methylamine
74-89-5

methylamine

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 50%
p-Trifluoromethylbenzylamine
3300-51-4

p-Trifluoromethylbenzylamine

polycarbonate

polycarbonate

A

N,N'-bis[[4-(trifluoromethyl)phenyl]methyl]urea

N,N'-bis[[4-(trifluoromethyl)phenyl]methyl]urea

B

BPA
80-05-7

BPA

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A 48%
B n/a
3-(TRIFLUOROMETHYL)BENZYLAMINE
2740-83-2

3-(TRIFLUOROMETHYL)BENZYLAMINE

polycarbonate

polycarbonate

A

BPA
80-05-7

BPA

B

C17H14F6N2O

C17H14F6N2O

Conditions
ConditionsYield
In ethanol; water at 80℃; for 12h; Green chemistry;A n/a
B 28%
Cumene hydroperoxide
80-15-9

Cumene hydroperoxide

Conditions
ConditionsYield
With hydrogenchloride; ethanethiol
With sulfuric acid; ethanethiol
prop-1-yne
74-99-7

prop-1-yne

phenol
108-95-2

phenol

Conditions
ConditionsYield
With boron trifluoride
Isopropenyl acetate
108-22-5

Isopropenyl acetate

phenol
108-95-2

phenol

Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid
With hydrogenchloride
With hydrogenchloride; zinc(II) chloride
4,4'-isopropylidenedicyclohexanol
13804-54-1, 13804-57-4, 13804-58-5, 80-04-6

4,4'-isopropylidenedicyclohexanol

Conditions
ConditionsYield
In 1,4-dioxane; water100%
With 10% Ru/C; hydrogen In isopropyl alcohol at 90℃; under 3800.26 Torr; for 21h;74%
With kieselguhr; ethanol; nickel at 180 - 200℃; under 51485.6 - 128714 Torr; Hydrogenation.Isolierung durch fraktionierte Krystallisation aus Aethanol-Benzol-Gemischen und aus Aceton;
benzocyclobutenone
3469-06-5

benzocyclobutenone

C31H28O4

C31H28O4

Conditions
ConditionsYield
at 200℃; for 2h;100%
glycerol
56-81-5

glycerol

3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol
5581-32-8

3-[4-[1-[4-(2,3-dihydroxypropoxy)phenyl]-1-methylethyl]phenoxy]propane-1,2-diol

Conditions
ConditionsYield
With potassium carbonate; Diethyl carbonate at 110℃; for 18h;100%
4,4'-(propane-2,2-diyl)bis(4,1-phenylene) disulfofluoridate
38184-64-4

4,4'-(propane-2,2-diyl)bis(4,1-phenylene) disulfofluoridate

Conditions
ConditionsYield
Stage #1: BPA With triethylamine In dichloromethane at 20℃; for 0.166667h;
Stage #2: With fluorosulfonyl fluoride In dichloromethane at 20℃; Sealed tube;
100%
Stage #1: BPA With triethylamine In dichloromethane at 20℃; for 0.166667h;
Stage #2: With fluorosulfonyl fluoride In dichloromethane at 20℃; Sealed tube;
100%
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h;98%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

dyanol 22
901-44-0

dyanol 22

Conditions
ConditionsYield
at 150℃; for 8h; Inert atmosphere;99%
With potassium carbonate In N,N-dimethyl-formamide at 145℃; for 3h;65%
Tetrabromobisphenol A
79-94-7

Tetrabromobisphenol A

Conditions
ConditionsYield
With potassium tribromide In water; acetonitrile at 30℃; for 0.0833333h;99%
With hydrogenchloride; sodium bromate; sodium dodecyl-sulfate; sodium bromide In tetrachloromethane; water at 10℃; for 4.5h;98.28%
With dihydrogen peroxide; bromine In dichloromethane; water96%
6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindan
1568-80-5

6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindan

Conditions
ConditionsYield
With methanesulfonic acid at 20℃; for 96h;99%
With methanesulfonic acid at 25℃; for 96h;95%
With methanesulfonic acid at 20℃; for 96h;90%
allyl bromide
106-95-6

allyl bromide

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
Stage #1: BPA With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux;
Stage #2: allyl bromide In acetone Reflux; Inert atmosphere;
99%
Hexamethylphosphorous triamide
1608-26-0

Hexamethylphosphorous triamide

polymer, Mr 15000, MP: 290-300 deg C; monomer(s): 2,2\-bis(4-hydroxyphenyl)propane; hexamethylphosphorous triamide

polymer, Mr 15000, MP: 290-300 deg C; monomer(s): 2,2\-bis(4-hydroxyphenyl)propane; hexamethylphosphorous triamide

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 80℃; for 5h;99%
Hexamethylphosphorous triamide
1608-26-0

Hexamethylphosphorous triamide

poly(phosphoramidite), MW: 15000, MP: 290-300 deg C; Monomer(s): 2,2\-(4-hydroxyphenyl)propane; hexamethylphosphorous triamide

poly(phosphoramidite), MW: 15000, MP: 290-300 deg C; Monomer(s): 2,2\-(4-hydroxyphenyl)propane; hexamethylphosphorous triamide

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 80℃; for 5h;99%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

C31H24N4O2
1020725-59-0

C31H24N4O2

Conditions
ConditionsYield
Stage #1: BPA With potassium carbonate In sulfolane; toluene at 20℃; for 0.75h;
Stage #2: 2-chloroquinoxaline at 80℃; for 48h; Further stages.;
99%
1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

4,4'-(isopropylidenediphenyl)-bis(4-bromobenzyl) ether
159639-83-5

4,4'-(isopropylidenediphenyl)-bis(4-bromobenzyl) ether

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;99%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2,2-bis(4-trifluoromethanesulfonyloxyphenyl)propane
139725-20-5

2,2-bis(4-trifluoromethanesulfonyloxyphenyl)propane

Conditions
ConditionsYield
Stage #1: BPA With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere;
98.5%
With pyridine for 25h; Ambient temperature;96%
With pyridine at 0 - 20℃;93%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(4,4'-(propane-2,2-diyl)bis(4,1-phenylene))bis(oxy)bis(tert-butyldimethylsilane)

(4,4'-(propane-2,2-diyl)bis(4,1-phenylene))bis(oxy)bis(tert-butyldimethylsilane)

Conditions
ConditionsYield
Stage #1: BPA With 1H-imidazole In dichloromethane at 20℃; for 0.166667h;
Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 24.5h;
98.5%
With 1H-imidazole In dichloromethane at 20℃; Sealed tube;98%
With 1H-imidazole; dmap In dichloromethane; N,N-dimethyl-formamide for 3h;96%
With 1H-imidazole In dichloromethane at 20℃;93%
With 1H-imidazole In dichloromethane
3,3-bis[4-(4-fluorobenzoyl)phenyl]phthalide
199334-40-2

3,3-bis[4-(4-fluorobenzoyl)phenyl]phthalide

cardo polyarene ether ketone

cardo polyarene ether ketone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 185℃; for 10h; Polymerization;98.5%
2,4'-difluorobenzophenone
342-25-6

2,4'-difluorobenzophenone

polymer; monomer(s): 2,4\-difluorobenzophenone; 2,2-bis(4\-hydroxyphenyl)propane

polymer; monomer(s): 2,4\-difluorobenzophenone; 2,2-bis(4\-hydroxyphenyl)propane

Conditions
ConditionsYield
With N,N-dimethyl acetamide; potassium carbonate In chlorobenzene at 185℃; for 50h;98.5%
4,4'-Difluorobenzophenone
345-92-6

4,4'-Difluorobenzophenone

polymer; monomer(s): 4,4\-difluorobenzophenone; 2,2-bis(4\-hydroxyphenyl)propane

polymer; monomer(s): 4,4\-difluorobenzophenone; 2,2-bis(4\-hydroxyphenyl)propane

Conditions
ConditionsYield
With N,N-dimethyl acetamide; potassium carbonate In chlorobenzene at 185℃; for 10h;98.5%
3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2,2-bis[4-(2-methylallyloxy)phenyl]propane
103915-73-7

2,2-bis[4-(2-methylallyloxy)phenyl]propane

Conditions
ConditionsYield
With sodium hydroxide In water at 20 - 30℃; for 6h;98.5%
Stage #1: BPA With potassium hydroxide In ethanol
Stage #2: 3-Chloro-2-methylpropene In ethanol for 10h; Reflux;
10.32 g
3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2,2-bis[3,5-dibromo-4-(2,3-dibromo-2-methylpropoxy)phenyl]propane

2,2-bis[3,5-dibromo-4-(2,3-dibromo-2-methylpropoxy)phenyl]propane

Conditions
ConditionsYield
Stage #1: BPA; 3-Chloro-2-methylpropene With sodium hydroxide In water at 50 - 60℃; for 12h; pH=8 - 10;
Stage #2: With hydrogen bromide; dihydrogen peroxide In water at 27 - 29℃; for 6h; Concentration;
98.3%
bromocyane
506-68-3

bromocyane

2,2-bis(4-cyanatophenyl)propane
1156-51-0

2,2-bis(4-cyanatophenyl)propane

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water; acetone98.1%
With hydrogenchloride; triethylamine In water; acetone98.1%
With triethylamine; isopropyl alcohol In acetone at -15 - -10℃; for 2h; Temperature;94%
With triethylamine In acetone at -30 - 20℃; for 1.5h;80%
With triethylamine In acetone at -5 - 0℃;
epichlorohydrin
106-89-8

epichlorohydrin

diphenylolpropane diglycidyl ether
1675-54-3

diphenylolpropane diglycidyl ether

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium hydroxide at 20℃; for 12h;98%
Stage #1: BPA With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;
Stage #2: epichlorohydrin In N,N-dimethyl-formamide at 20℃; for 18h;
72%
Stage #1: BPA; epichlorohydrin With N-benzyl-N,N,N-triethylammonium chloride at 80℃; for 12h;
Stage #2: With sodium hydroxide In water for 5h;
47%
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

4,4′-(propane-2,2-diyl)di(benzene-4,1-diyl) bis(N,N-diethyl-P-phenylphosphonamidite)
146733-97-3

4,4′-(propane-2,2-diyl)di(benzene-4,1-diyl) bis(N,N-diethyl-P-phenylphosphonamidite)

Conditions
ConditionsYield
at 115 - 120℃; a) 2 h, b) 10 mm Hg, 2 h, c) 1 mm Hg, 2 h;98%
at 115 - 120℃; for 1.5h;
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

Conditions
ConditionsYield
at 115 - 120℃; a) 2 h, b) 10 mm Hg, 2 h, c) 1 mm Hg, 2 h;98%
In xylene for 14h; Heating;85%
3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In ethanol for 24h; Heating;98%
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide at 40℃; for 6h;70%
With sodium hydroxide; calcium oxide In tert-butyl alcohol at 80℃; for 6h; Solvent; Reagent/catalyst; Temperature;
Stage #1: BPA With sodium hydroxide In ethanol at 78℃; for 8h;
Stage #2: 3-chloroprop-1-ene at 70℃; for 6h;
allyl methyl carbonate
35466-83-2

allyl methyl carbonate

bisphenol A diallyl ether
3739-67-1

bisphenol A diallyl ether

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 25℃; for 24h; Condensation;98%
With potassium carbonate In neat (no solvent) at 85℃; for 4h; Catalytic behavior;98%
propargyl bromide
106-96-7

propargyl bromide

4,4'-(propane-2,2-diyl)bis((prop-2-ynyloxy)benzene)
22235-02-5

4,4'-(propane-2,2-diyl)bis((prop-2-ynyloxy)benzene)

Conditions
ConditionsYield
With potassium carbonate In acetone for 22h; Heating;98%
Stage #1: BPA With sodium hydride In ethanol; N,N-dimethyl-formamide at -10 - 0℃; for 1.5h; Williamson Ether Synthesis; Inert atmosphere;
Stage #2: propargyl bromide With tetra-(n-butyl)ammonium iodide In ethanol; N,N-dimethyl-formamide at 0 - 20℃; for 2.5h; Williamson Ether Synthesis; Inert atmosphere;
92%
Stage #1: BPA With sodium hydroxide In water at 70℃;
Stage #2: propargyl bromide With tetrabutylammomium bromide In water; toluene at 70 - 90℃;
90%
Hexamethylphosphorous triamide
1608-26-0

Hexamethylphosphorous triamide

polymer, Mr 9500, MP: 252-260 deg C; monomer(s): 2,2\-bis(4-hydroxyphenyl)propane; hexamethylphosphorous triamide

polymer, Mr 9500, MP: 252-260 deg C; monomer(s): 2,2\-bis(4-hydroxyphenyl)propane; hexamethylphosphorous triamide

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 70 - 80℃; for 4h;98%
4,4'-Difluorobenzophenone
345-92-6

4,4'-Difluorobenzophenone

polymer, inherent viscosity 0.20 dL/g at 25 deg C; monomer(s): bisphenol A; 4,4\-difluorobenzophenone

polymer, inherent viscosity 0.20 dL/g at 25 deg C; monomer(s): bisphenol A; 4,4\-difluorobenzophenone

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide; toluene at 140 - 145℃; for 6h;98%
4,4'-Difluorobenzophenone
345-92-6

4,4'-Difluorobenzophenone

polymer, inherent viscosity 0.23 dL/g at 25 deg C; monomer(s): bisphenol A; 4,4\-difluorobenzophenone

polymer, inherent viscosity 0.23 dL/g at 25 deg C; monomer(s): bisphenol A; 4,4\-difluorobenzophenone

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one; toluene at 150 - 155℃; for 6h;98%
2,2-bis[4-(3-hydroxyphenyl)phenyl]propane
685561-32-4

2,2-bis[4-(3-hydroxyphenyl)phenyl]propane

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

polymer, Mn 29180 g/mol, PDI 1.6; monomer(s): 2,2-bis[4-(3-hydroxyphenyl)phenyl]propane; bisphenol A; triphosgene

polymer, Mn 29180 g/mol, PDI 1.6; monomer(s): 2,2-bis[4-(3-hydroxyphenyl)phenyl]propane; bisphenol A; triphosgene

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0 - 15℃; for 1h;98%

80-05-7Relevant articles and documents

Selective synthesis of Bisphenol-A over mesoporous MCM silica catalysts functionalized with sulfonic acid groups

Das, Debasish,Lee, Jyh-Fu,Cheng, Soofin

, p. 152 - 160 (2004)

Mesoporous MCM-41 and -48 silicas anchored with sulfonic acid (-SO 3H) groups via postsynthesis modification are very effective for the synthesis of Bisphenol-A by liquid-phase condensation of phenol with acetone. Higher amounts of thiol groups can be incorporated in MCM-48 silicas presumably due to the presence of larger number of surface silanol groups. However sulfur K-edge XANES spectroscopy reveals that effective oxidation of the precursor thiol (-SH) groups to the sulfonic acid (-SO3H) groups was necessary for obtaining samples of good catalytic activity. It was noted that when sulfur loadings exceed 1.5 meq/g solid a part of the sulfur atoms remains in the reduced form even after prolonged oxidation. MCM-41 silica anchored with sulfonic acid groups has comparable catalytic activity to that of commercial ion-exchange resin Amberlite-120 and the former also showed higher selectivity toward the desired p,p′ isomer. MCM-48 silica-anchored samples are equally effective for selective synthesis of Bisphenol-A.

Hydrolysis of polycarbonate in sub-critical water in fused silica capillary reactor with in situ Raman spectroscopy

Pan, Zhiyan,Chou, I-Ming,Burruss, Robert C.

, p. 1105 - 1107 (2009)

The advantages of using fused silica capillary reactor (FSCR) instead of conventional autoclave for studying chemical reactions at elevated pressure and temperature conditions were demonstrated in this study, including the allowance for visual observation

Synthesis, characterization, and catalytic activity of sulfonic acid-functionalized periodic mesoporous organosilicas

Yang, Qihua,Liu, Jian,Yang, Jie,Kapoor, Mahendra P.,Inagaki, Shinji,Li, Can

, p. 265 - 272 (2004)

Sulfonic acid-functionalized periodic mesoporous organosilicas were synthesized directly by cocondensation of (R′O)3SiRSi(OR′ )3 (R = CH2CH2 and C6H4; R′ = CH3 and C2H5) with 3-mercaptopropyltrimethoxysilane (MeO)3SiCH2CH 2CH2SH in the presence of H2O2 using nonionic oligomeric polymer surfactant C18H37(OCH 2CH2)10OH in acidic medium. The sulfonic acid functionalities (SO3H) were generated in situ by oxidation of the propylthiol using H2O2 as oxidant during the synthesis process. Powder X-ray diffraction patterns and nitrogen sorption indicate the formation of well-ordered mesoporous material with uniform porosity. The highest acid-exchange capacity (acid-base titration methods) was 1.72 H+ mmol/g. Complete oxidation of SH to SO3H was observed as evidenced by X-ray photoelectron spectroscopy. For comparison, the sulfonic acid-functionalized mesoporous organosilicas were also prepared by a grafting method. The catalytic properties of the materials were investigated in liquid-phase condensation of phenol with acetone to form Bisphenol A. All sulfonic acid-functionalized mesoporous organosilicas show high catalytic activity. The highest TOF obtained for the mesoporous organosilica is 17.2.

Optimization of process parameters for preparing a solid catalyst for bisphenol synthesis

Kozlova,Tereshchuk,Myznikov,Antonenko,Zubritskaya,Bazanov

, p. 406 - 413 (2016)

The results of optimization of the process parameters for preparing high-performance heterogeneous catalysts for bisphenol synthesis show that the performance of the solid acid catalyst is determined by its exchange capacity, acidity, pore structure, and specific surface area. Optimum process parameters for preparing highly active solid acid catalysts were revealed.

Photocatalytic Degradation of 4,4′-Isopropylidenebis(2,6-dibromophenol) on Magnetite Catalysts vs. Ozonolysis Method: Process Efficiency and Toxicity Assessment of Disinfection By-Products

Balawejder, Maciej,Barylyak, Adriana,Bobitski, Yaroslav,Kisa?a, Joanna,Tomaszewska, Anna

, (2022/03/31)

Flame retardants have attracted growing environmental concern. Recently, an increasing number of studies have been conducted worldwide to investigate flame-retardant sources, environmental distribution, living organisms’ exposure, and toxicity. The presented studies include the degradation of 4,4′-isopropylidenebis(2,6-dibromophenol) (TBBPA) by ozonolysis and photocatalysis. In the photocatalytic process, nano-and micro-magnetite (n-Fe3 O4 and μ-Fe3 O4) are used as a catalyst. Monitoring of TBBPA decay in the photocatalysis and ozonolysis showed photocatalysis to be more effective. Significant removal of TBBPA was achieved within 10 min in photocatalysis (ca. 90%), while for ozonation, a comparable effect was observed within 70 min. To determine the best method of TBBPA degradation concentration on COD and TOC, the removals were examined. The highest oxidation state was obtained for photocatalysis on μ-Fe3 O4, whereas for n-Fe3 O4 and ozonolysis, the COD/TOC ratio was lower. Acute toxicity results show noticeable differences in the toxicity of TBBPA and its degradation products to Artemia franciscana and Thamnocephalus platyurus. The EC50 values indicate that TBBPA degradation products were toxic to harmful, whereas the TBPPA and post-reaction mixtures were toxic to the invertebrate species tested. The best efficiency in the removal and degradation of TBBPA was in the photocatalysis process on μ-Fe3 O4 (reaction system 1). The examined crustaceans can be used as a sensitive test for acute toxicity evaluation.

PROCESS FOR PREPARING BISPHENOLE A (BPA) IN THE PRESENCE OF HYDROXYACETONE

-

Page/Page column 12-15, (2021/03/05)

The present invention relates to a process for preparing bisphenol A in the presence of hydroxyacetone without poisoning the catalyst system comprising an ion exchange resin catalyst and a sulfur containing cocatalyst, wherein at least part of the sulfur containing cocatalyst is not chemically bound to the ion exchange resin catalyst. Moreover, the present invention provides a process for preparing polycarbonate and a composition comprising bisphenol A and at least one specific impurity which is formed in the production of bisphenol A.

A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK

Pan, Wenjing,Li, Chenchen,Zhu, Haoyin,Li, Fangfang,Li, Tao,Zhao, Wanxiang

, p. 7633 - 7640 (2021/09/22)

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.

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