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131-17-9

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131-17-9 Usage

Chemical Properties

clear colourless to light yellow liquid

Uses

Diallyl Phthalate is used as a reagent in ring-closing ruthenium based reactions.

Preparation

Diallyl phthalate (DAP) is prepared by reaction of phthalic anhydride and allyl alcohol:

General Description

Clear pale-yellow liquid. Odorless.

Air & Water Reactions

Incompatible with water and oxygen. Should be stored air tight, with inhibitor, to prevent polymerization reaction .

Reactivity Profile

Diallyl phthalate can react with oxidizers. Diallyl phthalate can also react with acids and alkalis. Diallyl phthalate is incompatible with water and oxygen.

Fire Hazard

Diallyl phthalate is combustible.

Flammability and Explosibility

Notclassified

Safety Profile

Suspected carcinogen with experimental carcinogenic data. Moderately toxic by ingestion, skin contact, intraperitoneal, and subcutaneous routes. An eye irritant. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidzing materials. To fight fire, use CO2 or dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS and ESTERS.

Carcinogenicity

In the 103-week study referred to previously, a slight increase in MNCL was seen in female rats treated with 50 or 100 mg/kg/day of DAP. MNCL occurs in F344 control rats at a high incidence; however, the incidence of 51% in female rats at the high dose level was above historical control data for the laboratory (29%). No significant increases in tumor incidences were seen in male rats. Based on this study, DAP was considered to have demonstrated equivocal evidence for carcinogenicity in female F344 rats according to the NTP. In male and female B6C3F1 mice receiving 300 mg/kg of DAP by gavage for 103 weeks (5 days/week), the incidence of forestomach papillomas was significantly greater than that of controls. Because of the rarity of forestomach papillomas in control B6C3F1 mice and the concomitant observation of dose-related forestomach hyperplasia, the development of these tumors was considered to be test substance related. Compared to controls, a slight increase in the incidence of lymphomas was observed in males receiving 300 mg/kg/day of DAP. Because the increase was not statistically significant compared to historical control data, this effect was not considered to be test substance related.

Check Digit Verification of cas no

The CAS Registry Mumber 131-17-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 1 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 131-17:
(5*1)+(4*3)+(3*1)+(2*1)+(1*7)=29
29 % 10 = 9
So 131-17-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H14O4/c1-3-5-9-7-8-11(13(15)16)12(14(17)18)10(9)6-4-2/h3-4,7-8H,1-2,5-6H2,(H,15,16)(H,17,18)/p-2

131-17-9 Well-known Company Product Price

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  • Alfa Aesar

  • (B24648)  Diallyl phthalate, 97%   

  • 131-17-9

  • 100g

  • 202.0CNY

  • Detail
  • Alfa Aesar

  • (B24648)  Diallyl phthalate, 97%   

  • 131-17-9

  • 500g

  • 618.0CNY

  • Detail
  • Sigma-Aldrich

  • (36925)  Diallylphthalate  analytical standard

  • 131-17-9

  • 36925-250MG

  • 329.94CNY

  • Detail

131-17-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Diallyl Phthalate

1.2 Other means of identification

Product number -
Other names 1,2-Benzenedicarboxylic acid, di-2-propenyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:131-17-9 SDS

131-17-9Synthetic route

phthalic anhydride
85-44-9

phthalic anhydride

allyl alcohol
107-18-6

allyl alcohol

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
With 3,3′-(2,2-bis(hydroxymethyl)propane-1,3-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate for 2h; Dean-Stark; Reflux;100%
With diacidic ionic liquid supported on magnetic-silica nanoparticles In neat (no solvent) at 97℃; for 5h; Dean-Stark;95%
With phosphoric acid
Phthalic acid 1-allyl ester 2-prop-2-ynyl ester
182342-88-7

Phthalic acid 1-allyl ester 2-prop-2-ynyl ester

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
With indium In ethanol for 40h; Heating;95%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
Stage #1: benzene-1,2-dicarboxylic acid With copper; sodium iodide In water under 760.051 Torr; for 1h; Green chemistry;
Stage #2: 3-chloroprop-1-ene In water under 760.051 Torr; for 6h; Concentration; Time; Temperature; Reflux; Green chemistry;
91.7%
allyl bromide
106-95-6

allyl bromide

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;91%
Stage #1: benzene-1,2-dicarboxylic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: allyl bromide With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;
91%
With potassium hydroxide; Aliquat 336 1.) 60 deg C, 0.1 Torr, 6 h, 2.) 60 deg C, 16 h; Yield given. Multistep reaction;
phthalic anhydride
85-44-9

phthalic anhydride

allyl bromide
106-95-6

allyl bromide

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
With potassium carbonate; Katamin AB at 55 - 60℃; for 3h; Product distribution; or DMF, KOH powder; other catalysts;58.4%
With potassium carbonate; Katamin AB at 55 - 60℃; for 3h;58.4%
allyl chloride vapour

allyl chloride vapour

sodium-salt of phthalic acid monoallyl ester

sodium-salt of phthalic acid monoallyl ester

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
With netting agent; water at 100℃;
Allyl acetate
591-87-7

Allyl acetate

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
tin(IV) chloride
C11H10O4*C9H16N2
63770-79-6

C11H10O4*C9H16N2

allyl bromide
106-95-6

allyl bromide

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; chemoselective reaction;
phthalic anhydride
85-44-9

phthalic anhydride

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.17 h / 20 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
View Scheme
sodium 1,2-benzenedicarboxylate
827-27-0, 10197-71-4, 15968-01-1

sodium 1,2-benzenedicarboxylate

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

diallyl phthalate
131-17-9

diallyl phthalate

Conditions
ConditionsYield
at 40 - 60℃;
at 65℃; for 3h;
diallyl phthalate
131-17-9

diallyl phthalate

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

C18H26O6S2

C18H26O6S2

Conditions
ConditionsYield
With phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide at 20℃; Reagent/catalyst; Temperature; UV-irradiation;99%
diallyl phthalate
131-17-9

diallyl phthalate

C12H10O4
406911-89-5

C12H10O4

Conditions
ConditionsYield
With C46H54Cl2FeN2O3Ru In dichloromethane at 35℃; for 8h;97%
With C34H50B10Cl2N2O2Ru In dichloromethane at 40℃; for 8h; Reagent/catalyst; Time; Inert atmosphere;96%
With C96H111Cl6N9O3Ru3 In dichloromethane at 35℃; for 12h; Schlenk technique; Inert atmosphere;96%
diallyl phthalate
131-17-9

diallyl phthalate

(Z)-7,10-Dihydro-6,11-dioxa-benzocyclodecene-5,12-dione

(Z)-7,10-Dihydro-6,11-dioxa-benzocyclodecene-5,12-dione

Conditions
ConditionsYield
[2-((2,6-iPr2-Ph-imino)methyl)phenol][p-cymene][=CHPh]Ru2Cl3 In various solvent(s) at 70℃; for 4h; Product distribution; Further Variations:; Catalysts; Temperatures;96%
With diazomethyl-trimethyl-silane; ruthenium Schiff-base In toluene at 85℃; for 17h; ring-closing metathesis;94%
With diazomethyl-trimethyl-silane; ruthenium In toluene at 85℃; for 17h; Product distribution; Further Variations:; Catalysts;94%
hybrid N,O-bidentate Schiff base ruthenium complex In toluene at 85℃; for 17h;94%
Schiff base substituted ruthenium benzylidene; 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene In benzene-d6 at 55℃; for 4h; ring-closing metathesis;87 % Spectr.
(triethylsilyl)cobalt tetracarbonyl

(triethylsilyl)cobalt tetracarbonyl

diallyl phthalate
131-17-9

diallyl phthalate

(η-allyl)tricarbonylcobalt

(η-allyl)tricarbonylcobalt

Conditions
ConditionsYield
at -25 - 7℃; for 4.16h;94%
diallyl phthalate
131-17-9

diallyl phthalate

C26H24O8
1608129-88-9

C26H24O8

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV)isopropoxide In toluene at 80℃; for 0.75h; Inert atmosphere;91%
Triethoxysilane
998-30-1

Triethoxysilane

diallyl phthalate
131-17-9

diallyl phthalate

bis(3-(triethoxysilyl)propyl)phthalate

bis(3-(triethoxysilyl)propyl)phthalate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In dichloromethane at 20℃; Glovebox;80%
diallyl phthalate
131-17-9

diallyl phthalate

diethylamino magnesium bromide

diethylamino magnesium bromide

N,N-diethylallylamine
5666-17-1

N,N-diethylallylamine

Conditions
ConditionsYield
With palladium(II) acetylacetonate; triphenylphosphine In tetrahydrofuran at 50℃; for 5h;59%
diallyl phthalate
131-17-9

diallyl phthalate

benzyl bromide
100-39-0

benzyl bromide

4-Phenyl-1-butene
768-56-9

4-Phenyl-1-butene

Conditions
ConditionsYield
With palladium(II) acetylacetonate; triphenylphosphine; zinc In tetrahydrofuran at 60℃; for 5h;54%
diallyl phthalate
131-17-9

diallyl phthalate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

allyl [(2-thiocyanato-3-phenyl)propyl]phthalate

allyl [(2-thiocyanato-3-phenyl)propyl]phthalate

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone at -15 - -10℃; for 2.5h;48%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;48%
diallyl phthalate
131-17-9

diallyl phthalate

4-methoxybenzenediazonium tetrafluoroborate
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

phthalic acid 1-allyl ester 2-[3-(4-methoxy-phenyl)-2-thiocyanato-propyl] ester

phthalic acid 1-allyl ester 2-[3-(4-methoxy-phenyl)-2-thiocyanato-propyl] ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone44%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;44%
diallyl malonate
1797-75-7

diallyl malonate

diallyl phthalate
131-17-9

diallyl phthalate

A

C14H16O8

C14H16O8

B

C24H20O8

C24H20O8

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate In toluene at 80℃; Inert atmosphere;A 42%
B 38%
diallyl phthalate
131-17-9

diallyl phthalate

2-methylphenyl diazonium tetrafluoroborate
2093-46-1

2-methylphenyl diazonium tetrafluoroborate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-o-tolyl-propyl) ester

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-o-tolyl-propyl) ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone41%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;41%
diallyl phthalate
131-17-9

diallyl phthalate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-p-tolyl-propyl) ester

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-p-tolyl-propyl) ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone40%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;40%
diallyl phthalate
131-17-9

diallyl phthalate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

3-methylbenzenediazonium tetrafluoroborate
1422-76-0

3-methylbenzenediazonium tetrafluoroborate

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-m-tolyl-propyl) ester

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-m-tolyl-propyl) ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone38%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;38%
diallyl phthalate
131-17-9

diallyl phthalate

N-cyclohexylidenemethylamine
6407-35-8

N-cyclohexylidenemethylamine

A

2-allylcyclohexan-1-one
94-66-6

2-allylcyclohexan-1-one

B

(Z)-2,6-diallyl-1-cyclohexanone
115782-91-7

(Z)-2,6-diallyl-1-cyclohexanone

(E)-2,6-diallyl-1-cyclohexanone
36040-02-5, 115782-91-7, 115782-92-8

(E)-2,6-diallyl-1-cyclohexanone

Conditions
ConditionsYield
With ethylmagnesium bromide; triphenylphosphine; palladium(II) acetylacetonate 1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;
diallyl phthalate
131-17-9

diallyl phthalate

N-isopropyliden-cyclohexyl amine
6407-36-9

N-isopropyliden-cyclohexyl amine

A

1-hexen-5-one
109-49-9

1-hexen-5-one

B

nona-1,8-dien-5-one
74912-33-7

nona-1,8-dien-5-one

Conditions
ConditionsYield
With ethylmagnesium bromide Multistep reaction;
diallyl phthalate
131-17-9

diallyl phthalate

3,4,5,6-tetrahydrobenzo[c][1,6]dioxecine-1,8-dione
29246-20-6

3,4,5,6-tetrahydrobenzo[c][1,6]dioxecine-1,8-dione

Conditions
ConditionsYield
Grubbs catalyst first generation In 1,2-dichloro-ethane at 150℃; for 0.5h; MW irradiation;79 % Chromat.
diallyl phthalate
131-17-9

diallyl phthalate

A

C12H10O4
406911-89-5

C12H10O4

B

ethene
74-85-1

ethene

Conditions
ConditionsYield
With Grubbs catalyst first generation In dichloromethane
diallyl phthalate
131-17-9

diallyl phthalate

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: diallyl phthalate With dimethylaluminum chloride In toluene at 110℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; toluene at 20℃;
Stage #1: diallyl phthalate With dimethylaluminum chloride In toluene at 110℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; toluene at 20℃;

131-17-9Related news

New Diallyl phthalate (cas 131-17-9) resins for low pressure molding encapsulation of electronic components09/30/2019

The allylic resins are well known among thermosets for their excellent electrical characteristics and in particular for their ability to retain these properties under adverse environmental conditions. Properties are little affected on prolonged exposure to high temperatures, moisture and aqueous...detailed

Preparation and properties of cured Diallyl phthalate (cas 131-17-9) resin modified with dimeric acid polyamide derivatives09/29/2019

The allyl ester of dimeric acid polyamide, a compound which has a flexible unit in the main chain and reacts with the diallyl phthalate (DAP) resin to have an allyl group, was synthesized by the reaction of dimeric acid polyamide with allyl glycidyl ether. The allyl ester of dimeric acid polyami...detailed

Properties of novel Diallyl phthalate (cas 131-17-9) resin modified with sulfur‐containing allyl ester compounds10/01/2019

Sulfur‐containing allyl ester, which reacts with diallyl phthalate (DAP) resin to have allyl groups, was synthesized by the reaction of allyl phthalic acid with bisphenol having sulfur atoms. The sulfur‐containing allyl ester compound was blended with DAP resin to improve the adhesive properti...detailed

131-17-9Relevant articles and documents

Synthesis of unsaturated esters via highly efficient esterification catalyzed by polymer grafted quarternary ammonium salts as triphase catalysts

Liang, Zheng Yong,Wang, Li Li,Liu, Hui,Huang, Jin Shuo

, p. 1558 - 1561 (2013)

A series of unsaturated esters were prepared via condensation of sodium carboxylates and alkenyl halide under the condition of macroporous polystyrene grafted quarternary ammonium salt as recyclable phase transfer catalyst, NaI as co-catalyst, Cu powder as inhibitor and H2O as solvent. Under optimal conditions, products yields are 78.2~ 96.0%. The catalyst can be convenient recycled and reutilized for about five times without losing its activity obviously.

Diacidic ionic liquid supported on magnetic-silica nanocomposite: a novel, stable, and reusable catalyst for selective diester production

Fareghi-Alamdari, Reza,Nadiri Niri, Mehri,Hazarkhani, Hassan,Zekri, Negar

, p. 2615 - 2629 (2018/09/13)

Abstract: Supported diacidic ionic liquid on magnetic silica nanoparticles (SDAIL@magnetic nanoSiO2) was successfully prepared through a multi-step approach. 2,2- bis ((3- methylimidazolidin-1-yl) methyl) propane- 1,3- diol bromide salt was immobilized onto the surface of magnetic silica nanoparticles via covalent bonding to prepare a novel powerful acidic catalyst. The synthesized catalyst was characterized by FT-IR, SEM, TGA, VSM, N2 adsorption–desorption measurements and acid-base titration. The catalytic activity of the prepared SDAIL@magnetic nanoSiO2 was investigated for the selective diesterification of alcohols by phthalic anhydride to afford corresponding dialkyl plasticizers under solvent-free conditions. The nature of two acidic counter anions as well as the presence of Lewis acidic species (Fe3O4) on the magnetic nanosilica and high surface area of the nanosilica influenced the behavior of the catalyst. Surperisingly, the high acidic character of the catalyst facilitates the reaction with a short reaction time. Furthermore, TG analysis strongly demonstrates that major content of IL is still stable on the support up to 290?°C, so catalyst has a good thermal stability. Under the optimized conditions, the conversion of phthalic anhydride was 100% and diester plasticizers were obtained with excellent yields (80–100%). The SDAIL@magnetic nanoSiO2 catalyst showed a good reusability and could be easily separated from the reaction mixture using an external magnet thanks to its superparamagnetic behavior and reused for several runs without significant activity loss. An important advantage of the SDAIL@magnetic nanoSiO2 was its high-hydrophilicity resulted in excellent selectivity towards the formation of only diesters which are commonly used plasticizers in different industries. Graphical abstract [Figure not available: see fulltext.].

O-benzenedicarboxylic acid diallyl ester production technology

-

Paragraph 0002, (2017/07/19)

The invention discloses an o-benzenedicarboxylic acid diallyl ester production technology. O-benzenedicarboxylic acid diallyl ester is an important chemical product. The production technology comprises the following processes: 1, sodium phthalic anhydride synthesis: stirring 99% phthalic anhydride and 99% flake NaOH solid to react to generate sodium phthalic anhydride, wherein a boiling point of the 99% phthalic anhydride is 295 DEG C, the phthallic anhydride and the NaOH are fed according to a proportion of 1mol to 3.5mol, reaction time is 2h, a reaction conversion rate is calculated as 57.3% according to NaOH, and a production period is about 2h; 2, o-benzenedicarboxylic acid diallyl ester synthesis: indirectly heating and warming reaction fluid in a reaction kettle in the last step through steam, adding a catalyst, indirectly heating and warming temperature to 40 to 60 DEG C by steam, keeping the temperature unchanged, dropwise adding a certain amount of 99% chloropropene and performing condensation polymerization for 4 to 5h in normal pressure, wherein a boiling point of the 99% chloropropene is 45 DEG C, and a production period is about 5h; 3, washing: pumping a material generated by reaction in the last step into a washing kettle, adding technological purified water into the washing kettle, washing off impurities in a crude product, and then pumping the washed material into a decompressing rectifying kettle; 4, decompressing rectification: indirectly heating through steam, keeping distillate temperature as 120 to 130 DEG C, controlling tower temperature as 68 to 80 DEG C and receiving a rectified component into a stainless steel finished product tank when the rectified component is the o-benzenedicarboxylic acid diallyl ester stably.

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