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Diallyl phthalate

CAS：131-17-9
MW:246.25900
MF：C14H14O4

Clear pale-yellow liquid. Odorless.

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Diallyl phthalate

1.2 Synonyms: 1,2-Benzenedicarboxylic acid, di-2-propen-1-yl ester; DAP(Diallyl Phthalate); di-2-propenyl1,2-benzenedicarboxylate; Diallyl ester of phthalic acid; Diallyl ester o-phthalic acid; DIALLYL PHTHALATE OEKANAL, 250 MG; Diallylester kyseliny ftalove; Diallylester phthalic acid; diallylesterkyselinyftalove; diprop-2-en-1-yl benzene-1,2-dicarboxylate; EINECS 205-016-3; MFCD00008646; Phthalic Acid Diallyl Ester; Phthalic acid, diallyl ester (8CI);

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1.3 CAS No.: 131-17-9

1.4 CID: 8560

1.5 EINECS: 205-016-3

1.6 Molecular Formula: C14H14O4

1.7 Inchi: InChI=1S/C14H14O4/c1-3-9-17-13(15)11-7-5-6-8-12(11)14(16)18-10-4-2/h3-8H,1-2,9-10H2

1.8 InChkey: QUDWYFHPNIMBFC-UHFFFAOYSA-N

1.9 Canonical Smiles: C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C

1.10 Isomers Smiles: C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C

2. Properties

2.1 Vapour pressure: 8.3 (vs air)

2.2 Solubility: 0.18g/l

2.3 Viscosity: Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.

2.4 VaporDensity: 8.3 (vs air)

2.5 Appearance: Clear pale-yellow liquid. Odorless.

2.6 AutoIgnition: 385°C

2.7 Storage: Ambient temperatures.

2.8 Carcinogenicity: In the 103-week study referredto previously, a slight increase in MNCL was seen infemale rats treated with 50 or 100 mg/kg/day of DAP. MNCLoccurs in F344 control rats at a high incidence; however, theincidence of 51% in female rats at the high dose level wasabove historical control data for the laboratory (29%). Nosignificant increases in tumor incidences were seen in malerats. Based on this study, DAP was considered to havedemonstrated equivocal evidence for carcinogenicity infemale F344 rats according to the NTP.In male and female B6C3F1 mice receiving 300 mg/kg ofDAP by gavage for 103 weeks (5 days/week), the incidenceof forestomach papillomas was significantly greater than thatof controls. Because of the rarity of forestomachpapillomas in control B6C3F1 mice and the concomitantobservation of dose-related forestomach hyperplasia, thedevelopment of these tumors was considered to be testsubstance related. Compared to controls, a slight increasein the incidence of lymphomas was observed in malesreceiving 300 mg/kg/day of DAP. Because the increasewas not statistically significant compared to historical controldata, this effect was not considered to be test substancerelated. Diallyl phthalate Preparation Products And Raw materials Raw materials

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2.9 Chemical Properties: clear colourless to light yellow liquid

2.10 Color/Form: Nearly colorless, oily liquid

2.11 Decomposition: When heated to decomp it emits acrid smoke and irritating fumes.

2.12 Odor: mild lachrymatory

2.13 Physical: PHYSICAL DESCRIPTION: Clear pale-yellow liquid. Odorless. (NTP, 1992)

2.14 Water Solubility: 6 g/L (20 oC)

2.15 Spectral Properties: IR: 15173 (Sadtler Research Laboratories IR grating collection)
UV: 363 (American Petroleum Institute Collection)
Raman: 109 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 6707 (Sadtler Research Laboratories Spectral Collection)
MASS: 27836 (NIST/EPA/MSDC Mass Spectral database, 1990 version); 4647 (National Bureau of Standards)

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2.16 Stability: Stable under normal temperatures and pressures.

2.17 StorageTemp: Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 Description: Diallyl phthalate (CAS 131-17-9) is a colorless to pale yellow liquid with a strong odor. Its basic structure consists of two allyl groups attached to a phthalate ester. This chemical is sparingly soluble in water, but it is soluble in organic solvents such as ethanol and acetone. Diallyl phthalate has a boiling point of 324-325°C and a melting point of -35°C.

Applicable fields
Diallyl phthalate is commonly used in the following fields:

Plastics Industry: In the plastics industry, diallyl phthalate is used as a crosslinking agent and a plasticizer. It helps improve the flexibility, durability, and heat resistance of various plastic products. The mechanism of action involves forming covalent bonds with polymer chains, enhancing their crosslinking and overall performance.

Adhesive Industry: In the adhesive industry, this chemical is utilized as a reactive diluent. It helps reduce the viscosity of adhesives and improves their flow properties. Diallyl phthalate also enhances the adhesion and bonding strength of adhesives. The mechanism involves polymerization and crosslinking with other reactive components in the adhesive formulation.

Electronics Industry: Diallyl phthalate is used in the electronics industry as an encapsulant and a molding compound. It provides excellent electrical insulation properties and protects electronic components from moisture, dust, and mechanical stress. The mechanism of action involves polymerization and the formation of a protective barrier around the electronic devices.

Storage Conditions
Store in a cool, dry place.

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3.2 General Description: Clear pale-yellow liquid. Odorless.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]
H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes
P264, P270, P273, P301+P312, P330, P391, and P501

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3.4 Methods of Manufacturing: A general method for the preparation of allyl esters is the reaction of allyl alcohol; with the free acids, acid anhydrides, or acid chlorides. Catalysts frequently used are aromatic sulfonic acids (p-toluenesulfonic acid; and naphthalene-2-sulfonic acid;). Strong mineral acids are of less value because they can decompose the allyl alcohol;. Polymerizable acids are esterified in the presence of phenolic inhibitors. The following allyl esters are prepared by this method: diallyl phthalate;, diallyl isophthalate;, diallyl maleate;, diallyl fumarate;, triallyl cyanurate; (from cyanuric chloride; and allyl alcohol;), and diethylene glycol bis(allyl carbonate);. ...

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

4. Safety and Handling

4.1 Exposure Standards and Regulations: Diallyl phthalate is an indirect food additive for use only as a component of adhesives.

4.2 Octanol/Water Partition Coefficient: log Kow = 3.23

4.3 Fire Hazard: Diallyl phthalate is combustible.

4.4 Other Preventative Measures: Avoid contact with skin and eyes.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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4.5 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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4.6 Fire Fighting Procedures: Water or foam may cause frothing.

4.7 FirePotential: Limiting oxygen index (LOI): 26-36 /for diallyl phthalate/. This is a measure of the minimum concentration of oxygen in an oxygen-nitrogen atmosphere that is necessary to support a flame for at least 3 minutes under specified test conditions.

4.8 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.

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4.9 Reactivities and Incompatibilities: ...Can react with oxidizing materials.

4.10 Report: NTP Carcinogenesis Studies (gavage); Equivocal Evidence: rat NTPTR* ?? National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-284 ,1985. . Reported in EPA TSCA Inventory.

4.11 Safety

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 oxidizing materials. To fight fire, use CO₂ or dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety Information of Diallyl phthalate(131-17-9)
Hazard Codes:?? Harmful Xn, Dangerous N
Risk Statements: 22-50/53?
R22:Harmful if swallowed.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 24/25-60-61?
S24/25:Avoid contact with skin and eyes.?
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3082 9/PG 3
WGK Germany: 2
RTECS: CZ4200000
F: 19
HazardClass: 9
PackingGroup: III

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4.12 Specification: ? Diallyl phthalate (CAS NO.131-17-9), its Synonyms are 1,2-Benzenedicarboxylic acid, di-2-propenyl ester ; Allyl phthalate ; Dapon 35 ; Dapon R ; Di-2-propenyl 1,2-benzenedicarboxylate ; Diallylester kyseliny ftalove ; Phthalic acid, diallyl ester ; o-Phthalic acid, diallyl ester ; 1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester . It is clear colourless to light yellow liquid.

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4.13 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	oral	800mg/kg (800mg/kg)	?	National Technical Information Service. Vol. OTS0521092,
mouse	LDLo	oral	681mg/kg (681mg/kg)	?	National Toxicology Program Technical Report Series. Vol. NTP-TR-242, Pg. 1983,
rabbit	LD50	oral	1700mg/kg (1700mg/kg)	?	"Industrial Hygiene and Toxicology," 2nd ed., Patty, F.A., ed., New York, John Wiley & Sons, Inc., 1958-63Vol. 2, Pg. 1904, 1963.
rabbit	LD50	skin	3300mg/kg (3300mg/kg)	?	National Technical Information Service. Vol. OTS0521092,
rabbit	LDLo	subcutaneous	1gm/kg (1000mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 5, Pg. 191, 1946.
rat	LC50	inhalation	5200mg/m3/1H (5200mg/m3)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	National Technical Information Service. Vol. OTS0521092,
rat	LD50	oral	656mg/kg (656mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	National Toxicology Program Technical Report Series. Vol. NTP-TR-284, Pg. 1985,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 90 MHz in CDCl3

gas

IR : CCl4 solution

IR : liquid film

Raman : 4880 A,200 M,liquid

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

131-17-9Total: 8 Synthesis Route

85-44-9 310 Suppliers

131-17-9 192 Suppliers

182342-88-7

131-17-9 192 Suppliers

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8. Precursor and Product

precursor:

107-05-1

88-99-3

106-95-6

63770-79-6

182342-88-7

591-87-7

85-44-9

product:

768-56-9

115782-91-7

36040-02-5

94-66-6

74912-33-7

109-49-9

9. Computed Properties

Molecular Weight：246.25900g/mol
Molecular Formula：C₁₄H₁₄O₄
Compound Is Canonicalized：True
XLogP3-AA：246.08920892
Monoisotopic Mass：246.08920892
Complexity：290
Rotatable Bond Count：8
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：4
Topological Polar Surface Area：52.6
Heavy Atom Count：：18
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAAAAAADACgmAIwCIAABACIAiDSCAACAAAkAAAIiAEACMgIJjKANRiCMQAkwAEIqYfLyKCOgAAAAAAQAAAAAAAAACAAAAAAAAAAAA==

10.Other Information

BRN: 1880877

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.

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.

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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.

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11. Toltal 173 Suppliers View more

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12. Related Questions

: How to Prepare Diallyl Phthalate (DAP) and Its Application in LDPE/PET BlendsBackground and Overview[2] Diallyl phthalate (DAP) monomer is a new variety developed with the advancement of the petrochemical industry. It possesses many excellent properties, especially its heat re..

13. Realated Product Infomation