Draft:Diallyl phthalate
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==Applications====Applications==
[[File:Laying sewer hi res (2).jpg|thumb|upright|left|Phthalate plasticizers are essential for the utility of PVC, which is too brittle otherwise.{{cite book |last1=Lorz |first1=Peter M. |last2=Towae |first2=Friedrich K. |last3=Enke |first3=Walter |last4=Jäckh |first4=Rudolf |last5=Bhargava |first5=Naresh |last6=Hillesheim |first6=Wolfgang |display-authors=3|title=Ullmann's Encyclopedia of Industrial Chemistry |chapter=Phthalic Acid and Derivatives |year=2007 |doi=10.1002/14356007.a20_181.pub2 |isbn=978-3-527-30673-2 }}]][[File:Laying sewer hi res (2).jpg|thumb|upright|left|Phthalate plasticizers are essential for the utility of PVC, which is too brittle otherwise.{{cite book |last1=Lorz |first1=Peter M. |last2=Towae |first2=Friedrich K. |last3=Enke |first3=Walter |last4=Jäckh |first4=Rudolf |last5=Bhargava |first5=Naresh |last6=Hillesheim |first6=Wolfgang |display-authors=3|title=Ullmann's Encyclopedia of Industrial Chemistry |chapter=Phthalic Acid and Derivatives |year=2007 |doi=10.1002/14356007.a20_181.pub2 |isbn=978-3-527-30673-2 }}]]
Diallyl phthalate is a widely used for the production of [[polyvinyl chloride]] (PVC) plastic containers, medical devices, and packaging. It enhances [[tensile strength]] and elongation at break (the ratio of the final and initial lengths of material before breaking), and also acts as a chain extender due to the allyl groups that can form [[Cross-link|cross-links]] between PVC chains.{{cite web |title=Diallyl phthalate: a widely-used plasticizer |url=https://www.chemicalbook.com/article/diallyl-phthalate-a-widely-used-plasticizer.htm |website=chemicalbook.com |access-date=20 June 2026}}Diallyl phthalate is a widely used for the production of [[polyvinyl chloride]] (PVC) plastic containers, medical devices, and packaging. It enhances [[tensile strength]] and elongation at break (the ratio of the final and initial lengths of material before breaking), and also acts as a chain extender due to the allyl groups that can form [[Cross-link|cross-links]] between PVC chains.{{cite web |title=Diallyl phthalate: a widely-used plasticizer |url=https://www.chemicalbook.com/article/diallyl-phthalate-a-widely-used-plasticizer.htm |website=chemicalbook.com |access-date=20 June 2026}}
A plasticizer is an additive to polymers to make them more flexible, durable, and processable.{{cite web |title=PLASTICIZERS |url=http://kinampark.com/PL/files/Plasticizers.pdf |access-date=21 June 2026}}
⚫ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#movedpara_5_1_rhs)https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059DAP is a [[plasticizer]] used to produce [[thermosetting]] [[resins]], [[laminates]], and varnishes as well as impregnation of [[metal casting|metal castings]] in [[aerospace]] and military electrical components. This is due to its reliability in extreme conditions, with properties such as [[electrical insulation|electrical]] and [[thermal insulation]], water resistance, chemical resistance, and molding. It holds its shape in high-heat environments, such as [[soldering]].{{cite web |title=Diallyl Phthalate |url=https://www.univarsolutions.com/diallyl-phthalate-3398400 |website=univarsolutions.com |access-date=21 June 2026}}{{cite web |title=Material Options: DIALLYL PHTHALATE (DAP) |url=https://daviesmolding.com/resources/engineering-specifications/plastic-materials/diallyl-phthalate/ |website=daviesmolding.com |access-date=20 June 2026}} It is used in organic solvent-free [[UV curing|UV printing inks]] due to its quick-drying ability, as well as construction materials.{{cite web |title=Diallyl Phthalate Resin |url=https://www.osaka-soda.co.jp/en/prd/department/specialties/dially_phthalate-01.html |website=osaka-soda.co.jp |access-date=20 June 2026}}
⚫ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#movedpara_4_0_lhs)https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059DAP is a plasticizer used to produce [[thermosetting]] [[resins]], [[laminates]], and varnishes as well as impregnation of [[metal casting|metal castings]] in [[aerospace]] and military electrical components. This is due to its reliability in extreme conditions, with properties such as [[electrical insulation|electrical]] and [[thermal insulation]], water resistance, chemical resistance, and molding. It holds its shape in high-heat environments, such as [[soldering]].{{cite web |title=Diallyl Phthalate |url=https://www.univarsolutions.com/diallyl-phthalate-3398400 |website=univarsolutions.com |access-date=21 June 2026}}{{cite web |title=Material Options: DIALLYL PHTHALATE (DAP) |url=https://daviesmolding.com/resources/engineering-specifications/plastic-materials/diallyl-phthalate/ |website=daviesmolding.com |access-date=20 June 2026}} It is used in organic solvent-free [[UV curing|UV printing inks]] due to its quick-drying ability, as well as construction materials.{{cite web |title=Diallyl Phthalate Resin |url=https://www.osaka-soda.co.jp/en/prd/department/specialties/dially_phthalate-01.html |website=osaka-soda.co.jp |access-date=20 June 2026}}
==Toxicity====Toxicity==
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Diallyl phthalate[[1]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-pubchem-1)https://en.wikipedia.org/wiki/File:Diallylphthalate_Structural_Formula_V1.svg
Names
IUPAC name (https://en.wikipedia.org/wiki/Chemical_nomenclature)
bis(prop-2-enyl) benzene-1,2-dicarboxylate
Identifiers
CAS Number (https://en.wikipedia.org/wiki/CAS_Registry_Number)* 131-17-9 (https://commonchemistry.cas.org/detail?cas_rn=131-17-9)
3D model (JSmol (https://en.wikipedia.org/wiki/JSmol))* Interactive image (https://chemapps.stolaf.edu/jmol/jmol.php?model=C%3DCCOC%28%3DO%29C1%3DCC%3DCC%3DC1C%28%3DO%29OCC%3DC)
Abbreviations DAP
EC Number (https://en.wikipedia.org/wiki/European_Community_number)* 205-016-3
PubChem (https://en.wikipedia.org/wiki/PubChem)CID* 8560 (https://pubchem.ncbi.nlm.nih.gov/compound/8560)
InChI (https://en.wikipedia.org/wiki/International_Chemical_Identifier)
SMILES (https://en.wikipedia.org/wiki/Simplified_molecular-input_line-entry_system)
Properties
Chemical formula (https://en.wikipedia.org/wiki/Chemical_formula)C 6 H 4(CO 2 CH 2 CHCH 2)2
Molar mass (https://en.wikipedia.org/wiki/Molar_mass)246.26 g/mol
Appearance nearly colorless, pale-yellow, oily liquid
Odor (https://en.wikipedia.org/wiki/Odor)odorless
Density (https://en.wikipedia.org/wiki/Density)1.121 g/mL
Melting point (https://en.wikipedia.org/wiki/Melting_point)−70°C (−94°F; 203 K)
Boiling point (https://en.wikipedia.org/wiki/Boiling_point)157°C (315°F; 430 K)
Solubility in water (https://en.wikipedia.org/wiki/Aqueous_solution)0.015 g/100mL
log P (https://en.wikipedia.org/wiki/Partition_coefficient)3.23
Vapor pressure (https://en.wikipedia.org/wiki/Vapor_pressure)* 2.4 millimetres of mercury (320 Pa) (150°C (302°F; 423 K)
• 0.02 pascals (0.00015 mmHg) (25°C (77°F; 298 K))
Hazards
NFPA 704 (https://en.wikipedia.org/wiki/NFPA_704) (fire diamond)1 (https://en.wikipedia.org/wiki/NFPA_704#Blue)
1 (https://en.wikipedia.org/wiki/NFPA_704#Red)
1 (https://en.wikipedia.org/wiki/NFPA_704#Yellow)
Autoignition temperature (https://en.wikipedia.org/wiki/Autoignition_temperature)385°C (725°F; 658 K)
Related compounds
Related compounds* diethyl phthalate (https://en.wikipedia.org/wiki/Diethyl_phthalate)
• dimethyl phthalate (https://en.wikipedia.org/wiki/Dimethyl_phthalate)
• diethylhexyl phthalate (https://en.wikipedia.org/wiki/Diethylhexyl_phthalate)
• dibutyl phthalate (https://en.wikipedia.org/wiki/Dibutyl_phthalate)
• dioctyl phthalate (https://en.wikipedia.org/wiki/Dioctyl_phthalate)
Except where otherwise noted, data are given for materials in their standard state (https://en.wikipedia.org/wiki/Standard_state) (at 25°C [77°F], 100 kPa).
Infobox references (https://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox#References)
• *Diallyl phthalate (DAP**) is a phthalate (https://en.wikipedia.org/wiki/Phthalate)ester (https://en.wikipedia.org/wiki/Ester) with the formula C 6 H 4(CO 2 CH 2 CHCH 2)2 or C 14 H 14 O 4. It is a nearly-colorless pale-yellow oily liquid that is odorless.[[1]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-pubchem-1)
Diallyl phthalate is synthesized by reacting phthalic anhydride (https://en.wikipedia.org/wiki/Phthalic_anhydride) with allyl alcohol (https://en.wikipedia.org/wiki/Allyl_alcohol).[[2]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-2)
https://en.wikipedia.org/wiki/File:Laying_sewer_hi_res_(2).jpg
Phthalate plasticizers are essential for the utility of PVC, which is too brittle otherwise.[[3]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-3)
Diallyl phthalate is a widely used for the production of polyvinyl chloride (https://en.wikipedia.org/wiki/Polyvinyl_chloride) (PVC) plastic containers, medical devices, and packaging. It enhances tensile strength (https://en.wikipedia.org/wiki/Tensile_strength) and elongation at break (the ratio of the final and initial lengths of material before breaking), and also acts as a chain extender due to the allyl groups that can form cross-links (https://en.wikipedia.org/wiki/Cross-link) between PVC chains.[[4]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-chemicalbook-4)
A plasticizer is an additive to polymers to make them more flexible, durable, and processable.[[5]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-5)
DAP is a plasticizer used to produce thermosetting (https://en.wikipedia.org/wiki/Thermosetting)resins (https://en.wikipedia.org/wiki/Resins), laminates (https://en.wikipedia.org/wiki/Laminates), and varnishes as well as impregnation of metal castings (https://en.wikipedia.org/wiki/Metal_casting) in aerospace (https://en.wikipedia.org/wiki/Aerospace) and military electrical components. This is due to its reliability in extreme conditions, with properties such as electrical (https://en.wikipedia.org/wiki/Electrical_insulation) and thermal insulation (https://en.wikipedia.org/wiki/Thermal_insulation), water resistance, chemical resistance, and molding. It holds its shape in high-heat environments, such as soldering (https://en.wikipedia.org/wiki/Soldering).[[6]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-6)[[7]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-7) It is used in organic solvent-free UV printing inks (https://en.wikipedia.org/wiki/UV_curing) due to its quick-drying ability, as well as construction materials.[[8]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-8)
DAP has been detected in surface water at a concentration of 0.009 μg/L and in wastewater at 0.22 ± 0.31 μg/L.[[4]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-chemicalbook-4)
Diallyl phthalate is hazardous as it can act as an endocrine disruptor (https://en.wikipedia.org/wiki/Endocrine_disruptor). It can also cause developmental toxicity (https://en.wikipedia.org/wiki/Developmental_toxicity) and oxidative stress (https://en.wikipedia.org/wiki/Oxidative_stress).[[4]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-chemicalbook-4) Because of such hazards, phthalates such as DAP are being phased out in the United States (https://en.wikipedia.org/wiki/United_States) and Europe (https://en.wikipedia.org/wiki/Europe).[[1]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-pubchem-1)
DAP exposure in rats showed little effects, except for potentially relevant effects to the liver (https://en.wikipedia.org/wiki/Liver) and kidney (https://en.wikipedia.org/wiki/Kidney).[[9]](https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_note-9)
1. ^ Jump up to: a (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-pubchem_1-0)b (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-pubchem_1-1)c (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-pubchem_1-2)"Diallyl phthalate" (https://pubchem.ncbi.nlm.nih.gov/compound/8560). PubChem (https://en.wikipedia.org/wiki/PubChem). National Center for Biotechnology Information (https://en.wikipedia.org/wiki/National_Center_for_Biotechnology_Information). Retrieved 20 June 2026.
2. ^ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-2)"Diallyl phthalate synthesis" (https://www.chemicalbook.com/synthesis/diallyl-phthalate.htm). chemicalbook.com. Retrieved 20 June 2026.
3. ^ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-3)Lorz, Peter M.; Towae, Friedrich K.; Enke, Walter; et al. (2007). "Phthalic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi (https://en.wikipedia.org/wiki/Doi_(identifier)):10.1002/14356007.a20_181.pub2 (https://doi.org/10.1002%2F14356007.a20_181.pub2). ISBN (https://en.wikipedia.org/wiki/ISBN_(identifier))978-3-527-30673-2 (https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-30673-2).
4. ^ Jump up to: a (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-chemicalbook_4-0)b (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-chemicalbook_4-1)c (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-chemicalbook_4-2)"Diallyl phthalate: a widely-used plasticizer" (https://www.chemicalbook.com/article/diallyl-phthalate-a-widely-used-plasticizer.htm). chemicalbook.com. Retrieved 20 June 2026.
5. ^ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-5)"PLASTICIZERS" (http://kinampark.com/PL/files/Plasticizers.pdf)(PDF). Retrieved 21 June 2026.
6. ^ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-6)"Diallyl Phthalate" (https://www.univarsolutions.com/diallyl-phthalate-3398400). univarsolutions.com. Retrieved 21 June 2026.
7. ^ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-7)"Material Options: DIALLYL PHTHALATE (DAP)" (https://daviesmolding.com/resources/engineering-specifications/plastic-materials/diallyl-phthalate/). daviesmolding.com. Retrieved 20 June 2026.
8. ^ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-8)"Diallyl Phthalate Resin" (https://www.osaka-soda.co.jp/en/prd/department/specialties/dially_phthalate-01.html). osaka-soda.co.jp. Retrieved 20 June 2026.
9. ^ (https://en.wikipedia.org/w/index.php?title=Draft:Diallyl_phthalate&diff=1360474749&oldid=1360474059#cite_ref-9)"Human Health Hazard Assessment" (https://www.industrialchemicals.gov.au/sites/default/files/Diallyl%20phthalate%20DAP.pdf)(PDF). June 2008. Retrieved 20 June 2026.