Chemistry:Diallyl phthalate
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| Names | |
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| IUPAC name
bis(prop-2-enyl) benzene-1,2-dicarboxylate
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | DAP |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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PubChem CID
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| UNII | |
| UN number | 3082 |
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| Properties | |
| C6H4(CO2CH2CHCH2)2 | |
| Molar mass | 246.26 g/mol |
| Appearance | colorless oil |
| Odor | odorless |
| Density | 1.121 g/mL |
| Melting point | −70 °C (−94 °F; 203 K) |
| Boiling point | 157 °C (315 °F; 430 K) |
| 0.015 g/100mL | |
| log P | 3.23 |
| Vapor pressure |
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| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Warning |
| HH302Script error: No such module "Preview warning".Category:GHS errors, HH400Script error: No such module "Preview warning".Category:GHS errors, HH410Script error: No such module "Preview warning".Category:GHS errors | |
| NFPA 704 (fire diamond) | |
| 385 °C (725 °F; 658 K) | |
| Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Diallyl phthalate (DAP) is an organic compound with the formula C6H4(CO2CH2CHCH2)2. Like most other phthalate esters, it is a colorless oil although commercial samples can appear yellowish. It is synthesized by treating phthalic anhydride with allyl alcohol.[1]
Applications
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Diallyl phthalate is a widely used as a plasticizer in the production of polyvinyl chloride (PVC).[3] 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-links between PVC chains.[4]
DAP is a plasticizer used to produce thermosetting resins, laminates, and varnishes as well as impregnation of metal castings in aerospace and military electrical components. This is due to its reliability in extreme conditions, with properties such as electrical and thermal insulation, ability to withstand high humidity, water resistance, chemical resistance, and molding. It resists dimensional change in high-heat environments, such as soldering.[5][6] It is used in organic solvent-free UV printing inks due to its quick-drying ability, as well as construction materials.[7]
Environmental aspects
DAP has been widely studied, especially in as a potential endocrine disruptor.[8]
References
- ↑ "Diallyl phthalate synthesis". https://www.chemicalbook.com/synthesis/diallyl-phthalate.htm.
- ↑ Lorz, Peter M.; Towae, Friedrich K.; Enke, Walter et al. (2007). "Phthalic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a20_181.pub2. ISBN 978-3-527-30673-2.
- ↑ "PLASTICIZERS". http://kinampark.com/PL/files/Plasticizers.pdf.
- ↑ "Diallyl phthalate: a widely-used plasticizer". https://www.chemicalbook.com/article/diallyl-phthalate-a-widely-used-plasticizer.htm.
- ↑ "Diallyl Phthalate". https://www.univarsolutions.com/diallyl-phthalate-3398400.
- ↑ "Material Options: DIALLYL PHTHALATE (DAP)". https://daviesmolding.com/resources/engineering-specifications/plastic-materials/diallyl-phthalate/.
- ↑ "Diallyl Phthalate Resin". https://www.osaka-soda.co.jp/en/prd/department/specialties/dially_phthalate-01.html.
- ↑ Net, Sopheak; Sempéré, Richard; Delmont, Anne; Paluselli, Andrea; Ouddane, Baghdad (2015). "Occurrence, Fate, Behavior and Ecotoxicological State of Phthalates in Different Environmental Matrices". Environmental Science & Technology 49 (7): 4019–4035. doi:10.1021/es505233b. PMID 25730609. https://figshare.com/articles/journal_contribution/2179384.
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