Bis(2-ethylhexyl) phthalate

Base Information

• Chemical Name: Bis(2-ethylhexyl) phthalate
• CAS No.: 117-81-7
• Deprecated CAS: 126639-29-0,137718-37-7,205180-59-2,40120-69-2,50885-87-5,8033-53-2,275818-89-8,109630-52-6,607374-50-5,109630-52-6,137718-37-7,205180-59-2,275818-89-8,40120-69-2,607374-50-5,8033-53-2
• Molecular Formula: C24H38O4
• Molecular Weight: 390.563
• Hs Code.: 2917.34
• European Community (EC) Number: 204-211-0,617-060-4
• ICSC Number: 0271
• NSC Number: 17069
• UNII: C42K0PH13C
• DSSTox Substance ID: DTXSID5020607
• Nikkaji Number: J2.909B
• Wikipedia: Bis(2-ethylhexyl)_phthalate
• Wikidata: Q418492
• NCI Thesaurus Code: C44341
• Metabolomics Workbench ID: 49840
• ChEMBL ID: CHEMBL1242017
• Mol file: 117-81-7.mol

Synonyms:Bis(2-ethylhexyl)phthalate;DEHP;Di 2 Ethylhexylphthalate;Di(2-ethylhexyl)phthalate;Di-2-Ethylhexylphthalate;Diethylhexyl Phthalate;Dioctyl Phthalate;Phthalate, Diethylhexyl;Phthalate, Dioctyl

Chemical Property of Bis(2-ethylhexyl) phthalate

Chemical Property:

• Appearance/Colour: colorless to pale yellow oily liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: -50 °C
• Refractive Index: n20/D 1.488
• Boiling Point: 384.9 °C at 760 mmHg
• Flash Point: 204.5 °C
• PSA: 52.60000
• Density: 0.983 g/cm³
• LogP: 6.43300
• Water Solubility.: 0.27 mg/L at 25 ℃
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 16
• Exact Mass: 390.27700969
• Heavy Atom Count: 28
• Complexity: 394

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): T,F
• Hazard Codes: T:Toxic
• Statements: R60:; R61:
• Safety Statements: S45:; S53:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Phthalate Esters
• Canonical SMILES: CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract.
• Effects of Long Term Exposure: The substance may have effects on the testes. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Chemical Composition and Structure: Bis(2-ethylhexyl) phthalate (DEHP) is an ester of phthalic acid and 2-ethylhexanol. Its chemical structure consists of two ethylhexyl groups attached to the phthalate backbone.^[1]
• Uses: Bis(2-ethylhexyl) phthalate (DEHP) is widely used as a plasticizer in many plastics, such as polyvinyl chloride (PVC), and is commonly found in numerous consumer products such as vinyl flooring, wallpaper, vehicle interiors, and toys.^[3]
• Medical Uses: DEHP is used in medical devices, particularly in respiratory assistance devices.^[2]
• Health Risks: DEHP has been widely used as a plasticizer in various consumer products since the mid-20th century. It's potential health risks have led to regulatory scrutiny and risk assessments by organizations such as the European Food Safety Authority (EFSA). DEHP exposure can occur through various routes, including dietary intake, inhalation of contaminated air, and dermal contact with consumer products. DEHP contamination in aquatic environments can affect aquatic organisms, leading to potential ecological consequences.^[4]
• References: [1] Thyroid hormone disruption by bis-(2-ethylhexyl) phthalate (DEHP) and bis-(2-ethylhexyl) adipate (DEHA) in Japanese medaka Oryzias latipes; DOI 10.1016/j.aquatox.2022.106312; [2] Update of the risk assessment of di-butylphthalate (DBP), butyl-benzyl-phthalate (BBP), bis(2-ethylhexyl)phthalate (DEHP), di-isononylphthalate (DINP) and di-isodecylphthalate (DIDP) for use in food contact materials; DOI 10.2903/j.efsa.2019.5838; [3] Bis(2-ethylhexyl) phthalate transfer from polyvinyl chloride sheet to several kinds of particles; DOI 10.1016/j.chemosphere.2023.139438; [4] Estimation of dietary intake of bis(2-ethylhexyl)phthalate (DEHP) by consumption of food in the German population; DOI 10.1016/j.ijheh.2013.01.001

Technology Process of Bis(2-ethylhexyl) phthalate

There total 14 articles about Bis(2-ethylhexyl) phthalate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

phthalic anhydride (85-44-9) + 2-Ethylhexyl alcohol (104-76-7) → Di(2-ethylhexyl)phthalate (117-81-7,275818-89-8,50885-87-5,82208-43-3,607374-50-5,8033-53-2)

Guidance literature:

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;

DOI:10.1016/j.molliq.2016.11.121

Reference yield: 90.0%

2-Ethylhexyl alcohol (104-76-7) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) → Di(2-ethylhexyl)phthalate (117-81-7,275818-89-8,50885-87-5,82208-43-3,607374-50-5,8033-53-2)

Guidance literature:

With triflic acid on silica-encapsulated superparamagnetic iron oxide nanoparticles; In neat (no solvent); at 90 ℃; for 1h; Time; Reagent/catalyst; Catalytic behavior; Flow reactor; Green chemistry;

DOI:10.1039/C8RA07838F

Reference yield: 43.0%

phthalic anhydride (85-44-9) + 2-Ethylhexyl alcohol (104-76-7) + butan-1-ol (71-36-3) → Di(2-ethylhexyl)phthalate (117-81-7,275818-89-8,50885-87-5,82208-43-3,607374-50-5,8033-53-2) + Phthalic acid dibutyl ester (84-74-2) + 1,2-benzenedicarboxylic acid 1-butyl 2-ethylhexyl ester (85-69-8)

Guidance literature:

sulfuric acid; Title compound not separated from byproducts; Heating;

upstream raw materials:

phthalic anhydride

2-Ethylhexyl alcohol

benzene-1,2-dicarboxylic acid

butan-1-ol

Downstream raw materials:

(2-ethylhexyl) hydrogen phthalate

Bis(2-ethylhexyl) cyclohexane-1,2-dicarboxylate

Refernces

• 1、 Van Vugt-Lussenburg, Barbara M. A.,Van Es, Daan S.,Naderman, Matthijs,Le Notre, Jerome,Klis, Frits Van Der,Brouwer, Abraham,Van Der Burg, Bart. "Endocrine activities of phthalate alternatives; Assessing the safety profile of furan dicarboxylic acid esters using a panel of human cell based reporter gene assays". . p. 1873 - 1883. Retrieved 2020.
• 2、 Fareghi-Alamdari, Reza,Niri, Mehri Nadiri,Hazarkhani, Hassan. "A novel hydrogen-bonded silica-supported acidic ionic liquid: An efficient, recyclable and selective heterogeneous catalyst for the synthesis of diesters". . . Retrieved 2018.
• 3、 Fareghi-Alamdari, Reza,Nadiri Niri, Mehri,Hazarkhani, Hassan,Zekri, Negar. "Diacidic ionic liquid supported on magnetic-silica nanocomposite: a novel, stable, and reusable catalyst for selective diester production". . p. 2615 - 2629. Retrieved 2018/09/13.