16111-62-9

Basic information

• Product Name: Di-(2-ethylhexyl)peroxydicarbonate
• Synonyms: Di-(2-ethylhexyl)peroxydicarbonate;bis(2-ethylhexyl) peroxydicarbonate;2-Ethylhexyl percarbonate;Peroxydicarbonic acid, bis(2-ethylhexyl) ester;Di-(2-ethylhexyl)-peroxydicarbonat;bis(ethylhexyl) peroxydicarbonate;Initiating agent EHP;peroxydicarbonic acid, di(2-ethylhexyl) ester
• CAS NO: 16111-62-9
• Molecular Formula: C₁₈H₃₄O₆
• Molecular Weight: 346.45896
• EINECS: 240-282-4
• Mol File: 16111-62-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 401.18°C (rough estimate)
• Flash Point: 160.2 °C
• Appearance: Colorless liquid, unpleasant odor
• Density: 1.0722 (rough estimate)
• Vapor Pressure: 4.83E-06mmHg at 25°C
• Refractive Index: 1.4450 (estimate)
• Water Solubility: 880mg/L at 25℃
• Stability: Unstable if heated. Heating presents a potential risk of explosion. May be shock sensitive. Flammable. May react violently with
• CAS DataBase Reference: Di-(2-ethylhexyl)peroxydicarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: Di-(2-ethylhexyl)peroxydicarbonate(16111-62-9)
• EPA Substance Registry System: Di-(2-ethylhexyl)peroxydicarbonate(16111-62-9)

Safety Data

• RIDADR: 3117
• HazardClass: 5.2
• PackingGroup: II
• Hazardous Substances Data: 16111-62-9(Hazardous Substances Data)

Usage

Chemical Properties

It is colorless liquid with unpleasant odor. Thermally unstable with required continuous refrigeration below -10°C (-14°F). Refer to the Code for the Storage of Organic Peroxide Formulations. Storage incompatibility includes strong acids, oxidizing agents, alkaline materials, reducing agents, and amines. Also, it should be stored away from excessive heat, sources of ignition, and reactive materials (12b).

General Description

Di-(2-ethylhexyl)peroxydicarbonate is particularly sensitive to temperature rises. Above a given "Control Temperature" they decompose violently. They are generally stored or transported in a solvent slurry.

Reactivity Profile

DI-(2-ETHYLHEXYL) PEROXYDICARBONATE decomposes violently or explosively at temperatures 0-10° C. owing to self-accelerating exothermic decomposition; Several explosions were due to shock, heat or friction; amines and certain metals can cause accelerated decomposition [Bretherick, 1979 p. 156], Danger of explosion when dry

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes. See also PEROXIDES, ORGANIC

InChI:InChI=1/C18H34O6/c1-5-9-11-15(7-3)13-21-17(19)23-24-18(20)22-14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3

Synthetic route

2-Ethylhexyl chloroformate (24468-13-1) → di-(2-ethylhexyl)-peroxydicarbonate (16111-62-9)

Conditions	Yield
With dihydrogen peroxide In water at 30 - 35℃;	92%
With dihydrogen peroxide; sodium carbonate In water at 0 - 10℃; for 0.0618333h; Temperature; Reagent/catalyst; Flow reactor;	90.4%
With sodium hydroxide; water; dihydrogen peroxide

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) + 1,4-Divinylbenzene (105-06-6) + di-(2-ethylhexyl)-peroxydicarbonate (16111-62-9) → 2-(2-ethylhexyloxycarbonyloxy)-1-(2',2',6',6'-tetramethyl-1'-piperidinyloxy)-1-(4'-vinylphenyl)ethane

Conditions	Yield
at 0 - 55℃; for 5h;	69.6%

di-(2-ethylhexyl)-peroxydicarbonate (16111-62-9) → C9H17O3 (115827-75-3)

Conditions	Yield
at 20℃; Irradiation; laser flash photolysis (LFP);

5,5-Dimethyl-1-pyrroline N-oxide + di-(2-ethylhexyl)-peroxydicarbonate (16111-62-9) → C6H11NOCO3C8H17

Conditions	Yield
In benzene at 26.84 - 59.84℃; Product distribution; Decomposition; addition;

2,4,6-tri-tert-butyl-1-nitrosobenzene (24973-59-9) + di-(2-ethylhexyl)-peroxydicarbonate (16111-62-9) → C6H5NO(C4H8)3C8H17CO3

Conditions	Yield
In benzene at 79.84℃; Product distribution; Decomposition; addition;	51 % Spectr.

N-[2H5]benzylidene-[2H9]tert-butylamine N-oxide (119391-92-3) + di-(2-ethylhexyl)-peroxydicarbonate (16111-62-9) → C4D9NOCHC6D5CO3C8H17

Conditions	Yield
In benzene at 26.84 - 39.84℃; Product distribution; Decomposition; addition;

Upstream product

• 24468-13-1 2-Ethylhexyl chloroformate 

Relevant articles and documents

ONLINE CONTINUOUS FLOW PROCESS FOR THE SYNTHESIS OF ORGANIC PEROXIDES USING HYDROGEN PEROXIDE AS RAW MATERIAL

An online continuous flow production process for directly preparing organic peroxides by using hydrogen peroxide as a raw material. This production process uses hydrogen peroxide, catalyst, and an oxidation substrate as a raw material. Substrate will be turned to designated peroxides sequentially through oxidation and workup. This process is performed in a plug-and-produce integrated continuous flow reactor, and the raw materials are continuously fed to the reactor. So, specified peroxide can be continuously obtained at the outlet of the plug-and-produce integrated continuous flow reactor.

METHOD FOR PREPARING ORGANIC PEROXIDES ON SITE

The present invention relates to a process for preparing an organic peroxide and the subsequent use thereof in a (co)polymerization reaction, wherein the process comprises the steps (a), b1 (or b2), (c), (d), and (e), said steps being: (a) the reaction of chlorine with carbon monoxide, (b1) the reaction of phosgene formed in step (a) with one or more alcohols in order to prepare chloroformate, (b2) the reaction of phosgene formed in step (a) with one or more organic acids to prepare acid chloride, optionally in the presence of a catalyst suitable to effect the reaction of phosgene with said one or more organic acids, (c) the reaction of chloroformate, acid chloride, or mixture thereof with (in)organic hydroperoxide and base in an aqueous environment, (d) the transfer of organic peroxide formed in step (c) to a polymerization vessel, and (e) the (co)polymerization of monomer in the polymerization vessel in the presence of one or more organic peroxides transferred in step (d), wherein all of steps (a)-(e) are conducted at one site.