3025-88-5

Basic information

• Product Name: 2,5-DIMETHYLHEXANE-2,5-DIHYDROPEROXIDE
• Synonyms: 2,5-BIS(HYDROPEROXY)2,5-DIMETHYLHEXANE;2,5-DI(HYDROPEROXY)-2,5-DIMETHYLHEXANE;2,5-Dimethy-2,5-dihydroperoxyhexane(not more than 82%,with water);2,5-DIMETHYLHEXANE-2,5-DIHYDROPEROXIDE;(1,1,4,4-tetramethyl-1,4-butanediyl)bis-hydroperoxid;(1,1,4,4-tetramethyl-1,4-butanediyl)bis-Hydroperoxide;2,5-dimethyl-2,5-dihydroperoxyhexane,notmorethan82%withwater;2,5-Dimethylhexane-2,5-dihydroxyperoxide
• CAS NO: 3025-88-5
• Molecular Formula: C₈H₁₈O₄
• Molecular Weight: 178.23
• EINECS: 221-184-0
• Mol File: 3025-88-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 230.46°C (rough estimate)
• Flash Point: 145.5 °C
• Appearance: White wet solid
• Density: 1.0268 (rough estimate)
• Vapor Pressure: 3.33E-05mmHg at 25°C
• Refractive Index: 1.4209 (estimate)
• PKA: 12.28±0.50(Predicted)
• CAS DataBase Reference: 2,5-DIMETHYLHEXANE-2,5-DIHYDROPEROXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYLHEXANE-2,5-DIHYDROPEROXIDE(3025-88-5)
• EPA Substance Registry System: 2,5-DIMETHYLHEXANE-2,5-DIHYDROPEROXIDE(3025-88-5)

Safety Data

• RIDADR: 3102
• HazardClass: 5.2
• PackingGroup: II
• Hazardous Substances Data: 3025-88-5(Hazardous Substances Data)

Usage

General Description

White wet solid. May float or sink in water. 2,5-DIMETHYLHEXANE-2,5-DIHYDROPEROXIDE is particularly sensitive to temperature rises. Above a given "Control Temperature" they decompose violently. 2,5-DIMETHYLHEXANE-2,5-DIHYDROPEROXIDE is generally stored or transported in a water slurry.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Peroxides, such as 2,5-DIMETHYL-2,5-DIHYDROPEROXY HEXANE, are good oxidizing agents. Organic compounds can ignite on contact with concentrated peroxides. Strongly reduced material such as sulfides, nitrides, and hydrides may react explosively with peroxides. There are few chemical classes that do not at least produce heat when mixed with peroxides. Many produce explosions or generate gases (toxic and nontoxic). Generally, dilute solutions of peroxides (<70%) are safe, but the presence of a catalyst (often a transition metal such as cobalt, iron, manganese, nickel, or vanadium) as an impurity may even then cause rapid decomposition, a buildup of heat, and even an explosion. Solutions of peroxides often become explosive when evaporated to dryness or near-dryness. Decomposes in contact with many metals and acids [USCG, 1999].

Health Hazard

Contact with eyes or skin causes irritation.

Fire Hazard

Behavior in Fire: Decomposes violently when heated in fire. Can increase intensity of fire when in contact with combustible material. Containers may explode.

InChI:InChI=1/C8H18O4/c1-7(2,11-9)5-6-8(3,4)12-10/h9-10H,5-6H2,1-4H3

Synthetic route

2,5-dimethyl-2,5-hexanediol (110-03-2) → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide
With dihydrogen peroxide
With dihydrogen peroxide

2,5-dimethylhexane (592-13-2) → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5)

Conditions	Yield
With oxygen

2,5-dimethylhexane (592-13-2) → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + 5-hydroperoxy-2,5-dimethyl-hexan-2-ol (99233-61-1)

Conditions	Yield
With oxygen

2,5-dimethylhexane (592-13-2) → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + 2-Hydroperoxy-2,5-dimethylhexane (90951-87-4)

Conditions	Yield
With oxygen at 95℃;

2,5-dimethyl-2,5-hexanediol (110-03-2) + sulfuric acid (7664-93-9) + dihydrogen peroxide (7722-84-1) → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5)

Conditions	Yield
at 25 - 30℃;

2,5-dimethylhexane (592-13-2) + air → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5)

Conditions	Yield
at 20℃; Autoxydation;

2,5-dimethylhexane (592-13-2) + oxygen → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + 2-Hydroperoxy-2,5-dimethylhexane (90951-87-4)

Conditions	Yield
at 120℃;
at 95℃;

2,2,5,5-tetramethyltetrahydrofuran (15045-43-9) → 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide In water

sebacoyl chloride (111-19-3) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + terephthaloyl chloride (100-20-9) → 4-(4-{4-[4-(9-{4-[9-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-nonanoylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-nonanoylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	98%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + α-bromosebacoyl chloride (42875-57-0) → C90H157Br5O31 (78499-33-9)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	97%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + α-bromoglutaryl chloride (42875-51-4) → C52H86Br4O25 (78491-80-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	95%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + α-bromoadipoyl chloride (42875-52-5) → C56H94Br4O25 (78491-81-3)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	95%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + succinoyl dichloride (543-20-4) + Phthaloyl dichloride (88-95-9) → 2-(4-{2-[4-(3-{4-[3-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-propionylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-propionylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid (78491-83-5)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	95%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + tert-butyl alcohol (75-65-0) → 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane (78-63-7)

Conditions	Yield
With spherical polyvinyl alcohol complex amino acid C In pentane at 70 - 80℃; for 8h; Reagent/catalyst;	94.3%
With sulfuric acid In water at 40 - 45℃; for 2h; Industry scale;
With sulfuric acid at 50℃; Temperature;
With sulfuric acid In water; tert-butyl alcohol at 15 - 40℃; for 4.33333h;

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + α-chloroazelaoyl chloride (42875-56-9) → C68H118Cl4O25 (78491-82-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1.5h;	93%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + phenyl chloroformate (1885-14-9) → C22H26O8

Conditions	Yield
With pyridine In pentane at 10℃;	71%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + (+-)-5,5,6exo-trimethyl-norbornan-2-one (3292-05-5, 3649-86-3, 3767-44-0, 26399-21-3, 63814-38-0, 63814-39-1, 68330-85-8) → 6,6,9,9-tetramethyl-3-(5,5,6-trimethylbicyclo<2.2.1>heptyl)-1,2,4,5-tetraoxacyclononane (120676-78-0)

Conditions	Yield
With cation-exchange resin KRS-40t In diethyl ether at 20 - 23℃; for 8h;	59.5%

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + 1,7-dicarba-closo-dodecarborane-1-carboxylic acid chloride (40101-88-0) → 2,5-dimethyl-2,5-di(m-carboranoylperoxy)hexane (140701-98-0)

Conditions	Yield
In pyridine; dichloromethane addn. of a soln. of B-compound in CH2Cl2 to a mixt. of organic compound, pyridine and CH2Cl2 at -5 to 0°C, raising temp. slowly to room temp., stirring for 12-14 h; diluting mixt. with hexane, washing (tartaric acid soln., water, sodium bicarbonate), drying (sodium sulfate), column chromy. (silica gel/benzene or hexane-ether), elem. anal.;	54%

pyridine (110-86-1) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + 4-nitro-benzoyl chloride (122-04-3) → 2,5-dimethyl-2,5-bis-(4-nitro-benzoylperoxy)-hexane

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → 3,3,6,6-tetramethyl-1,2-dioxane (22431-89-6)

Conditions	Yield
With lead(IV) acetate; acetic acid

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → 3,3,6,6,9,9-hexamethyl-1,2,4,5-tetraoxacyclononane (22397-33-7)

Conditions	Yield
With hydrogenchloride; acetone
With copper(II) sulfate; acetone

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + benzoyl chloride (98-88-4) → 2,5-dimethyl-2,5-di(benzoylperoxy)-hexane (2618-77-1)

Conditions	Yield
With pyridine

succinic acid anhydride (108-30-5) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → 3-[4-(3-Carboxy-propionylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-propionic acid (58551-92-1)

Conditions	Yield
With sodium acetate In tetrahydrofuran

butanoic acid anhydride (106-31-0) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → 2,5-Dimethyl-2,5-hexandiyl-diperbutyrat (14619-70-6)

Conditions	Yield
With pyridine

glutaric anhydride, (108-55-4) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → 4-[4-(4-Carboxy-butyrylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-butyric acid (58551-93-2)

Conditions	Yield
With sodium acetate In tetrahydrofuran

phthalic anhydride (85-44-9) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → 2,5-Dimethylhexan-2,5-bis(acid-peroxy-phthalat) (58551-94-3)

Conditions	Yield
With sodium acetate In tetrahydrofuran

chloro-trimethyl-silane (75-77-4) + 2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → C14H34O4Si2 (17630-14-7)

Conditions	Yield
With ammonia In diethyl ether

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + n-heptanoic anhydride (626-27-7) → 2,5-Dimethyl-2,5-hexandiyl-diperoenthat (14619-48-8)

Conditions	Yield
With pyridine

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + pentanoic anhydride (2082-59-9) → 2,5-Dimethyl-2,5-hexadiyl-dipervalerat (14619-46-6)

Conditions	Yield
With pyridine

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + 4-methylpentanoic anhydride (83594-04-1) → 4-Methyl-pentaneperoxoic acid 1,1,4-trimethyl-4-(4-methyl-pentanoylperoxy)-pentyl ester

Conditions	Yield
With pyridine

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + capric anhydride (2082-76-0) → 2,5-Dimethyl-2,5-hexandiyl-dipercaprat (13052-08-9)

Conditions	Yield
With pyridine

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + Triphenylsilyl chloride (76-86-8) → C44H46O4Si2 (55606-92-3)

Conditions	Yield
With ammonia In diethyl ether

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) → 5-hydroperoxy-2,5-dimethyl-hexan-2-ol (99233-61-1)

Conditions	Yield
With (thermolysis) In benzene at 143.9 - 164℃; Kinetics;

2,5-dimethyl-2,5-dihydroperoxyhexane (3025-88-5) + acetic anhydride (108-24-7) → 2,5-Dimethylhexan-2,5-bis(peroxyacetat) (14619-45-5)

Conditions	Yield
With pyridine

Upstream product

• 110-03-2 2,5-dimethyl-2,5-hexanediol 
• 592-13-2 2,5-dimethylhexane 
• 15045-43-9 2,2,5,5-tetramethyltetrahydrofuran 
• 7664-93-9 sulfuric acid 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 78-63-7 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane 
• 5168-50-3 (1,1,4,4-tetramethyltetramethylene)bis[tert-pentyl] peroxide 
• 71352-00-6 3,3,6,6,9,9-Hexamethyl-1,2,4,5-tetraoxa-3-silacyclononan 
• 58551-97-6 C₂₄H₂₄Cl₂O₈ 
• 7553-56-2 iodine 
• 78491-83-5 2-(4-{2-[4-(3-{4-[3-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-propionylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-propionylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid 
• 136664-86-3 2,5-bis(o-benzoylbenzoyldioxy)-2,5-dimethylhexane 
• 55606-92-3 C₄₄H₄₆O₄Si₂ 
• 2618-77-1 2,5-dimethyl-2,5-di(benzoylperoxy)-hexane 
• 22397-33-7 3,3,6,6,9,9-hexamethyl-1,2,4,5-tetraoxacyclononane 
• 22431-89-6 3,3,6,6-tetramethyl-1,2-dioxane 

Relevant articles and documents

Process for producing organic peroxides

The present invention relates to a method for producing organic peroxides and separating, purifying and concentrating sulfuric acid from aqueous effluents of said organic peroxide production process.

De-coloring method for 2,5-dimethyl-2,5-bis(tertiary butyl peroxy) hexane

The invention relates to a de-coloring method for 2,5-dimethyl-2,5-bis(tertiary butyl peroxy) hexane and belongs to the technical field of organic peroxide product preparation. The method comprises the following steps: firstly, putting a dilute acid solution into a reaction vessel with a stirring device and controlling the temperature of the reaction vessel at 10-40 DEG C and pressure at 0.1MPa; adding the to-be-de-colored 2,5-dimethyl-2,5-bis(tertiary butyl peroxy) hexane into the reaction vessel and starting the stirring device to stir; after ending the stirring, standing by and layering, recycling the separated lower layer dilute acid solution and acquiring the upper layer of de-colored 2,5-dimethyl-2,5-bis(tertiary butyl peroxy) hexane. The operation is simple; the severe use requirement can be met; the solid waste discharge can be reduced; the environmental protection property is reflected; the resources are saved; the pollution is avoided.

Preparation of 2,5-dimethylhexane-2,5-dihydroperoxide and derivatives thereof

A one-step process for preparing 2,5-dimethylhexane-2,5-dihydroperoxide and its alkyl derivatives comprises: (1) adding sulfuric acid to a 60-70% hydrogen peroxide solution to form a first reaction mixture where the first mixture is controlled at a temperature in the range of from about -10° C. to about 10° C.; (2) adding 2,5-dimethyl-2,5-dihydroxy hexane to the mixture held at a temperature in the range of from about -10° C. to about 10° C. or lower to form a second reaction mixture and maintaining the second mixture at a temperature in the range of from about 20° C. to about 50° C. for about 5 minutes to about 5 hours to form a slurry containing the solid product of 2,5-dimethylhexane-2,5-dihydroperoxide, unreacted reactants and impurities; (3) lowering the temperature of the slurry to the range of from about -10° C. to about 10° C.; (4) removing unreacted reactants and impurities from the solid product and optionally, washing the solid product; and (5) adding sulfated alkyl alcohol, which is prepared by adding the alkyl alcohol to sulfuric acid, to the solid product to form a third reaction mixture and maintaining the third mixture at about 30° C. to about 60° C. for about 1 to about 5 hours to prepare the alkyl derivatives.