849-99-0

Basic information

• Product Name: DICYCLOHEXYL ADIPATE
• Synonyms: Adipic acid, dicyclohexyl ester;adipicacid,dicyclohexylester;adipicaciddicyclohexylester;Dicyclohexyl hexanedioate;Ergoplast ADC;ergoplastadc;Hexanedioic acid, dicyclohexyl ester;hexanedioicacid,dicyclohexylester
• CAS NO: 849-99-0
• Molecular Formula: C₁₈H₃₀O₄
• Molecular Weight: 310.43
• EINECS: 212-702-6
• Mol File: 849-99-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 35°C
• Boiling Point: 410.58°C (rough estimate)
• Flash Point: 192.7°C
• Appearance: /
• Density: 1.0490 (rough estimate)
• Vapor Pressure: 1.1E-06mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• CAS DataBase Reference: DICYCLOHEXYL ADIPATE(CAS DataBase Reference)
• NIST Chemistry Reference: DICYCLOHEXYL ADIPATE(849-99-0)
• EPA Substance Registry System: DICYCLOHEXYL ADIPATE(849-99-0)

Safety Data

• Hazardous Substances Data: 849-99-0(Hazardous Substances Data)

Usage

Safety Profile

Mildly toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and fumes.

InChI:InChI=1/C18H30O4/c19-17(21-15-9-3-1-4-10-15)13-7-8-14-18(20)22-16-11-5-2-6-12-16/h15-16H,1-14H2

Synthetic route

carbon monoxide (201230-82-2) + buta-1,3-diene (106-99-0) + cyclohexanol (108-93-0) → dicyclohexyl adipate (849-99-0)

Conditions	Yield
With palladium(II) trifluoroacetate; toluene-4-sulfonic acid; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In toluene at 120℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	73%
With palladium(II) trifluoroacetate; HeMaRaphos; toluene-4-sulfonic acid In toluene at 120℃; under 30003 Torr; for 24h; regioselective reaction;	83 %Chromat.

diphenyl 1,6-hexanedioate (3195-37-7) → dicyclohexyl adipate (849-99-0)

Conditions	Yield
With nickel at 150℃; under 73550.8 Torr; Hydrogenation;

cyclohexanone (108-94-1) + cyclohexanol (108-93-0) → dicyclohexyl adipate (849-99-0)

Conditions	Yield
With potassium permanganate; air at 85℃;

Adipic acid (124-04-9) + cyclohexanol (108-93-0) → dicyclohexyl adipate (849-99-0)

Conditions	Yield
at 140℃;
With hydrogenchloride
With sulfuric acid; water; copper(II) sulfate

dicyclohexyl ether (4645-15-2) → dicyclohexyl adipate (849-99-0)

Conditions	Yield
With ozone In ethyl acetate at 8 - 10℃;

succinic acid (110-15-6) + cyclohexanol (108-93-0) → dicyclohexyl adipate (849-99-0)

Conditions	Yield
With adipic acid anhydride In benzene at 120℃; for 1h;	0.0125 mol

cyclohexyl nitrite (5156-40-1) + air → Adipic acid (124-04-9) + dicyclohexyl adipate (849-99-0) + cyclohexanone (108-94-1) + cyclohexanol (108-93-0)

cyclohexane (110-82-7) → Adipic acid (124-04-9) + dicyclohexyl adipate (849-99-0) + cyclohexanone (108-94-1)

Conditions	Yield
With N-hydroxyphthalimide; bromine; oxygen; 1,10-phenanthroline hydrate In tetrachloromethane; acetonitrile at 99.85℃; under 2250.18 Torr; for 5h;

Adipic acid (124-04-9) + cyclohexanol (108-93-0) → dicyclohexyl adipate (849-99-0) + monocyclohexyl adipate (54812-72-5)

Conditions	Yield
In 1,2-dichloro-benzene at 160℃; Kinetics; Temperature;

cyclohexane (110-82-7) → Adipic acid (124-04-9) + dicyclohexyl adipate (849-99-0) + cyclohexanone (108-94-1) + cyclohexanol (108-93-0)

Conditions	Yield
With oxygen at 150℃; under 7500.75 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Autoclave; High pressure;

dicyclohexyl adipate (849-99-0) → Adipic acid (124-04-9)

Conditions	Yield
With water; Aliquat 336; sodium hydroxide In cyclohexane; cyclohexanone; cyclohexanol at 70℃; for 1.5h; Reagent/catalyst;

Upstream product

• 3195-37-7 diphenyl 1,6-hexanedioate 
• 4645-15-2 dicyclohexyl ether 
• 110-15-6 succinic acid 
• 108-93-0 cyclohexanol 
• 5156-40-1 cyclohexyl nitrite 
• 201230-82-2 carbon monoxide 
• 106-99-0 buta-1,3-diene 
• 110-82-7 cyclohexane 
• 124-04-9 Adipic acid 
• 108-94-1 cyclohexanone 

Downstream Products

• 124-04-9 Adipic acid 

Relevant articles and documents

Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters

The dicarbonylation of 1,3-butadiene to adipic acid derivatives offers the potential for a more cost-efficient and environmentally benign industrial process. However, the complex reaction network of regioisomeric carbonylation and isomerization pathways, make a selective and direct transformation particularly difficult. Here, we report surprising solvent effects on this palladium-catalysed process in the presence of 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, which allow adipate diester formation from 1,3-butadiene, carbon monoxide, and methanol with 97 % selectivity and 100 % atom-economy under scalable conditions. Under optimal conditions a variety of di- and triesters from 1,2- and 1,3-dienes can be obtained in good to excellent yields.

Catalytic oxidation of cyclohexane to KA oil by zinc oxide supported manganese 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin

A series of manganese metalloporphyrins were prepared and tested in cyclohexane oxidation. It has been found that the manganese 5,10,15,20-tetrakis(4-nitrophonyl) porphyrin (Mn-TNPP) presents better catalytic performance. The Mn-TNPP was then immobilized on different supports, and characterized by UV-vis, FT-IR, XRD, TG/DTG and ICP. Among these supported Mn-TNPP catalysts, Mn-TNPP/ZnO exhibits the best selectivity to KA oil and higher turnover number in cyclohexane oxidation. The influence of the reaction conditions and the recycle of the catalysts are discussed. Mn-TNPP/ZnO catalyst presents the average cyclohexane conversion of 7.17%, KA oil selectivity of 91.18%, and the average catalytic turnover number of 6.53 × 104 after six times of recycle under 150 °C and 1.0 MPa.

Highly efficient and metal-free aerobic hydrocarbons oxidation process by an o-phenanthroline-mediated organocatalytic system

A highly efficient o-phenanthroline-mediated, metal-free catalytic system has been developed for oxidation of hydrocarbons with dioxygen in the presence of N-hydroxyphthalimide; various hydrocarbons were efficiently and high selectively oxidized, e.g., ethylbenzene to acetophenone in 97% selectivity and 76% conversion, under mild conditions.