94133-80-9

Usage

Chemical structure

1,7-diisopropylnaphthalene is composed of a naphthalene ring with two isopropyl groups attached at the 1 and 7 positions.

Physical state

It is a colorless liquid.

Odor

It has a pungent odor.

Solubility

Insoluble in water, but soluble in organic solvents.

Industrial applications

Primarily used as a high-temperature heat transfer fluid due to its thermal stability and low volatility.

Additional uses

Utilized as a plasticizer in the production of polymers and as a lubricant additive.

Safety precautions

Handle with care as it is considered harmful if swallowed, inhaled, or in contact with skin and eyes.

InChI:InChI=1/C16H20/c1-11(2)14-9-8-13-6-5-7-15(12(3)4)16(13)10-14/h5-12H,1-4H3

Upstream product

• 91-20-3 naphthalene 
• 187737-37-7 propene 
• 67-63-0 isopropyl alcohol 
• 1121-05-7 2,3-dimethylcyclopent-2-enone 

Relevant academic research and scientific papers

The isopropylation of naphthalene over USY zeolite with FAU topology. The selectivities of the products

The isopropylation of naphthalene (NP) over USY zeolite (FAU06, SiO2/Al2O3 = 6) gave all eight possible diisopropylnaphthalene (DIPN) isomers: β,β- (2,6- and 2,7-), α,β- (1,3-, 1,6-, and 1,7-), and α,α- (1,4- and 1,5-). Th

Reaction routes in catalytic reforming of poly(3-hydroxybutyrate) into renewable hydrocarbon oil

Poly(3-hydroxybutyrate) or PHB is an energy storage material of microbial organisms and can be reformed into hydrocarbon oils rich with aromatic compounds. This work investigated the main reaction routes from PHB to the key intermediates and final hydrocarbons. The main sequential reactions under catalysis of phosphoric acid at moderate temperatures (200-230 °C) consist of: (1) decomposition of PHB into crotonic acid, a major monomeric intermediate, (2) deoxygenation of crotonic acid, and (3) combination of the deoxygenated molecules. The oxygen in PHB is removed as CO2 and H2O in stage (2), involving decarboxylation and ketonization of crotonic acid. The main aromatic compounds are formed in stage (3) from propylene and 2,3-dimethyl-2-cyclopenten-1-one as two key intermediates, the former from decarboxylation and the latter from ketonization of crotonic acid. The reaction routes reveal that the formation of aromatics is affected to a great extent by the concentrations of phosphoric acid and water in the reaction, which can be used to control the composition of hydrocarbon oil.

The isopropylation of naphthalene with propene over H-mordenite: The catalysis at the internal and external acid sites

The isopropylation of naphthalene (NP) with propene over H-Mordenite (MOR) was studied under a wide range of reaction parameters: temperature, propene pressure, period, and NP/MOR ratio. Selective formation of 2,6-diisopropylnaphthalene (2,6-DIPN) was observed at reaction conditions, such as at low reaction temperature, under high propene pressure, and/or with high NP/MOR ratio. However, the decrease in the selectivities for 2,6-DIPN was observed at reaction conditions such as at high temperature, under low propene pressure, and/or with low NP/MOR ratio. The selectivities for 2,6-DIPN in the encapsulated products were remained high and constant under all reaction conditions. These results indicate that the selective formation of 2,6-DIPN occurs through the least bulky transition state due to the exclusion of the bulky isomers by the MOR channels. The decrease in the selectivities for 2,6-DIPN are due to the isomerization of 2,6-DIPN to 2,7-DIPN at the external acid sites, directing towards thermodynamic equilibrium of DIPN isomers.

Isopropylation of naphthalene by isopropanol over conventional and Zn- and Fe-modified USY zeolites

Catalytic performances of USY, MOR, and BEA zeolites were compared for the isopropylation of naphthalene by isopropyl alcohol in a high-pressure, fixed-bed reactor. The USY catalyst showed a high conversion of 86% and good stability but a low 2,6-/2,7-DIPN shape selectivity ratio of 0.94. In contrast, over the MOR catalyst, 2,6-DIPN was selectively synthesized with a high 2,6-/2,7-DIPN ratio of 1.75, but low naphthalene conversions and fast deactivation of the catalyst were observed. The USY catalyst was modified by Zn and Fe using the wet impregnation method to enhance the selectivity for 2,6-DIPN. The highest conversion (~95%) and selectivity for 2,6-DIPN (~20%) were achieved with 4% Zn/USY catalyst. It appeared that small metal oxide islands formed in the USY pores to decrease the effective pore size and thus render it mildly shape-selective. Zn loading also decreased the number of strong acid sites responsible for coke formation and increased the number of weak acid sites. The high conversion and stability of Zn-modified catalysts were ascribed to the presence of a suitable admixture of weak and strong acid sites with less coke deposition. The Fe-modified USY catalysts were less effective because the modification increased the number of the strong acid sites.

Shape-selective synthesis of 2,6-diisopropylnaphthalene on H-mordenite catalysts

To finally dispel any doubts on the shape-selective formation of 2,6-diisopropylnaphthalene (2,6-DIPN) over H-MOR zeolites, naphthalene alkylation was carried out over high-silica H-MOR catalysts with propylene or isopropanol as an alkylating agent and with or without cyclohexane as a solvent. Isomeric composition of DIPN's, determined by one-dimensional GC analysis, was additionally confirmed with advanced two-dimensional GC × GC. Our results proved beyond any doubt shape-selective formation of 2,6-DIPN over these H-MOR catalysts from naphthalene and propylene and without cyclohexane as a solvent. The DIPN mixture contained 60-64% 2,6-DIPN, and the ratio of 2,6-DIPN/2,7-DIPN was in the range 2.5-2.8. We also showed that shape-selective formation of 2,6-DIPN over H-MOR catalyst was depressed by using isopropanol instead of propylene and in the presence of cyclohexane.

Shape-selective diisopropylation of naphthalene in H-Mordenite: Myth or reality?

Selective diisopropylation of naphthalene to 2,6-diisopropylnaphthalene is a challenging goal in sustainable catalysis. Ultrastable Y and H-Mordenite zeolites are the best catalysts reported in the literature with respect to 2,6-diisopropylnaphthalene selectivity. It is generally accepted that in the case of H-Mordenite, shape-selectivity is responsible for the observed 2,6-diisopropylnaphthalene selectivity, while on Ultrastable Y-zeolite, the observed selectivity reflects the internal thermodynamic equilibrium of positional isomers. Revisiting both the experimental and the computational work in this field now leads to the conclusion that shape-selectivity of whatever kind can be ruled out in the case of H-Mordenite. H-Mordenite catalysts produce usually a kinetically controlled mixture of diisopropylnaphthalene isomers which can shift to the direction of a thermodynamical distribution at high reaction temperatures or over more active catalysts.

The alkylation of naphthalene over one-dimensional fourteen-membered ring zeolites. the influence of zeolite structure and alkylating agent on the selectivity for dialkylnaphthalenes

The alkylation, i.e., isopropylation, s-butylation, and t-butylation, of naphthalene (NP) was examined over one-dimensional fourteen-membered (14-MR) zeolites: CIT-5 (CF1), UTD-1 (DON), and SSZ-53 (SFH), and compared to the results over H-mordenite (MOR)

Shape-selective Synthesis of 2,6-Diisopropylnaphthalene over H-Mordenite Catalyst

2,6-Diisopropylnaphthalene is selectively produced in the liquid phase alkylation of naphthalene with propene or propan-2-ol over H-mordenite catalyst.