18970-30-4

Basic information

• Product Name: 4,4'-DIISOPROPYLBIPHENYL
• Synonyms: 4,4'-DIISOPROPYLBIPHENYL;1,1'-Biphenyl, 4,4'-bis-(1-methylethyl);1,1'-Biphenyl, 4,4'-diisopropyl;-Diisopropylbiphenyl;4,4'-Bis(1-methylethyl)-1,1'-biphenyl;4,4''-DIISOPROPYLBIPHENYL 98+%;4,4'-Diisopropyl-1,1'-biphenyl;1-(propan-2-yl)-4-[4-(propan-2-yl)phenyl]benzene
• CAS NO: 18970-30-4
• Molecular Formula: C₁₈H₂₂
• Molecular Weight: 238.37
• Mol File: 18970-30-4.mol

Chemical Properties

• Melting Point: 66°C
• Boiling Point: 330.6°Cat760mmHg
• Flash Point: 161.7°C
• Appearance: /
• Density: 0.935g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4,4'-DIISOPROPYLBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIISOPROPYLBIPHENYL(18970-30-4)
• EPA Substance Registry System: 4,4'-DIISOPROPYLBIPHENYL(18970-30-4)

Safety Data

• Hazardous Substances Data: 18970-30-4(Hazardous Substances Data)

Usage

Uses

Used in Industrial Applications:
4,4'-Diisopropylbiphenyl is used as a high-temperature heat transfer fluid for its ability to maintain stability and performance in high-temperature processes. It is particularly favored in heat exchangers and cooling systems due to its low environmental impact and safety profile when handled with proper precautions.
Used in Heat Transfer Systems:
In the heat transfer industry, 4,4'-Diisopropylbiphenyl serves as a reliable heat transfer medium, ensuring efficient temperature regulation and heat distribution across various systems. Its resistance to oxidation and low volatility contribute to its longevity and effectiveness in these applications.
Used in Cooling Systems:
4,4'-Diisopropylbiphenyl is utilized in cooling systems to manage and dissipate heat generated by industrial processes or equipment. Its thermal properties make it an ideal choice for maintaining optimal operating temperatures and preventing overheating.
Used in Environmentally Friendly Applications:
Recognized for its low environmental impact, 4,4'-Diisopropylbiphenyl is selected for applications where reducing the ecological footprint is a priority. Its relative safety in industrial settings aligns with environmentally conscious practices and regulations.

Upstream product

• 586-61-8 4-iso-propylbromobenzene 
• 17356-09-1 4-iodocumene 
• 98-82-8 Isopropylbenzene 
• 61434-46-6 3,4'-di-isopropylbiphenyl 
• 92-52-4 biphenyl 
• 187737-37-7 propene 
• 16152-51-5 (4-isopropylphenyl)boronic acid 
• 403-48-5 4-(isopropyl)benzenediazonium tetrafluoroborate 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 141987-55-5 4-(1-hydroxy-1-methylethyl)-4'-(1-methylethyl)biphenyl 
• 1279720-39-6 bis(1-methyl-1-(4'-isopropylbiphenyl-4-yl)ethyl)peroxide 
• 102714-30-7 1-(4'-(1-methylethyl)biphenyl-4-yl)ethanone 
• 22726-67-6 4,4'-bis(2-hydroxy-2-propyl)biphenyl 
• 92-88-6 4,4'-Dihydroxybiphenyl 

Relevant articles and documents

The isopropylation of biphenyl over transition metal substituted aluminophosphates: MAPO-5 (M: Co and Ni)

The isopropylation of biphenyl (BP) was examined over transition metal substituted aluminophosphates (MAPO-5; M: Co and Ni) with 12-membered (12-MR) oxygen ring pore-entrances of AFI topology. The MAPO-5 samples were synthesized by dry gel conversion method using trimethylamine as a structure directing agent, and their properties were characterized by XRD, XPS, SEM, N2 adsorption, NH3-TPD, pyridine adsorption, and o-xylene uptake. They are clear crystals without impurity phases and agglomerates, and found small amounts of Br?nsted acid sites which are expecting active for acid catalysis. The isopropylation of BP over both of Co(5)APO-5 and Ni(5)APO-5 at 250 °C gave the high selectivities for 4,4′-DIPB: 65-75%. 4-IPBP is almost exclusive precursor of 4,4′- and 3,4′-DIPB. 3-IPBP was not significantly concerned even though 3-IPBP was predominant among IPBP isomers at the late stages: the MAPO-5 channels allow preferential access of 4-IPBP, and prevent the access of 3-IPBP due to reactant selectivity mechanism. The selective formation of 4,4′-DIPB occurred by preferential exclusion of bulkier 3,4′-DIPB and other isomers through the steric interaction of transition states with the channels by the restricted transition state selectivity mechanism. MAPO-5 (M: Co and Ni) has the same level of the selectivities for 4,4′-DIPB to SSZ-24 and other MAPO-5 (M: Si, Mg, and Zn), and these selectivities were originated by the AFI channels. The selectivities for 4,4′-DIPB were kept 65-75% at low and moderate temperatures over MAPO-5 (M: Co and Ni); however, they were decreased by the isomerization to stable 3,4′-DIPB with the increase in temperature.

Preparation of [Fe]-SSZ-24 through the isomorphous substitution of [B]-SSZ-24 with iron, and its catalytic properties in the isopropylation of biphenyl

[Fe]-SSZ-24, a ferrosilicate with AFI topology, was prepared through an isomorphous substitution of [B]-SSZ-24 with iron, and applied for the isopropylation of biphenyl (BP) to understand the mechanism of shape-selective catalysis. The substitution of [B]-SSZ-24 with an aqueous solution of a limited amount of Fe(NO3)3·6H2O effectively gave [Fe]-SSZ-24, and its XRD gave clear patterns of AFI topology without the peaks assigned to Fe2O3. [Fe]-SSZ-24 exhibited enhanced catalytic activity for the isopropylation of BP. Shape-selective formation of 4,4′-diisopropylbiphenyl (4,4′-DIPB) occurred at moderate temperatures (250-300 °C); however, the decreases of the selectivity for 4,4′-DIPB occurred at high temperatures (325-350 °C). On the other hand, the selectivities for 4,4′-DIPB in encapsulated products remained almost constant (ca 75%), irrespective of the reaction temperature and the SiO2/Fe2O3 ratios. The differences in the selectivities for 4,4′-DIPB between bulk and encapsulated products indicate that shape-selective formation of 4,4′-DIPB occurs in the [Fe]-SSZ-24 channels, and these channels prevent the isomerization of 4,4′-DIPB, even at 350 °C. These results suggest that the channels of SSZ-24 can discriminate 4,4′-DIPB from other possible DIPB isomers at their transition states although high reaction temperatures cause isomerization at external acid sites. Large pore molecular sieves of AFI topology, [Fe]-SSZ-24, [Al]-SSZ-24, MgAPO-5, ZnAPO-5, and SAPO-5, gave similar levels of selectivities for 4,4′-DIPB in the isopropylation of BP. These results indicate that the framework of AFI topology primarily controls shape-selective formation of 4,4′-DIPB, although catalytic activities of the materials were dependent on acidic properties.

Shape-selective isopropylation of aromatic hydrocarbons over h-mordenite in supercritical carbon dioxide medium

The isopropylation of aromatic hydrocarbons isobutylbenzene (IBB), naphthalene (NP), and biphenyl (BP) was examined over H-mordenite (MOR), H-β (BEA), and H-Y (FAU) zeolites in supercritical carbon dioxide (sc-CO2) medium. MOR was only selective for the formation of the least bulky 4-isobutylcumene (4-IBC) in the isopropylation of IBB. In particular, the catalytic activity and selectivity for 4-IBC were enhanced by the dealumination of MOR; MOR with 110 of SiO2/Al2O3 ratio rendered the highest performance; however, the catalytic activity was decreased by further dealumination. Thermogravimetric analyses confirmed the reduction of coke formation on the catalysts in sc-CO2 medium, preventing the deactivation of MOR. Shape-selective formation of the least bulky isomers, 2,6- diisopropylnaphthalene (2,6-DIPN) and 4,4′-diisopropylbiphenyl (4,4′-DIPB), was also observed in the isopropylation of NP and BP over MOR in sc-CO2. sc-CO2 works as an efficient medium to access and/or replace substrates and their products to/from acidic sites in the MOR channels. In particular, the removal of coke precursors from acidic sites on the zeolite is enhanced by the sc-CO2 medium, resulting in decreased coke formation.

Isopropylation of biphenyl over ZSM-12 zeolites

ZSM-12 zeolites, ZSM-12L and ZSM-12S, with MTW topology were synthesized by using methyltriethylammonium bromide (MTEABr) and tetraethylammnoium bromide (TEABr) as structure directing agents (SDA), respectively, for the isopropylation of biphenyl (BP) usi

Lanthanoid exchanged mordenites as catalysts for the isopropylation of biphenyl

Liquid-phase isopropylation of biphenyl (BP) with propene was studied to understand the acidities resulting from lanthanoid exchanged sodium mordenite (Ln,NaMOR; Ln: La, Ce, Pr, Sm, Dy, and Yb). The acidities of La3+ exchanged sodium mordenite (La,NaMOR) appeared at around 0.60-.8 exchange calculated from La/3Al molar ratio. Similar acidities appeared with all Ln,NaMORs. The resultant zeolites have Bronsted acidic sites appearing near unsaturated lanthanoid cations. The isopropylation of BP predominantly afforded 4,4'-diisopropylbiphenyl (4,4'-DIPB) among DIPB isomers over all Ln,NaMORs. These catalyses occur on the acidic sites in the channels. The exchanged catalysts had high selectivities for 4,4'-DIPB even at temperatures as high as 300 °C although the selectivities decreased by the isomerization of 4,4'-DIPB over H-mordenite (HMOR) with similar SiO2/Al 2O3 ratio. These results indicate the external acid sites are lowly active for the isopropylation of BP and the isomerization of 4,4'-DIPB. The combustion of coke-deposits on Ln,NaMORs, particularly Ce,NaMOR, used for the isopropylation occurred at lower temperatures than that on HMOR because the lanthanoids dispersed in MOR channels work as an oxidation catalyst.

Copper quinolate: A simple and efficient catalytic complex for coupling reactions

We describe an effective and novel method to prepare N-aryl imidazoles via the copper quinolate-catalyzed N-arylation of aryl halides and imidazoles. A wide range of products were obtained in moderate to excellent yields under the optimal reaction conditions. Applying standard conditions, the model reaction could be performed on a gram scale. This method also presents a new avenue to the “click” reaction of terminal alkynes, benzyl bromide, and sodium azide and to the construction of C–C bonds by homocoupling of phenylboronic acid or phenylacetylene derivatives with the aid of copper quinolate.

Shape-selective alkylation of biphenyl with propylene using zeolite and amorphous silica-alumina catalysts

The influence of zeolite structure for the alkylation of biphenyl with propylene was studied over various zeolites such as HY, HZSM-5, and dealuminated mordenite (DMOR), as well as amorphous SiO2/Al2O 3, in a stirred tank reactor. Biphenyl conversion was found to increase with reaction time for HZSM-5 and DMOR zeolites and reach a leveling off in 4 h, whereas for HY and amorphous SiO2/Al2O 3 a leveling off was reached within an hour. DMOR displayed the highest selectivity for 4,4′-diisopropylbiphenyl (4,4′-DIPB) even at temperatures as high as 300 °C, whereas for HY, HZSM-5 and amorphous SiO2/Al2O3 selectivities fell in the range of 10-35%; they were significantly lower than observed for DMOR. These differences in selectivity might be due to the structure and pore channels of the zeolites. DMOR was found to be an active catalyst, the selectivity for 4-isopropylbiphenyl (4-IPB) and (4,4′-DIPB) was high among isopropylbiphenyl (IPB) and diisopropylbiphenyl (DIPB) isomers, respectively, indicating DMOR possesses shape-selectivity. The selectivity of 4,4′-DIPB increased with time, while the corresponding selectivity of 4-IPB decreased for DMOR catalyst. Alkylation of biphenyl with propylene occurred with predominant formation of 4-IPB in the first step. 4-IPB is only a source in the second step of alkylation of biphenyl with propylene for the formation of 4,4′-DIPB, while 3-IPB does not participate in the formation of DIPB isomers.

Ferrous salt-promoted homocoupling of arenediazonium tetrafluoroborates under mild conditions

A simple and efficient protocol has been developed for the synthesis of various symmetrical biaryls in good to excellent yields from the homocoupling reactions of arenediazonium salts with ferrous salt in carbon tetrachloride solution under mild reaction conditions. Moreover, the novel homocoupling has been demonstrated to proceed via an electron transfer reaction mechanism.

Cobalt-catalyzed homo-coupling of aryl and alkenyl bromide using atmospheric oxygen as oxidant

An efficient procedure for the synthesis of symmetric biphenyl and olefinic compounds was reported by cobalt-catalyzed direct homo-coupling reaction of aryl and alkenyl bromide in the presence of metallic magnesium using atmospheric oxygen as the oxidant. All tested aromatic bromides could give corresponding biaryls in good yields (up to 85%). Moreover, under the same conditions, β-bromostyrene could also afford the corresponding conjugated dienes in moderate yields, and the coupling is highly stereoselective to give trans-products. This mild and practicable method opened a new way to the preparation of symmetric biaryls and conjugated dienes.

The alkylation of biphenyl over one-dimensional twelve-membered ring zeolites. the influence of zeolite structure and alkylating agent on the selectivity for 4,4'-dialkylbiphenyl

Alkylation, i.e., isopropylation, s-butylation, and t-butylation, of biphenyl (BP) was examined over one-dimensional twelve-membered (12-MR) zeolites: Mordenite (MOR) and SSZ-24 (AFI) with straight channels, and SSZ-55 (ATS) and SSZ-42 (IFR) with corrugated channels. Types of zeolites and alkylating agents highly influenced the selectivities for dialkylbiphenyl (DABP) isomers. Shape-selective formation of 4,4'-diisopropylbiphenyl (4,4'-DIPB) was observed over MOR and AFI; however, ATS and IFR gave 4,4'-DIPB only in low selectivities at 250°C: 87% over MOR, 60% over AFI, 20% over ATS, and 30% over IFR. The selectivities for 4,4'-di-s-butylbiphenyl (4,4'-DSBB) in the,s-butyl-ation were higher than those for 4,4'-DIPB: 95% over MOR, 85% over AFI, 75% over ATS, and 50% over IFR. The t-butylation afforded selectively 4,4'-di-t-butylbiphenyl (4,4'-DTBB) over the zeolites: 96-97% over MOR and AFI, 90% over ATS, and 80% over IFR. These results in the alkylation indicate the exclusion of 4,4'-DABP from other bulky DABP isomers by steric restriction in zeolite channels is an important key for the high shape-selectivity. Even zeolites with large channels, such as ATS and IFR, can have shape-selective nature if the bulky moieties, such as,s-butyl and t- butyl groups, are large enough to differentiate the transition state of the least bulky 4,4'-DABP from those of the other isomers inside their channels. The selectivity for 4,4'-DABP decreased at high temperatures in some alkylations: isopropylation over MOR, and s-butylation and t-butylation over MOR, AFI, and ATS. The decreases are due to the iso-merization of 4,4'-DABP at external acid sites, because the channels are not large enough for the isomerization of 4,4'-DABP to bulkier 3,4'-DABP. However, the isopropylation over AFI was accompanied by the isomerization of 4,4'-DIPB at external and internal acid sites, because the channels are large enough for the isomerization of 4,4'-DIPB.