19550-40-4

Basic information

• Product Name: 3,6-dimethylcyclohexene
• Synonyms: Cyclohexene, 3,6-dimethyl-
• CAS NO: 19550-40-4
• Molecular Formula: C₈H₁₄
• Molecular Weight: 110.1968
• Mol File: 19550-40-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 122.5°C at 760 mmHg
• Flash Point: 6.8°C
• Density: 0.788g/cm³
• Vapor Pressure: 16.7mmHg at 25°C
• Refractive Index: 1.438
• CAS DataBase Reference: 3,6-dimethylcyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-dimethylcyclohexene(19550-40-4)
• EPA Substance Registry System: 3,6-dimethylcyclohexene(19550-40-4)

Safety Data

• Hazardous Substances Data: 19550-40-4(Hazardous Substances Data)

Upstream product

• 74-85-1 ethene 
• 592-46-1 hexa-2,4-diene 
• 108667-06-7 (+/-)-toluene-4-sulfonic acid-(2t,5c-dimethyl-cyclohex-r-yl ester) 
• 932-51-4 2,5-dimethylcyclohexanone 
• 3809-32-3 2,5-dimethylcyclohexanol 
• 917-64-6 methyl magnesium iodide 
• 21592-97-2 cis-4-methylcyclohex-2-en-1-ol 
• 21592-97-2 (±)-(1R*,4R*)-4-methylcyclohex-2-enol 
• 7560-64-7 4-methyl-cyclohex-3-enecarbaldehyde 
• 78-79-5 isoprene 
• 5194-51-4 (2E,4E)-hexa-2,4-diene 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 1692-53-1 1-chloro-2-pentafluorosulfanylcyclohexane 
• 106-42-3 para-xylene 

Relevant articles and documents

Selective production of bio-based: Para -xylene over an FeOx -modified Pd/Al2O3catalyst

para-Xylene (PX) is a basic building block of polyethylene terephthalate, which is currently produced from petroleum resources. Developing a renewable route to PX is highly desirable to address both economic and environmental concerns. Several attempts used noble metal catalysts, e.g. Pd/Al2O3, to synthesize PX from biomass-derived 4-methyl-3-cyclohexene-1-carboxaldehyde (4-MCHCA), but suffered from a severe decarbonylation reaction, resulting in toluene as the main product. In this paper, we report an FeOx modification strategy to suppress the decarbonylation reaction on a Pd/Al2O3 catalyst, leading to a drastic shift in selectivity towards PX with a yield up to 81percent via a cascade dehydroaromatization-hydrodeoxygenation (DHA-HDO) pathway. Characterization and control experiments revealed that the electron density of Pd sites decreased in an FeOx-modified Pd/Al2O3 catalyst compared to Pd/Al2O3, thus tuning the preferential adsorption mode of the substrate from η2-(C,O), the key transition state of the decarbonylation reaction, to the η1-(O) mode that favors the hydrodeoxygenation process. Notably, this designed catalyst is highly stable and is readily applicable in the selective synthesis of a broad range of desired aromatic chemicals via the same DHA-HDO pathway from cyclohex-3-enecarbaldehyde derivatives. Overall, this work develops a controllable catalyst modification strategy that tailors an efficient catalyst for petroleum-independent bio-PX synthesis.

SYNTHESIS OF PARA-XYLENE AND TOLUENE

A method of making para-xylene or toluene is carried out by: (a) reacting a C5 or C6 linear monoene (itself, or formed from a C5 or C6 linear alkane) with a hydrogen acceptor in the presence of a hydrogen transfer catalyst to produce a C5 or C6 diene; (b) reacting the C5-C6 diene with ethylene to produce a cyclohexene having 1 or 2 methyl groups substituted thereon; and then (c) either (i) dehydrogenating the cyclohexene in the presence of a hydrogen acceptor with a hydrogen transfer catalyst to produce a compound selected from the group consisting of para-xylene and toluene, or (ii) dehydrogenating the cyclohexene in the absence of a hydrogen acceptor with a dehydrogenation catalyst, to produce para-xylene or toluene.

Stereochemical Aspects of the Nickel-Catalyzed Alkylation of Allylic Alcohols

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