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Terpene product derivatives from isoprene oligomerization

Journal Article · · Ind. Eng. Chem., Prod. Res. Dev.; (United States)
DOI:https://doi.org/10.1021/i360072a006· OSTI ID:6389102
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Products of isoprene oligomerization at 65/sup 0/-95/sup 0/C with modified Ziegler-type catalysts were separated by distillation into dimer (40/sup 0/-60/sup 0/C bp), trimer (115/sup 0/-140/sup 0/C), and polymer fractions, which were analyzed by gas chromatography. The ratio of cycle to linear dimers, i.e., 2,4-dimethyl-4- vinyl-1-cyclohexene (DMVCH) and 2,6-dimethyl- 1,3-6-octatriene (DMOT), was correlated with the electronic factor (basicity) of the ligands. In pilot-plant studies, maximum yields of DMVCH, 66% at 80/sup 0/C, and DMOT, 64% at 75/sup 0/C, were obtained with Ziegler systems composed of titanium tetrachloride or tetraiodide, respectively, plus diethylaluminum chloride (DEAC) and 1,4-dioxane. The yields of cyclotrimers, mainly 1,6,9- (A) and 1,5,9- (B) trimethyl- 1,5,9-cyclodecatrienes, depended also on the steric factor (cone angle) of the ligands and the nature of the central atom and were highest, 65% at 65/sup 0/C and 63% at 95/sup 0/C, respectively, with catalysts composed of titanium trichloride, p-NO/sub 2/,o-chlorobenzaldehyde, and DEAC (A) and nickel octooate, triethylaluminum, and certain phosphines (B). Potential applications of oligomer derivatives are discussed.

Research Organization:
Mitsubishi Petrochem. Co. Ltd.
OSTI ID:
6389102
Journal Information:
Ind. Eng. Chem., Prod. Res. Dev.; (United States), Journal Name: Ind. Eng. Chem., Prod. Res. Dev.; (United States) Vol. 18:4; ISSN IEPRA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALDEHYDES
ALKENES
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
CATALYSTS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CHROMATOGRAPHY
CORRELATIONS
CYCLOALKENES
DIENES
DIMERS
DIOXANE
DISTILLATION
FUNCTIONAL MODELS
GAS CHROMATOGRAPHY
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HIGH TEMPERATURE
HYDROCARBONS
IODIDES
IODINE COMPOUNDS
ISOPRENE
LIGANDS
MEDIUM TEMPERATURE
NICKEL COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PH VALUE
PHOSPHINES
PHOSPHORUS COMPOUNDS
PILOT PLANTS
POLYENES
POLYMERIZATION
POLYMERS
SEPARATION PROCESSES
STEREOCHEMISTRY
TERPENES
TITANIUM CHLORIDES
TITANIUM COMPOUNDS
TITANIUM IODIDES
TRANSITION ELEMENT COMPOUNDS
USES
YIELDS
ZIEGLER CATALYST