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The composition of a higher olefin fraction from targetted ethylene oligomerisation processes and use in detergent applications

IP.com Disclosure Number: IPCOM000149847D
Publication Date: 2007-Apr-10
Document File: 6 page(s) / 103K

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The IP.com Prior Art Database

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The composition of a higher olefin fraction from targetted ethylene oligomerisation processes and use in detergent applications

Introduction

Commercially important higher olefins (C6+) are used in applications such as comonomers and as feedstocks for surfactant raw materials[i].  These olefins are produced as non-targetted products and separated from various process streams.  Newer processes such as oligomerisation produce a distribution of the olefins throughout the range.  These non-targetted routes lead to the production of a range of olefins that need to be sold into other applications than the target olefin range.  Targetted olefin production by trimerisation and tetramerisation produces target olefins – hexene and octene in higher concentrations.   A comparison of some oligomerisation processes shown in figure 1 shows the typical distribution of the olefins from oligomerisation processes.      

 

 

 

 

 

Figure 1: A comparison of product distributions from ethylene oligomerisationibid

Targetted Olefin Oligomerisation

The non-targetted oligomerisation processes such as the Chevron, Innovene and Shell processes produce olefins in the co-monomer and detergent ranges.  The trimerisation and tetramerisation process produces, in addition to co-monomer range olefin, other secondary products olefins in the detergent range (figure 1). 

  

Figure 2: An example of PNP based ligands used for tetramerisation and trimerisation of ethylene[ii]

An example of such a catalyst system (figure 2) shows a chromium-based catalyst system with polar-substituted diphosphinoamine ligands.  This system is selective for either trimerisation or tetramerisation of ethylene, depending on the position of the polar groups on the aryl rings.

The trimerisation and tetramerisation reactions produce in addition to hexene and octene other secondary reaction products in the C10-C14 range.

Mechanism of production of Secondary Products

The production of secondary products in trimerisation and tetramerisation has been reported.  The formation of branched C10 products may then readily be explained by co-trimerisation reactions of ethylene with formed 1-hexene.

Figure 3: The Possible Mechanism for the Formation of C10-C14 Branched Secondary Products[iii]

Similarly the formation of C12 products may be explained by the co-tetramerisation of ethylene with 1-hexene and co-trimerisation of ethylene with 1-octene and finally, branched C14 products arise from the co-tetramerisation of ethylene with 1-octene. For example, Overett et al[iv] have demonstrated that the major branched C14 product in a tetramerisation reaction mixture is 7-methylenetridecane, indicating that the oxidative addition of ethylene and 1-octene/1-hexene occurs in a 1,2-regioselective fashion. This premise is also consistent with recent observations by Bowen and Wass[v] on t...