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Stabilization of olefin metathesis product mixtures

A product mixture and olefin metathesis technology, which is applied in the preparation of organic compounds, hydrocarbons, hydrocarbon purification/separation, etc., can solve the unsolved problems of stable olefin metathesis product mixtures against double bond isomerization and decomposition

Inactive Publication Date: 2007-07-25
DOW GLOBAL TECH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The problem with homogeneous catalysts, even with exceptional activity and selectivity, is that the catalyst (including the catalytic metal) should be recovered from the olefin metathesis product mixture for economical purposes
References address decolorization of polymers but do not address stabilization of olefin metathesis product mixtures against double bond isomerization and decomposition

Method used

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  • Stabilization of olefin metathesis product mixtures
  • Stabilization of olefin metathesis product mixtures
  • Stabilization of olefin metathesis product mixtures

Examples

Experimental program
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preparation example Construction

[0059] Preparation of Olefin Metathesis Product Mixture

[0060] In a dry box, a toluene solution of the catalytic ruthenium complex (0.01 M) was prepared, bis(tricyclohexylphosphine)benzylidene ruthenium dichloride (Grubb's catalyst). Methyl oleate (Aldrich Company) was degassed with nitrogen and passed through an activated alumina column before use. In a dry box, the following reagents were added to the reactor: methyl oleate (3.50 g, refined as described above), tetradecane (0.50 g, used as an internal standard for gas chromatographic analysis), and catalyst solution (265 µl, 0.01M solution). The molar ratio of methyl oleate to ruthenium is 4452 / 1. The reactor was sealed, removed from the dry box, and connected to an ethylene manifold (ethylene, 99.8% purity, polymer grade). Olefin metathesis was carried out at 60 psig ethylene (413.7 kPa) and 30°C for 4 hours. An aliquot sample was removed from the reactor and analyzed by gas chromatography. A mixture of olefin meta...

Embodiment 1-14

[0062] A general method for stabilizing olefin metathesis product mixtures and removing catalytic metals from such mixtures is described below. The crude metathesis product mixture obtained above containing 65 parts per million ruthenium (10 ml aliquots) was slurried with adsorbent (700 mg) in air at room temperature (22 °C) and ambient pressure for 3 h . At the end of the contact time, the mixture was filtered through a Teflon brand tetrafluoroethylene fluorocarbon polymer filter (0.45 micron diameter) to obtain a stable mixture of olefin metathesis products. The stable mixture was analyzed for ruthenium content by inductively coupled plasma mass spectrometry (ICP-MS).

[0063] The general method above was performed with each of the following sorbents: Westvaco Nucal TM SA brand charcoal (Exp.1), once used Westvaco Nuchar TM SA brand carbon (Exp.2), WestvacoNuchar TM SN brand charcoal (Exp.3), Westvaco Nuchar modified by copper TM Brand Charcoal (Exp.4), Cabot Monarch...

Embodiment 15-16

[0070] Examples 15-16: Evaluation of stability of metathesis reaction mixtures

[0071] To determine the stability of olefin metathesis product mixtures to olefin isomerization, two such products containing 9-decenoate methyl ester and ruthenium concentrations of 100 ppb (Ex. 15) and 423 ppb (Ex. 16) were included The mixture was heated to 200-220°C and olefin isomerization was monitored by gas chromatographic analysis. Table 2 illustrates the effect of heating cycles on the isomerization of methyl 9-decenoate.

[0072] Table 2. Effect of [Ru] on the stability of olefin metathesis product mixtures

[0073] Example

[Ru](ppb)

heating temperature

(℃)

heating time

(h)

% isomerized 9-decane

methyl acrylate

15 a

100

210-220

2.7

0.2

16 b

423

200

1.0

26.3

[0074] CE-1 c

66,500

175

175

1.0

4.0

27.5

48.1

...

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Abstract

The invention relates a process of stabilizing an olefin metathesis product mixture, preferably, against double bond isomerization and thermal and chemical degradation. The process involves (a) contacting an olefin metathesis product mixture comprising one or more olefins produced in a metathesis process, a metathesis catalyst comprising a catalytic metal and one or more ligands, optionally, one or more metathesis catalyst degradation products, and optionally, one or more metals derived from sources other than the catalyst or catalyst degradation product(s), with an adsorbent, more preferably carbon; or alternatively, (b) subjecting the olefin metathesis product mixture to a two-step distillation, preferably, including short path wiped-film evaporation. A stabilized olefin metathesis product mixture is disclosed containing one or more olefins obtained in a metathesis process and having a total concentration of metal(s) of less than about 30 parts per million by weight.

Description

[0001] This application is a divisional application of a Chinese patent application with the application number 03824598.1, the filing date is September 26, 2003, and the invention title is "Stabilization of Olefin Metathesis Product Mixture". [0002] Cross References to Related Applications [0003] This application claims the benefit of US Provisional Patent Application Serial No. 60 / 421,355, filed October 24,2002. Background of the invention [0004] In a first aspect, the present invention relates to a method of stabilizing olefin metathesis product mixtures, preferably against double bond isomerization and against thermal and chemical degradation. In a second aspect, the present invention relates to stable olefin metathesis product compositions. In a third aspect, the present invention is directed to a method of removing metals from an olefin metathesis product mixture. [0005] Olefin metathesis processes generally involve the conversion of two reactant olefins to on...

Claims

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Application Information

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IPC IPC(8): C07C7/00C07C7/04C07C11/02C07C7/12C07C67/54C07C69/533C07C67/56C07C69/54
CPCC07C67/54C07C7/12C07C7/04C07C67/56C07C7/005
Inventor K·A·伯德特B·R·莫洪P·H·欧阳
Owner DOW GLOBAL TECH LLC
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