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Removal of alcohols and water from a methylcyclopentadiene recycle stream in a process for the synthesis of methylcyclopentadienyl manganese tricarbonyl

a technology of methylcyclopentadiene and recycle stream, applied in the field of synthesis, can solve the problems of compromising the overall mmt yield and becoming expensiv

Inactive Publication Date: 2006-01-19
AFTON CHEMICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0006] One aspect of the invention relates to a method of extracting water and alcohol from a mixture comprising methylcyclopentadiene, water and alcohol, comprising (a) providing an organic material comprising methylcyclopentadiene, water and alcohol; (b) adding water to the organic material to create organic and aqueous fractions; and (c) separating the organic and aqueous fractions; wherein the separated organic fraction comprises less w

Problems solved by technology

These alkoxides and hydroxide will compete with MCP-Na chemistry further down the process for making MMT, hence compromising overall MMT yield.
If allowed to continue, this can become expensive because the levels of these contaminants in the process are being boosted as more are generated from DMC cleavage each cycle.

Method used

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  • Removal of alcohols and water from a methylcyclopentadiene recycle stream in a process for the synthesis of methylcyclopentadienyl manganese tricarbonyl
  • Removal of alcohols and water from a methylcyclopentadiene recycle stream in a process for the synthesis of methylcyclopentadienyl manganese tricarbonyl

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0027] An MCP recycle stream from a MMT purification system was found to contain 0.361 wt % methanol, 0.39 wt % water and 1.078 wt % 2-methoxyethanol. To an aliquot of this organic material was added 2.5 vol % water. The resulting biphasic product was agitated to extract the three protic impurities into the aqueous layer. The liquid mixture was allowed to settle and the organic layer separated from the aqueous layer. Analysis of the organic layer showed a dramatic decrease in methanol of 82.8%, water of 55.9%, and 2-methoxyethanol of 64.7%. The process was repeated on a fresh aliquot of recycle MCP, but this time the wash was carried out with 5 vol % water. This doubling of the water layer did not significantly improve on the purification process (see Table 1).

TABLE 1Removal of protic contaminants methanol, water, and 2-methoxyethanolfrom MCP recycle stream in a commercial scale MMT productionprocess by washing the organic material with waterImpurityInitial2.5% H2OImpurity5.0% H2O...

example 2

[0028] An MCP recycle stream from one of the MMT purification systems was found to contain 0.68 wt % methanol, 0.69 wt % water and 1.62 wt % 2-methoxyethanol. This material was contacted with a bed of UOP AZ molecular sieve. Subsequent analysis of the sieve treated MCP recycle showed a significant decrease in methanol of 79.4%, water of 97.1%, and 2-methoxyethanol of 77.2%. (see Table 2).

TABLE 2Removal of protic contaminants methanol, water,and 2-methoxyethanol from MCP recycle stream ina commercial scale MMT production process by treatingthe organic with UOP AZ molecular sieve.UOP AZImpurityInitialMolecularImpurityComponentwt %SieveRemoved (%)Methanol0.680.1479.4Water0.690.0297.12-Methoxyethanol1.620.3777.2

[0029] It is to be understood that the reactants and components referred to by chemical name anywhere in the specification or claims hereof, whether referred to in the singular or plural, are identified as they exist prior to coming into contact with another substance referred ...

example 3

Optimization of Water Amount into the Liquid / Liquid Separator

[0031] The LX 204 Liquid / Liquid Extractor (Rousselet Robatel, Annonay, France) was fed with a MCP stream contaminated with 2.87% DMC, 0.57% 2-methoxyethanol, 0.02% water, and 0.08% methanol. The LX 204 Liquid / Liquid Extractor was run with the water wash stream in batches of 0.0%, 0.75%, 2.00% and 4.00%, respectively. As the amount of water in the secondary stream into the Extractor increases, the level of contaminants in the MCP stream exiting the Extractor decreases, as shown in FIG. 1.

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Abstract

The field of the present invention is the synthesis of a manganese-containing organometallic compound—methylcyclopentadienyl manganese tricarbonyl. More specifically, a key raw material in the synthesis process is treated to reduce the amount of protic side products in the material, thereby improving the yield of the overall synthesis.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This patent application is a continuation-in-part of patent application Ser. No. 10 / 800,784 filed Mar. 15, 2004, which is hereby incorporated herein by reference in its entirety.FIELD OF THE INVENTION [0002] The field of the present invention is the synthesis of a manganese-containing organometallic compound—methylcyclopentadienyl manganese tricarbonyl. More specifically, a key raw material in the synthesis process is treated to reduce the amount of protic side products in the material, thereby improving the yield of the overall synthesis. BACKGROUND OF THE INVENTION [0003] Methylcyclopentadiene (“MCP”) is a key raw material in the synthesis of methylcyclopentadienyl manganese tricarbonyl (“MMT”). The first step of the reaction sequence involves reacting excess MCP with sodium metal in an ether solvent to generate a process intermediate complex, MCP-Na. For economic reasons, the excess MCP is recovered in the product distillation step, ...

Claims

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Application Information

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IPC IPC(8): B01D11/00C07C7/10C07C7/13C07F13/00
CPCC07C7/10C07C7/13C07C2101/10C07C13/08C07C2601/10
Inventor MARCHAND, DAVID MARKKADKHODAYAN, ABBAS
Owner AFTON CHEMICAL