{"id":42292,"date":"2021-03-17T17:11:32","date_gmt":"2021-03-17T21:11:32","guid":{"rendered":"https:\/\/seniordesign.digitalscholar.rochester.edu\/che2021\/?p=65"},"modified":"2022-04-13T11:39:26","modified_gmt":"2022-04-13T15:39:26","slug":"ducklifors","status":"publish","type":"post","link":"https:\/\/www.hajim.rochester.edu\/senior-design-day\/ducklifors\/","title":{"rendered":"Purification of LUV Dye Using Column Chromatography"},"content":{"rendered":"\n
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Purification of LUV Dye Using Column Chromatography<\/h2>\n\n\n\n

Quinton Dang, Waad Magram, Zhiwei Wang<\/em><\/p>\n<\/div>\n<\/div>\n\n\n\n

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Project Mentor<\/h3>\n\n\n\n

Mark Juba, University of Rochester <\/strong><\/p>\n<\/div>\n\n\n\n

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Project Sponsor<\/h3>\n\n\n\n

Brian Cleary, Kodak <\/strong><\/p>\n<\/div>\n<\/div>\n\n\n\n

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Motivation<\/h2>\n\n\n\n

At Eastman Kodak, specialty chemicals, inks, and dispersions are manufactured for application in imaging products and photographic films. <\/p>\n\n\n\n

The LUV dye, [3-(dihexylamino)allylidene]malononitrile, is one such chemical that is used in the production of photographic film. Kodak manufactures crude LUV dye containing impurities that must be removed prior to being implemented into motion picture film.<\/p>\n<\/div><\/div>\n\n\n\n

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In the crude LUV dye, there are two main impurities present. These impurities have boiling points that are both below and above the boiling point of the pure LUV dye. Specifically, the impurity dihexylamine has a boiling point of 192-195o<\/sup>C1<\/sup>. The other impurity, quat-propylamine, has a boiling point greater than 400.6o<\/sup>C. For pure LUV dye, the boiling point is 400.6o<\/sup>C at 1 atm2<\/sup>.<\/p>\n\n\n\n

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Figure 1: Impurities in Crude LUV Dye. Dihexylamine (left), Quat-propylamine cation (middle), and Quat-propylamine anion (right). <\/figcaption><\/figure><\/div>\n\n\n\n

At Kodak, the current practice for the purification of pure LUV dye involves contracting a toll manufacturer to use a two-pass wiped-film evaporator to separate the impurities from the crude LUV dye. However, given the cost associated with contracting the toll manufacturer for the purification process, Kodak sought out the team to devise a lab-scale purification process which upon scale-up would be able to purify 2 kilograms of crude LUV dye per day.<\/p>\n<\/div>\n<\/div>\n\n\n\n\n\n\n\n

Project Background<\/h2>\n\n\n\n

To purify the crude LUV dye at Kodak, a toll manufacturer is contracted to operate a wiped-film evaporator (WFE) for the separation of dihexylamine and quat-propylamine from the crude LUV dye. Prior to the start of the project, the cost associated with purifying a kilogram of crude dye was $500\/kg. At Kodak, 5 to 7 kg of crude LUV dye were purified annually, making the cost of the process approximately $2,500-3,500 per year. Also, purification of the crude dye via WFE netted a percent yield of 70% pure LUV dye recovered. With this in mind, the team was tasked with creating a lab-scale purification process that could:<\/p>\n\n\n\n

  1. Produce purified LUV dye with the impurities being below the upper specification limits (USL) set by Kodak<\/li>
  2. Obtain percent yields that are equal to or greater than the percent yield associated with the WFE purification process<\/li>
  3. Create a process that is cheap, easily operated, and scalable from the lab prototypes to a process that can purify 2 kg\/day in-house<\/li><\/ol>\n\n\n\n
    Analytical Method<\/strong><\/td>Impurity<\/strong><\/td>USL<\/strong><\/td>Measured<\/strong><\/td>Boiling Point (\u00b0C)<\/strong><\/td><\/tr>
    UV-Vis Spectroscopy<\/td>Quat-proplymine<\/td>0.1% W\/W%<\/td>3.4 wt%<\/td>>400.6<\/td><\/tr>
    GC with Flame-Ionization Detector (GC-FID)<\/td>Dihexylamine<\/td>1.0 area%
    0.5 area%<\/td>    		0.4 area%
    0.7 area%<\/td>    		192-195<\/td><\/tr><\/tbody><\/table>
    Table 1: Impurities concentrations and boiling points <\/figcaption><\/figure>\n\n\n\n

    Stakeholder Impact <\/h2>\n\n\n\n

    Eastman Kodak Company, both the project sponsor and main stakeholder, was greatly involved with the team throughout the semester. When constructing the lab-scale process, Kodak impacted and assisted the team in the following ways: <\/p>\n\n\n\n