Name: Arya

Message: I am suppose to make a project for chemistry in which I am supposed to make dye out of general reagents available in an ordinary lab. Could you help?

I remember a series of labs in my advanced chemistry class in high school in which, if I recall correctly, we used toluene to make nitrobenzene, which we then used to make aniline. The final step was to use our products to make dyes, presumably azo dyes.  It was great fun. In my case, I selected the blue dye option, but made some slight error and ended up with green. We mordanted cotton shirts with alum and then dyed them with the dyes we had made, but, as none of us knew anything about dyeing at the time, all of the dyes washed out the first time they were laundered. I remember that just a tiny amount of color remained in my shirt, enough to make it look dirty, but not to give it any real color.

A very old chemistry lab manual, William Simon's 1898 Manual of Chemistry, A Guide to Lectures and Laboratory Work for Beginners in Chemistry, on page 545 says that aniline and toluidine, when "treated with oxidizing agents such as arsenic oxide, hypochlorites [such as household bleach], chromic or nitric acid, etc., various substances are oobtained which are either themselves distinguished by beautiful colors or may be converted into numerous derivatives showing all the various shades of red, blue, violet, green, etc." You can read this book online in Google Books.

Your library should be able to get you the following article via interlibrary loan, if they don't subscribe to the Journal of Chemical Education: "Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions" (James V. McCullagh, and Kelly A.Daggett, J. Chem. Educ. 2007, 84: 1799). Here is the abstract:

An online laboratory guide for making dye in a college organic chemistry lab can be found in the Online Chemistry Lab Turtorials at Washington University, in a chapter entitled "Aromatic Chemistry: Synthesis of o-Nitroaniline and p-Nitroaniline via a Multi-Step Sequence":

Another lab experiment is detailed in "Diazonium Coupling Reaction of p-Nitrobenzenediazonium sulfate and N,N -Dimethylaniline: Synthesis of p-(4-nitrobenzeneazo)-N,N-dimethylaniline ", or try "Multi-step Synthesis: Preparation of Organic Dyes".
 
You can view a video of a lab in which naphthol dyes are synthesized. Here are links to the description of the experiment and to the video.

For methods of synthesizing Procion MX (dichlorotriazine) dyes, see David R. Waring and Geoffrey Hallas's 1990 book,  "The Chemistry and Application of Dyes (Topics in Applied Chemistry)".  At $192, it is too expensive for a student to buy, but you may be able to find it at the public library or in the library of your educational institution. There are also recipes for the synthesis of dichlorotriazine dyes in the appendix of Victor B. Ivanov's Reactive Dyes in Biology.

With all of these possibilities, I think you should not have any trouble in selecting a suitable method for synthesizing dye out of the reagents available in an ordinary lab.

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