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  1. #1
    Nikola Dulgiarov's Avatar
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    Glycin Synthesis/Production

    So, I've had this idea in my head ever since I read about glycin and decided to try it as a developing agent. Originally, I tried to buy it from dealers in chemical reagents, only to discover prices in the range or $10-15 to the gram, shipping from Artcraft/Photoformulary is out of the question (I live in Bulgaria).
    I do have p-aminophenol, which I mix Rodinal with; and from what I gather, hydroxyphenyl-glycine can be synthesized from it and monochloroacetic acid(MCA). My search did turn up one old thread there on APUG, but it had only references to science articles and no relevant experiences.
    I have two of the articles outlined in the merck index, but they are somewhat vague as to procedure, focusing more on the structure and properties of the derivatives. What I have done, to no success, is to mix p-aminohenol and MCA in aqueous solution and reflux until dissolution and a color change.
    However, instead of glycin, ongly slightly soluble in water, I get, upon cooling down to 0C, crystals that dissolve readily and respond to a test for paraamniophenol, suggesting presumably a conversion to the HCl salt.
    Has anyone actually done this? I have no relevant experience in organic chemistry, besides very rudimentary reactions like nitrations, dehydrations, etc.
    My chemistry teacher is also not too well acquainted (11-graders here learn nothing ). So anyone, who can chime in with some practical advice, I'd be deeply indebted . Also, if all goes well, I will post a detailed account and references, so that anyone else without access to glycin may try it out.
    PS: I follow safety procedures, and I'm well aware of the toxicity of the compounds above, I have no intentions to harm myself in the process
    Cheers,
    Nick

  2. #2

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    Quote Originally Posted by Nikola Dulgiarov View Post
    ...11-graders here learn nothing ...
    I have no knowledge about Glycin synthesis, but feel compelled to chime in. You clearly learned something, namely excellent English as well as the ability to think logically. Would that most US 11th graders possessed your skills in those areas!

    Best wishes for success. The photography world needs a second source of Glycin; producing it could be a business for you.

  3. #3
    Nikola Dulgiarov's Avatar
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    Thanks Not to wander off-topic too much, but what I have noticed is that students worldwide are becoming more and more alike, mainly due to the spreading popularity of the internet as a means of communicating. But even with a sea of information at their fingertips, students would rather use the net for entertainment and socializing, but that is a whole 'nother story
    Vis. my English... it's a necessity; knowing foreign languages empowers one so
    I do mix developers and chemistry for friends who shoot film, but even at prices 1/2 of store ones, photochemistry is on the bottom of the shopping-priority-list of Bulgarians

  4. #4

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    After a brief search on the net The only reference to a synthesis was that p-aminophenol and chloroacetic acid were allowed to react in a solvent. I assume that the solvent is not water. The solvent may have to be basic in nature to catalyse the reaction.

    Since you have no experience in chemical synthesis I would strongly suggest that you do not attempt to make this chemical. If the solvent is the one I am thinking about then it is particularly nasty to work with.

    So many photographers seem to be ignorant of the lesson of the marketplace. The reason why Glycin and other older developing agents are no longer used is that they did not provide an advantage to counter their increased cost.
    Last edited by Gerald C Koch; 05-19-2013 at 11:32 AM. Click to view previous post history.
    A rock pile ceases to be a rock pile the moment a single man contemplates it, bearing within him the image of a cathedral.

    ~Antoine de Saint-Exupery

  5. #5

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    Quote Originally Posted by Nikola Dulgiarov View Post
    ...I do mix developers and chemistry for friends who shoot film, but even at prices 1/2 of store ones, photochemistry is on the bottom of the shopping-priority-list of Bulgarians...
    I was suggesting that, should you make Glycin available commercially, your market would be worldwide, not limited to Bulgaria. And you'd only have one competitor anywhere else on the globe!

  6. #6
    Nikola Dulgiarov's Avatar
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    The two solvents that I have seen referred to are water and diethyl ether, by Vater in 1888. Meldola in 1917 worked in aqueous solution with the addition of sodium acetate, although a particular reason was not disclosed. He claims precipitating glycin "after digesting a mixture of molar quantities of p-aminophenol and MCA in 20 parts water", but no times, temperatures or experimental setup beyond that are given.
    Working in ether didn't yield a considerably different result, apart from a phase separation of the crystallization water of my chloroacetic acid. Upon evaporating the ether, needle-like crystals of pap.HCl still formed.
    Just as I was speaking about language as empowering, I do have a request to make, a favor to ask anyone, who knows German, maybe also is aware of basic chemistry terminology. Vater's article is and old sca in pdf, OCR fails on it; I am unable to translate the full text, so I only have had a cursory idea of what it says. If anyone is willing to read through some pages that I need and interpret a passage or two, I would be grateful PM me if you you'd like to help, and I'll send you the pdf( I would upload it here, but since it's still copyrighted, I am unwilling to share it publicly; still, if you are interested in having the articles, feel free to contact me )
    Sal, if my plan to enter a US institute of technology and study chemical engineering doesn't get derailed, I expect your suggestion to become more than viable
    Last edited by Nikola Dulgiarov; 05-19-2013 at 11:25 AM. Click to view previous post history. Reason: style

  7. #7

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    nikola

    have you tried the people mentioned in this thread?
    http://www.apug.org/forums/forum37/2...er-europe.html
    or at fadu?
    http://www.film-and-darkroom-user.or...ead.php?t=5192

    it might be easier to find a already made source rather than make it yourself,
    from what i remember, it takes 2 weeks to manufacture from start to finish ...

    good luck !
    john
    silver magnets, trickle tanks sold
    artwork often times sold for charity
    PM me for details

  8. #8
    Nikola Dulgiarov's Avatar
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    Thank you, John. I have seen the links and I have talked to suppliers and importers, who can offer me similar prices. The point of the whole endeavor, I am unwilling to admit, is to satisfy my own interest in chemistry, and to see if I can make a viable point. Purchasing it is the least worry I have, I stressed the price in my first point to kinda "justify" trying to do something that will eventually end up being more expensive and tiresome
    You comment on the time it takes to make glycin makes me wonder if the conversion doesn't occur at a much slower rate than I had imagined (no more than 24hrs), much like Gainer's Metonal, or Rodinal itself, taking several weeks to reach stability. of course, the commercial process probably involves purification steps, such as recrystallization, sublimation, desiccating the final product (although that shouldn't take that long ). But there could be something to it.
    I'll keep trying, keeping in mind safety and sanity

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    Quote Originally Posted by Nikola Dulgiarov View Post
    Thank you, John. I have seen the links and I have talked to suppliers and importers, who can offer me similar prices. The point of the whole endeavor, I am unwilling to admit, is to satisfy my own interest in chemistry, and to see if I can make a viable point. Purchasing it is the least worry I have, I stressed the price in my first point to kinda "justify" trying to do something that will eventually end up being more expensive and tiresome
    You comment on the time it takes to make glycin makes me wonder if the conversion doesn't occur at a much slower rate than I had imagined (no more than 24hrs), much like Gainer's Metonal, or Rodinal itself, taking several weeks to reach stability. of course, the commercial process probably involves purification steps, such as recrystallization, sublimation, desiccating the final product (although that shouldn't take that long ). But there could be something to it.
    I'll keep trying, keeping in mind safety and sanity

    aaahhh, i geddit ..
    totally understand the "i gotta try to make this stuff" point of view
    i just wasn't sure if hadn't seen the other "pre made" alternatives.
    i learned about the time period years ago when you could ask the good
    folks at TPF to send you "the freshest - stuff" and they would say it takes 2 weeks
    and at the end is when it is crushed .. i have no idea what it is, how it is made
    or much else, it just seems to take its time ( drying out ? ) before it can be used.
    and then it has to be used before it becomes use-less ..
    have fun with your mad-science
    john
    silver magnets, trickle tanks sold
    artwork often times sold for charity
    PM me for details

  10. #10

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    Some years ago a friend of mine was severely burned doing a routine synthesis that he had done many times before. On that particular day the reaction mixture decided to explode.

    AS A TRAINED CHEMIST, I WILL SAY IT AGAIN -- UNLESS YOU HAVE A DEGREE IN CHEMISTRY AND ARE FAMILIAR WITH ORGANIC SYNTHESIS AND HAVE ALL THE NECESSARY EQUIPMENT INCLUDING AN EXHAUST HOOD DO NOT ATTEMPT TO MAKE THIS DEVELOPING AGENT OR ANY OTHER ONE.

    I was suggesting that, should you make Glycin available commercially, your market would be worldwide, not limited to Bulgaria. And you'd only have one competitor anywhere else on the globe!
    Encouraging someone to undertake a dangerous synthesis is really not being helpful.
    A rock pile ceases to be a rock pile the moment a single man contemplates it, bearing within him the image of a cathedral.

    ~Antoine de Saint-Exupery

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