[Eduardo Orjuela]

Hello, i am trying to understand this reaction. I am not sure if the OH group is actally reacting or the OH from the acid is going to react. What conditions will it need? Will it happen?

[Babcock_Hall]

At neutral pH values, is the hydroxyl group at carbon-6 of the glucose residue a good leaving group?  If not, how could it be converted into a good leaving group.

[orgopete]

Is that the product from that reaction or are you trying to propose how this modified cellulose could be prepared? The product written is one of the least likely products I'd predict from this acid catalyze do reactions. Am I just on the wrong trail?

[Eduardo Orjuela]

At neutral pH values, is the hydroxyl group at carbon-6 of the glucose residue a good leaving group?  If not, how could it be converted into a good leaving group.

It is turned into water and expulsed by the molecule of the glycolic acid.

[Eduardo Orjuela]

Is that the product from that reaction or are you trying to propose how this modified cellulose could be prepared? The product written is one of the least likely products I'd predict from this acid catalyze do reactions. Am I just on the wrong trail?

I found this rection on the literature. The industrial process is done by another reaction (using monochloro acetic acid) but i am not sure why this one isnt used. That is what i am not understanding and what i need to know.

[orgopete]

I agree with the chloroacetic acid route. I'm still disbelieving the other supposed route.

[Arkcon]

I found this rection on the literature. The industrial process is done by another reaction (using monochloro acetic acid) but i am not sure why this one isnt used. That is what i am not understanding and what i need to know.

That's not really an organic chemistry question, however.  This is more of a process chemistry question, dealing with concepts of massive scale, or cost of materials, and the like.  You can try to infer, by comparing the two reactions -- does one generate too much heat, that in large bulk would cause side-reactions or other failure, etc.  You can't be surprised however, if this simply ends up being a trade secret, and that no one who even knows, will actually want to tell you.

[Babcock_Hall]

At neutral pH values, is the hydroxyl group at carbon-6 of the glucose residue a good leaving group?  If not, how could it be converted into a good leaving group.

It is turned into water and expulsed by the molecule of the glycolic acid.

With all due respect, you did not exactly answer my questions.  For the moment, let's set aside the question of whether or not this is the way in which this gel is actually produced, and just look at this as a mechanistic problem.  The hydroxyl group is not a good leaving group, because it would depart as hydroxide ion, which is a very poor leaving group.  How can it be made into a better one with acid.

[orgopete]

I'm not a sugar chemist, but can one treat a sugar with acid and selectively replace the primary alcohol without affecting the glycoside linkage? I would have said no, but the comment suggests I am wrong. Please elaborate.

[Babcock_Hall]

orgopete,

You raise a good point, and I also doubt that the route originally provided is the actual synthetic process.