Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Mixed carboxylic-phosphoric acid anhydride
morsagh
Hazard to Others
***




Posts: 187
Registered: 20-2-2014
Member Is Offline

Mood: No Mood

[*] posted on 12-1-2016 at 08:03
Mixed carboxylic-phosphoric acid anhydride


How can be mixed carboxylic-phosphoric acid anhydride (like 1,3-bisphosphoglycerate) prepared synthetically? For example if i want to produce phosphoacetic anhydride i canĀ“t just boil phosphoric acid with acetic because normal acetic anhydride is produced, so are there any other ways? Thank you for help
View user's profile View All Posts By User
Kagutsuchi
Hazard to Self
**




Posts: 51
Registered: 21-6-2015
Location: Hungary
Member Is Offline

Mood: Happy

[*] posted on 12-1-2016 at 08:27


It is mere speculation, but maybe it can be produced by the carbonylation of organic alcohol-phosphoric acid-esters, for example the phosphoacetic anhydride could be produced from methyl-phosphate.
View user's profile View All Posts By User
DraconicAcid
International Hazard
*****




Posts: 4356
Registered: 1-2-2013
Location: The tiniest college campus ever....
Member Is Offline

Mood: Semi-victorious.

[*] posted on 12-1-2016 at 08:39


If we're going to speculate, I would guess the reaction of acetic acid with POCl3.



Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
View user's profile View All Posts By User
morsagh
Hazard to Others
***




Posts: 187
Registered: 20-2-2014
Member Is Offline

Mood: No Mood

[*] posted on 12-1-2016 at 09:33


I think POCl3 with carboxylic acid produce just acyl chloride? Carbonylation seems very extreme to try... No studies about preparation of these anhydrides?
View user's profile View All Posts By User
Nicodem
Super Moderator
Thread Moved
12-1-2016 at 09:57
UC235
National Hazard
****




Posts: 565
Registered: 28-12-2014
Member Is Offline

Mood: No Mood

[*] posted on 12-1-2016 at 10:55


There's literature on them, but it is fairly scarce. A search for a model compound, acetylphosphoric acid (acetyl phosphate) gives this paper which uses ketene and phosphoric acid.

https://gmwgroup.harvard.edu/pubs/pdf/69.pdf

The references list contains preps using acetyl chloride, namely http://www.jbc.org/content/153/2/571.full.pdf

Acetyl chloride and Silver Diammonium Phosphate give ~70% yield isolated as the silver salt.

Isopropenyl acetate can be coaxed into reacting with phosphoric acid in the presence of sulfuric acid to gives 60-70% yield isolated as dilithium acetylphosphate.

http://www.jbc.org/content/185/2/549.full.pdf

An excess of acetic anhydride reacts with triethylammonium dihydrogen phosphate to give acetyl phosphate which is isolated as the dilithium salt. No yield seems to be given, but it is substantially free of contaminating inorganic phosphate.

http://www.jbc.org/content/244/7/1846.full.pdf
View user's profile View All Posts By User

  Go To Top