Author Topic: Succinaldehyd  (Read 3715 times)

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politoxicomania

  • Guest
Succinaldehyd
« on: September 09, 2003, 01:39:00 PM »
someone out there who prepared succinaldeyd before ?
i figuered out 2,5-dimethoxytetrahydrofuran as a precursor
but it is very expansive,
could someone give a ref about a syntheses from
2,4-butandiacid  or butandiacidanhydrid ?
must be possible!
thanks
:)

Vitus_Verdegast

  • Guest
2,5-dimethoxytetrahydrofuran
« Reply #1 on: September 09, 2003, 03:36:00 PM »
It is not THAT expensive, Fisher has it for $30/100 g and I've seen one photographical supplier that sold it for $3.95/10 g.

Please provide a link or a reference to the procedure you mean.


politoxicomania

  • Guest
Price
« Reply #2 on: September 09, 2003, 04:17:00 PM »

politoxicomania

  • Guest
no sources
« Reply #3 on: September 09, 2003, 04:52:00 PM »
sorry sorry sorry
i sould read the manual before posting

roger2003

  • Guest
succindialdehyde
« Reply #4 on: September 11, 2003, 04:55:00 AM »
2,5 Diemthoxytetrahydrofuran can be converted in quantitative yield to succindialdehyde with HCL or H2SO4 in aqueous solutions without workup.

There is also a way from 1,4 - butanediol to succindialdehyde. If i remember right, there is a patent, maybe 1975, to BASF

Ullmann`s:

Succinaldehyde (1,4-Butanedial)

Some physical properties of succinaldehyde and its CAS registry number are given in Table (8). To avoid spontaneous polymerization of anhydrous succinaldehyde, it is best stored as a cyclic acetal, e.g., 2,5 dimethoxytetrahydrofuran. Aqueous solutions consist mainly of the cyclic hemiacetal 2,5-dihydroxytetrahydrofuran.
Production. Succinaldehyde is prepared by various routes, e.g., reaction of chlorine with tetrahydrofuran and subsequent acid hydrolysis. Hydroformylation of acrolein acetals (mostly cyclic) yields a mixture of 2- and 3-(1,3-dioxan-2-yl)propanal. Hydrolysis of the latter forms 1,4-butanedial Post 141 (not existing).
 
Due to the similar chemical properties, succinaldehyde has been replaced extensively by glutardialdehyde, diminishing its commercial importance significantly.
Uses. Succinaldehyde is used as disinfectant, biological fixative, and cross-linker in thermosetting resins.


Post 141 (not existing)  M. Tamura, S. Kumano, Chem. Econ. Eng. Rev. 12  (1980) 32.J. Maeda, R. Yoshida, Bull Chem. Soc. Jpn. 41 (1968) 2969.BASF, DE 2 401 553, 1975(R. Kummer).


Rhodium

  • Guest
synthesis of succindialdehyde
« Reply #5 on: September 11, 2003, 06:25:00 AM »
I researched the synthesis of succindialdehyde a few years ago, and I found that there is really no better method (in terms of ease, time and money) than the acid hydrolysis of commercially available 2,5-dimethoxytetrahydrofuran, even if it isn't the cheapest of chemicals. The second best method is the ring-opening of pyrrole with hydroxylamine, followed by hydrolysis of the formed  succindialdehyde dioxime. Refs upon request.

roger2003

  • Guest
succindialdehyde
« Reply #6 on: September 12, 2003, 06:51:00 AM »
There are also a lot of ways from furan to 2,5 - dimethoxytetrahydrofuran

Organic Syntheses CV 5, 403

Rhodium

  • Guest
2,5-Dimethoxy-tetrahydrofuran from Furan
« Reply #7 on: September 12, 2003, 11:23:00 AM »

Organic Syntheses, CV 5, 403

(http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0403) is unfortunately a synthesis of  2,5-dimethoxy-2,5-dihydrofuran from furan - to arrive at 2,5-dimethoxy-tetrahydrofuran you need to subject the dihydrofuran to catalytic hydrogenation (best accomplished with Raney-Ni/80–100°C/1700–2000 psi./45–60 min.), see the following ref:

Preparation and Reactions of Dialkoxytetrahydrofurans
Jørgen Fakstorp, Dolores Raleigh, L. E. Schniepp
J. Am. Chem. Soc. 72(2), 869-874 (1950)

politoxicomania

  • Guest
too expensive
« Reply #8 on: September 12, 2003, 12:39:00 PM »
good post
good refs
but too expensive
better keep it simple, slow and cheap

pHarmacist

  • Guest
i see...
« Reply #9 on: September 12, 2003, 09:18:00 PM »
better keep it simple, slow and cheap

...and that would bee?