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All 10 posts Subject: Succinaldehyd Please login to post Down

politoxicomania
(Stranger)
09-09-03 20:39
No 457963
      Succinaldehyd

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
smile

Vitus_Verdegast
(Hive Bee)
09-09-03 22:36
No 457988
User Picture       2,5-dimethoxytetrahydrofuran

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.

A Dream Within A Dream (http://www.poedecoder.com/Qrisse/works/dreamw.html)

politoxicomania
09-09-03 23:17
      Price
(Rated as: no sources!)

politoxicomania
(Stranger)
09-09-03 23:52
No 458006
      no sources

sorry sorry sorry
i sould read the manual before posting

roger2003
(Hive Bee)
09-11-03 11:55
No 458404
      succindialdehyde

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).

roger2003

Rhodium
(Chief Bee)
09-11-03 13:25
No 458411
User Picture       synthesis of succindialdehyde

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
(Hive Bee)
09-12-03 13:51
No 458658
      succindialdehyde

There are also a lot of ways from furan to 2,5 - dimethoxytetrahydrofuran

Organic Syntheses CV 5, 403

Rhodium
(Chief Bee)
09-12-03 18:23
No 458701
User Picture       2,5-Dimethoxy-tetrahydrofuran from Furan
(Rated as: good read)

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
(Stranger)
09-12-03 19:39
No 458720
      too expensive

good post
good refs
but too expensive
better keep it simple, slow and cheap

pHarmacist
(pHantasticant)
09-13-03 04:18
No 458796
User Picture       i see...

better keep it simple, slow and cheap

...and that would bee?

Point... Counter Point...

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	All 10 posts		Subject: Succinaldehyd		Please login to post		Down


		politoxicomania (Stranger) 09-09-03 20:39 No 457963				Succinaldehyd
						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 (Hive Bee) 09-09-03 22:36 No 457988				2,5-dimethoxytetrahydrofuran
						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. A Dream Within A Dream (http://www.poedecoder.com/Qrisse/works/dreamw.html)



		politoxicomania 09-09-03 23:17				Price (Rated as: no sources!)



		politoxicomania (Stranger) 09-09-03 23:52 No 458006				no sources
						sorry sorry sorry i sould read the manual before posting



		roger2003 (Hive Bee) 09-11-03 11:55 No 458404				succindialdehyde
						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). roger2003



		Rhodium (Chief Bee) 09-11-03 13:25 No 458411				synthesis of succindialdehyde
						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 (Hive Bee) 09-12-03 13:51 No 458658				succindialdehyde
						There are also a lot of ways from furan to 2,5 - dimethoxytetrahydrofuran Organic Syntheses CV 5, 403



		Rhodium (Chief Bee) 09-12-03 18:23 No 458701				2,5-Dimethoxy-tetrahydrofuran from Furan (Rated as: good read)
						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 (Stranger) 09-12-03 19:39 No 458720				too expensive
						good post good refs but too expensive better keep it simple, slow and cheap



		pHarmacist (pHantasticant) 09-13-03 04:18 No 458796				i see...
						better keep it simple, slow and cheap ...and that would bee? Point... Counter Point...

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