Solubility of Cellulose in Ammonia Salt Solutions

Scherer, Philip C.

doi:10.1021/ja01362a012

Cited by 18 publications

(9 citation statements)

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“…The results of Wagner and Pacsu [34] are not included' as they were unable to separate the mixture of degradation products completely. ' The discrepancy between Rivlin's and our work can be understood because his permethylation procedure by the Haworth-Pacsu method [ 11,12,19] followed by an &dquo;exchange methylation&dquo; [ 14,28,29,30] gave formaldehyde losses of 25% and 14% with the highest and medium DS samples, respectively.…”

Section: Resultscontrasting

confidence: 75%

“…They include moisture regain [5,30] , infrared deuteration [11. 12, 13, 16, 28], formylation [ 18,21,24], iodine sorption [26], acid hydrolysis [20,23,25,27], and periodate~oxi-dation [ 2,6,29 ] . ' A series of cotton and partially methylated cotton fabrics have been examined by these techniques and the results obtained have been compared.…”

Section: Discussionmentioning

confidence: 99%

“…. Our permethylation process consists essentially of a 4-8-fold methylation with dimethylsulfate and 'sodium hydroxide in dimethylsulfoxide [32] followed , by a 2-4-fold &dquo;exchange&dquo; methylation of sodium cellulosate (made with sodium butoxide) by methyl iodide [14,28,29,30] . The completeness of methylation was confirmed by infrared spectroscopy (disappearance of OH stretching band).…”

Section: And D Q U O ;mentioning

confidence: 99%

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Investigations on the Chemical Constitution of Cotton Cross-Linked With Formaldehyde

Patel

Rivlin

Samuelson

et al. 1968

Textile Research Journal

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Cotton was cross-linked with formaldehyde by various methods (Form D, W, and V processes). The cellulose formals containing 1-4% formaldehyde were permethylated by a series of dimethylsulfate/dimethylsulfoxide treatments followed by exchange methylations of sodium cellulosate with methyl iodide in n -butanol. The permethylated cellulose formals were hydrolyzed in sulfuric acid and the methyl glucoses thus formed were reduced to the respective sorbitols. The mixture of these sorbitols, after suitable blocking of the free hydroxyl groups, was separated and quantitatively analyzed by gas-liquid phase chromatography. The results indicate a decreasing reactivity of the hydroxyl groups in the sequence C(6)>C(2)>C(3), the occurrence of 2,3-methylene linkages, and an average length of the oxymethylene cross links of between 1,3 and 2,0. The constitution of these cellulose formals is influenced by the type of formaldehyde application. Discrepancies between our results and those of other investigators are explained by their incomplete methylation, substitution of methylene cross links by methyl groups in permethylations, and incomplete separation of the degradation products.

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Section: Resultscontrasting

confidence: 75%

Section: Discussionmentioning

confidence: 99%

Section: And D Q U O ;mentioning

confidence: 99%

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Investigations on the Chemical Constitution of Cotton Cross-Linked With Formaldehyde

Patel

Rivlin

Samuelson

et al. 1968

Textile Research Journal

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“…Solubility of Cellulose in the Ethylenediamine/Salt System In the early work, 1,18,19 it was revealed that several inorganic salts such as NH 4 SCN, LiSCN, NaSCN, KSCN, NaNO 3 , NaI, and NH 4 I were dissolved in liquid NH 3 and NH 2 NH 2 and that some of the solutions had high dissolving power for cellulose. However, in the NH 3 system, only the solution of NH 4 SCN was kept liquid state under ambient conditions of temperature and pressure.…”

Section: Resultsmentioning

confidence: 99%

New Solvents for Cellulose. II. Ethylenediamine/Thiocyanate Salt System

Hattori

Abe

Yoshida

et al. 2004

Polym J

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ABSTRACT:The ethylenediamine/thiocyanate salt system was found to be a new solvent for cellulose. The solubility, dissolution behavior, solution properties, and cellulose recovered from the solutions were investigated. The dissolution took place at room temperature, and the maximum solubility achieved was 16 % (w/w) for cellulose of DP210 in the ethylenediamine/sodium thiocyanate 54/46 (w/w). The dependence of cellulose solubility on DP is also described. Tracing the dissolution behavior of the cellulose by CP/MAS 13 C NMR measurements revealed the polymorphic conversion of cellulose I to III to amorphous structure during the dissolution process. The cellulose dissolved was stable for 30 days storage at room temperature. Microscopic observations and steady-shear viscosity measurements of the solutions indicated mesophase formation of cellulose in the ethylenediamine/sodium thiocyanate system. This anisotrpoic phase appeared from ca. 10 % (w/w) cellulose with DP210 and greatly depended on the cellulose concentrations. Coagulation studies disclosed that cellulose II and amorphous cellulose were recovered from the cellulose/ethylenediamine/thiocyanate salt solutions when water and alcohol were used as a coagulant, respectively. It was suggested that this solvent system has high potential for cellulosic fiber and film formations.KEY WORDS Cellulose / Cellulose Solvent / Cellulose Solution / Amine / Thiocyanate / Dissolution Mechanism / Regenerated Cellulose / Cellulose is a linear and high molecular weight polymer as well as a natural, renewable, and biodegradable material. However, due to its considerable inter-and intramolecular hydrogen bonds, cellulose neither melts nor dissolves readily in common solvents. The complicated crystalline and amorphous morphology has also been preventing cellulose from being exploited to its fullest potential. Any process which simplifies or hastens the dissolution of cellulose represents a significant step forward in the development of cellulose as a viable, ecologically favorable polymer source. Furthermore, the ability of cellulose and cellulose derivatives to form mesophase in certain solvents has resulted in attempts to develop high-performance cellulosic fibers and membrane. At present, there are a few solvents that can directly dissolve cellulose without heavy metal complexation and any chemical derivatization, which are lithium chloride/dimethyl acetamide (LiCl/DMAc), 3 N-methylmorpholine-N-oxide/water (NMMO/H 2 O), 4 calcium thiocyanate/water (Ca(SCN) 2 /H 2 O), 5 etc. Quite recently, ionic liquids containing 1-butyl-3-methylimidazolium cations were discovered to dissolve high M w pulp (DP % 1000) with 10 % (w/w) at elevated temperatures. 6 However, almost known solvents still have some undesirable points, for example, chemical safety, environmental concern, degradation of cellulose, requirements of high temperatures and/or pretreatment of cellulose, poor mechanical properties of the cellulose recovered, and high cost for commercial use.We have been studied new solvent for ...

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“…( 1) with a correlation coefficient of 0.99 613 = 1.5325 -0 . 7 2 5~ (1) where w is weight fraction of NH4SCN in the solvent.…”

Section: Methodsmentioning

confidence: 99%

Lyotropic mesophases of cellulose in the ammonia/ammonium thiocyanate solvent system: Phase relationships

Yang

Cuculo

Theil

1992

J Polym Sci B Polym Phys

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Mesophase formation of the cellulose/NH3/NH4SCN system has been studied as a function of system composition at 25°C. Compositions for incipience of mesophase formation and for wholly anisotropic phase formation have been determined and relevant phase diagrams constructed. The biphasic gap narrowed when the solvent composition approached 75.5 weight percent NH4SCN and as the cellulose concentration decreased. As solvent composition was changed, the minimum cellulose volume fraction for mesophase formation ranged between 0.02 to 0.045.

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Solubility of Cellulose in Ammonia Salt Solutions

Cited by 18 publications

References 0 publications

Investigations on the Chemical Constitution of Cotton Cross-Linked With Formaldehyde

Investigations on the Chemical Constitution of Cotton Cross-Linked With Formaldehyde

New Solvents for Cellulose. II. Ethylenediamine/Thiocyanate Salt System

Lyotropic mesophases of cellulose in the ammonia/ammonium thiocyanate solvent system: Phase relationships

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