US1817994A - Process of making cellulose nitro acetate - Google Patents

Process of making cellulose nitro acetate Download PDF

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US1817994A
US1817994A US392257A US39225729A US1817994A US 1817994 A US1817994 A US 1817994A US 392257 A US392257 A US 392257A US 39225729 A US39225729 A US 39225729A US 1817994 A US1817994 A US 1817994A
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cellulose
weight
acid
parts
acetate
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US392257A
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Lock Ludwig
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B7/00—Preparation of cellulose esters of both organic and inorganic acids

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  • the present invention relates to a process of preparing cellulose nitro acetates.
  • the bleached cellulose serving as the starting material is preliminarily nitrated by a mild treatment with a weakly acting example, to a nitrogen content of 2%, freed from adhering acid, washed and dried, after which acetylation is effected in the second stage of the process by one of the known technical methods.
  • the present invention describes a new process of producing cellulose nitro acetates in one and the same process in a technically easy and simple manner. sists in acetylating the cellulose at temperatures between about and 100 C. by means of acetic acid and acetic anhydride in the presence of a calculated amount of a salt of nitric acid with a weak inorganic or organicase, such as for example ammonium nitrate, zinc nitrate, aniline nitrate and urea nitrate, with the addition of a small amount, say about 0.21% calculated on the amount of the cellulose to be acidylated, of a free mineral acid, especially sulfuric acid.
  • a weak inorganic or organicase such as for example ammonium nitrate, zinc nitrate, aniline nitrate and urea nitrate
  • the quantity of the salt of the nitric acid to be added to the reaction mixture depends on the desired nitrogen content of the cellulose nitro acetate to be prepared. Thus, there- 7 are obtainable cellulose nitro acetates w1th a nitrogen content of about 0.1 to 1.8%.
  • nitro acetates obtained in this manner are extraordinarily clear and viscous and b form a valuable material for the film industry, which is distinguished among others from the products obtained from non-ni- The process contrated cellulose acetate by cuted water stretchability.
  • Example 1 One part by weight of cellulose is heated at 70 C. with 5 parts by weight of acetic anhydride, 3 parts by weight of glacial acetic acid and 0.05 parts by weight of ammonium nitrate with the addition of 0.003 parts by weight of sulfuric acid until atest portion is found to be soluble in chloroform.
  • the triacetate contains 0.6% of nitrogen (calculated on the cellulose).
  • the resulting nitro acetate is then hydrolized according to one of the known processes.
  • the triacetate contains 0.8% of nitrogen, (calculated on the cellulose) it is then hydrolized according to one of the known processes.

Description

i arate processes.
" ing to the process nitrating acid mixture, for
ble effect of having combined two expensive Patented Aug. 11, 1931 UNITED STATES PATENT OFFICE LUDWIG LOCK, OF DORMAGEN-ON-THE-RHINE, GERMANY, ASSIGNOR TO I. G. F-ABBENP INDUSTRIE AI KTIENGESELLSGHAF'I', OF FRANKFORT-ON-THE-MAIN, GER-MARY, A
CORPORATION" OF GERMANY PROCESS OF MAKING CELLULOSE NITRO ACETATE No Drawing. Application filed September 12, 1929, Serial No. 392,257, and in Germany September 19, 1929.
The present invention relates to a process of preparing cellulose nitro acetates.
The manufacture of cellulose nitro acetates has hitherto been carried out in two sep- Thus, forexample, accordof the German Patent No. 295,889, the bleached cellulose serving as the starting material is preliminarily nitrated by a mild treatment with a weakly acting example, to a nitrogen content of 2%, freed from adhering acid, washed and dried, after which acetylation is effected in the second stage of the process by one of the known technical methods.
The present invention describes a new process of producing cellulose nitro acetates in one and the same process in a technically easy and simple manner. sists in acetylating the cellulose at temperatures between about and 100 C. by means of acetic acid and acetic anhydride in the presence of a calculated amount of a salt of nitric acid with a weak inorganic or organicase, such as for example ammonium nitrate, zinc nitrate, aniline nitrate and urea nitrate, with the addition of a small amount, say about 0.21% calculated on the amount of the cellulose to be acidylated, of a free mineral acid, especially sulfuric acid. The quantity of the salt of the nitric acid to be added to the reaction mixture depends on the desired nitrogen content of the cellulose nitro acetate to be prepared. Thus, there- 7 are obtainable cellulose nitro acetates w1th a nitrogen content of about 0.1 to 1.8%.
'In addition to the extraordinarily valuaseparate processes into a single reaction, which is readily and securely carried out the new and technically equally important feature must be considered of being able to predetermine in this manner the nitrogen conb tent of the ultimate cellulose nitroacetate.
The nitro acetates obtained in this manner are extraordinarily clear and viscous and b form a valuable material for the film industry, which is distinguished among others from the products obtained from non-ni- The process contrated cellulose acetate by duced water stretchability.
The invention is illustrated by the following examples, withoutbeing limited thereto:
Example 1.One part by weight of cellulose is heated at 70 C. with 5 parts by weight of acetic anhydride, 3 parts by weight of glacial acetic acid and 0.05 parts by weight of ammonium nitrate with the addition of 0.003 parts by weight of sulfuric acid until atest portion is found to be soluble in chloroform. The triacetate contains 0.6% of nitrogen (calculated on the cellulose). The resulting nitro acetate is then hydrolized according to one of the known processes.
Ewample 2.O ne part by weight of cellulose is heated at 100 C. with 4 parts by weight of acetic anhydride, 2 parts by weight of glacial acetic acid and 0.5 parts by weight of ammonium nitrate with the addition of 0.004 parts by weight of sulfuric acid until a test portion is found to be soluble in chloroform. The triacetate contains 1.5% of nitrogen calculated on the cellulose. It is then hydrolized according to one of the known processes. "1
E trample 3.-One part by weight of cellulose is heated at 80 C. with 3 parts by weight of acetic anhydride, 3 parts by weight of glacial acetic acid and 0.1 part by weight of urea nitrate with the addition of 0.005 parts by weight of sulfuric a considerably reacid until a test portion is foundto be soluble in chloroform.
The triacetate contains 0.8% of nitrogen, (calculated on the cellulose) it is then hydrolized according to one of the known processes.
I claim: 1. The process which comprises acet lating cellulose between about 50 and 100 means of acetic acid and acetic anhydride in the presence of a small amount of mineral acid and of a salt of nitric acid with a weak ase. 11 2. The process which comprises acetylating cellulose between about 50 and 100 C. y means of acetic acid and acetic anhydride in t 'e presence of a small amount of sulfuric acid and of a salt of nitric acid with a; weak base.
3. The process which comprises acetylating cellulose between about 50 and 100 C. by means of acetic acid and acetic anhydride in the presence of Oil-1% (calculated on the 5 amount of the cellulose) of sulfuric acid and of a salt of nitric acid with a weak base.
4. The process which comprises acetylating cellulose between about 50 and 100 C. by means of acetic acid and acetic anhydride in the presence of 0.24% (calculated on the amount of the cellulose) of sulfuric acid and of urea nitrate.
In testimony whereof, I afiix m signature.
LUDWI LOCK.
US392257A 1929-09-19 1929-09-12 Process of making cellulose nitro acetate Expired - Lifetime US1817994A (en)

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