GB578067A - Improvements in or relating to cellulose derivatives - Google Patents

Improvements in or relating to cellulose derivatives

Info

Publication number
GB578067A
GB578067A GB1194944A GB1194944A GB578067A GB 578067 A GB578067 A GB 578067A GB 1194944 A GB1194944 A GB 1194944A GB 1194944 A GB1194944 A GB 1194944A GB 578067 A GB578067 A GB 578067A
Authority
GB
United Kingdom
Prior art keywords
carboxycellulose
ester
alcohol
heating
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1194944A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to GB1194944A priority Critical patent/GB578067A/en
Publication of GB578067A publication Critical patent/GB578067A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
    • C08B15/04—Carboxycellulose, e.g. prepared by oxidation with nitrogen dioxide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

Carboxycellulose, which may be obtained by the oxidation of cellulose with periodic acid or lead tetra-acetate, is esterified by heating with an alcohol in the presence of an esterification catalyst. An ester of carboxycellulose with a low boiling alcohol, prepared as above, may be treated at an elevated temperature with a higher boiling alcohol, whereby an exchange of alcohol radicals takes place and an ester of the higher alcohol obtained. Suitable ester-exchange catalysts for this reaction are caustic alkalies, zinc chloride, ferric chloride, ammonium chloride, boron trifluoride, sulphonium iodides, hydrochloric acid, phosphoric acid and p-toluene sulphonic acid. Examples are given of the preparation of carboxycellulose, and of (1) methyl ester of carboxycellulose containing 0.049 ester groups, by heating carboxycellulose containing 0.138 carboxyl group with methyl alcohol in the presence of sulphuric acid; (2) ethyl ester of carboxycellulose containing 0.060 ester group, by heating carboxycellulose containing 0.231 carboxyl group with ethyl alcohol in the presence of sulphuric acid; (3) n-propyl ester of carboxycellulose containing 0.050 ester group by heating carboxycellulose containing 0.321 carboxyl group with n-propyl alcohol in the presence of sulphuric acid; (4) methyl ester of carboxycellulose containing 0.40 ester group, by heating carboxycellulose containing 0.45 carboxyl group with methyl alcohol in the presence of hydrogen chloride gas; and (5) a mixed ester containing both methyl and butyl groups, by heating the methyl ester of carboxycellulose, obtained as described in examples (1) and (4), with butanol in the presence of sodium hydroxide. The amounts of ester and carboxyl groups given above are calculated with respect to the glucose unit. A large number of alcohols suitable for use in the process are specified. The lowly esterified materials are, in general, insoluble in organic solvents, but where they contain free carboxyl groups they are partially or completely soluble in aqueous alkali. The highly esterified materials are generally soluble in organic solvents and may also be soluble in aqueous alkali if sufficient free carboxyl groups are present. The carboxycellulose esters are more stable than the carboxycellulose itself, and may be used for the production of filaments, films and moulding powders.
GB1194944A 1944-06-23 1944-06-23 Improvements in or relating to cellulose derivatives Expired GB578067A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1194944A GB578067A (en) 1944-06-23 1944-06-23 Improvements in or relating to cellulose derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1194944A GB578067A (en) 1944-06-23 1944-06-23 Improvements in or relating to cellulose derivatives

Publications (1)

Publication Number Publication Date
GB578067A true GB578067A (en) 1946-06-13

Family

ID=9995598

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1194944A Expired GB578067A (en) 1944-06-23 1944-06-23 Improvements in or relating to cellulose derivatives

Country Status (1)

Country Link
GB (1) GB578067A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2912430A (en) * 1954-12-07 1959-11-10 Henkel & Compagnie G M B H Method of preparing esters of cellulose ether carboxylic acids
WO2008035975A2 (en) * 2006-09-22 2008-03-27 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Paint additive

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2912430A (en) * 1954-12-07 1959-11-10 Henkel & Compagnie G M B H Method of preparing esters of cellulose ether carboxylic acids
WO2008035975A2 (en) * 2006-09-22 2008-03-27 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Paint additive
WO2008035975A3 (en) * 2006-09-22 2008-11-20 Tno Paint additive

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