GB686311A - Improvements in the production of cellulose and cellulose derivatives - Google Patents

Improvements in the production of cellulose and cellulose derivatives

Info

Publication number
GB686311A
GB686311A GB2306949A GB2306949A GB686311A GB 686311 A GB686311 A GB 686311A GB 2306949 A GB2306949 A GB 2306949A GB 2306949 A GB2306949 A GB 2306949A GB 686311 A GB686311 A GB 686311A
Authority
GB
United Kingdom
Prior art keywords
chloro
acetic acid
chlorinated
ethyl
chlorhydrins
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
GB2306949A
Inventor
Stanley Charles Bate
Walter Alan Rogerson
Francis George Peach
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.)
Acordis UK Ltd
Original Assignee
British Celanese Ltd
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 British Celanese Ltd filed Critical British Celanese Ltd
Priority to GB2306949A priority Critical patent/GB686311A/en
Publication of GB686311A publication Critical patent/GB686311A/en
Expired legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21CPRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C3/00Pulping cellulose-containing materials
    • D21C3/003Pulping cellulose-containing materials with organic compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B1/00Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
    • C08B1/02Rendering cellulose suitable for esterification

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)
  • Chemical And Physical Treatments For Wood And The Like (AREA)

Abstract

Cellulose is produced from lignocellulosic material by heating the material with a homogeneous mixture of (1) a halogenated organic compound (other than a chlorinated lower fatty acid) containing aliphatically bound halogen and also oxygen or sulphur, and (2) an organic diluent for the halogenated compound. The halogenated compound preferably has the formula X.R.Y.R1, where X represents chlorine or bromine, Y represents oxygen or sulphur, R is a hydrocarbon radical such that the link X-R is aliphatic in nature, and R1 represents hydrogen, a monovalent hydrocarbon group, a divalent hydrocarbon group bound by the second valency to R, or an acyl group. More particularly preferred are chlorhydrins (i.e. compounds containing one or more aliphatically-bound chlorine atoms and one or more aliphatically bound hydroxyl groups) and chlorinated mercaptans, especially such as contain 2 or 3 carbon atoms in the molecule; esters of the chlorhydrins, particularly with lower fatty acids; ethers and thioethers derived from the chlorhydrins and mercaptans, especially lower alkyl and chlorinated lower alkyl ethers and thioethers; chlorinated epoxides and chlorinated saturated and unsaturated cyclic ethers and thioethers. The term "lower fatty acid" denotes fatty acids containing 2-4 carbon atoms in the molecule, and the term "lower alkyl" denotes alkyl groups containing 1-4 carbon atoms. The halogenated compounds are best employed diluted with lower fatty acids, especially acetic acid. Other diluents may, however, be employed, e.g. aromatic or other saturated hydrocarbons such as ethyl benzene and the xylenes, normally liquid nitro-and halogeno-aromatic hydrocarbons, and fatty acid esters boiling above 110 DEG C. More volatile diluents such as ethyl acetate, acetone or chloroform may be used, but less conveniently. The proportion of diluent may be about 15-65 per cent and especially 25-45 per cent of the weight of the mixture. Mineral acids and water are preferably absent. Particularly good results are given by mixtures of ethylene chlorhydrin, 2-chloro-ethyl acetate, or epichlorhydrin with a lower fatty acid, especially acetic acid, or with xylenes or other hydrocarbons of similar boiling range. Other examples of halogenated compounds which may be used, diluted preferably with lower fatty acids, are 1- and 2-glycerol chlorhydrins, 1-chloro-2-hydroxy-propane, and 1-hydroxy-2,3-dichloropropane; methyl, ethyl, and 2-chloro - ethyl ethers of those chlorhydrins; 2 - chloro - ethyl mercaptan and 2 - chloro - ethyl methyl sulphide; 2 - chloro - furan (under pressure), 2,3-dichloro-1,4-dioxane, and 2 - chloro - thiophene. The lignocellulosic material may be cereal straws and particularly woods such as spruce, larch, pine, fir, poplar, beech and eucalyptus. After the treatment of the lignocellulosic material the cellulose produced may be filtered off and washed, preferably either with further quantities of the diluent, e.g. acetic acid, or with a more volatile solvent for the halogenated compound, e.g. acetone, or with xylene followed by acetone. If the cellulose has been washed with acetic acid it is washed free from acid with water. The washed cellulose may be bleached and whether bleached or unbleached, may be further refined by treatment with a warm solution containing 15-22 grams of caustic soda per 100 c.c. of water, as described in Specifications 640,490 and 679,832. In an example eucalyptus chips are boiled under a reflux with a mixture of equal parts by weight of ethylene chlorhydrin and glacial acetic acid. The cellulose produced is filtered off, washed with acetic acid, bleached, washed again and treated with warm 18 per cent by weight aqueous caustic soda solution to reduce its pentosan content. The filtrate and washings are either mixed with water to precipitate the lignin and treated to recover the halogenated compounds present, or re-used for treating further wood after fortifying with acetic acid. In other examples wood chips are similarly treated with mixtures of epichlorhydrin and glacial acetic acid, epichlorhydrin and xylene, and 2-chloro-ethyl acetate and glacial acetic acid, respectively. Specification 679,833 also is referred to.ALSO:Lignin is recovered from lignocellulosic material by heating the material with a homogeneous mixture of (1) a halogenated organic compound (other than a chlorinated lower fatty acid) containing aliphatically bound halogen and also oxygen or sulphur, and (2) an organic diluent for the halogenated compound. The halogenated compound preferably has the formula X.R.Y.R1, where X represents chlorine or bromine, Y represents oxygen or sulphur, R is a hydrocarbon radical such that the link X-R is aliphatic in nature, and R1 represents hydrogen, a monovalent hydrocarbon group, divalent hydrocarbon group bound by the second valency to R, or an acyl group. More particularly preferred are chlorohydrins (i.e. compounds containing one or more aliphatically bound chlorine atoms and one or more aliphatically bound hydroxyl groups) and chlorinated mercaptans, especially such as contain 2 or 3 carbon atoms in the molecule; esters of the chlorhydrins, particularly with lower fatty acids; ethers and thio-ethers derived from the chlorhydrins and mercaptans, especially alkyl and chlorinated lower alkyl ethers and thioethers; chlorinated lower alkyl ethers and thioethers; chlorinated epoxides and chlorinated saturated and unsaturated cyclic ethers and thioethers. The term "lower fatty acid" denotes fatty acids containing 2-4 carbon atoms in the molecule and the term "lower alkyl" denotes alkyl groups containing 1-4 carbon atoms. Corresponding bromine compounds can also be used. The halogenated compounds are best employed diluted with lower fatty acids, especially acetic acid. Other diluents may, however, be employed, e.g. aromatic or other saturated hydrocarbons such as ethyl benzene and the xylenes, normally liquid nitro- and halogeno-aromatic hydrocarbons, and fatty acid esters boiling above 110 DEG C. More volatile diluents such as ethyl acetate, acetone or chloroform may be used, but less conveniently. The proportion of diluent may be about 15-65 per cent and especially about 25-45 per cent of the weight of the mixture. Mineral acids and water are preferably absent from the mixture. Particularly good results are given by mixtures of ethylene chlorhydrin, 2-chloro-ethyl acetate, or epichlorhydrin with a lower fatty acid, especially acetic acid, or with xylenes or other hydrocarbons of similar boiling range. Alternatively there may be used (diluted preferably with lower fatty acids), 1- and 2-glycerol chlorhydrins, 1 - chloro - 2 - hydroxy - propane, and 1 - hydroxy - 2,3 - dichloropropane; methyl, ethyl and 2-chloro-ethyl ethers of these chlorhydrins; 2-chloroethyl mercaptan and 2-chloro-ethyl methyl sulphide; 2-chloro-furan (under pressure), 2-3-dichloro-1,4-dioxane, and 2-chlorothiophene. The ligno-cellulosic material may be cereal straws and particularly woods such as spruce, larch, pine, fir, poplar, beech and eucalyptus. In an example eucalyptus chips are refluxed with a mixture of ethylene chlorhydrin and glacial acetic acid the cellulose filtered off and further purified for use in artificial silk manufacture (see Group IV (a)). The filtrate is mixed with water to precipitate the lignin and treated to recover the solvents. The filtrate may be fortified with acetic acid and re-used for treating further wood before finally precipitating the lignin. In other examples wood chips are similarly treated with epichlorhydrin and acetic acid, epichlorhydrin and xylene and 2-chloro-ethyl acetate and acetic acid respectively. Specification 679,833, [Group IV (a)], is referred to.
GB2306949A 1949-09-06 1949-09-06 Improvements in the production of cellulose and cellulose derivatives Expired GB686311A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2306949A GB686311A (en) 1949-09-06 1949-09-06 Improvements in the production of cellulose and cellulose derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2306949A GB686311A (en) 1949-09-06 1949-09-06 Improvements in the production of cellulose and cellulose derivatives

Publications (1)

Publication Number Publication Date
GB686311A true GB686311A (en) 1953-01-21

Family

ID=10189616

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2306949A Expired GB686311A (en) 1949-09-06 1949-09-06 Improvements in the production of cellulose and cellulose derivatives

Country Status (1)

Country Link
GB (1) GB686311A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003054022A1 (en) * 2001-12-21 2003-07-03 Rhodia Acetow Gmbh Method for improving the colour index of cellulose esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003054022A1 (en) * 2001-12-21 2003-07-03 Rhodia Acetow Gmbh Method for improving the colour index of cellulose esters

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