GB1585200A - Method for the preparation of esters of carbohydrates and other organic compounds containing hydroxyl groups - Google Patents
Method for the preparation of esters of carbohydrates and other organic compounds containing hydroxyl groups Download PDFInfo
- Publication number
- GB1585200A GB1585200A GB4284777A GB4284777A GB1585200A GB 1585200 A GB1585200 A GB 1585200A GB 4284777 A GB4284777 A GB 4284777A GB 4284777 A GB4284777 A GB 4284777A GB 1585200 A GB1585200 A GB 1585200A
- Authority
- GB
- United Kingdom
- Prior art keywords
- water
- glucose
- solution
- stirred
- poured
- 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
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title claims description 8
- 150000002894 organic compounds Chemical class 0.000 title claims description 8
- 150000001720 carbohydrates Chemical class 0.000 title description 4
- 235000014633 carbohydrates Nutrition 0.000 title description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 36
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 21
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- 239000005457 ice water Substances 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 230000021736 acetylation Effects 0.000 claims description 10
- 238000006640 acetylation reaction Methods 0.000 claims description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- SQUHHTBVTRBESD-UHFFFAOYSA-N (2,3,4,5,6-pentaacetyloxycyclohexyl) acetate Chemical compound CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 229920002472 Starch Polymers 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000008107 starch Substances 0.000 claims description 6
- 235000019698 starch Nutrition 0.000 claims description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- 239000011592 zinc chloride Substances 0.000 claims description 5
- 235000005074 zinc chloride Nutrition 0.000 claims description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- MKRNVBXERAPZOP-UHFFFAOYSA-N Starch acetate Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OC(C)=O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 MKRNVBXERAPZOP-UHFFFAOYSA-N 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000011135 tin Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 239000001083 [(2R,3R,4S,5R)-1,2,4,5-tetraacetyloxy-6-oxohexan-3-yl] acetate Substances 0.000 claims description 2
- NJVBTKVPPOFGAT-XMTFNYHQSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentaacetyloxyhexyl] acetate Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)COC(C)=O NJVBTKVPPOFGAT-XMTFNYHQSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 claims description 2
- 238000010908 decantation Methods 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 2
- 229960000367 inositol Drugs 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- -1 HYDROXYL GROUPS Chemical group 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/02—Esters
- C08B31/04—Esters of organic acids, e.g. alkenyl-succinated starch
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
(54) A METHOD FOR THE PREPARATION OF ESTERS OF
CARBOHYDRATES AND OTHER ORGANIC COMPOUNDS
CONTAINING HYDROXYL GROUPS
(71) We, AHMEDABAD TEXTILE
INDUSTRY'S RESEARCH ASSOCIA
TION, a Society registered under Societies
Registration Act of 1856, of P.O. Polytechnic, Ahmedabad-380 015, Gujarat, India, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
This invention relates to a method for the preparation of esters of carbohydrates and other organic compounds containing hydroxyl groups.
Polysaccharides are polymeric materials composed of monosaccharides, and are found abundantly in nature e.g. cellulose, starch and gums. Cotton is composed essentially of cellulose.
Esters of cellulose, starch and gums are of great industrial importance and find application in textile, paper. food and pharmaceutical industries. These esters are prepared by reacting the alcoholic compounds with an acid anhydride in the presence of an acidic or alkaline catalyst~such as sulfuric acid, perchloric acid. zinc chloride, pyridine, sodium hydroxide and sodium acetate. Depending upon the polysaccharide and the catalyst used, preparation of a simple derivative like acetate can take a long time, sometimes as much as 16 to 18 hours.
This invention is related to the use of a new catalyst system. which greatly enhances the rate of esterification of organic compounds. Thus, esterification of organic compounds, whether a monomer or a polymer, can be now completed within a short time.
The catalyst system as proposed herein consists of anhydrous ferric chloride or anhydrous ferric chloride in combination with chlorides of bi- and tri-valent metals.
The reaction is very quick and for simple carbohydrates like p-glucose and p-glucitol (sorbitol) complete esterification can be achieved in just five minutes whereas in the case of polysaccharides like cellulose esterification can be completed in a few hours.
The process of this invention also permits preparation of mixed esters by employing a mixture of acid anhydrides.
According to this invention there is provided a process for esterification of organic hydroxylic compounds comprising reacting the compound with an acid anhydride and a catalyst which is anhydrous ferric chloride with or without the addition of anhydrous chlorides of other di- and tri-valent metals, such as tin, aluminium and zinc, and isolating the ester by pouring the reaction mixture in cold water followed by filtration or decantation.
In one aspect of this invention the hydroxylic compound is added to a solution or suspension of the catalyst in an acid anhydride with stirring until the compound is esterified to the desired level.
In another aspect of this invention the acid anhydride and the catalyst are dissolved or suspended in a non-reactive organic solvent followed by addition of the organic compound. The reaction may be carried out at between 20 to 1000C.
An inert solvent may be used to minimize the use of the anhydride. Without in anyway limiting the scope of this invention, the following examples are cited.
EXAMPLE 1
Acetylation of D-glucose
D-Glucose (6 g.) is stirred in acetic anhydride (35 ml) containing anhydrous ferric chloride (0.6 g). Within a few minutes (about 5 minutes) a clear solution is obtained which is poured into ice water. The precipitated material is filtered and washed with water to give a (-D-glucose pentacetate in 90% yield; m.p. 111-112"C and [a]D + 103 (c 1, CHCl3).
EXAMPLE 2
Acetylation of sorbitol
Sorbitol (6 g) is added to a stirred solution of anhydrous ferric chloride (0.4 g) in acetic anhydride (35 ml). Within 5 minutes, a clear solution is obtained. This is poured into ice-water with stirring to give a solid. This is filtered, washed thoroughly with water and dried to give sorbitol hexaacetate; 11.4 g (82% yield), m.p. 97-98"C and [a]D + 9.9 (c 2, acetone).
EXAMPLE 3
Preparation of myo-inositol hexaacetate
Dry myo-inositol (5.2 g) is added to a stirred solution of anhydrous ferric chloride (0.1 g) in acetic anhydride (30 ml). After 5-10 minutes, the reaction mixture is filtered and the residue washed with water. The filtrate is poured into ice-water and the precipitated acetate is filtered and washed.
Both the residue (10.2 g) and regenerated solid (2 g) are found to give the same melting point 211-212"C corresponding to the myo-inositol hexaacetate. Total yield
12.2 g (97%).
EXAMPLE 4
Acetylation of ss-naphthol Powdered Bnaphthol (10 g) is added to a stirred solution of anhydrous ferric chloride (1 g) in ascetic anhydride (40 ml). Within 2-3 minutes a clear solution is obtained. This is kept stirred for 10 minutes and poured into ice-water with stirring. Shortly, a colourless solid separates, with lumps. The lumps are broken. the broken solids filtered, washed and dried. Yield is 13 g (93%). m.p. 67-78 .
Recrystallization from petroleum ether (60 80"C) gives Il g (80%) recrystallized solid
having m.p. 7()-71 C.
EXAMPLE 5 Preparnrion of cellobiose octapropionate To propionic anhydride (70 ml) 4-0-(3-D- glucopyranosyl-D-glucose (cellobiose, 10 g) and anhydrous ferric chloride (0.6 g) are added. The mixture is stirred at room temperature (30-35"C) for 18 hr., when a clear solution is obtained. It is poured with stirring into 500 ml ice-water to give 22.7 g of the propionate derivative as a solid (yield 98%) m.p. 174-175 , [a]D + 35 (CHCl3).
EXAMPLE 6
Preparation of starch acetate
Dry Starch (14 g) is added to a solution of anhydrous ferric chloride (0.5 g) in acetic anhydride (40 ml) at 65"C. This is stirred for 48 hr., when almost all the starch goes into solution. The solution is poured with stirring into ice-water (1.1) to give 21 g. starch acetate (yield: 84% based on triacetate), m.p. 145-150"C, [a]D + 157.1 (C 1,
CHCl3); having an acetyl content of 43.82% corresponding to a D.S. of 2.88.
EXAMPLE 7
Acetylation of D-glucose in the presence of a solvent
D-Glucose (10 g) is stirred in dioxan (10 ml), as solvent, and acetic anhydride (8 ml) containing anhydrous ferric chloride (0.4 g) is added. The mixture is stirred for 15 minutes and then poured into ice-water mixture to give ci-D-glucose pentaacetate in 80% yield. After recrystallization the product has m.p. 111-112 C [a]D + 102" (CHCl3).
EXAMPLE 8
Acetylation of D-glucose using mixed catalyst
To a stirred solution of anhydrous ferric chloride (0.2 g) and fused zinc chloride (0.2 g) in acetic anhydride (30 ml), D-glucose (10 g) is added. After 15 minutes, the solution is poured into 200 ml of ice-water mixture with vigorous stirring. The solid separated is filtered, washed and dried (yield 75%).
Recrystallization from ethyl alcohol gives a-D-glucose pentaacetate, m.p. 111-112 [cilD + 103 (c 2 CHCl3).
Process of the Example 8 can be successfully repeated by use of equivalent amounts of anhydrous tin chloride or anhydrous aluminium chloride instead of the zinc chloride. In these cases, however, a suspension of the chloride and not a solution will be formed.
WHAT WE CLAIM IS:
1. A process for esterification of organic hydroxylic compounds comprising reacting the compound with an acid anhydride and a catalyst which is anhydrous ferric chloride with or without the addition of anhydrous chloride of other di- and tri-valent metals, such as tin, aluminium and zinc, and isolating the ester by pouring the reaction mixture in cold water followed by filtration or
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (5)
1. A process for esterification of organic hydroxylic compounds comprising reacting the compound with an acid anhydride and a catalyst which is anhydrous ferric chloride with or without the addition of anhydrous chloride of other di- and tri-valent metals, such as tin, aluminium and zinc, and isolating the ester by pouring the reaction mixture in cold water followed by filtration or
decantation.
2. A process as claimed in claim 1 in which the hydroxylic compound is added to a solution or suspension of the catalyst in an acid anhydride with stirring until the compound is esterified to the desired level.
3. A process as claimed in claim 1 in which the acid anhydride and the catalyst are dissolved or suspended in a non-reactive organic solvent followed by addition of the organic compound.
4. A process as claimed in claim 1 or 2 in which the reaction is carried out at a temperature ranging from 20"-100"C.
5. A process for esterification of organic hydroxylic compounds substantially as herein described particularly with reference to the examples.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4284777A GB1585200A (en) | 1978-04-12 | 1978-04-12 | Method for the preparation of esters of carbohydrates and other organic compounds containing hydroxyl groups |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4284777A GB1585200A (en) | 1978-04-12 | 1978-04-12 | Method for the preparation of esters of carbohydrates and other organic compounds containing hydroxyl groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1585200A true GB1585200A (en) | 1981-02-25 |
Family
ID=10426233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4284777A Expired GB1585200A (en) | 1978-04-12 | 1978-04-12 | Method for the preparation of esters of carbohydrates and other organic compounds containing hydroxyl groups |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1585200A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6977275B2 (en) | 2002-01-16 | 2005-12-20 | Eastman Chemical Company | Carbohydrate esters and polyol esters as plasticizers for polymers, compositions and articles including such plasticizers and methods of using the same |
| DE102007005927A1 (en) * | 2007-02-06 | 2008-08-14 | Emsland - Stärke GmbH | Process for the preparation of a hydrophobic starch derivative, hydrophobic starch derivative and use of the process |
| CN106977555A (en) * | 2017-03-28 | 2017-07-25 | 华东师范大学 | A kind of method of complete acetylization of saccharides in presence of solid acid catalyst |
| CN116217375A (en) * | 2021-12-03 | 2023-06-06 | 中国科学院宁波材料技术与工程研究所 | A kind of preparation method of highly selective calcium gluconate |
-
1978
- 1978-04-12 GB GB4284777A patent/GB1585200A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6977275B2 (en) | 2002-01-16 | 2005-12-20 | Eastman Chemical Company | Carbohydrate esters and polyol esters as plasticizers for polymers, compositions and articles including such plasticizers and methods of using the same |
| US7276546B2 (en) | 2002-01-16 | 2007-10-02 | Eastman Chemical Company | Carbohydrate esters and polyol esters as plasticizers for polymers, compositions and articles including such plasticizers and methods of using the same |
| DE102007005927A1 (en) * | 2007-02-06 | 2008-08-14 | Emsland - Stärke GmbH | Process for the preparation of a hydrophobic starch derivative, hydrophobic starch derivative and use of the process |
| DE102007005927B4 (en) * | 2007-02-06 | 2011-05-05 | Emsland - Stärke GmbH | Process for the preparation of a hydrophobic starch derivative |
| CN106977555A (en) * | 2017-03-28 | 2017-07-25 | 华东师范大学 | A kind of method of complete acetylization of saccharides in presence of solid acid catalyst |
| CN116217375A (en) * | 2021-12-03 | 2023-06-06 | 中国科学院宁波材料技术与工程研究所 | A kind of preparation method of highly selective calcium gluconate |
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