US1962829A - Production of mixed esters of cellulose in an ester of a halogenated fatty acid - Google Patents
Production of mixed esters of cellulose in an ester of a halogenated fatty acid Download PDFInfo
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- US1962829A US1962829A US566799A US56679931A US1962829A US 1962829 A US1962829 A US 1962829A US 566799 A US566799 A US 566799A US 56679931 A US56679931 A US 56679931A US 1962829 A US1962829 A US 1962829A
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- cellulose
- ester
- fatty acid
- esters
- acid
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- 229920002678 cellulose Polymers 0.000 title description 41
- 235000014113 dietary fatty acids Nutrition 0.000 title description 36
- 229930195729 fatty acid Natural products 0.000 title description 36
- 239000000194 fatty acid Substances 0.000 title description 36
- 239000001913 cellulose Substances 0.000 title description 35
- 150000002148 esters Chemical class 0.000 title description 31
- 150000004665 fatty acids Chemical class 0.000 title description 30
- 238000004519 manufacturing process Methods 0.000 title description 7
- 235000010980 cellulose Nutrition 0.000 description 34
- 239000002904 solvent Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 16
- 230000032050 esterification Effects 0.000 description 14
- 238000005886 esterification reaction Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 229920002301 cellulose acetate Polymers 0.000 description 11
- 125000005907 alkyl ester group Chemical group 0.000 description 10
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 9
- -1 fatty acid esters Chemical class 0.000 description 9
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001242 acetic acid derivatives Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 229920006218 cellulose propionate Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZKYQOYYTRWJQLQ-UHFFFAOYSA-N acetic acid hexadecanoic acid octadecanoic acid Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCC)(=O)O.C(C)(=O)O ZKYQOYYTRWJQLQ-UHFFFAOYSA-N 0.000 description 1
- IIOPVJIGEATDBS-UHFFFAOYSA-N acetic acid;dodecanoic acid Chemical compound CC(O)=O.CCCCCCCCCCCC(O)=O IIOPVJIGEATDBS-UHFFFAOYSA-N 0.000 description 1
- SPTSIOTYTJZTOG-UHFFFAOYSA-N acetic acid;octadecanoic acid Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O SPTSIOTYTJZTOG-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940106135 cellulose Drugs 0.000 description 1
- HKQOBOMRSSHSTC-UHFFFAOYSA-N cellulose acetate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 HKQOBOMRSSHSTC-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical class OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- QJZNRCWAXUGABH-UHFFFAOYSA-N propyl 2-chloroacetate Chemical compound CCCOC(=O)CCl QJZNRCWAXUGABH-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/16—Preparation of mixed organic cellulose esters, e.g. cellulose aceto-formate or cellulose aceto-propionate
Definitions
- the present invention relates to the production of the mixed organic esters of cellulose such as cellulose acetate-stearate in which an ester of a halogenated fatty acid is employed as the solvent.
- esters of the halogenated fatty acids exhibit the valuable solvent properties of the halogenated fatty acids without the accompanying disadvantageous property of those acids of being highly corrosive.
- the esters of the halogenated fatty acids are suitable as solvents for various types of esterification processes such as, for example, those in which partially deacetylated cellulose acylates such as commercially available acetone soluble hydrolyzed cellulose acetate are employed as the initial cellulosic material.
- these esters of halogenated fatty acids are also suitable for use as solvents in reaction mixtures for the esterification of cellulose itself.
- Our solvent is of especial value in the esterification of the lower fatty acid esters of cellulose with the higher fatty acid anhydrides such as stearic anhydride as there are few solvents in which both of these materials are compatible.
- chloracetic acid which is suitable as a solvent for a mixture of a higher fatty acid anhydride and a lower ester of cellulose is corrosive and severe on the reaction vessels.
- esters of the halogenated fatty acids will dissolve both lower fatty acid esters of cellulose and the higher fatty acid anhydrides without the corrosive effect on equipment, which is characteristic of the solvents previously employed, which makes it eminently suitable as a solvent in esterification processes in which higher fatty acid anhydrides are employed.
- Example I 55 About 50 lbs. of an acetone-soluble cellulose acetate having an acetyl content of about 38% was introduced into an esterifying bath comprising about 406 lbs. of methyl chloracetate, 100 lbs. of stearic' anhydride and 1 lb. of benzene sulfonic acid and the whole was agitated and maintained at about 80 1' until a sample from the bath showed that the product formed was soluble in hot toluene. The solution was then poured into isopropyl ether to precipitate out the product, which was washed with isopropyl ether all as disclosed in Malm and Fordyce application Serial No. 553,646 and dried. A cellulose acetatestearate having a stearyl content of about 40% was obtained.
- Example 11 About lbs. of bleached cotton tissue was placed in an esterifying bath comprising about 250 lbs. of commercial stearic acid, 150 lbs. of acetic anhydride, 400 lbs. of ethyl chloracetate and .5 lb. of perchloric acid and the whole was agitated and maintained at (SO- C. until a clear dope resulted (about 5 hours). The product was precipitated out from the reaction mass by pouring into iso-propyl ether. It was then washed with isopropyl ether and dried. The ester formed was a'cellulose acetate-palmitate-stearate (palniitic acid being present in commercial stearic acid) and was soluble in acetone.
- Example III About 50 lbs. of cellulose acetate having an acetyl content of 38% was treated with an esteri fication bath comprising about 50 lbs. of propionic anhydride, 400 lbs. of methyl chloracetate and 1 lb. of benzene sulfonic acid at about F. with vigorous stirring. When a sample showed that the product was soluble in ethylene chloride, the solution was poured into methyl alcohol, washed with alcohol and dried. A cellulose acetate-propionate soluble in acetone, ethylene chloride, and ethyl acetate was obtained.
- Altho the allayl esters of the halogenated fatty acids such as methyl, ethyl or propyl chloracetate are the preferred solvents for use in esterification baths, nevertheless any other compatible liquid aliphatic ester of the halogenated fatty acids which is suitable may be employed as a solvent in baths for the esterification of cellulose or cellulosic materials, for example the esters of halogenated fatty acids with other monoor polyhydroxy alcohols may be employed as solvents in esterification baths.
- esters of the bromacetic and iodo-acetic acids may find use as solvents according to the present invention however at present because of the availability of the chloracetic acids and the usefulness of their esters, it is preferred to employ the esters of the chloracetic acids in that connection.
- cellulosic material as employed herein, is intended to define both partially esterified cellulose esters and materials such as cotton linters, pulp, etc. which are composed mainly of cellulose.
- esters of cellulose are possible according to our process by merely substituting for the fatty acids or anhydrides employed in the examples equimolecular proportions of other fatty acids or anhydrides, the groups of which are de-- sired in the cellulose molecule.
- the fatty acids or anhydrides employed in the examples equimolecular proportions of other fatty acids or anhydrides, the groups of which are de-- sired in the cellulose molecule.
- 70 lbs. of lauric anhydride may be employed and in that case the resulting product would be a cellulose acetate-laurate.
- the starting material should obviously be a partially esterified cellulose propionate (or butyrate) instead of the cellulose acetate which is employed in the examples.
- Typical examples of esters which may be prepared according to our invention, by methods analogous to those shown in the examples, are:
- Cellulose acetate-propionate Cellulose acetate-butyrate
- Cellulose acetate-laurate Cellulose acetate-stearate
- Cellulose acetate-oleate Cellulose propionate-stearate Cellulose butyrate-stearate.
- the step which comprises treating cellulosic material with an esterifying bath comprising a fatty acid anhydride and an alkyl ester of a halogenated acetic acid which is a liquid solvent of the cellulose ester formed.
- the step which comprises treating cellulosic material with an esterifying bath comprising a fatty acid anhydride and an alkyl ester of chloracetic acid.
- step 7 which comprises treating cellu' losic material with an esterifying bath compris-- ing a fatty acid anhydride and methyl chloracetate.
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- 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)
Description
Patented June 12, 1934 PATENT FFIQE PRODUCTION FATTY ACID Carl J. Malm and Charles OFIMIXED ESTERS OF CELLU- LOSE IN AN ESTER OF A HALOGENATED R. Fordyce, Rochester,
N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New York No Drawing. Application October 3, 1931, Serial No. 566,799
19 Claims.
The present invention relates to the production of the mixed organic esters of cellulose such as cellulose acetate-stearate in which an ester of a halogenated fatty acid is employed as the solvent.
It has been previously known to employ the halogenated lower fatty acids such as chloracetic acid as a solvent in esterification baths, which are quite satisfactory except for the fact that they are very corrosive which obviously leads to deterioration of equipment and accompanying contamination of the product.
We have now found that the esters of the halogenated fatty acids exhibit the valuable solvent properties of the halogenated fatty acids without the accompanying disadvantageous property of those acids of being highly corrosive. We have found that the esters of the halogenated fatty acids are suitable as solvents for various types of esterification processes such as, for example, those in which partially deacetylated cellulose acylates such as commercially available acetone soluble hydrolyzed cellulose acetate are employed as the initial cellulosic material. On the other hand these esters of halogenated fatty acids are also suitable for use as solvents in reaction mixtures for the esterification of cellulose itself.
Our solvent permits of use in the production of mixed esters of cellulose in which either acid anhydrides such as acetic anhydride or the high fatty acid anhydrides are employed.
Our solvent is of especial value in the esterification of the lower fatty acid esters of cellulose with the higher fatty acid anhydrides such as stearic anhydride as there are few solvents in which both of these materials are compatible. As pointed out previously chloracetic acid which is suitable as a solvent for a mixture of a higher fatty acid anhydride and a lower ester of cellulose is corrosive and severe on the reaction vessels. However we have found that the esters of the halogenated fatty acids will dissolve both lower fatty acid esters of cellulose and the higher fatty acid anhydrides without the corrosive effect on equipment, which is characteristic of the solvents previously employed, which makes it eminently suitable as a solvent in esterification processes in which higher fatty acid anhydrides are employed.
The following specific examples illustrate the applicaton of our invention to esterfication processes. It is to be understood however that our invention is not 1i ted to the details given in those examples.
Example I 55 About 50 lbs. of an acetone-soluble cellulose acetate having an acetyl content of about 38% was introduced into an esterifying bath comprising about 406 lbs. of methyl chloracetate, 100 lbs. of stearic' anhydride and 1 lb. of benzene sulfonic acid and the whole was agitated and maintained at about 80 1' until a sample from the bath showed that the product formed was soluble in hot toluene. The solution was then poured into isopropyl ether to precipitate out the product, which was washed with isopropyl ether all as disclosed in Malm and Fordyce application Serial No. 553,646 and dried. A cellulose acetatestearate having a stearyl content of about 40% was obtained.
Example 11 About lbs. of bleached cotton tissue was placed in an esterifying bath comprising about 250 lbs. of commercial stearic acid, 150 lbs. of acetic anhydride, 400 lbs. of ethyl chloracetate and .5 lb. of perchloric acid and the whole was agitated and maintained at (SO- C. until a clear dope resulted (about 5 hours). The product was precipitated out from the reaction mass by pouring into iso-propyl ether. It was then washed with isopropyl ether and dried. The ester formed was a'cellulose acetate-palmitate-stearate (palniitic acid being present in commercial stearic acid) and was soluble in acetone.
Example III About 50 lbs. of cellulose acetate having an acetyl content of 38% was treated with an esteri fication bath comprising about 50 lbs. of propionic anhydride, 400 lbs. of methyl chloracetate and 1 lb. of benzene sulfonic acid at about F. with vigorous stirring. When a sample showed that the product was soluble in ethylene chloride, the solution was poured into methyl alcohol, washed with alcohol and dried. A cellulose acetate-propionate soluble in acetone, ethylene chloride, and ethyl acetate was obtained.
Altho the allayl esters of the halogenated fatty acids such as methyl, ethyl or propyl chloracetate are the preferred solvents for use in esterification baths, nevertheless any other compatible liquid aliphatic ester of the halogenated fatty acids which is suitable may be employed as a solvent in baths for the esterification of cellulose or cellulosic materials, for example the esters of halogenated fatty acids with other monoor polyhydroxy alcohols may be employed as solvents in esterification baths. Also the esters of the bromacetic and iodo-acetic acids may find use as solvents according to the present invention however at present because of the availability of the chloracetic acids and the usefulness of their esters, it is preferred to employ the esters of the chloracetic acids in that connection.
The term cellulosic material as employed herein, is intended to define both partially esterified cellulose esters and materials such as cotton linters, pulp, etc. which are composed mainly of cellulose.
Various mixed esters of cellulose are possible according to our process by merely substituting for the fatty acids or anhydrides employed in the examples equimolecular proportions of other fatty acids or anhydrides, the groups of which are de-- sired in the cellulose molecule. For instance, in Example I given herein instead of 100 lbs. of stearic anhydride, 70 lbs. of lauric anhydride may be employed and in that case the resulting product would be a cellulose acetate-laurate. If a cellulose propionate (or butyrate) -higher acylate is desired the starting material should obviously be a partially esterified cellulose propionate (or butyrate) instead of the cellulose acetate which is employed in the examples. Typical examples of esters which may be prepared according to our invention, by methods analogous to those shown in the examples, are:
Cellulose acetate-propionate Cellulose acetate-butyrate Cellulose acetate-laurate Cellulose acetate-stearate Cellulose acetate-oleate Cellulose propionate-stearate Cellulose butyrate-stearate.
What we claim as our invention and desire to be secured by Letters Patent of the United States: 1. The esterification of cellulosic material with an aliphatic acid compound in the presence of an alkyl ester of a halogenated acetic acid which is a liquid solvent of the cellulose ester formed.
2. The esterification of cellulosic material with an aliphatic acid compound in the presence of an ester of a halogenated acetic acid which is a liquid solvent of the cellulose ester formed selected from the groups consisting of the methyl, the ethyl, and the propyl esters of the halogenated acetic acids.
3. The esterification of cellulosic material with an aliphatic acid compound in the presence of an alkyl ester of a chloracetic acid.
4. The esterification of cellulosic material with an aliphatic acid compound in the presence of methyl chloracetate.
5. In the production of a mixed ester of cellulose, the step which comprises treating cellulosic material with an esterifying bath comprising a fatty acid anhydride and an alkyl ester of a halogenated acetic acid which is a liquid solvent of the cellulose ester formed.
6. In the manufacture of a mixed ester of cellulose, the step which comprises treating cellulosic material with an esterifying bath comprising a fatty acid anhydride and an alkyl ester of chloracetic acid.
7. In the manufacture of a mixed ester of cellulose, the step which comprises treating cellu' losic material with an esterifying bath compris-- ing a fatty acid anhydride and methyl chloracetate.
8. The process of making mixed esters of cellulose which comprises esterifying a partially esterified lower fatty acid ester of cellulose with the anhydride of a higher fatty acid in the presence of an alkyl ester of a halogenated acetic acid which is a liquid solvent of the cellulose ester formed. 7
9. The process of making mixed esters of cellulose which comprises esterifying a partially esterified lower fatty acid ester of cellulose with the anhydride of a higher fatty acid in the presence of an alkyl ester of a chloracetic acid.
10. The process of making mixed esters of cellulose which comprises esterifying a partially esterified lower fatty acid ester of cellulose with the anhydride of a higher fatty acid in the presence of methyl chloracetate.
11. The process of making mixed esters of cellulose which comprises esterifying a partially esterified cellulose acetate with a higher fatty acid anhydride in the presence of an alkyl ester of a halogenated acetic acid which is a liquid solvent of the cellulose ester formed.
12. The process of making mixed esters of cellulose which comprises esterifying a partially esterified cellulose acetate with a higher fatty acid anhydride in the presence of an alkyl chloracetate.
13. The process of making mixed esters of cellulose which comprises esterifying a partially esterified cellulose acetate with a higher fatty acid anhydride in the presence of a methyl chloracetate.
14. The process of making cellulose acetatestearate which comprises esterifying a partially esterified cellulose acetate with stearic anhydride in the presence of an alkyl ester of a halogenated acetic acid which is a liquid solvent of the cellulose ester formed. 7 I 7 15. The process of making cellulose acetatestearate which comprises esterifying a partially esterified cellulose acetate with stearic anhydride in the presence of an alkyl chloracetate.
16. The process of making cellulose acetatestearate which comprises esterifying a partially esterified cellulose acetate with stearic anhydride in the presence of a methyl chloracetate.
17. The esterification of cellulosic material with an aliphatic acid compound in the presence of an alkyl ester of monochloracetic acid.
18. The process of making mixed esters of cellulose which comprises esterifying a partially esterified lower fatty acid ester of cellulose with the anhydride of a higher fatty acid in the presence of an alkyl ester of monochloracetic acid.
19. The process of making a mixed ester of cellulose which comprises esterifying a partially esterified, cellulose acetate with a higher fatty acid anhydride in the presence of methyl monochloracetate.
CARL J. MALM.
I CHARLES R. FORDYCE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US566799A US1962829A (en) | 1931-10-03 | 1931-10-03 | Production of mixed esters of cellulose in an ester of a halogenated fatty acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US566799A US1962829A (en) | 1931-10-03 | 1931-10-03 | Production of mixed esters of cellulose in an ester of a halogenated fatty acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1962829A true US1962829A (en) | 1934-06-12 |
Family
ID=24264419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US566799A Expired - Lifetime US1962829A (en) | 1931-10-03 | 1931-10-03 | Production of mixed esters of cellulose in an ester of a halogenated fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1962829A (en) |
-
1931
- 1931-10-03 US US566799A patent/US1962829A/en not_active Expired - Lifetime
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