USRE21291E - Production of fatty acid esters - Google Patents
Production of fatty acid esters Download PDFInfo
- Publication number
- USRE21291E USRE21291E US RE21291 E USRE21291 E US RE21291E
- Authority
- US
- United States
- Prior art keywords
- fatty acid
- fatty acids
- starch
- acid
- hydrol
- Prior art date
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title description 84
- 239000000194 fatty acid Substances 0.000 title description 84
- -1 fatty acid esters Chemical class 0.000 title description 18
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000004665 fatty acids Chemical class 0.000 description 66
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- 229920002472 Starch Polymers 0.000 description 46
- 235000019698 starch Nutrition 0.000 description 46
- 239000008107 starch Substances 0.000 description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 239000002253 acid Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- 235000000346 sugar Nutrition 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 150000008064 anhydrides Chemical class 0.000 description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 150000001805 chlorine compounds Chemical class 0.000 description 14
- 238000004821 distillation Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 229940053200 antiepileptics Fatty acid derivatives Drugs 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- 235000014633 carbohydrates Nutrition 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000005712 crystallization Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000003472 neutralizing Effects 0.000 description 6
- 239000001187 sodium carbonate Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 150000008163 sugars Chemical class 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 235000021313 oleic acid Nutrition 0.000 description 4
- 150000002943 palmitic acids Chemical class 0.000 description 4
- 239000001184 potassium carbonate Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 2
- DLRVVLDZNNYCBX-LIZSDCNHSA-N Gentiobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-LIZSDCNHSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 241000209149 Zea Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000012084 conversion product Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000005824 corn Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 230000001804 emulsifying Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000000772 tip-enhanced Raman spectroscopy Methods 0.000 description 2
- 150000004043 trisaccharides Chemical class 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
Definitions
- This invention relates to the production of fatty acid esters from fatty acid containing byproducts or Waste products of the starch industry, particularly the corn products industry, such as refinery mud or acidulated soap stock, and sugar containing by-products such as starch sugar hydrol.
- Refinery mud is the sludge filtered from neutralized converter liquors and contains a 30 relatively large percentage of fatty acids such as palmitic, oleic and linoleic acids.
- Acidulated soap stock consists of fatty acids, with impurities, produced by acidification of the caustic wash liquors derived from the refining of corn oil.
- the material contains a mixture of stearic, palmitic, oleic and linoleic acids.
- Starch sugar hydrol ordinarily called hydrol in the starch and starch sugar industries is the mother liquor left after crystallization of dextrose from the acid conversion products of corn starch, removed by centrifuging or pressing and contains a mixture of dextrose and certain diand trisaccharides together with complex impurities the di-saccharides being gentiobiose and its isomers.
- This invention provides a process where a valuable product useable as a fat or emulsifying agent may be obtained from the above mentioned or all similar waste products.
- the fatty acids obtained from sources (1) and/or (2) by vacuum distillation or solvent extraction (with petroleum ether, chloroform, or benzene) or by other suitable means are treated to produce their anhydrides or chlorides; and the hydrol is dehydrated, dissolved with an acid removing catalyst, such as pyridine, or mixed pyridine bases, is reacted by heating with the fatty acid derivatives dissolved in a suitable solvent such as chloroform or carbon tetrachloride.
- a preferred method of treating the hydrol or other sugar containing liquid is as follows:
- the product depending upon the extent of its purification, is dark brown to yellow in color and consists of a fatty crystalline mass having emulsifying properties.
- its melting point is between 70 and 100 C. It has a slight fatty odor and taste and is slightly dextro-rotary in chloroform solution.
- E'scamplea 500 grams of refinery mud was boiled with 1 liter of methanol, filtered, and the resulting residue extracted with 100 cubic centimeters of ethyl ether. The mixed solvents were removed and dry potassium carbonate added to the residue until reaction ceased; six normal sulfuric acid was added in excess and the solution refrigerated. 120 grams of fatty acids were obtained in this way.
- Process of producing carbohydrate fatty acid esters from starch factory b-y-products which comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; and reacting said derivative products in solution with a solution of starch converted sugars in the presence of an acid removing catalyst, and removing the solvents.
- Process of producing carbohydrate fatty acid esters from starch factory by-products which comprises: extracting fatty acids from fatty acid containing starch factory residues;. converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; and reacting said derivative products in solution with a solution of dried starch sugar hydrol in the presence of an acid removing catalyst; and removing the solvents.
- Process of producing carbohydrate fatty acid esters from starch factory "by-products which comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; and reacting said derivative products in solution with a solution of starch converted sugars in the presence of pyridine bases; removing the pyridine hydrochloride, neutralizing the acid and removing the solvent of the fatty acid derivatives by distillation.
- Process of producing carbohydrate fatty acid esters from starch factory by-products which comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; dissolving said derivative products in a solvent; drying starch sugar hydrol; dissolving the dried hydrol in pyridine bases; mixing the aforesaid solutions and heating the mixture at reflux temperature under a reflux condenser; removing the pyridine with an acid; neutralizing the acid and washing out the salt; and distilling off the solvent of the fatty acid derivatives.
- Process of producing carbohydrate fatty acid esters from starch factory lay-products which comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and 01110- rides of said fatty acids; dissolving said derivative products in a solvent; drying starch sugar hydrol; dissolving the dried hydrol in pyridine bases; mixing the aforesaid solutions and heating the mixture at reflux temperature under a reflux condenser; removing the pyridine with an acid; neutralizing the acid and washing out the salt; and distilling off the solvent of the fatty acid derivatives and crystallizing the esters from alcohol.
- composition of matter comprising the esters of the fatty acids of fatty acid containing starch factory residues, and the sugars contained in starch sugar hydrol.
Description
Reissued Dec. 12, 1939 UNITED STATEE? OFFICE PRODUCTION OF FATTY ACID ES'TERS FROM STARCH FACTORY BYPRODUCTS New Jersey No Drawing. Original No. 2,147,241, dated February 14, 1939, Serial No. 159,111, August 14,
1937. Serial No. 281,753
6 Claims.
This invention relates to the production of fatty acid esters from fatty acid containing byproducts or Waste products of the starch industry, particularly the corn products industry, such as refinery mud or acidulated soap stock, and sugar containing by-products such as starch sugar hydrol.
(1) Refinery mud is the sludge filtered from neutralized converter liquors and contains a 30 relatively large percentage of fatty acids such as palmitic, oleic and linoleic acids.
(2) Acidulated soap stock consists of fatty acids, with impurities, produced by acidification of the caustic wash liquors derived from the refining of corn oil. The material contains a mixture of stearic, palmitic, oleic and linoleic acids.
(3) Starch sugar hydrol ordinarily called hydrol in the starch and starch sugar industries (Henry Berlin, Journal American Chemical So 20 ciety, vol. 49, pp. 26-27 (1926)), is the mother liquor left after crystallization of dextrose from the acid conversion products of corn starch, removed by centrifuging or pressing and contains a mixture of dextrose and certain diand trisaccharides together with complex impurities the di-saccharides being gentiobiose and its isomers.
This invention provides a process where a valuable product useable as a fat or emulsifying agent may be obtained from the above mentioned or all similar waste products. In accordance with the invention the fatty acids obtained from sources (1) and/or (2) by vacuum distillation or solvent extraction (with petroleum ether, chloroform, or benzene) or by other suitable means are treated to produce their anhydrides or chlorides; and the hydrol is dehydrated, dissolved with an acid removing catalyst, such as pyridine, or mixed pyridine bases, is reacted by heating with the fatty acid derivatives dissolved in a suitable solvent such as chloroform or carbon tetrachloride. This mixture is then flushed into water and the chloroform solution thus obtained is washed with dilute hydrochloric acid to remove pyridine, then with dilute sodium carbonate to remove acid and finally with water, The chloroform is removed by distillation and the crude esters used as such or further purified by crystallization from 95% ethyl 1.1001101.
One of the following methods may be used for vroducing the anhydrides or chlorides of the atty acids:
(0.) The crude fatty acids from sources (1) rid/or (2) are refluxed with a excess of :etic anhydride for six hours. The excess acetic Application for reissue June 28, 1939,
anhydride and acetic acid are removed by vacuum distillation.
(b) The crude fatty acids are dissolved in an equal volume of dioxane or benzene and treated with an excess of thionyl chloride at 80 C. The uncombined thionyl chloride is removed by vacuum distillation. The product will be fatty acid anhydrides or chlorides or mixtures of the same according to the extent to which the reaction is carried.
(c) The crude fatty acids from (1) and/or (2) are dissolved in twice their volume of dry toluene and treated with a 10% excess of phosphorous pentachloride, phosphorous trichloride or phosphorous oxychloride. The mixture is treated under a reflux condenser for 3-4 hours, then distilled in vacuo. The material consists of fatty acid chlorides.
A preferred method of treating the hydrol or other sugar containing liquid is as follows:
(d) The hydrol is evaporated to dryness in vacuo or by distillation with toluene and is dissolved by slight warming in 7 to 10 times its weight of pyridine.
Further steps ofthe process are preferably as follows:
(6) The fatty acid derivatives from (a), (b), or (c) are dissolved in '7 to 10 times their weight of chloroform and added to the dissolved hydrol at 20 C. and the mixture heated to 100 Cy'for from 8 to 12 hours to bring about esterification.
(f) The material is then flushed into an equal amount of water, the chloroform solution washed With dilute hydrochloric acid to remove the pyridine, with sodium carbonate to remove acid and finally with water. The chloroform is removed by distillation. Purification of the esters may be effected by crystallization from 95% alcohol.
The product, depending upon the extent of its purification, is dark brown to yellow in color and consists of a fatty crystalline mass having emulsifying properties. When purified its melting point is between 70 and 100 C. It has a slight fatty odor and taste and is slightly dextro-rotary in chloroform solution.
The following is a specific example of the application of the invention to practice:
E'scamplea.500 grams of refinery mud was boiled with 1 liter of methanol, filtered, and the resulting residue extracted with 100 cubic centimeters of ethyl ether. The mixed solvents were removed and dry potassium carbonate added to the residue until reaction ceased; six normal sulfuric acid was added in excess and the solution refrigerated. 120 grams of fatty acids were obtained in this way.
100 grams of the crude fatty acids dissolved in 100 cubic centimeters of dioxane were placed in a one liter, three necked flask and 46 cubic centimeters of thionyl chloride added, drop by drop, over a two hour period with the temperature at 50-80 C. Excess of thionyl chloride was removed by distillation on a steam bath. The dioxane was removed by distillation at a vacuum of 50 millimeters of mercury.
30 grams of dried hydrol was partially dissolved in 200 cubic centimeters of dry pyridine and to this, placed in a flask, was added the mixture of fatty acid chlorides and anhydrides which had been dissolved in 200 cubic centimeters of chloroform. The mixture was under a reflux condenser at reflux temperature for 12 hours.
Pyridine was removed by washing twice with 200 cubic centimeter portions of six normal hydrochloric acid; excess of acid was removed by washing twice with two normal sodium carbonate and finally the base was removed by repeated washing with water. The chloroform solution was dried over anhydrous potassium carbonate. The chloroform was removed by distillation and the resulting oil taken up in 400 cubic centimeters of ethyl alcohol. Crystallization resulted in a 40% yield of crude esters.
I claim:
1. Process of producing carbohydrate fatty acid esters from starch factory b-y-products which comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; and reacting said derivative products in solution with a solution of starch converted sugars in the presence of an acid removing catalyst, and removing the solvents.
2. Process of producing carbohydrate fatty acid esters from starch factory by-products which comprises: extracting fatty acids from fatty acid containing starch factory residues;. converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; and reacting said derivative products in solution with a solution of dried starch sugar hydrol in the presence of an acid removing catalyst; and removing the solvents.
3. Process of producing carbohydrate fatty acid esters from starch factory "by-products which comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; and reacting said derivative products in solution with a solution of starch converted sugars in the presence of pyridine bases; removing the pyridine hydrochloride, neutralizing the acid and removing the solvent of the fatty acid derivatives by distillation.
4. Process of producing carbohydrate fatty acid esters from starch factory by-productswhich comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and chlorides of said fatty acids; dissolving said derivative products in a solvent; drying starch sugar hydrol; dissolving the dried hydrol in pyridine bases; mixing the aforesaid solutions and heating the mixture at reflux temperature under a reflux condenser; removing the pyridine with an acid; neutralizing the acid and washing out the salt; and distilling off the solvent of the fatty acid derivatives.
5. Process of producing carbohydrate fatty acid esters from starch factory lay-products which comprises: extracting fatty acids from fatty acid containing starch factory residues; converting said fatty acids into one of the group of substances consisting of the anhydrides and 01110- rides of said fatty acids; dissolving said derivative products in a solvent; drying starch sugar hydrol; dissolving the dried hydrol in pyridine bases; mixing the aforesaid solutions and heating the mixture at reflux temperature under a reflux condenser; removing the pyridine with an acid; neutralizing the acid and washing out the salt; and distilling off the solvent of the fatty acid derivatives and crystallizing the esters from alcohol.
6. Composition of matter comprising the esters of the fatty acids of fatty acid containing starch factory residues, and the sugars contained in starch sugar hydrol.
SIDNEY MARK'GANTOR.
Family
ID=
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