US2876174A - Bleaching and color stabilization of fatty acids and related materials - Google Patents
Bleaching and color stabilization of fatty acids and related materials Download PDFInfo
- Publication number
- US2876174A US2876174A US622736A US62273656A US2876174A US 2876174 A US2876174 A US 2876174A US 622736 A US622736 A US 622736A US 62273656 A US62273656 A US 62273656A US 2876174 A US2876174 A US 2876174A
- Authority
- US
- United States
- Prior art keywords
- fatty acids
- color
- ndt
- hypophosphorous acid
- bleaching
- 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 - Lifetime
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 32
- 229930195729 fatty acid Natural products 0.000 title claims description 32
- 239000000194 fatty acid Substances 0.000 title claims description 32
- 150000004665 fatty acids Chemical class 0.000 title claims description 32
- 238000004061 bleaching Methods 0.000 title description 2
- 239000000463 material Substances 0.000 title description 2
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 10
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 3
- 235000012343 cottonseed oil Nutrition 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229910001380 potassium hypophosphite Inorganic materials 0.000 description 1
- CRGPNLUFHHUKCM-UHFFFAOYSA-M potassium phosphinate Chemical compound [K+].[O-]P=O CRGPNLUFHHUKCM-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
- C11C1/10—Refining by distillation
- C11C1/103—Refining by distillation after or with the addition of chemicals
Definitions
- Fat acids as used in this invention relate to straight chained-mono-carboxylic acids containing -6 to 22 carbon atoms.
- Common sources of these acids are naturally occurring fats and oils, soapstock and tall oil.
- Illustrative fats and oils are soybean oil, cottonseed oil, corn oil, rapeseed oil, castor oil, linseed oil, sugar cane oil, and so forth.
- These acids arev used extensively in the preparation of soaps, detergents, cosmetics and numerous other uses. It will be appreciated that in many of these applications the color and color stability of the products are .of primary importance. Accordingly, fatty acids having the :best color and color stability demand a premium price from these users.
- the principal methods employed to purify fatty acids commercially are crystallization and distillation. This invention deals only with the distillation of these acids at elevated temperatures, i. e., 175 to 300 C. and at reduced pressures, i. e., 4 to 60 millimeters of mercury. It has been discovered that the objects and advantages of this invention may be accomplished by adding hypophosphorous acid and the alkali salts of hypophosphorous acid to the fatty acids prior to their distillation. Sodium and potassium hypophosphite are two illustrative salts.
- Step 1 Hydrophilicity of the fatty acids or one of its alkali metal salts is added to the fatty acids prior to their introduction into the stills.
- Step 2. The fatty acids are heated under reduced pressure to vaporize them and simultaneously therewith phosphine is generated when hypophosphorous acid or its alkali salts are heated at distillation temperatures.
- Step 3 The vaporized fatty acids are cooled and condensed to yield the improved acids made possible 'by this invention.
- NDT'throughout refers-tonot; darkerthan on-the Gardnerscale.
- the B methodformeasuring-colorstability is substantally thesame as the A method except that the sample is heated for 3 hours.
- the process of distilling fatty acids containing 6 to 22 carbon atoms which comprises adding a compound selected from the group consisting of hypophosphorous acid and the alkali salts of hypophosphorous acid to the fatty acids prior. to distillation, heating the fatty acids to 175 to 300% C. at a reduced pressure of from 4 to millimeters of mercury to simultaneously vaporize the fatty acids and generate phosphine, and cooling said vapors to condense the improved fatty acids which have been bleached and have improved color stability at elevated temperatures and good color reversion characteristics at room temperature.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
BLEACHING AND COLOR sTAamz Tro or FATTY ACIDS AND- RELATED MATERIALS 7 John M. Preston, Gilman, Ill., assignor to General Mills, Inc., a corporation of Delaware NoDrawing. Application November-12.1956 I Serial No. 622,736
2 Claims. (Cl. 202-57) This invention relates to an improved method for .dis- 'tilling fatty acids.
*Fatty acids as used in this invention relate to straight chained-mono-carboxylic acids containing -6 to 22 carbon atoms. Common sources of these acids are naturally occurring fats and oils, soapstock and tall oil. Illustrative fats and oils are soybean oil, cottonseed oil, corn oil, rapeseed oil, castor oil, linseed oil, sugar cane oil, and so forth. These acids arev used extensively in the preparation of soaps, detergents, cosmetics and numerous other uses. It will be appreciated that in many of these applications the color and color stability of the products are .of primary importance. Accordingly, fatty acids having the :best color and color stability demand a premium price from these users. I
It is, therefore, an object of this invention to teach an improved process for distilling fatty acids. The principal advantages of this improved process are that the fatty acids treated in the manner hereinafter described are bleached and have good color reversion characteristics at room temperature and good color stability at elevated temperatures.
Other objects and advantages to the process will become apparent upon reading the subsequent specification.
The principal methods employed to purify fatty acids commercially are crystallization and distillation. This invention deals only with the distillation of these acids at elevated temperatures, i. e., 175 to 300 C. and at reduced pressures, i. e., 4 to 60 millimeters of mercury. It has been discovered that the objects and advantages of this invention may be accomplished by adding hypophosphorous acid and the alkali salts of hypophosphorous acid to the fatty acids prior to their distillation. Sodium and potassium hypophosphite are two illustrative salts.
The steps involved in the practice of this invention are as follows:
Step 1.-Hypophosphorous acid or one of its alkali metal salts is added to the fatty acids prior to their introduction into the stills.
Step 2.-The fatty acids are heated under reduced pressure to vaporize them and simultaneously therewith phosphine is generated when hypophosphorous acid or its alkali salts are heated at distillation temperatures.
Step 3.-The vaporized fatty acids are cooled and condensed to yield the improved acids made possible 'by this invention.
This invention may be illustrated further by reference to the following examples in which all parts are expressed as parts by weight and all percentages are ex-' pressed as percent by weight, unless specified otherwise.
EXAMPLE I 200 gram samples of technical grade lauric acid from coconut soapstock and coconut oil were distilled at 5 mm. of mercury subsequent to the addition of 0.5% Na(H PO (Nata-Because of the phosphine generated during 2,8 76,1 74 Patented Mar. -3, 1959 2 distillation itis important to carry out the distillation in a well vented .fhood.)
In each instance the percent of distillate and residue was in the order of and 4%, respectively. Table .I shows a comparison of various treated and the original acids.
Ta le ,-I
I Coconut Soapstoclr' Coconut Oil Crude .Crude'Lauric Acid. Laurie Acid Original; Treated Original Treated Distillate Distillate .Gardner Color LT .1 LT 1 LT'l LT 1 ColorStability A NDT 4 LT l NDT 3 -L'I 1' Color Stability B NDT 7 NDT 4 NDT 7 NDI 2 1 LT throughout refers to "lighter than on the Gardner scale.
NDT'throughoutrefers-tonot; darkerthan on-the Gardnerscale.
3 The "A method for measuring color stability is a measurement of the color developed by heating-s25 ml. sample of the fatty acids at 250=l=5 C for 30 minutes, cooling to room temperature, and taking a Gardner color reading.
-The B methodformeasuring-colorstability is substantally thesame as the A method except that the sample is heated for 3 hours.
EXAMPLE II 300 gram samples of crude cottonseed fatty acids were alembjically distilled at a pressure of 5 mm. Hg and a maximum pot temperature of 275 C. To each of these samples was added prior to distillation the amount of solid Na(H 'PO shown in Table II.
EXAMPLE III Crude soybean fatty acids and crude tallow fatty acids were alembically distilled as described in Example II and the results are shown in Table III.
Table III SOYBEAN FATTY ACIDS Gardner Color Color Percent of N 3(H2P02) Added Color Stability Stalgillty 0 NDT 4 NDT 9 NDT 13 2.0 NDT 3 NDT 6 NDT 12 TALLOW FATTY ACIDS 0 NDT 2 NDT 5 LT 13 2.0 NDT 1 NDT 3 NDT 11 EXAMPLE IV Hypophosphorous acid was added to 200 gram samples of crude cottonseed fatty acids and the mixtures distilled at 5 mm. Hg and at a maximum pot temperature of. 275 C. The hypophosphorous acid was added in the form of a 50% solution. In Sample A the amount of hypophosphorous acidadded was equivalent on a mole basis to the addition of 0.1% Na(H PO and in sample color tests run on the B to 1-.0%"Na (H,PO,). The results are 'shown a Table Table IV Gardner" Color 06101- Sample Color Stability Stability I I 1A1! H BY! Control.....' 8 12 16 A s 9 13 B 4 9 EXAMPLE V r- 0.2% Na(H,PO,) was added to a crude mixture of fatty acids containing approximately 3% caproic acid,
56% caprylic acid, 34% capric acid, and 7% lauric acid and the mixture distilled in a large scale commercial operation. Table Y shows the comparison between the color characteristics of acids treated in the above manner and untreated commercially distilled acids of the same composition.
Table V Gardner Color Color Color Stability Stability H A" B Treated LT 1 ND'I 6 'NDT 11 Untreated LT 1 NDT 8 NDT 13 In the large scale treatment of acids as in Example V, precautions must be taken to safely vent the phosphine generated, It has been observed, however, that only 'minute quantities of phosphine will be carried over into v the condensed fatty acids.
-As demonstrated by the preceding Examplesflt is possible to improve the quality of distilled fatty acids by the addition of from 0.01 to 2.0% by weight of hypophosphorous acid or its alkali salts. However, the preferred range is from 0.1 to 1% Therefore, many modifications and variations of the invention as hereinbefore set forth may be made with out departing from the spirit and scope thereof and therefore only such limitations should be imposed as are indicated in the appended claims.
What is claimed:
1. The process of distilling fatty acids containing 6 to 22 carbon atoms which comprises adding a compound selected from the group consisting of hypophosphorous acid and the alkali salts of hypophosphorous acid to the fatty acids prior. to distillation, heating the fatty acids to 175 to 300% C. at a reduced pressure of from 4 to millimeters of mercury to simultaneously vaporize the fatty acids and generate phosphine, and cooling said vapors to condense the improved fatty acids which have been bleached and have improved color stability at elevated temperatures and good color reversion characteristics at room temperature.
2. Theprocess of claim 1 in which the phosphite compound added prior to distillation is sodium hypophosphite.
References Cited in the file of this patent UNITED STATES PATENTS 1,909,605
Belden May' 16, 1933 2,062,837 Sheely Dec. 1, 1936 2,259,968 Andersen Oct. 21, 1941 2,483,414 Henderson Oct. 4, 1949
Claims (1)
1. THE PROCESS OF DISTILLING FATTY ACIDS CONTAINING 6 TO 22 CARBON ATOMS WHICH COMPRISES ADDING A COMPOUND SELECTED FROM THE GROUP CONSISTING OF HYPOPHOSPHOROUS ACID AND THE ALKALI SALTS OF HYPOPHOSPHOROUS ACID TO THE FATTY ACIDS PRIOR TO DISTILLATION, HEATING THE FATTY ACIDS TO 175 TO 300% C. AT A REDUCED PRESSURE OF FROM 4 TO 60 MILLIMETRES OF MERCURY TO SIMULTANEOUSLY VAPORIZE THE FATTY ACIDS AND GENERATE PHOSPHINE, AND COOLING SAID VAPORS TO CONDENSE THE IMPROVED FATTY ACIDS WHICH HAVE BEEN BLEACHED AND HAVE IMPROVED COLOR STABILITY AT ELEVATED TEMPERATURES AND GOOD COLOR REVERSION CHARACTERISTICS AT ROOM TEMPERATURE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US622736A US2876174A (en) | 1956-11-19 | 1956-11-19 | Bleaching and color stabilization of fatty acids and related materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US622736A US2876174A (en) | 1956-11-19 | 1956-11-19 | Bleaching and color stabilization of fatty acids and related materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2876174A true US2876174A (en) | 1959-03-03 |
Family
ID=24495318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US622736A Expired - Lifetime US2876174A (en) | 1956-11-19 | 1956-11-19 | Bleaching and color stabilization of fatty acids and related materials |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2876174A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3146267A (en) * | 1961-03-03 | 1964-08-25 | Nopco Chem Co | Production and decolorization of quaternary ammonium compounds |
| US3168578A (en) * | 1961-03-30 | 1965-02-02 | Nopco Chem Co | Process for production of alkyl phenols of improved color |
| US4599143A (en) * | 1982-07-23 | 1986-07-08 | Hermann Stage | Process for deodorizing and/or physical refining of high-boiling organic edible oils, fats and esters |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1909605A (en) * | 1929-05-20 | 1933-05-16 | Filtrol Company Of California | Process of distilling and purifying fatty materials |
| US2062837A (en) * | 1935-10-16 | 1936-12-01 | Armour & Co | Process of preparing color-stable fatty acids |
| US2259968A (en) * | 1938-09-30 | 1941-10-21 | Lever Brothers Ltd | Method of decolorizing oils |
| US2483414A (en) * | 1945-01-03 | 1949-10-04 | Lever Brothers Ltd | Process of bleaching fats and oils and making soap therefrom |
-
1956
- 1956-11-19 US US622736A patent/US2876174A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1909605A (en) * | 1929-05-20 | 1933-05-16 | Filtrol Company Of California | Process of distilling and purifying fatty materials |
| US2062837A (en) * | 1935-10-16 | 1936-12-01 | Armour & Co | Process of preparing color-stable fatty acids |
| US2259968A (en) * | 1938-09-30 | 1941-10-21 | Lever Brothers Ltd | Method of decolorizing oils |
| US2483414A (en) * | 1945-01-03 | 1949-10-04 | Lever Brothers Ltd | Process of bleaching fats and oils and making soap therefrom |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3146267A (en) * | 1961-03-03 | 1964-08-25 | Nopco Chem Co | Production and decolorization of quaternary ammonium compounds |
| US3168578A (en) * | 1961-03-30 | 1965-02-02 | Nopco Chem Co | Process for production of alkyl phenols of improved color |
| US4599143A (en) * | 1982-07-23 | 1986-07-08 | Hermann Stage | Process for deodorizing and/or physical refining of high-boiling organic edible oils, fats and esters |
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