US1840349A - Fat cleavage - Google Patents
Fat cleavage Download PDFInfo
- Publication number
- US1840349A US1840349A US388638A US38863829A US1840349A US 1840349 A US1840349 A US 1840349A US 388638 A US388638 A US 388638A US 38863829 A US38863829 A US 38863829A US 1840349 A US1840349 A US 1840349A
- Authority
- US
- United States
- Prior art keywords
- water
- cleavage
- alcohol
- fatty acid
- fat
- 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
- 238000003776 cleavage reaction Methods 0.000 title description 9
- 230000007017 scission Effects 0.000 title description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- -1 fatty acid esters Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000002366 lipolytic effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 101100386518 Caenorhabditis elegans dbl-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000725101 Clea Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 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
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N lauric acid triglyceride Natural products CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000010792 warming Methods 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
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
Definitions
- the lipolysis or cleavage of fats and oils has been performed hitherto without employing high pressures by heating the same with pure water or water which is only 5 slightly acidulated', the fat or oil to be treated having a cleavage facilitating a ent added to it in the form of a product obtained by the sulphonation of a mixture of a fatty acid (or a hardened castor oil) with a hydrocarbon of the benzene series. .
- the use of sulpho-acids of the petroleum hydrocarbons has also been proposed for the samepurpose.
- the object of the present invention is to provide an alternative class of suchclevage facilitating additions.
- Such are the substances formed by the sulphonation of mixtures of the alcohols corresponding to the higher fatty o bons. These are. excellently suited for the cleavage of fatty acid esters of all kinds, particularly of fats and oils, and are considerably superior in their efficacy to the hitherto known lipolytic agents, especially to the arcmatic fatty sulpho-acids. Their greater suitability exhibits itself both in the more rapid progress of the cleavage process and alsoin the particular purity of the cleavage products obtained which are almost pure white. The differences are due presumably to the better emulsifying powers of the novel cleavage a ents towards water-insoluble substances suc as fatt acid esters.
- the lipolytic me ia employed according to this invention may be prepared, for example, as follows Molecular proportions of olein alcohol and naphthaline are mixed while warming. The m ixtu-re is treated with a sulphonating agent 40 such as concentrated sulphuric acid, and is allowed to stand until the reaction is completed. Excess sulphuric acid may be washed .out of the reaction mixture with water.
- a sulphonating agent 40 such as concentrated sulphuric acid
- the oily- 'sulp'honation product is added to the fatty acid ester to be treated, for instance the fat or oil, the necessary pro ortion generally not exceeding 1%.
- the w ole isthen heated with water whereby smooth clea'rageof the ester into fatty acid and acids with benzene hydrocar-' alcohol takes place without any substantial decomposition or discolouration of the 'cleav age products.
- laurin alcohol As examples of the alcohols which maybe employed .in the formation'of the fat-splitting reagent, there may be named laurin alcohol, olein alcohol, cet 1 alcohol and stemin alcohol.
- These alcoho s may be referred to generically and definitely as those alcohols I derived from higher fatty acids having more tha'i0 8 (iarbon attomlsl, b Hrezpgcement of the car on yt e 2 cup.
- An of the fnembers of the b ehzene series may lie employed, including benzene, naphthalene, an anthracene.
- Example 1 One part by weight of the sulphonationproduct derived by sulphonating olein alcohol in the presence of naphthalene is added to and stirred carefully into 100 parts by weight of molten tallow. Then 50 parts by weight of water are added 'and t e mass brought to a boil by the introduction .of
- I claim 1 The process of cleaving fatty acid esters comprising heating a fatty acid ester in the presence of water and an agent composed of a sulphonation product derived from the treatment with a sulphonating agent of a mixture ofa hydrocarbon of the benzene series.
- the step comprising treating said fatty acid esters during said heating in the presence of water, with an alkyl derivative of a sulphonated aromatic hydrocarbon in which said alkvl radical corres onds to a higher fatty aci in the number carbon atoms contained therein.
- the step comprising treating said esters during said heatin in the presence of water also with a sma quantity of a fat splitting agent derived from the treatment with a sulphonating agent of a mixture of a hydrocarbon of the benzene series with an alcohol derived from a higher fatty acid havin more than 8 carbon atoms by rrzplacement o? the carboxyl group by the CH H group.
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
' Patented Jan. 12, 1932 UNITED STATES- PATENT OFFICE-f HEINRICH nausea, or cnmrmrz, (minim, assmnon ro n. rm. 120m mrmr- GESELLSCHAI'T, or cnrmm'rz, (1mm, x conrona'rzox or onnmr ra'r omavaen Ho Drawing. Application and August as, 1920, Serial m. asacas, and in Germany October 17', ms.
The lipolysis or cleavage of fats and oils has been performed hitherto without employing high pressures by heating the same with pure water or water which is only 5 slightly acidulated', the fat or oil to be treated having a cleavage facilitating a ent added to it in the form of a product obtained by the sulphonation of a mixture of a fatty acid (or a hardened castor oil) with a hydrocarbon of the benzene series. .The use of sulpho-acids of the petroleum hydrocarbons has also been proposed for the samepurpose.
The object of the present invention is to provide an alternative class of suchclevage facilitating additions. Such are the substances formed by the sulphonation of mixtures of the alcohols corresponding to the higher fatty o bons. These are. excellently suited for the cleavage of fatty acid esters of all kinds, particularly of fats and oils, and are considerably superior in their efficacy to the hitherto known lipolytic agents, especially to the arcmatic fatty sulpho-acids. Their greater suitability exhibits itself both in the more rapid progress of the cleavage process and alsoin the particular purity of the cleavage products obtained which are almost pure white. The differences are due presumably to the better emulsifying powers of the novel cleavage a ents towards water-insoluble substances suc as fatt acid esters.
The lipolytic me ia employed according to this invention may be prepared, for example, as follows Molecular proportions of olein alcohol and naphthaline are mixed while warming. The m ixtu-re is treated with a sulphonating agent 40 such as concentrated sulphuric acid, and is allowed to stand until the reaction is completed. Excess sulphuric acid may be washed .out of the reaction mixture with water.
The oily- 'sulp'honation product is added to the fatty acid ester to be treated, for instance the fat or oil, the necessary pro ortion generally not exceeding 1%. The w ole isthen heated with water whereby smooth clea'rageof the ester into fatty acid and acids with benzene hydrocar-' alcohol takes place without any substantial decomposition or discolouration of the 'cleav age products.
As examples of the alcohols which maybe employed .in the formation'of the fat-splitting reagent, there may be named laurin alcohol, olein alcohol, cet 1 alcohol and stemin alcohol. These alcoho s may be referred to generically and definitely as those alcohols I derived from higher fatty acids having more tha'i0 8 (iarbon attomlsl, b Hrezpgcement of the car on yt e 2 cup.
An of the fnembers of the b ehzene series may lie employed, including benzene, naphthalene, an anthracene.
The exact structure of the reage'nt'cannot be definitel given. However, it is believed that the aliyl radical of the alcohol joins directly with the aryl radical of the hydrocarbon thereby eliminating water, and that the simultaneous or subsequent sulphonation introduces'a sulphonic group at another point on the aryl radical.
Example One part by weight of the sulphonationproduct derived by sulphonating olein alcohol in the presence of naphthalene is added to and stirred carefully into 100 parts by weight of molten tallow. Then 50 parts by weight of water are added 'and t e mass brought to a boil by the introduction .of
steam. After about 10 hours, the cleavage is substantially complete. The mass is then allowed tosettle. Finally, the glycerin and water are drawn ofi.
I claim 1. The process of cleaving fatty acid esters comprising heating a fatty acid ester in the presence of water and an agent composed of a sulphonation product derived from the treatment with a sulphonating agent of a mixture ofa hydrocarbon of the benzene series.
and an 9.100 01 correspondin in the number of carbon atomsto a higher atty acid.
2. Inthe process of cleaving fatty acidesters by heating in the presence of water, the step comprising treating said fatty acid esters during said heating in the presence of water, with an alkyl derivative of a sulphonated aromatic hydrocarbon in which said alkvl radical corres onds to a higher fatty aci in the number carbon atoms contained therein.
3., The process of cleaving fats and oils 55 comprising adding thereto a sulphonation product produced by sulphonating a mixture of a hydrocarbon or" the benzene series with an alcohol derived from a higher fatty acid by replacement of the carbonyl group with re a (ll-LOH group, and then heating in the presence of Water 4. A process according to claim 3 wherein the proportion of the .sulphonation product does not exceed about one per cent.
5. In the process of splitting fatty acid esters by heating in the presence of water, the step comprising treating said esters during said heatin in the presence of water also with a sma quantity of a fat splitting agent derived from the treatment with a sulphonating agent of a mixture of a hydrocarbon of the benzene series with an alcohol derived from a higher fatty acid havin more than 8 carbon atoms by rrzplacement o? the carboxyl group by the CH H group.
DR. HEINRICH BEBTSCH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1840349X | 1928-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1840349A true US1840349A (en) | 1932-01-12 |
Family
ID=7745537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US388638A Expired - Lifetime US1840349A (en) | 1928-10-17 | 1929-08-26 | Fat cleavage |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1840349A (en) |
-
1929
- 1929-08-26 US US388638A patent/US1840349A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US1659790A (en) | Method of producing commercial stearic acid | |
| US2383599A (en) | Treating fatty glycerides | |
| US1840349A (en) | Fat cleavage | |
| US1701703A (en) | Hantjfacttjre | |
| US2333093A (en) | Cosmetic preparation | |
| GB379534A (en) | Soap and like preparations | |
| US2378005A (en) | Process for treating fats and fatty oils | |
| US1823815A (en) | Production of esters of sulphonic acids | |
| US3102128A (en) | Mixed esters and process for their preparation | |
| US2427717A (en) | Cosmetic preparation containing triethanol amine salts of sulfurized fatty acids | |
| US2478354A (en) | Preparation of partial esters | |
| US2190769A (en) | Washing and cleansing agent and process of making same | |
| DE871893C (en) | Process for the preparation of sulfosuccinic acid esters | |
| US1928582A (en) | Esterification of fatty acids | |
| US2042411A (en) | Process of decomposing fats or oils into fatty acids and glycerine | |
| GB391610A (en) | Improvements in or relating to the manufacture and use of wetting-out, equalising, peptising and cleansing agents | |
| US2352698A (en) | Process of preparing a sulphonated product | |
| GB334022A (en) | Improvements in or relating to the cleavage of fatty acid esters | |
| US2056272A (en) | Wetting | |
| US1993375A (en) | Production and purification of sulphonated products | |
| US2126527A (en) | Method of making a synthetic teaseed oil | |
| GB427641A (en) | Improvements in and relating to processes for manufacturing substances having wetting, washing, emulsifying and like properties, and the products obtained thereby | |
| DE913418C (en) | Process for the production of organic sulfuric acid drops | |
| US2039989A (en) | Sulphonation of oils and greases | |
| SU15720A1 (en) | The method of deodorization of acids obtained by the oxidation of petroleum or similar hydrocarbon oils |