DE271985C - - Google Patents
Info
- Publication number
- DE271985C DE271985C DENDAT271985D DE271985DA DE271985C DE 271985 C DE271985 C DE 271985C DE NDAT271985 D DENDAT271985 D DE NDAT271985D DE 271985D A DE271985D A DE 271985DA DE 271985 C DE271985 C DE 271985C
- Authority
- DE
- Germany
- Prior art keywords
- water
- acid
- percent
- hydrogen
- esters
- 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.)
- Active
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 2
- -1 hydrogen esters Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-Aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 231100000614 Poison Toxicity 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N Propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- RILTWTZTURZUEO-UHFFFAOYSA-N formic acid;nickel Chemical compound [Ni].OC=O RILTWTZTURZUEO-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
- C11C3/123—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation using catalysts based principally on nickel or derivates
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 271985 KLASSE 12 o. GRUPPE- M 271985 CLASS 12 or GROUP
KARL WIMMER in BREMEN.KARL WIMMER in BREMEN.
Bei den Verfahren, organische Körper durch Wasserstoff mittels Katalysatoren zu reduzieren bzw. zu hydrogenisieren, zeigt es sich, daß während des Prozesses unliebsame Spaltungen eintreten können. Bei der Hydrogenisation von Glyzeriden der Fettsäuren z. B. tritt häufig eine Spaltung in Glyzerin und freie Fettsäure ein, wodurch der Gehalt an freien Fettsäuren im Fett erhöht wird, was speziell beiIn the process of reducing organic bodies with hydrogen using catalysts or to hydrogenate, it turns out that unpleasant splits during the process can enter. In the hydrogenation of glycerides of fatty acids z. B. occurs frequently a breakdown into glycerol and free fatty acid, reducing the free fatty acid content in fat is increased, which is especially in
ίο Fetten, die als Speisefett Verwendung finden sollen, sehr nachteilig ist.ίο Fats that are used as edible fat should, is very disadvantageous.
Es wurde nun gefunden, daß derartige Spaltungen vermieden werden können, wenn man dem zu reduzierenden Körper oder dem Katalysator wasserbindende Substanzen, wie z. B. geglühtes Natriumsulfat, Magnesiumsulfat usw., vor oder während des Prozesses zusetzt. Als solche Körper kommen alle diejenigen in Betracht, welche die Fähigkeit haben, Wasser aufzunehmen und zu binden, sofern sie nicht Katalysatorgifte sind.It has now been found that such divisions can be avoided if one of the body to be reduced or the catalyst water-binding substances, such as z. B. calcined sodium sulfate, magnesium sulfate, etc., is added before or during the process. Such bodies are all those who have the ability to consume water absorb and bind, provided they are not catalyst poisons.
500 g Cottonöl werden mit 3 bis 10 Prozent geglühtem Natriumsulfat und mit 2 bis 3 Prozent gepulvertem, ameisensaurem Nickel verrieben. Diese Mischung wird hierauf in einem geeigneten Apparat erwärmt und gleichzeitig Wasserstoff oder Wassergas durchgeleitet. Nach einigen Stunden ist der Ester der ölsäure größtenteils hydrogenisiert und in den Ester der Stearinsäure umgewandelt.500 g cotton oil are made with 3 to 10 percent calcined sodium sulfate and with 2 to 3 percent powdered, formic acid nickel. This mixture is then in one heated suitable apparatus and at the same time passed through hydrogen or water gas. After a few hours the ester of oleic acid is largely hydrogenated and in the Converted to esters of stearic acid.
Ein Erdnußöl mit 0,5 Prozent freier Säure ergab beim Hydrogenisieren nach vorstehender Arbeitsweise einen Säuregehalt von 0,42 Prozent, während bei gleicher Arbeitsweise, aber ohne Zusatz von Natriumsulfat, das gehärtete öl einen Säuregehalt von 0,72 Prozent hatte.A peanut oil with 0.5 percent free acid when hydrogenated gave the above Working method an acid content of 0.42 percent, while with the same working method, but without the addition of sodium sulfate, the hydrogenated oil had an acidity of 0.72 percent.
Ähnlich wie vorstehend ist die Hydrogenisation in Gegenwart wasserbindender Körper auch bei anderen Estern durchführbar, z. B. bei der Überführung von Allylacetat in Propylacetat. Würde rhari die Reduktion in Gegenwart von Wasser durchführen, so würde der Ester zelegt werden und sich Essigsäure und Propylalkohol bilden. Behandelt man Metanitrobenzoesäureäthylester wie angegeben bei etwa i6o°, so entsteht in Gegenwart wasserbindender Körper quantitativ Metaaminobenzoesäureäthylester, während bei der Abwesenheit wasserbindender Körper ein Gemisch von Metaaminobenzoesäure, Metaamin obenzoesäureäthylester und Äthylalkohol entsteht.The hydrogenization in the presence of water-binding bodies is similar to the above also feasible with other esters, e.g. B. when converting allyl acetate into propyl acetate. Would rhari the reduction in the present of water, the ester would break down and acetic acid and propyl alcohol would be formed. Treated one Ethyl metanitrobenzoate, as indicated at about 160 °, is formed in the presence of water-binding Body quantitatively metaaminobenzoic acid ethyl ester, while in the absence of water-binding body a mixture of Metaaminobenzoic acid, metaamin ethyl acetate and ethyl alcohol are formed.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE271985C true DE271985C (en) |
Family
ID=528592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT271985D Active DE271985C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE271985C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1174414A1 (en) * | 1999-04-27 | 2002-01-23 | Showa Denko Kabushiki Kaisha | Process for producing hydrogenated ester, hydrogenation catalyst for use therein, and process for producing the catalyst |
| US6936730B1 (en) | 1999-04-27 | 2005-08-30 | Showa Denko K.K. | Process for producing hydrogenated ester, hydrogenating catalyst used therefor and process for producing the catalyst |
| WO2009064012A1 (en) * | 2007-11-14 | 2009-05-22 | Showa Denko K.K. | Method of producing n-propyl acetate and allyl acetate |
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0
- DE DENDAT271985D patent/DE271985C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1174414A1 (en) * | 1999-04-27 | 2002-01-23 | Showa Denko Kabushiki Kaisha | Process for producing hydrogenated ester, hydrogenation catalyst for use therein, and process for producing the catalyst |
| EP1174414A4 (en) * | 1999-04-27 | 2004-04-21 | Showa Denko Kk | Process for producing hydrogenated ester, hydrogenation catalyst for use therein, and process for producing the catalyst |
| US6936730B1 (en) | 1999-04-27 | 2005-08-30 | Showa Denko K.K. | Process for producing hydrogenated ester, hydrogenating catalyst used therefor and process for producing the catalyst |
| WO2009064012A1 (en) * | 2007-11-14 | 2009-05-22 | Showa Denko K.K. | Method of producing n-propyl acetate and allyl acetate |
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