DE1271701B - Process for the production of higher molecular fatty acid esters - Google Patents
Process for the production of higher molecular fatty acid estersInfo
- Publication number
- DE1271701B DE1271701B DEP1271A DE1271701A DE1271701B DE 1271701 B DE1271701 B DE 1271701B DE P1271 A DEP1271 A DE P1271A DE 1271701 A DE1271701 A DE 1271701A DE 1271701 B DE1271701 B DE 1271701B
- Authority
- DE
- Germany
- Prior art keywords
- fatty acid
- higher molecular
- cadmium
- copper
- production
- 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.)
- Pending
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 31
- 239000000194 fatty acid Substances 0.000 title claims description 31
- 229930195729 fatty acid Natural products 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 11
- -1 fatty acid esters Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 24
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- 229910052793 cadmium Inorganic materials 0.000 claims description 9
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000344 soap Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 7
- 239000001993 wax Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004164 Wax ester Substances 0.000 description 2
- 150000001661 cadmium Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229940066675 ricinoleate Drugs 0.000 description 2
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000019386 wax ester Nutrition 0.000 description 2
- JXSRRBVHLUJJFC-UHFFFAOYSA-N 7-amino-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound N1=CC(C#N)=C(N)N2N=C(SC)N=C21 JXSRRBVHLUJJFC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000011 cadmium carbonate Inorganic materials 0.000 description 1
- 229940065285 cadmium compound Drugs 0.000 description 1
- 150000001662 cadmium compounds Chemical class 0.000 description 1
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 1
- GWOWVOYJLHSRJJ-UHFFFAOYSA-L cadmium stearate Chemical compound [Cd+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O GWOWVOYJLHSRJJ-UHFFFAOYSA-L 0.000 description 1
- GKDXQAKPHKQZSC-UHFFFAOYSA-L cadmium(2+);carbonate Chemical compound [Cd+2].[O-]C([O-])=O GKDXQAKPHKQZSC-UHFFFAOYSA-L 0.000 description 1
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 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
- C11C3/126—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation using catalysts based principally on other metals 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
Verfahren zur Herstellung von höhermolekularen Fettsäureestern Die Erfindung betrifft ein Verfahren zur Herstellung von höhermolekularen Fettsäureestern durch katalytische Druckhydrierung von Fettsäuren.Process for the preparation of higher molecular weight fatty acid esters The invention relates to a process for the production of higher molecular weight fatty acid esters by catalytic pressure hydrogenation of fatty acids.
Es sind bereits folgende Verfahren zur Herstellung von solchen Estern bekannt: a) Veresterung höhermolekularer Fettsäuren mit sogenannten FettalkohoIen in Gegenwart von Katalysatoren, wie Schwefelsäure oder Phosphorsäure; b) Umsetzung von Fettsäurechloriden mit Fettalkoholen und e) Umsetzung von Fettsäuren mit Alkylehloriden in Gegenwart eines Chlorwasserstoff bindenden Stoffes, wie Pyridin. The following processes for the preparation of such esters are already known: a) esterification of higher molecular weight fatty acids with so-called fatty alcohols in the presence of catalysts such as sulfuric acid or phosphoric acid; b) reaction of fatty acid chlorides with fatty alcohols and e) reaction of fatty acids with alkyl chlorides in the presence of a substance that binds hydrogen chloride, such as pyridine.
Nach den bisherigen Verfahren wurden Wachsester durch Umsetzen von Fettsäure(n) oder Fettsäurechloriden mit Fettalkoholen hergestellt. Das vorliegende Verfahren geht dagegen ausschließlich von Fettsäuren aus. Gemäß diesem Verfahren werden Wachsester durch teilweise Reduktion der Fettsäure zu dem entsprechenden Fettalkohol und Veresterung des letzteren mit der nichtreduzierten Fettsäure erhalten.According to the previous process, wax esters were made by reacting Fatty acid (s) or fatty acid chlorides made with fatty alcohols. The present Process, on the other hand, is based exclusively on fatty acids. According to this procedure wax esters become the corresponding ones by partial reduction of the fatty acid Fatty alcohol and esterification of the latter with the unreduced fatty acid.
Die Erfindung ermöglicht die Herstellung einer großen Anzahl von Estern jeder gewünschten Art, von harten, hochschmelzenden und gesättigten bis zu ungesättigten, flüssigen Estern, und besteht darin, daß man zur Herstellung höhermolekularer Fettsäureester höhermolekulare Fettsäuren oder Gemische solcher Fettsäuren in Gegenwart eines Mischkatalysators, bestehend aus Kupfer und Cadmium in Form ihrer Salze oder Fettsäureseifen, bei einer Temperatur zwischen 100 und 4001 C und unter einem Wasserstoffdruck zwischen etwa 72 und 360 at hydriert.The invention enables the production of a large number of esters of any desired type, from hard, high-melting and saturated to unsaturated, liquid esters, and consists in that, for the production of higher molecular weight fatty acid esters, higher molecular weight fatty acids or mixtures of such fatty acids in the presence of a mixed catalyst consisting of Copper and cadmium in the form of their salts or fatty acid soaps, hydrogenated at a temperature between 100 and 4001 C and under a hydrogen pressure between about 72 and 360 at.
Die erfindungsgemäß hergestellten Ester können die natürlichen Esterwachse auf zahlreichen Anwendungsgebieten ersetzen. Die natürlichen Hartwachse werden als Fußboden-, Auto- und Bootspolituren sowie für die Herstellung von Kohlepapieren und Wachsmatrizen und bei der Holzbearbeitung verwendet. Die flüssigen Ester werden zur Schmierung von schnellaufenden Maschinen, für die Metallbearbeitung und als Transformatorenöle gebraucht. Eines der wichtigsten Naturwachse, Camaubawachs, hat einen Schmelzpunkt von 841 C, besitzt viele freie sekundäre Hydroxylgruppen (woraus sich eine Acetylzahl von etwa 55 ergibt) und einen hohen Sättigungsgrad (Jodzahl etwa 10). Ein wichtiges flüssiges Wachs, Joioba, hat eine Jodzahl von 83. Der Katalysator wird der zu hydrierenden Fettsäure wie folgt einverleibt: Ein Kupfersalz einer schwachen Säure, beispielsweise Kupfercarbonat oder Kupferacetat, wird zu einem überschuß der zu hydrierenden Fettsäure bzw. dem Fettsäuregemisch gegeben. In gleicher Weise wird mit einem Cadmiumsalz einer schwachen Säure, beispielsweise Cadmiumcarbonat oder Cadmiumoxyd, verfahren. Selbstverständlich können die Kupfer- und Cadmiumverbindungen nach vorheriger Mischung auch gemeinsam zu der Fettsäure bzw. dem Fettsäuregemisch zugegeben werden. Anschließend wird die katalysatorhaltige Fettsäure bzw. das Fettsäuregemisch erhitzt und auf diese Weise aus den Metallsalzen die entsprechenden fettsauren Kupfer- und Cadmiumseifen gebildet. Die Masse wird schließlich unter vermindertem Druck auf 1201 C erhitzt, um das entstandene Wasser abzutreiben.The esters produced according to the invention can replace the natural ester waxes in numerous fields of application. The natural hard waxes are used as floor, car and boat polishes as well as for the production of carbon papers and wax matrices and in woodworking. The liquid esters are used for the lubrication of high-speed machines, for metalworking and as transformer oils. One of the most important natural waxes, camauba wax, has a melting point of 841 C, has many free secondary hydroxyl groups (resulting in an acetyl number of around 55 ) and a high degree of saturation (iodine number around 10). An important liquid wax, joioba, has an iodine number of 83. The catalyst is incorporated into the fatty acid to be hydrogenated as follows: A copper salt of a weak acid, for example copper carbonate or copper acetate, is added to an excess of the fatty acid or fatty acid mixture to be hydrogenated. The same procedure is used with a cadmium salt of a weak acid, for example cadmium carbonate or cadmium oxide. Of course, the copper and cadmium compounds can also be added together to the fatty acid or fatty acid mixture after prior mixing. Then the catalyst-containing fatty acid or the fatty acid mixture is heated and in this way the corresponding fatty acid copper and cadmium soaps are formed from the metal salts. The mass is finally heated to 1201 ° C. under reduced pressure in order to drive off the water formed.
Wenn das Kupfer- oderCadmiumsalz wasserlöslich ist, kann dieses auch zuerst in Wasser gelöst und dann die Lösung einer wäßrigen Lösung des Natriumsalzes der Fettsäure oder des Gemisches der Fettsäuren zugefügt werden. Die ausgeschiedenen Kupfer-und Cadmiumseifen können dann durch Dekantieren oder Filtrieren abgetrennt worden.If the copper or cadmium salt is water soluble, so can first dissolved in water and then the solution of an aqueous solution of the sodium salt the fatty acid or the mixture of fatty acids are added. The eliminated Copper and cadmium soaps can then be separated by decanting or filtering been.
Beispiel 1 Ein Mischkatalysator aus Kupfer- und Cadmiumseife mit einem Metallgehalt von 1 g Kupfer und 3,3 g Cadmium (Metallgehalt insgesamt 4,3 g), entsprechend 10,2 g Kupferricinoleat und 21,0 g Cadmiumricinoleat, wurde zu 100 g Ricinolsäure gegeben. Die verwendete Ricinolsäure zeigte folgende Analysenwerte: Säurezahl 188, Jodzahl 84,6, Hydroxylzahl 186,0. Example 1 A mixed catalyst of copper and cadmium soap with a metal content of 1 g of copper and 3.3 g of cadmium (total metal content of 4.3 g), corresponding to 10.2 g of copper ricinoleate and 21.0 g of cadmium ricinoleate, was added to 100 g of ricinoleic acid . The ricinoleic acid used showed the following analytical values: acid number 188, iodine number 84.6, hydroxyl number 186.0.
Die Hydrierung wurde bei einer Temperatur von 2001 C und einem Wasserstoffdruck von 275 at durchgeführt. Das Endprodukt zeigte folgende Analysenwerte (die theoretischen Werte des erwarteten Esters hierbei in Klammern): Säurezahl 2,4 (0), Verseifungszahl 94 (99), Hydroxylzahl 181 (199), Jodzahl 84 (90). Dies entspricht einem Gehalt von 92 % Ricinoleylrieinoleat.The hydrogenation was carried out at a temperature of 2001 C and a hydrogen pressure of 275 at. The end product showed the following analytical values (the theoretical values of the expected ester in brackets): acid number 2.4 (0), saponification number 94 (99), hydroxyl number 181 (199), iodine number 84 (90). This corresponds to a content of 92 % ricinoleyl rinoleate.
Beispiel 2 Gemäß Beispiel 1 wurde Stearinsäure bei einer Temperatur von 2501 C und einem Wasserstoffdruck von 275 at hydriert, und zwar in Gegenwart eines Mischkatalysators aus Kupferstearat und Cadmiumstearat mit einem Metallgehalt von 1 g Kupfer und 3,3 g Cadmium (Metallgehalt insgesamt 4,3 g). Das Endprodukt zeigte folgende Analysenwerte: Säurezahl 1,4 (0), Verseifungszahl 93,5 (104,7), Hydroxylzahl 0 (0), Schmelzpunkt 65,61 C. Dies entsprach einem Gehalt von 88% Stearylstearat.Example 2 As in Example 1 , stearic acid was hydrogenated at a temperature of 2501 C and a hydrogen pressure of 275 atm, in the presence of a mixed catalyst of copper stearate and cadmium stearate with a metal content of 1 g copper and 3.3 g cadmium (total metal content 4.3 G). The end product showed the following analytical values: acid number 1.4 (0), saponification number 93.5 (104.7), hydroxyl number 0 (0), melting point 65.61 C. This corresponded to a content of 88% stearyl stearate.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1271A DE1271701B (en) | 1964-09-05 | 1964-09-05 | Process for the production of higher molecular fatty acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1271A DE1271701B (en) | 1964-09-05 | 1964-09-05 | Process for the production of higher molecular fatty acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1271701B true DE1271701B (en) | 1968-07-04 |
Family
ID=5661539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP1271A Pending DE1271701B (en) | 1964-09-05 | 1964-09-05 | Process for the production of higher molecular fatty acid esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1271701B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409148A (en) * | 1981-12-09 | 1983-10-11 | Uop Inc. | Process for the reduction of unsaturated carboxylic acids |
| US4724100A (en) * | 1986-03-26 | 1988-02-09 | Sherex Chemical Company, Inc. | Liquid phase process for producing esters |
-
1964
- 1964-09-05 DE DEP1271A patent/DE1271701B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409148A (en) * | 1981-12-09 | 1983-10-11 | Uop Inc. | Process for the reduction of unsaturated carboxylic acids |
| US4724100A (en) * | 1986-03-26 | 1988-02-09 | Sherex Chemical Company, Inc. | Liquid phase process for producing esters |
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