DE185932C - Process for the preparation of aldehydes - Google Patents
Process for the preparation of aldehydesInfo
- Publication number
- DE185932C DE185932C DE1905185932D DE185932DA DE185932C DE 185932 C DE185932 C DE 185932C DE 1905185932 D DE1905185932 D DE 1905185932D DE 185932D A DE185932D A DE 185932DA DE 185932 C DE185932 C DE 185932C
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- aldehydes
- preparation
- lead
- glass
- 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
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000001299 aldehydes Chemical class 0.000 title claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 239000008262 pumice Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 235000002639 sodium chloride Nutrition 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000004575 stone Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
ben &a\"on Ι'ανη Ib. ben & a \ "on Ι'α νη Ib.
ιοίviacHtat bet ιοίvi acHtat bet
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Bekanntlich ist es bisher nicht möglich gewesen, Aldehyde der aliphatischen Reihe durch Reduktion der entsprechenden Carbonsäuren direkt darzustellen; man war vielmehr gezwungen, den Umweg über die Säurechloride oder die Anhydride der Fettsäuren einzuschlagen, nach welchen Verfahren indessen Formaldehyd naturgemäß überhaupt nicht erhalten werden kann.It is known that it has not been possible to date to use aldehydes of the aliphatic series to be prepared directly by reducing the corresponding carboxylic acids; one was rather forced to take the detour via the acid chlorides or the anhydrides of fatty acids, according to which processes, however Naturally, formaldehyde cannot be obtained at all.
ίο Es hat sich nun gezeigt, daß z. B. die Ameisensäure sich direkt in Formaldehyd überführen läßt, wenn man sie in Dampf form im Gemisch mit Wasserstoff bei höheren Temperaturen über gewisse Metalle, wie Eisen, Nickel, Zink, Zinn, Blei, Silber und dergl., leitet. Dabei ist es vorteilhaft, diese Metalle in kompakter Form zu verwenden.ίο It has now been shown that z. B. the Formic acid can be converted directly into formaldehyde if it is in vapor form in a mixture with hydrogen at higher temperatures over certain metals, such as Iron, nickel, zinc, tin, lead, silver and the like., Conducts. It is advantageous to do this To use metals in compact form.
Es' wurde weiterhin gefunden, daß an Stelle der genannten Metalle auch andere feste Körper wie Glas, z. B. in Form von Glaswolle oder Glasperlen, sowie Bimsstein, Kochsalz usw. benutzt werden können; in diesem Falle wird die Temperatur zweckmäßig noch höher gewählt.It 'was further found that in place of the metals mentioned also other solid bodies such as glass, e.g. B. in the form of glass wool or glass beads, as well as pumice stone, table salt, etc. can be used; in this Case the temperature is expediently chosen even higher.
Man mischt Wasserstoff (beliebigen Ursprungs) mit Dämpfen von Ameisensäure, was man in einfacher Weise dadurch bewirken kann, daß man den Wasserstoff durch erhitzte Ameisensäure leitet, und läßt sodann das Gemisch der beiden Gase durch ein Rohr gehen, welches mit linsengroßen Stückchen von Blei gefüllt und auf etwa 300 ° erhitzt ist. Der Formaldehyd wird aus den entweichenden Gasen in bekannter Weise isoliert.Mix hydrogen (of any origin) with formic acid vapors, which can be done in a simple manner by passing the hydrogen through heated formic acid and then leaving it the mixture of the two gases go through a tube, which is made with lentil-sized pieces filled with lead and heated to about 300 °. The formaldehyde is made from the escaping Gases isolated in a known manner.
^Zu ungefähr dem gleichen Resultat gelangt man, wenn man in vorstehendem Beispiel statt des Bleis Glasperlen benutzt und diese auf etwa 450 bis 500 ° erhitzt.^ Reached roughly the same result if one uses glass beads instead of lead in the above example and these heated to about 450 to 500 °.
In ähnlicher Weise wie Formaldehyd lassen sich unter Verwendung von Essigsäure usw. auch Acetaldehyd usw. gewinnen.In a similar way to formaldehyde, using acetic acid, etc. also gain acetaldehyde, etc.
Das vorliegende Verfahren ist prinzipiell verschieden von demjenigen des Patents 141029. Zwar werden auch nach jenem Patent Fettsäuren (bezw. deren Glyceride) mit Wasserstoff bei Gegenwart von Kontaktmitteln, von denen besonders Nickel erwähnt ist, behan-' delt. Zweck und Erfolg dieser Behandlung ist indessen die Anlagerung von Wasserstoff an die ungesättigte Gruppe— CH= CH—, die in die gesättigte — CH2 — CH2 — übergeführt wird, während im übrigen das Molekül keine Veränderung erfährt. So entsteht aus Ölsäure bei genügend langer Einwirkung quantitativ Stearinsäure (vergl. Patentschrift S. i, Z. 50/51).The present process is fundamentally different from that of patent 141029. According to that patent, fatty acids (or their glycerides) are treated with hydrogen in the presence of contact agents, of which nickel is particularly mentioned. The purpose and success of this treatment, however, is the addition of hydrogen to the unsaturated group - CH = CH -, which is converted into the saturated group - CH 2 - CH 2 - while the rest of the molecule does not undergo any change. Thus, if the effect is long enough, oleic acid is quantitatively converted into stearic acid (see patent specification p. I, line 50/51).
Typisch verschieden von der Erfindung des Patents 141029 ist das gegenwärtige Ver-, fahren, nach welchem die Carboxylgruppe aliphatischer Carbonsäuren durch Wasserstoff katalylisch in die Aldehydgruppe übergeführt wird. Hierbei findet also durch die Wasserstoffkatalyse eine Wegnahme von Sauerstoff aus der Carboxylgruppe (unter Bildung von Wasser) statt, während bei den obigen Reaktionen lediglich Wasserstoff an Kohlen-Typically different from the invention of patent 141029 is the current drive, according to which the carboxyl group of aliphatic carboxylic acids by hydrogen is converted catally into the aldehyde group. This takes place through hydrogen catalysis a removal of oxygen from the carboxyl group (with formation of water) takes place during the above reactions only hydrogen to carbon
wasserstoffreste angelagert wird unter Herstellung der einfachen Bindung.hydrogen residues are deposited with the production of the simple bond.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE185932T | 1905-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE185932C true DE185932C (en) | 1907-06-07 |
Family
ID=42040421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1905185932D Expired DE185932C (en) | 1905-12-14 | 1905-12-14 | Process for the preparation of aldehydes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE185932C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040414B1 (en) * | 1980-05-19 | 1983-06-08 | Kuraray Co., Ltd. | Process for producing acetaldehyde |
| EP0178718A1 (en) * | 1984-10-15 | 1986-04-23 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of aldehydes |
| WO2018163003A1 (en) * | 2017-03-08 | 2018-09-13 | Sabic Global Technologies B.V. | Formaldehyde from formic acid with production of metal oxide |
-
1905
- 1905-12-14 DE DE1905185932D patent/DE185932C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040414B1 (en) * | 1980-05-19 | 1983-06-08 | Kuraray Co., Ltd. | Process for producing acetaldehyde |
| EP0178718A1 (en) * | 1984-10-15 | 1986-04-23 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of aldehydes |
| WO2018163003A1 (en) * | 2017-03-08 | 2018-09-13 | Sabic Global Technologies B.V. | Formaldehyde from formic acid with production of metal oxide |
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