DE903931C - Process for the production of nitriles of fatty aromatic hydrocarbons - Google Patents
Process for the production of nitriles of fatty aromatic hydrocarbonsInfo
- Publication number
- DE903931C DE903931C DEK8885A DEK0008885A DE903931C DE 903931 C DE903931 C DE 903931C DE K8885 A DEK8885 A DE K8885A DE K0008885 A DEK0008885 A DE K0008885A DE 903931 C DE903931 C DE 903931C
- Authority
- DE
- Germany
- Prior art keywords
- aromatic hydrocarbons
- nitriles
- production
- fatty aromatic
- bromide
- 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 5
- 150000002825 nitriles Chemical class 0.000 title claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 3
- 239000003513 alkali Substances 0.000 claims description 7
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 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 claims description 3
- 239000011734 sodium Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 description 2
- WWHJLVMBXXXUFO-UHFFFAOYSA-N 4-(chloromethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CCl)C=C1OC WWHJLVMBXXXUFO-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal cyanides Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-LZFNBGRKSA-N Potassium-45 Chemical compound [45K] ZLMJMSJWJFRBEC-LZFNBGRKSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 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
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
Description
Verfahren zur Herstellung von Nitrilen fettaromatischer Kohlenwasserstoffe Im Patent 896 344 ist ein Verfahren zur Herstellung von Nitrilen durch Erhitzen von in der Seitenkette chlor- oder bromsubstituierten fettaromatischen Kohlenwasserstoffen mit Alkalicyaniden in Gegenwart organischer Lösungsmittel beschrieben, das dadurch gekennzeichnet ist, daß man die Umsetzung in Gegenwart einer, geringen Menge eines löslichen Alkalijodids, wie Natrium-oder Kaliumjodid, in einem indifferenten organischen Lösungsmittel vornimmt, in dem das verwendete Cyanid mindestens teilweise löslich ist.Process for the preparation of nitriles of fatty aromatic hydrocarbons In the patent 896 344 a process for the preparation of nitriles by heating in the side chain chlorine or bromine-substituted fatty hydrocarbons with alkali metal cyanides in the presence of organic solvents is described, which is characterized in that the reaction is carried out in the presence of a , small amount of a soluble alkali iodide, such as sodium or potassium iodide, in an inert organic solvent in which the cyanide used is at least partially soluble.
Es wurde nun weiterhin gefunden, daß man dieselben hohen Ausbeuten an Arvlalky lcyaniden erzielt, wenn man unter sonst gleichen Bedingungen an Stelle des Zusatzes von Alkalijodid einen solchen von Alkalibromid, wie Natrium- oder Kaliumbromid, anwendet. Der Ersatz des kostspieligen Alkalijodids durch das wohlfeile Alkalibromid bedeutet zumal bei der großtechnischen Anwendung des vorliegenden Verfahrens einen wesentlichen Vorteil.It has now also been found that the same high yields can be obtained on Arvlalky lcyaniden achieved if under otherwise identical conditions in place the addition of alkali iodide such as alkali bromide, such as sodium or potassium bromide, applies. The replacement of the expensive alkali iodide by the cheap alkali bromide especially in the large-scale application of the present process means one substantial advantage.
Beispiel i 5o g farbloses, reines kristallisiertes '#,eratrylchlori:d vom F. 46 bis 48°, erhalten aus rohem Veratrylchlorid durch Kurzwegdestillation (i torr) im Luftbad von etwa 15.0°, werden in 3oo ccm Aceton gelöst, mit 22 g Kaliumcyanid und 45 g Natriumbromid versetzt und 6'Stunden am Rückfluß erhitzt. Darauf wird vom Salzrückstand abgesaugt, das Lösungsmittel verdampft und der ölige Rückstand in Äther gelöst. Die erhaltene Ätherlösung wird mit Wasser geschüttelt, über Calciumchlorid getrocknet und im Vakuum destilliert. Das Veratrylcyanid geht bei Kpl 148° als, farbloses Öl über, das rasch zu weißen Kristallen vom F. 65 bis 67° erstarrt. Ausbeute: 45,19 - 9,5 °/o der Theorie. Beispiel 2 i io g rohes Veratrylchlorid, erhalten durch Chlormethylierung von 12:5 g Veratrol, werden in 7,50 ccm Aceton gelöst, mit 89 g Natriumcyanid und io g Natriumbromid versetzt und etwa 30 Stunden unter Rückfluß gekocht. Nach Abtrennung der abgeschiedenen Salze wird das Filtrat eingedampft und aus dem Rückstand das, Veratrylcyanid durch fraktionierte Destillation im Vakuum (Kp. 14o°/ i mm) in einer Ausbeute von 770/0 .der Theorie, berechnet auf Veratral (nach Abzug des zurückgewonnenen Veratrols), erhalten.EXAMPLE I 50 g of colorless, pure crystallized '#, eratrylchlori: d with a melting point of 46 to 48 °, obtained from crude veratryl chloride by short-path distillation (i torr) in an air bath at about 15.0 °, are dissolved in 300 cc of acetone with 22 g of potassium cyanide and 45 g of sodium bromide are added and the mixture is refluxed for 6 'hours. The salt residue is then suctioned off, the solvent is evaporated and the oily residue is dissolved in ether. The ether solution obtained is shaken with water, dried over calcium chloride and distilled in vacuo. The veratryl cyanide passes over at Kpl 148 ° as a colorless oil, which quickly solidifies to white crystals with a melting point of 65 to 67 °. Yield: 45.19-9.5% of theory. EXAMPLE 2 100 g of crude veratryl chloride obtained by chloromethylation of 12: 5 g of veratrole are dissolved in 7.50 cc of acetone, 89 g of sodium cyanide and 10 g of sodium bromide are added and the mixture is refluxed for about 30 hours. After the separated salts have been separated off, the filtrate is evaporated and the veratryl cyanide is removed from the residue by fractional distillation in vacuo (boiling point 140 ° / i mm) in a yield of 770/0. Of theory, calculated on veratral (after deduction of the recovered veratrole ), obtain.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK8885A DE903931C (en) | 1951-02-03 | 1951-02-03 | Process for the production of nitriles of fatty aromatic hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK8885A DE903931C (en) | 1951-02-03 | 1951-02-03 | Process for the production of nitriles of fatty aromatic hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE903931C true DE903931C (en) | 1954-02-11 |
Family
ID=7212183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK8885A Expired DE903931C (en) | 1951-02-03 | 1951-02-03 | Process for the production of nitriles of fatty aromatic hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE903931C (en) |
-
1951
- 1951-02-03 DE DEK8885A patent/DE903931C/en not_active Expired
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