DE2003932B - Process for the distillation of benzyl chloride or mixtures of the same containing it - Google Patents
Process for the distillation of benzyl chloride or mixtures of the same containing itInfo
- Publication number
- DE2003932B DE2003932B DE2003932B DE 2003932 B DE2003932 B DE 2003932B DE 2003932 B DE2003932 B DE 2003932B
- Authority
- DE
- Germany
- Prior art keywords
- benzyl chloride
- mixtures
- distillation
- chloride
- determined
- 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
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 title claims description 11
- 229940073608 benzyl chloride Drugs 0.000 title claims description 11
- 238000004821 distillation Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 title description 5
- 150000003951 lactams Chemical class 0.000 claims description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 2
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 caprylic lactam Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Description
Bekanntlich spaltet Benzylchlorid, besonders bei hohen Temperaturen, verhältnismäßig leicht Chlorwasserstoff ab unter Bildung wertloser, meist tiefgefärbter Kondensationsprodukte. Diese Zersetzung wird schon durch Spuren von Metallen und ihren Verbindungen, insbesondere Eisenoxiden und -salzen, die in der Technik ohne großen Aufwand nie ganz vermieden werdsn können, stark gefördert.It is known that benzyl chloride splits hydrogen chloride relatively easily, especially at high temperatures with the formation of worthless, mostly deeply colored condensation products. This decomposition is already caused by traces of metals and their compounds, especially iron oxides and salts, which can never be completely avoided in technology without great effort.
Die Zersetzung des Benzylchlorids macht sich beim Destillieren desselben oder dieses enthaltender Gemische, z. B. Gemische mit Benzalchlorid und Benzotrichlorid, wie sie bei der technischen Her-Stellung des Benzylchlorids anfallen, besonders unangenehm bemerkbar, da sich die DeiHillierkolonnert durch Abscheidung der Kondensationsprodukte schon in verhältnismäßig kurzer Zeit zusetzen und sich im Sumpf undestillierbare Rückstände anreichern.The decomposition of the benzyl chloride takes place on distillation of the same or more containing it Mixtures, e.g. B. Mixtures with benzal chloride and benzotrichloride, as used in technical manufacture of the benzyl chloride are obtained, which is particularly noticeable because the DeiHillierkolonnert clog by the separation of the condensation products in a relatively short time and in the Enrich sump undistillable residues.
Gegenband der Erfindung ist daher ein verbessertes Verfahren zum Destillieren von Benxylchlorid oder von dieses enthaltenden Gemischen, das dadurch gekennzeichnet ist, daß man in Gegenwart eines Lactams, zweckmäßig in einer Menge zwischen etwa 0,01 und etwa 1,0 Gewichtsprozent, destilliert.Opposite tape of the invention is therefore an improved method for distilling or benxyl chloride of this containing mixtures, which is characterized in that in the presence of a Lactams, suitably in an amount between about 0.01 and about 1.0 percent by weight, distilled.
Die Zersetzung des Benzylchlorids und die damit verbundenen Nachteile beim Destillieren werden durch den Zusatz eines Lactams weitgehend vermieden.The decomposition of the benzyl chloride and the associated disadvantages when distilling are largely avoided by adding a lactam.
Geeignete Lactame sind z. B. Pyrrolidon-(2). p-Caprolactam, Capryllactam und <u-Laurinlactam.Suitable lactams are e.g. B. Pyrrolidone- (2). p-caprolactam, caprylic lactam and <u-laurolactam.
Die stabilisierende Wirksamkeit tf ,K> Zusatzes von Lactamen zeigt der folgende Test:The stabilizing effectiveness tf, K > addition of lactams is shown in the following test:
Zu reinem Benzylchlorid wurden 1 Gewichtsprozent sublimiertes Eisen(III)-chlorid und 0,1,0,5 und 1,0 Gewichtsprozent verschiedener Lactame zugegeben. Dann wurde der Zersetzungsgrad des Benzylchlorids in Prozent nach 90 Minuten, yemessen an der Menge des abgespaltenen Chlorwasserstoffs, bei Raumtemperatur, bei 50 und bei 95° C bestimmt, wie aus der folgenden Tabelle hervorgeht:1 percent by weight of sublimed ferric chloride and 0.1, 0.5 and 1.0 percent by weight were added to pure benzyl chloride various lactams added. Then the degree of decomposition of the benzyl chloride became in percent after 90 minutes, measured on the amount of the split off hydrogen chloride, at room temperature, determined at 50 and 95 ° C, as can be seen from the following table:
Beim Destillieren von Benzylchlorid aus einem technischen Gesnisch von Toluol, Benzylchlorid, Benzalchlorid und Benzotrichlorid tritt in Gegenwart von nur etwa 0,01 bis etwa 0,05 Gewichtsprozent Caprolactam eine nur kaum noch meßbare Zersetzung ein. da das Ausgangsmaterial nur Spuren zersetzender Metallverbindungen enthält im Unterschied zu den obigen Tests, die mit einem vergleichsweise sehr hohen EisenchlortHßeliialt durchgeführt wurden.When distilling benzyl chloride from a technical mixture of toluene, benzyl chloride, benzal chloride and benzotrichloride occurs in the presence of only about 0.01 to about 0.05 weight percent caprolactam a hardly measurable decomposition. as the starting material only contains traces of decomposing metal compounds In contrast to the above tests, it contains the one with a comparatively very high level of EisenchlorotHßeliialt were carried out.
Da die Siedepunkte der Lactame viel höher liegen als die der Toluolchlorierungsprodukte, ist es [ I'Since the boiling points of the lactams are much higher than those of the toluene chlorination products, it is [I '
ausgeschlossen, daß Lactamantcile mit überdestillieren. Auf diese Weise wird vermieden, daß die gewui.
zersetzungshemmendc Wirkung während der Destillation zu einer unerwünschten reaktionshemmenden Wirkung
bei der Weitervefwendung des Benzylchlorids wird. ruled out that lactamantcile distill over with. In this way it is avoided that the Gewui.
The anti-decomposition effect during the distillation becomes an undesirable reaction-inhibiting effect when the benzyl chloride is reused.
Claims (1)
Family
ID=
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