DE1070616B - - Google Patents
Info
- Publication number
- DE1070616B DE1070616B DENDAT1070616D DE1070616DA DE1070616B DE 1070616 B DE1070616 B DE 1070616B DE NDAT1070616 D DENDAT1070616 D DE NDAT1070616D DE 1070616D A DE1070616D A DE 1070616DA DE 1070616 B DE1070616 B DE 1070616B
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- carboxylic acid
- benzoyl chloride
- nucleus
- found
- 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
- 239000000460 chlorine Substances 0.000 claims description 7
- -1 aromatic carboxylic acid chlorides Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 210000004940 Nucleus Anatomy 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 2
- LLRZUDIHEZXFGV-UHFFFAOYSA-N (4-methylphenyl) benzoate Chemical compound C1=CC(C)=CC=C1OC(=O)C1=CC=CC=C1 LLRZUDIHEZXFGV-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N Phenylpropanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(fr CbOL(for CbOL
BEKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
\USLEGESCHRIFT: 10. DEZEMBER 1959 NOTICE
THE REGISTRATION
AND ISSUE OF THE
\ USLEGALSCRIPT: DECEMBER 10, 1959
In der Patentanmeldung I 11940 IVb/12o wird ein Verfahren zur Herstellung aromatischer Carbonsäurechloride durch Einwirkung von Chlor auf gegebenenfalls im Kern substituierte Benzoesäuremethylester in Gegenwart von Licht bei Temperaturen von 100 bis 220° C beschrieben.Patent application I 11940 IVb / 12o describes a process for the preparation of aromatic carboxylic acid chlorides by the action of chlorine on methyl benzoate optionally substituted in the nucleus in Presence of light at temperatures from 100 to 220 ° C described.
Es wurde nun gefunden, daß man weiterhin zu aromatischen Carbonsäurechloriden gelangen kann, wenn man von Verbindungen ausgeht, in denen die Methylgruppe durch einen aromatischen Rest substituiert ist. also von gegebenenfalls im Kern substituierten Benzoesäureestern der allgemeinen FormelIt has now been found that aromatic carboxylic acid chlorides can still be obtained, when starting from compounds in which the methyl group is substituted by an aromatic radical is. that is to say of benzoic acid esters of the general formula which may be substituted in the nucleus
COO-CH2-RCOO-CH 2 -R
Verfahren zur Herstellung
aromatischer CarbonsäurechlorideMethod of manufacture
aromatic carboxylic acid chlorides
Zusatz zur Patentanmeldung I 11940 IVb/12 ο
(Auslegesciirift 1 064 495) Addition to patent application I 11940 IVb / 12 ο
(Disposal lift 1 064 495)
U oooiU oooi
Anmelder:Applicant:
Chemische Werke WittenChemical works in Witten
Gesellschaft mit beschränkter Haftung,Company with limited liability,
Witten, Arthur-Imhausen-Str. 92 aWitten, Arthur-Imhausen-Str. 92 a
in der R einen aromatischen Rest darstellt.in which R represents an aromatic radical.
210 g Benzoesäurebenzylester wurden unter Belichtung bei 150° C 90 Minuten chloriert. Es wurden 282 g Chlorierungsprodukt erhalten und destilliert. Von 79 bis 80° C/15 mm gingen 256 g Benzoylchlorid = 91,5 «/o der Theorie mit einer VZ = 805 über.210 g of benzyl benzoate were chlorinated with exposure to light at 150 ° C. for 90 minutes. 282 g of chlorination product were obtained and distilled. From 79 to 80 ° C./15 mm, 256 g of benzoyl chloride = 91.5% of theory with a VZ = 805 were transferred.
113 g Benzoesäure-p-toluylester werden unter Belichtung chloriert. Die Temperatur beträgt bei Beginn der Chloreinleitung 50° C, nach 1 Stunde 120° C, nach insgesamt 2 Stunden 135° C, nach insgesamt 3 Stunden 160° C und nach insgesamt 4 Stunden 175° C. Es werden 213 g eines flüssigen und schwachgelbgefärbten Reaktionsproduktes erhalten, das über eine kleine Glaskolonne destilliert wird. Dabei wurden folgende Fraktionen erhalten:113 g of p-toluyl benzoate are obtained with light exposure chlorinated. The temperature at the beginning of the introduction of chlorine is 50 ° C, after 1 hour 120 ° C, after a total of 2 hours 135 ° C, after a total of 3 hours 160 ° C and after a total of 4 hours 175 ° C. 213 g of a liquid and pale yellow-colored reaction product are obtained, which over a small glass column is distilled. The following fractions were obtained:
Fraktion 1 (75 bis 79° C/12 mm):Fraction 1 (75 to 79 ° C / 12 mm):
59 g = 84,5 °/o der Theorie Jjenzoylchlorid
VZ: 803 gefunden, 800 berechnet,
Cl: 25,5«/o gefunden, 25,3% berechnet.59 g = 84.5% of the theory Jjen zoylchlorid
VZ: 803 found, 800 calculated,
Cl: 25.5% found, 25.3% calculated.
Fraktion 2 (148 bis 153° C/12 mm):Fraction 2 (148 to 153 ° C / 12 mm):
109 g = 84,2% der Theorie u-Trichlormetb.ylbenzoylchlorid 109 g = 84.2% of theory of u-trichlorometb.yl benzoyl chloride
VZ: 1254 gefunden. 1300 berechnet,
Cl: 55.2% gefunden. 55,0% berechnet.VZ: 1254 found. 1300 calculated,
Cl: 55.2% found. 55.0% calculated.
Destillationsrückstand: 39g.Distillation residue: 39g.
Es ist bereits vorgeschlagen worden, Benzoylchlorid durch Einwirkung von Chlor auf Benzylacetat herzustellen.
Abgesehen davon, daß hierbei als Ausgangs-Dipl.-Chem. Ewald Katzschmann, Dortmund-Kruckel,
ist als Erfinder genannt wordenIt has been proposed to prepare benzoyl chloride by the action of chlorine on benzyl acetate. Apart from the fact that here as the starting Dipl.-Chem. Ewald Katzschmann, Dortmund-Kruckel,
has been named as the inventor
produkt der Benzylester einer aliphatischen Carbonsäure verwendet wird und dabei das Benzoylchlorid mit Acetylchlorid verunreinigt anfällt und erst von diesem befreit werden muß, wird angenommen, daß ein Teil des Chlors auch in den Kern wandert, so daßproduct of the benzyl ester of an aliphatic carboxylic acid is used and the benzoyl chloride is contaminated with acetyl chloride and only from this must be freed, it is assumed that part of the chlorine also migrates into the core, so that
a5 sich diese Methode zur Herstellung von insbesondere Benzoylchlorid technisch nicht durchgesetzt hat. Demgegenüber gestattet das vorliegende Verfahren, bei welchem in Gegenwart von Licht gearbeitet wird, z. B. die Herstellung von äußerst reinem Benzoylchlorid in nahezu theoretischer Ausbeute. a 5 this method for the production of benzoyl chloride in particular has not established itself technically. In contrast, the present method, which is carried out in the presence of light, z. B. the production of extremely pure benzoyl chloride in almost theoretical yield.
Claims (1)
Britische Patentschrift Nr. 465 038;
russische Patentschrift Nr. 56693, referiert in »Chemisches Zentralblatt«, 1940, II., S. 2552.Considered publications:
British Patent No. 465,038;
Russian patent specification No. 56693, reported in "Chemisches Zentralblatt", 1940, II., p. 2552.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1070616B true DE1070616B (en) | 1959-12-10 |
Family
ID=595478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1070616D Pending DE1070616B (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1070616B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0078993A1 (en) * | 1981-11-07 | 1983-05-18 | Bayer Ag | Process for the preparation of benzoyl chloride |
-
0
- DE DENDAT1070616D patent/DE1070616B/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0078993A1 (en) * | 1981-11-07 | 1983-05-18 | Bayer Ag | Process for the preparation of benzoyl chloride |
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