GB945162A - Improvements in or relating to the preparation of aryl alkyl aminoketones - Google Patents
Improvements in or relating to the preparation of aryl alkyl aminoketonesInfo
- Publication number
- GB945162A GB945162A GB34326/59A GB3432659A GB945162A GB 945162 A GB945162 A GB 945162A GB 34326/59 A GB34326/59 A GB 34326/59A GB 3432659 A GB3432659 A GB 3432659A GB 945162 A GB945162 A GB 945162A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vessel
- pipe
- continuously
- product
- halogen
- 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
- -1 aryl alkyl aminoketones Chemical class 0.000 title 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000012433 hydrogen halide Substances 0.000 abstract 3
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- 150000003335 secondary amines Chemical class 0.000 abstract 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 2
- 230000026030 halogenation Effects 0.000 abstract 2
- 238000005658 halogenation reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000004983 alkyl aryl ketones Chemical class 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000110 cooling liquid Substances 0.000 abstract 1
- 238000007872 degassing Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1868—Stationary reactors having moving elements inside resulting in a loop-type movement
- B01J19/1875—Stationary reactors having moving elements inside resulting in a loop-type movement internally, i.e. the mixture circulating inside the vessel such that the upwards stream is separated physically from the downwards stream(s)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00076—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements inside the reactor
- B01J2219/00083—Coils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
<PICT:0945162/C2/1> Aminoketones of the general formula: <FORM:0945162/C2/1> (wherein R represents hydrogen or an alkyl group and R2 and R3 represent alkyl groups, which may be alike or different, or together with the nitrogen atom form a 5 or 6 member heterocyclic ring) are produced by continuously feeding an alkyl aryl ketone having at least one hydrogen atom attached to the alpha carbon atom of the alkyl group, and a halogen to a closed reaction vessel, continuously removing the hydrogen halide formed, effecting the halogenation in a forced cycle with continuous removal of part of the halogenated product, continuously reacting the withdrawn halogenation product with a secondary amine and treating the reaction mixture with an aqueous alkali metal hydroxide solution, and continuously removing the fixed halogen hydracid. Preferably the reaction mixture is pumped through the cooled interior of a jacket vessel within the closed reaction vessel under the action of light. As shown, halogen is fed through pipe 15 and ketone is fed through pipe 16 into a reaction chamber 10. The agitator 13 causes the reaction mixture to circulate through the jacket vessel 11 and the annular space between that vessel and the wall of the chamber 10. Cooling liquid is passed through coil 12. Gaseous hydrogen halide which is formed is discharged through pipe 17, and halogenated product is removed through pipe 18. The halogenated product passes to a further vessel where residual hydrogen halide is removed by washing with water or by degassing at a higher temperature preferably under vacuum. The halogenated product is then passed to a reaction vessel in the form of a long horizontally arranged container provided with stirring arms and is mixed with a secondary amine. The mixture is then treated with soda lye at the end of the same vessel or in a further vessel, and the amine phase is then continuously separated from the aqueous phase. As secondary amines these may be used diethylamine, piperidine, piperazine, pyrrolidine, or morpholine. Examples describe the continuous bromination of propiophenone and the amination of the brominated product with diethylamine and pyrrolidine. Reference has been directed by the Comptroller to Specification 849,755.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET16340A DE1164388B (en) | 1959-03-02 | 1959-03-02 | Process and apparatus for the production of aryl alkyl bromoketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB945162A true GB945162A (en) | 1963-12-23 |
Family
ID=7548212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34326/59A Expired GB945162A (en) | 1959-03-02 | 1959-10-09 | Improvements in or relating to the preparation of aryl alkyl aminoketones |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3340305A (en) |
| DE (1) | DE1164388B (en) |
| GB (1) | GB945162A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308400A (en) * | 1977-12-22 | 1981-12-29 | Ciba-Geigy A.G. | Sensitizers for photopolymerization |
| EP1357117A2 (en) * | 2002-04-26 | 2003-10-29 | Chingfan Chris Chiu | Novel aminoketone derivatives and preparation process and uses of the same as photoinitiators |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1242241B (en) * | 1964-04-08 | 1967-06-15 | Boehringer Sohn Ingelheim | Process for the preparation of substituted phenyl-alpha-aminoketones and their acid addition salts or their optical antipodes |
| DE1270022B (en) * | 1966-08-26 | 1968-06-12 | Kalk Chemische Fabrik Gmbh | Process for the preparation of alpha-bromoalkylaryl ketones |
| WO2000075094A2 (en) * | 1999-06-03 | 2000-12-14 | Ishihara Sangyo Kaisha, Ltd. | Method for producing a halogenated acetophenone |
| CN100560563C (en) * | 2007-07-06 | 2009-11-18 | 浙江普洛医药科技有限公司 | The synthetic method of BUPROPIONE HCl |
| CN104741062A (en) * | 2014-07-09 | 2015-07-01 | 季永东 | Heat resistant type electrical heating reaction vessel |
| CN106268567A (en) * | 2016-09-27 | 2017-01-04 | 冀州天大天久精细化工科技有限公司 | A kind of enamel reaction still |
| CN111545131B (en) * | 2020-04-29 | 2021-10-08 | 北京航空航天大学 | Control method of waste heat recovery type sealed hydrothermal reaction kettle |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2116893A (en) * | 1935-11-05 | 1938-05-10 | Ig Farbenindustrie Ag | Process of chlorinating and brominating carbonyl compounds |
| DE696772C (en) * | 1935-11-06 | 1940-09-28 | I G Farbenindustrie Akt Ges | Process for the chlorination or bromination of ketones |
| US2107905A (en) * | 1937-03-09 | 1938-02-08 | Armour & Co | Chlorinated aralkyl ketones |
| US2155194A (en) * | 1938-10-27 | 1939-04-18 | Kamlet Jonas | Preparation of alpha-alkylaminoacylophenones |
| DE859146C (en) * | 1943-11-19 | 1952-12-11 | Temmler Werke | Process for the production of ª ‡ -bromopropiophenone |
| NL93401C (en) * | 1954-10-23 | |||
| US2784193A (en) * | 1955-01-19 | 1957-03-05 | Merck & Co Inc | Phenalkylamines |
-
1959
- 1959-03-02 DE DET16340A patent/DE1164388B/en active Pending
- 1959-10-09 GB GB34326/59A patent/GB945162A/en not_active Expired
-
1964
- 1964-07-07 US US381945A patent/US3340305A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308400A (en) * | 1977-12-22 | 1981-12-29 | Ciba-Geigy A.G. | Sensitizers for photopolymerization |
| EP1357117A2 (en) * | 2002-04-26 | 2003-10-29 | Chingfan Chris Chiu | Novel aminoketone derivatives and preparation process and uses of the same as photoinitiators |
| EP1357117A3 (en) * | 2002-04-26 | 2003-12-17 | Chingfan Chris Chiu | Novel aminoketone derivatives and preparation process and uses of the same as photoinitiators |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1164388B (en) | 1964-03-05 |
| US3340305A (en) | 1967-09-05 |
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