DE2152646A1 - Verfahren zur herstellung von gemischen aus benzylcyanid und beta-phenylaethylamin - Google Patents
Verfahren zur herstellung von gemischen aus benzylcyanid und beta-phenylaethylaminInfo
- Publication number
- DE2152646A1 DE2152646A1 DE19712152646 DE2152646A DE2152646A1 DE 2152646 A1 DE2152646 A1 DE 2152646A1 DE 19712152646 DE19712152646 DE 19712152646 DE 2152646 A DE2152646 A DE 2152646A DE 2152646 A1 DE2152646 A1 DE 2152646A1
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- phenylethylamine
- mixtures
- catalyst
- preparation
- 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
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- VLRQRRQHXZCEDL-UHFFFAOYSA-N 2-cyclohexylideneacetonitrile Chemical compound N#CC=C1CCCCC1 VLRQRRQHXZCEDL-UHFFFAOYSA-N 0.000 claims description 9
- 229910052697 platinum Inorganic materials 0.000 claims description 9
- -1 platinum metals Chemical class 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 239000011787 zinc oxide Substances 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE790446D BE790446A (fr) | 1971-10-22 | Procede de preparation de melanges de cyanure de benzyle et de beta-phenylethylamine | |
| DE19712152646 DE2152646A1 (de) | 1971-10-22 | 1971-10-22 | Verfahren zur herstellung von gemischen aus benzylcyanid und beta-phenylaethylamin |
| CA152,820A CA978550A (en) | 1971-10-22 | 1972-09-28 | PROCESS FOR THE PRODUCTION OF MIXTURES CONSISTING OF BENZYL CYANIDE AND .beta.-PHENYLETHYLAMINE |
| NL7214033A NL7214033A (OSRAM) | 1971-10-22 | 1972-10-17 | |
| CH1520872A CH570974A5 (OSRAM) | 1971-10-22 | 1972-10-18 | |
| IT7230772A IT969777B (it) | 1971-10-22 | 1972-10-20 | Processo per la produzione di miscele di benzilcianuro e beta feniletilammina |
| JP47104575A JPS4849730A (OSRAM) | 1971-10-22 | 1972-10-20 | |
| US00299211A US3835178A (en) | 1971-10-22 | 1972-10-20 | Process for the production of mixtures consisting of benzyl cyanide and {62 -phenylethylamine |
| FR7237229A FR2250349A5 (OSRAM) | 1971-10-22 | 1972-10-20 | |
| GB4869072A GB1383009A (en) | 1971-10-22 | 1972-10-23 | Process for the preparation of benzyl cyanide and beta-phenylethy lamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712152646 DE2152646A1 (de) | 1971-10-22 | 1971-10-22 | Verfahren zur herstellung von gemischen aus benzylcyanid und beta-phenylaethylamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152646A1 true DE2152646A1 (de) | 1973-04-26 |
Family
ID=5823087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152646 Pending DE2152646A1 (de) | 1971-10-22 | 1971-10-22 | Verfahren zur herstellung von gemischen aus benzylcyanid und beta-phenylaethylamin |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3835178A (OSRAM) |
| JP (1) | JPS4849730A (OSRAM) |
| BE (1) | BE790446A (OSRAM) |
| CA (1) | CA978550A (OSRAM) |
| CH (1) | CH570974A5 (OSRAM) |
| DE (1) | DE2152646A1 (OSRAM) |
| FR (1) | FR2250349A5 (OSRAM) |
| GB (1) | GB1383009A (OSRAM) |
| IT (1) | IT969777B (OSRAM) |
| NL (1) | NL7214033A (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3219704A (en) * | 1961-02-02 | 1965-11-23 | Monsanto Co | Manufacture of aromatic amines from alicyclic ketones |
-
0
- BE BE790446D patent/BE790446A/xx unknown
-
1971
- 1971-10-22 DE DE19712152646 patent/DE2152646A1/de active Pending
-
1972
- 1972-09-28 CA CA152,820A patent/CA978550A/en not_active Expired
- 1972-10-17 NL NL7214033A patent/NL7214033A/xx unknown
- 1972-10-18 CH CH1520872A patent/CH570974A5/xx not_active IP Right Cessation
- 1972-10-20 FR FR7237229A patent/FR2250349A5/fr not_active Expired
- 1972-10-20 JP JP47104575A patent/JPS4849730A/ja active Pending
- 1972-10-20 US US00299211A patent/US3835178A/en not_active Expired - Lifetime
- 1972-10-20 IT IT7230772A patent/IT969777B/it active
- 1972-10-23 GB GB4869072A patent/GB1383009A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT969777B (it) | 1974-04-10 |
| FR2250349A5 (OSRAM) | 1975-05-30 |
| CH570974A5 (OSRAM) | 1975-12-31 |
| CA978550A (en) | 1975-11-25 |
| JPS4849730A (OSRAM) | 1973-07-13 |
| US3835178A (en) | 1974-09-10 |
| BE790446A (fr) | 1973-04-24 |
| NL7214033A (OSRAM) | 1973-04-25 |
| GB1383009A (en) | 1975-02-05 |
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