JPS584706B2 - ジフエニルアミンの製造方法 - Google Patents
ジフエニルアミンの製造方法Info
- Publication number
- JPS584706B2 JPS584706B2 JP51052876A JP5287676A JPS584706B2 JP S584706 B2 JPS584706 B2 JP S584706B2 JP 51052876 A JP51052876 A JP 51052876A JP 5287676 A JP5287676 A JP 5287676A JP S584706 B2 JPS584706 B2 JP S584706B2
- Authority
- JP
- Japan
- Prior art keywords
- aniline
- boron
- reaction
- water
- weight
- 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
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title claims description 68
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 122
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000011541 reaction mixture Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 24
- 229910015900 BF3 Inorganic materials 0.000 claims description 21
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 21
- 229910052796 boron Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 16
- 150000002222 fluorine compounds Chemical class 0.000 claims description 16
- 150000001639 boron compounds Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- -1 ammonium fluoroborate Chemical compound 0.000 claims description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 4
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 2
- KVBCYCWRDBDGBG-UHFFFAOYSA-N azane;dihydrofluoride Chemical compound [NH4+].F.[F-] KVBCYCWRDBDGBG-UHFFFAOYSA-N 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical compound [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
- 230000035484 reaction time Effects 0.000 description 15
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002912 waste gas Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 238000000326 densiometry Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/64—Preparation of compounds containing amino groups bound to a carbon skeleton by disproportionation
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2521293A DE2521293C3 (de) | 1975-05-13 | 1975-05-13 | Verfahren zur Herstellung von Diphenylamin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51138628A JPS51138628A (en) | 1976-11-30 |
| JPS584706B2 true JPS584706B2 (ja) | 1983-01-27 |
Family
ID=5946450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51052876A Expired JPS584706B2 (ja) | 1975-05-13 | 1976-05-11 | ジフエニルアミンの製造方法 |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS584706B2 (cg-RX-API-DMAC10.html) |
| BE (1) | BE841762A (cg-RX-API-DMAC10.html) |
| BR (1) | BR7602968A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1067519A (cg-RX-API-DMAC10.html) |
| CH (1) | CH608781A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2521293C3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES447825A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2310997A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1483173A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1061268B (cg-RX-API-DMAC10.html) |
| LU (1) | LU74916A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL7605129A (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA762832B (cg-RX-API-DMAC10.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19756146A1 (de) * | 1997-12-17 | 1999-06-24 | Bayer Ag | Herstellung von N-Phenyl-1-naphthylamin |
| DE19756158A1 (de) * | 1997-12-17 | 1999-06-24 | Bayer Ag | Herstellung von sekundären Diarylaminen |
| DE19756145A1 (de) * | 1997-12-17 | 1999-06-24 | Bayer Ag | Herstellung von N-Phenyl-1-naphthylamin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE694781C (de) * | 1938-06-15 | 1940-08-07 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Phenolen |
| FR1231215A (fr) * | 1959-04-10 | 1960-09-27 | Cfmc | Nouveau procédé de préparation de la diphénylamine |
| US3071619A (en) * | 1959-06-09 | 1963-01-01 | Goodrich Co B F | Preparation of secondary aryl amines |
-
1975
- 1975-05-13 DE DE2521293A patent/DE2521293C3/de not_active Expired
-
1976
- 1976-05-10 CH CH765843A patent/CH608781A5/xx not_active IP Right Cessation
- 1976-05-11 IT IT49411/76A patent/IT1061268B/it active
- 1976-05-11 GB GB19349/76A patent/GB1483173A/en not_active Expired
- 1976-05-11 CA CA252,188A patent/CA1067519A/en not_active Expired
- 1976-05-11 JP JP51052876A patent/JPS584706B2/ja not_active Expired
- 1976-05-11 LU LU74916A patent/LU74916A1/xx unknown
- 1976-05-12 ZA ZA762832A patent/ZA762832B/xx unknown
- 1976-05-12 BR BR7602968A patent/BR7602968A/pt unknown
- 1976-05-12 ES ES447825A patent/ES447825A1/es not_active Expired
- 1976-05-13 FR FR7614490A patent/FR2310997A1/fr active Granted
- 1976-05-13 NL NL7605129A patent/NL7605129A/xx not_active Application Discontinuation
- 1976-05-13 BE BE2055024A patent/BE841762A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE841762A (fr) | 1976-11-16 |
| NL7605129A (nl) | 1976-11-16 |
| BR7602968A (pt) | 1977-05-31 |
| ZA762832B (en) | 1977-04-27 |
| DE2521293C3 (de) | 1987-12-03 |
| DE2521293A1 (de) | 1976-11-18 |
| JPS51138628A (en) | 1976-11-30 |
| CH608781A5 (en) | 1979-01-31 |
| ES447825A1 (es) | 1977-07-01 |
| GB1483173A (en) | 1977-08-17 |
| IT1061268B (it) | 1983-02-28 |
| FR2310997A1 (fr) | 1976-12-10 |
| CA1067519A (en) | 1979-12-04 |
| FR2310997B1 (cg-RX-API-DMAC10.html) | 1979-08-10 |
| LU74916A1 (cg-RX-API-DMAC10.html) | 1977-02-11 |
| DE2521293B2 (de) | 1979-07-12 |
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