CA2499306C - Preparation of substituted aromatic amines - Google Patents

Preparation of substituted aromatic amines Download PDF

Info

Publication number: CA2499306C
Authority: CA; Canada
Prior art keywords: aniline; complex; hydrogen; ferrate; vessel
Prior art date: 1996-04-04
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 - Fee Related

Application number

CA 2499306

Other languages

English (en)

French (fr)

Other versions

CA2499306A1 (en

Inventor

Edward Lockwood Wheeler

Russell Edward Malz, Jr.

Mark W. Simon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Uniroyal Chemical Co Inc

Original Assignee

Uniroyal Chemical Co Inc

Priority date (The priority date 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 date listed.)

1996-04-04

Filing date

1997-03-13

Publication date

2008-08-05

1997-03-13 Application filed by Uniroyal Chemical Co Inc filed Critical Uniroyal Chemical Co Inc

1997-03-13 Priority claimed from CA002250850A external-priority patent/CA2250850C/en

1997-10-16 Publication of CA2499306A1 publication Critical patent/CA2499306A1/en

2008-08-05 Application granted granted Critical

2008-08-05 Publication of CA2499306C publication Critical patent/CA2499306C/en

2017-03-13 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000004982 aromatic amines Chemical class 0.000 title abstract description 6
238000002360 preparation method Methods 0.000 title description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 claims abstract description 10
238000004519 manufacturing process Methods 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims description 30
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
239000000908 ammonium hydroxide Substances 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
229960002089 ferrous chloride Drugs 0.000 claims description 4
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 2
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 2
230000000977 initiatory effect Effects 0.000 claims 1
238000001556 precipitation Methods 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 76
239000003054 catalyst Substances 0.000 abstract description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 26
239000001301 oxygen Substances 0.000 abstract description 26
229910052760 oxygen Inorganic materials 0.000 abstract description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 24
229910052751 metal Inorganic materials 0.000 abstract description 20
239000002184 metal Substances 0.000 abstract description 20
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 14
239000003446 ligand Substances 0.000 abstract description 14
229910021529 ammonia Inorganic materials 0.000 abstract description 12
ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 abstract description 10
UPHDFMNLYLLXDF-UHFFFAOYSA-N iron(2+);pentacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UPHDFMNLYLLXDF-UHFFFAOYSA-N 0.000 abstract description 9
150000001412 amines Chemical group 0.000 abstract description 6
125000005265 dialkylamine group Chemical group 0.000 abstract description 5
238000005984 hydrogenation reaction Methods 0.000 abstract description 5
150000003973 alkyl amines Chemical class 0.000 abstract description 4
230000002829 reductive effect Effects 0.000 abstract description 4
125000005270 trialkylamine group Chemical group 0.000 abstract description 4
125000003118 aryl group Chemical group 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 33
239000001257 hydrogen Substances 0.000 description 28
229910052739 hydrogen Inorganic materials 0.000 description 28
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
238000007254 oxidation reaction Methods 0.000 description 18
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 17
230000003647 oxidation Effects 0.000 description 17
229910052708 sodium Inorganic materials 0.000 description 16
239000011734 sodium Substances 0.000 description 16
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 12
239000000243 solution Substances 0.000 description 12
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000007800 oxidant agent Substances 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
238000007792 addition Methods 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000010410 layer Substances 0.000 description 6
-1 trisodium pentacyano ferrate-(II) complexes Chemical class 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000002638 heterogeneous catalyst Substances 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
229940011051 isopropyl acetate Drugs 0.000 description 3
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
229910052707 ruthenium Inorganic materials 0.000 description 3
ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical class OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
238000006025 oxidative dimerization reaction Methods 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
238000005086 pumping Methods 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229940072049 amyl acetate Drugs 0.000 description 1
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
229940039407 aniline Drugs 0.000 description 1
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003940 butylamines Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
235000014413 iron hydroxide Nutrition 0.000 description 1
NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical class [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
230000027756 respiratory electron transport chain Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
229940075931 sodium dithionate Drugs 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
238000013022 venting Methods 0.000 description 1
239000002699 waste material 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
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C3/00—Cyanogen; Compounds thereof
- C01C3/08—Simple or complex cyanides of metals
- C01C3/12—Simple or complex iron cyanides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Toxicology (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)

CA 2499306 1996-04-04 1997-03-13 Preparation of substituted aromatic amines Expired - Fee Related CA2499306C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/628,181		1996-04-04
US08/628,181 US5728882A (en)	1996-04-04	1996-04-04	Preparation of substituted aromatic amines
CA002250850A CA2250850C (en)	1996-04-04	1997-03-13	Preparation of substituted aromatic amines

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002250850A Division CA2250850C (en)	1996-04-04	1997-03-13	Preparation of substituted aromatic amines

Publications (2)

Publication Number	Publication Date
CA2499306A1 CA2499306A1 (en)	1997-10-16
CA2499306C true CA2499306C (en)	2008-08-05

Family

ID=24517818

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2499306 Expired - Fee Related CA2499306C (en)	1996-04-04	1997-03-13	Preparation of substituted aromatic amines

Country Status (20)

Country	Link
US (2)	US5728882A (sk)
EP (2)	EP1316531A1 (sk)
JP (2)	JP3200441B2 (sk)
KR (1)	KR100497955B1 (sk)
CN (2)	CN1158216C (sk)
AR (1)	AR006498A1 (sk)
AU (1)	AU712906B2 (sk)
BR (1)	BR9708481A (sk)
CA (1)	CA2499306C (sk)
CZ (1)	CZ294051B6 (sk)
EA (1)	EA001708B1 (sk)
ID (1)	ID16552A (sk)
IL (1)	IL126294A0 (sk)
NO (2)	NO311758B1 (sk)
PL (2)	PL188191B1 (sk)
SG (1)	SG87055A1 (sk)
SK (2)	SK283813B6 (sk)
TR (1)	TR199801985T2 (sk)
TW (1)	TW427967B (sk)
WO (1)	WO1997037965A1 (sk)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5728882A (en) *	1996-04-04	1998-03-17	Uniroyal Chemical Company, Inc.	Preparation of substituted aromatic amines
US5925790A (en) *	1997-03-13	1999-07-20	Uniroyal Chemical Company, Inc.	Preparation of substituted aromatic amines
US6069279A (en) *	1999-06-14	2000-05-30	Simon; Mark W.	Preparation of substituted aromatic amines
US6229035B1 (en)	1999-06-16	2001-05-08	Uniroyal Chemical Company, Inc.	Preparation of substituted aromatic amines

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL127232C (sk) *	1963-03-12	1900-01-01
GB1440767A (en) *	1972-11-24	1976-06-23	Ici Ltd	Oxidation process for the manufacture of 4-aminodiphenylamine and related higher amines
US4760186A (en) *	1986-09-15	1988-07-26	Monsanto Company	Preparation of substituted aromatic amines
ES2003074T3 (es) *	1986-12-17	1994-08-01	Monsanto Co	Preparacion de aminas aromaticas sustituidas.
US5117063A (en) *	1991-06-21	1992-05-26	Monsanto Company	Method of preparing 4-aminodiphenylamine
US5728882A (en) *	1996-04-04	1998-03-17	Uniroyal Chemical Company, Inc.	Preparation of substituted aromatic amines

1996
- 1996-04-04 US US08/628,181 patent/US5728882A/en not_active Expired - Lifetime
1997
- 1997-03-13 CN CNB001374303A patent/CN1158216C/zh not_active Expired - Fee Related
- 1997-03-13 KR KR10-2004-7016795A patent/KR100497955B1/ko not_active IP Right Cessation
- 1997-03-13 CN CNB971941475A patent/CN1168699C/zh not_active Expired - Fee Related
- 1997-03-13 EP EP02025719A patent/EP1316531A1/en not_active Withdrawn
- 1997-03-13 CZ CZ19983212A patent/CZ294051B6/cs not_active IP Right Cessation
- 1997-03-13 EP EP97909033A patent/EP1021393A1/en not_active Withdrawn
- 1997-03-13 PL PL97361695A patent/PL188191B1/pl not_active IP Right Cessation
- 1997-03-13 JP JP53620497A patent/JP3200441B2/ja not_active Expired - Fee Related
- 1997-03-13 CA CA 2499306 patent/CA2499306C/en not_active Expired - Fee Related
- 1997-03-13 TR TR1998/01985T patent/TR199801985T2/xx unknown
- 1997-03-13 AU AU20785/97A patent/AU712906B2/en not_active Ceased
- 1997-03-13 EA EA199800890A patent/EA001708B1/ru not_active IP Right Cessation
- 1997-03-13 SK SK186-2003A patent/SK283813B6/sk unknown
- 1997-03-13 SG SG9904937A patent/SG87055A1/en unknown
- 1997-03-13 BR BR9708481A patent/BR9708481A/pt not_active IP Right Cessation
- 1997-03-13 IL IL12629497A patent/IL126294A0/xx not_active IP Right Cessation
- 1997-03-13 SK SK1374-98A patent/SK283812B6/sk unknown
- 1997-03-13 WO PCT/US1997/003966 patent/WO1997037965A1/en not_active Application Discontinuation
- 1997-03-13 PL PL97329158A patent/PL188156B1/pl not_active IP Right Cessation
- 1997-03-19 TW TW086103411A patent/TW427967B/zh not_active IP Right Cessation
- 1997-04-03 AR ARP970101338A patent/AR006498A1/es active IP Right Grant
- 1997-04-03 ID IDP971115A patent/ID16552A/id unknown
- 1997-11-12 US US08/968,623 patent/US5858321A/en not_active Expired - Lifetime
1998
- 1998-10-02 NO NO19984614A patent/NO311758B1/no unknown
2001
- 2001-04-05 JP JP2001106962A patent/JP2001293372A/ja active Pending
- 2001-06-27 NO NO20013219A patent/NO20013219D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
BR9708481A (pt)	1999-08-03
EA001708B1 (ru)	2001-06-25
CN1216976A (zh)	1999-05-19
AR006498A1 (es)	1999-08-25
CN1309084A (zh)	2001-08-22
US5728882A (en)	1998-03-17
TW427967B (en)	2001-04-01
SK283812B6 (sk)	2004-02-03
CZ294051B6 (cs)	2004-09-15
CZ321298A3 (cs)	1999-01-13
KR100497955B1 (ko)	2005-06-29
EP1316531A1 (en)	2003-06-04
EA199800890A1 (ru)	1999-04-29
PL188156B1 (pl)	2004-12-31
NO20013219D0 (no)	2001-06-27
NO311758B1 (no)	2002-01-21
KR20040097372A (ko)	2004-11-17
NO984614L (no)	1998-11-26
IL126294A0 (en)	1999-05-09
NO984614D0 (no)	1998-10-02
AU712906B2 (en)	1999-11-18
CN1168699C (zh)	2004-09-29
CA2499306A1 (en)	1997-10-16
EP1021393A1 (en)	2000-07-26
SK137498A3 (en)	1999-03-12
NO20013219L (no)	1998-11-26
US5858321A (en)	1999-01-12
AU2078597A (en)	1997-10-29
SG87055A1 (en)	2002-03-19
CN1158216C (zh)	2004-07-21
JP2000507598A (ja)	2000-06-20
PL188191B1 (pl)	2004-12-31
SK283813B6 (sk)	2004-02-03
ID16552A (id)	1997-10-09
PL329158A1 (en)	1999-03-15
WO1997037965A1 (en)	1997-10-16
TR199801985T2 (xx)	1999-01-18
JP3200441B2 (ja)	2001-08-20
JP2001293372A (ja)	2001-10-23

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Date	Code	Title	Description
2005-03-18	EEER	Examination request
2010-03-15	MKLA	Lapsed

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