NL1001238C2 - Nitrering van pyridine-2,6-diamines. - Google Patents

Nitrering van pyridine-2,6-diamines. Download PDF

Info

Publication number: NL1001238C2
Authority: NL; Netherlands
Prior art keywords: sulfuric acid; pyridine; nitric acid; oleum; nitration
Prior art date: 1995-09-19

Application number

NL1001238A

Other languages

English (en)

Dutch (nl)

Inventor

Doetze Jakob Sikkema

Original Assignee

Akzo Nobel Nv

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.)

1995-09-19

Filing date

1995-09-19

Publication date

1997-03-20

1995-09-19 Application filed by Akzo Nobel Nv filed Critical Akzo Nobel Nv

1995-09-19 Priority to NL1001238A priority Critical patent/NL1001238C2/nl

1996-09-02 Priority to DE69605131T priority patent/DE69605131T2/de

1996-09-02 Priority to CN96197061A priority patent/CN1089756C/zh

1996-09-02 Priority to JP51235197A priority patent/JP3179114B2/ja

1996-09-02 Priority to PCT/EP1996/003841 priority patent/WO1997011058A1/en

1996-09-02 Priority to AT96930999T priority patent/ATE186529T1/de

1996-09-02 Priority to CA002232463A priority patent/CA2232463C/en

1996-09-02 Priority to EP96930999A priority patent/EP0873314B1/de

1997-03-20 Application granted granted Critical

1997-03-20 Publication of NL1001238C2 publication Critical patent/NL1001238C2/nl

1998-03-12 Priority to US09/041,882 priority patent/US5945537A/en

Links

238000006396 nitration reaction Methods 0.000 title claims abstract description 22
VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical class NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 title claims abstract description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 37
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 19
229910017604 nitric acid Inorganic materials 0.000 claims abstract description 19
239000000203 mixture Substances 0.000 claims abstract description 12
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000000391 smoking effect Effects 0.000 claims description 3
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 3
238000011835 investigation Methods 0.000 claims 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 4
235000011149 sulphuric acid Nutrition 0.000 abstract 1
239000001117 sulphuric acid Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
-1 2,6-dichloropyridine nitrates Chemical class 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
FHIDEWWHKSJPTK-UHFFFAOYSA-N (3,5-dinitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 FHIDEWWHKSJPTK-UHFFFAOYSA-N 0.000 description 1
ZLJZDCVHRYAHAW-UHFFFAOYSA-N 3,5-dinitropyridine-2,6-diamine Chemical compound NC1=NC(N)=C([N+]([O-])=O)C=C1[N+]([O-])=O ZLJZDCVHRYAHAW-UHFFFAOYSA-N 0.000 description 1
KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000002360 explosive Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920003252 rigid-rod polymer Polymers 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL1001238A 1995-09-19 1995-09-19 Nitrering van pyridine-2,6-diamines. NL1001238C2 (nl)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
NL1001238A NL1001238C2 (nl)	1995-09-19	1995-09-19	Nitrering van pyridine-2,6-diamines.
DE69605131T DE69605131T2 (de)	1995-09-19	1996-09-02	Nitrierung von pyridin-2,6-diamine
CN96197061A CN1089756C (zh)	1995-09-19	1996-09-02	吡啶－2,6－二胺的硝化
JP51235197A JP3179114B2 (ja)	1995-09-19	1996-09-02	ピリジン−２，６−ジアミンのニトロ化
PCT/EP1996/003841 WO1997011058A1 (en)	1995-09-19	1996-09-02	Nitration of pyridine-2,6-diamines
AT96930999T ATE186529T1 (de)	1995-09-19	1996-09-02	Nitrierung von pyridin-2,6-diamine
CA002232463A CA2232463C (en)	1995-09-19	1996-09-02	Nitration of pyridine-2,6-diamines
EP96930999A EP0873314B1 (de)	1995-09-19	1996-09-02	Nitrierung von pyridin-2,6-diamine
US09/041,882 US5945537A (en)	1995-09-19	1998-03-12	Nitration of pyridine-2, 6-diamines

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1001238A NL1001238C2 (nl)	1995-09-19	1995-09-19	Nitrering van pyridine-2,6-diamines.
NL1001238		1995-09-19

Publications (1)

Publication Number	Publication Date
NL1001238C2 true NL1001238C2 (nl)	1997-03-20

Family

ID=19761596

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1001238A NL1001238C2 (nl)	1995-09-19	1995-09-19	Nitrering van pyridine-2,6-diamines.

Country Status (8)

Country	Link
EP (1)	EP0873314B1 (de)
JP (1)	JP3179114B2 (de)
CN (1)	CN1089756C (de)
AT (1)	ATE186529T1 (de)
CA (1)	CA2232463C (de)
DE (1)	DE69605131T2 (de)
NL (1)	NL1001238C2 (de)
WO (1)	WO1997011058A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20090089903A (ko)	2006-12-12	2009-08-24	이 아이 듀폰 디 네모아 앤드 캄파니	3-하이드록시글루타로니트릴의 합성 방법
KR20100050524A (ko)	2007-08-01	2010-05-13	이 아이 듀폰 디 네모아 앤드 캄파니	다이아미노피리딘 및 관련 화합물의 합성 방법
CN117069651B (zh) *	2023-08-22	2026-04-24	福建桦智工程技术有限公司	一种2-氯-4-氨基-5-甲基吡啶的连续合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4310671A (en) *	1978-08-21	1982-01-12	Olin Corporation	Process for producing 2,6-dichloro-3-nitropyridine
DE3920336A1 (de) *	1989-06-21	1991-01-10	Deutsch Franz Forsch Inst	Sprengstoffmasse mit geringer empfindlichkeit

1995
- 1995-09-19 NL NL1001238A patent/NL1001238C2/nl not_active IP Right Cessation
1996
- 1996-09-02 JP JP51235197A patent/JP3179114B2/ja not_active Expired - Fee Related
- 1996-09-02 CA CA002232463A patent/CA2232463C/en not_active Expired - Fee Related
- 1996-09-02 EP EP96930999A patent/EP0873314B1/de not_active Expired - Lifetime
- 1996-09-02 DE DE69605131T patent/DE69605131T2/de not_active Expired - Lifetime
- 1996-09-02 WO PCT/EP1996/003841 patent/WO1997011058A1/en not_active Ceased
- 1996-09-02 CN CN96197061A patent/CN1089756C/zh not_active Expired - Fee Related
- 1996-09-02 AT AT96930999T patent/ATE186529T1/de not_active IP Right Cessation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4310671A (en) *	1978-08-21	1982-01-12	Olin Corporation	Process for producing 2,6-dichloro-3-nitropyridine
DE3920336A1 (de) *	1989-06-21	1991-01-10	Deutsch Franz Forsch Inst	Sprengstoffmasse mit geringer empfindlichkeit

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
H. RITTER ET AL.: "Synthesis and reactions of dinitrated amino and diaminopyridines", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 32, no. 2, March 1995 (1995-03-01), PROVO US, pages 585 - 590, XP002003030 *
R.L. WILLIAMS ET AL.: "The chemistry of aryltetraamines. II. The synthesis of 2,3,5,6-tetraaminopyridine.", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 8, 1971, PROVO US, pages 841 - 843, XP002003031 *

Also Published As

Publication number	Publication date
DE69605131D1 (de)	1999-12-16
JPH11504942A (ja)	1999-05-11
JP3179114B2 (ja)	2001-06-25
CA2232463C (en)	2007-11-06
CN1089756C (zh)	2002-08-28
EP0873314B1 (de)	1999-11-10
CN1196723A (zh)	1998-10-21
EP0873314A1 (de)	1998-10-28
DE69605131T2 (de)	2000-05-25
CA2232463A1 (en)	1997-03-27
WO1997011058A1 (en)	1997-03-27
ATE186529T1 (de)	1999-11-15

Legal Events

Date	Code	Title	Description
1997-05-01	PD2B	A search report has been drawn up
2000-06-05	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20000401

Publication	Publication Date	Title
US5945537A (en)	1999-08-31	Nitration of pyridine-2, 6-diamines
Pouramiri et al.	2023	Saccharin based ionic liquid: novel and recyclable catalyst for eco-friendly mechanosynthesis of Biginelli and Hantzcsh heterocycles under solvent-free conditions
EP0873314B1 (de)	1999-11-10	Nitrierung von pyridin-2,6-diamine
CH682917A5 (fr)	1993-12-15	Composés organogermanium.
WO2009018502A2 (en)	2009-02-05	Process for the synthesis of diaminopyridine and related compounds
WO1995016726A1 (de)	1995-06-22	Verfahren zur herstellung von polymerisaten des maleinimids und ihre verwendung
Malesa et al.	1999	Separation of ammonium dinitramide from reaction mixture
CN117715887A (zh)	2024-03-15	2-硝基-4-甲砜基苯甲酸的制备方法
Hoffman et al.	1919	The preparation of hexanitro-diphenylamine from chlorobenzene. 3
JP3817736B2 (ja)	2006-09-06	６−置換−２（１ｈ）−キノキサリノンの製法
KR20100050524A (ko)	2010-05-13	다이아미노피리딘 및 관련 화합물의 합성 방법
DE2216925A1 (de)	1972-10-19	Pyrazinderivate und Verfahren zu ihrer Herstellung
RU2760432C1 (ru)	2021-11-25	Способ сульфатирования арабиногалактана древесины лиственницы сульфаминовой кислотой
US5424436A (en)	1995-06-13	Processes for the synthesis of unsymmetrical secondary amines
SU1395646A1 (ru)	1988-05-15	Способ получени аммонийной соли тетрасульфофталоцианиновых металлокомплексов
JPWO1995022531A1 (ja)	1996-07-30	６−置換−２（１ｈ）−キノキサリノンの製法
KR900006208B1 (ko)	1990-08-25	신규 염소화 방법
GB1560719A (en)	1980-02-06	Process for the preparation of p-nitrosodiphenyl hydroxylamines
Jennings et al.	1953	The heat treatment of bisdiphenylene‐ethylene
Manvatkar	2021	POLYANILINE: SYNTHESIS, CHARACTERIZATION and CATALYTIC PROPERTIES
Bojarska‐Dahlig	1959	On the synthesis of derivatives of N‐(4‐pyridonyl)‐oxyacetic acid
DE2226588A1 (de)	1972-12-14	Cyanoäthylierung von Aminophenolen
US3882140A (en)	1975-05-06	Salts of 2,4,5-trisubstituted imidazoles and their preparation
Roizard et al.	1989	Design and synthesis of biomimetic polyacrylamides
FR2580636A1 (fr)	1986-10-24	Nouveaux derives acryliques de l'uree