IL138700A - Method for making hydrazine hydrate - Google Patents

Method for making hydrazine hydrate

Info

Publication number: IL138700A
Authority: IL; Israel
Prior art keywords: methyl ethyl; ethyl ketone; azine; hydrazine hydrate; oxime
Prior art date: 1998-05-14

Application number

IL13870099A

Other languages

English (en)

Hebrew (he)

Other versions

IL138700A0 (en

Original Assignee

Atofina

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.)

1998-05-14

Filing date

1999-05-06

Publication date

2004-09-27

1999-05-06 Application filed by Atofina filed Critical Atofina

2001-10-31 Publication of IL138700A0 publication Critical patent/IL138700A0/xx

2004-09-27 Publication of IL138700A publication Critical patent/IL138700A/en

Links

NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 title claims abstract description 33
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 title claims abstract description 33
238000000034 method Methods 0.000 title claims abstract description 26
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 78
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 48
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 48
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 26
239000012224 working solution Substances 0.000 claims abstract description 22
229910021529 ammonia Inorganic materials 0.000 claims abstract description 13
239000000203 mixture Substances 0.000 claims abstract description 13
WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims abstract description 11
238000004064 recycling Methods 0.000 claims abstract description 7
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
230000001172 regenerating effect Effects 0.000 claims abstract description 3
238000004821 distillation Methods 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 4
150000002923 oximes Chemical class 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
229910001868 water Inorganic materials 0.000 description 15
238000006460 hydrolysis reaction Methods 0.000 description 14
150000001408 amides Chemical class 0.000 description 13
230000007062 hydrolysis Effects 0.000 description 13
239000002253 acid Substances 0.000 description 12
150000003863 ammonium salts Chemical class 0.000 description 12
-1 CH3 oxime Chemical class 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 10
239000000376 reactant Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
150000007513 acids Chemical class 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical class [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
LAWAERKRWYQEEN-FKJILZIQSA-N (e)-n-[(z)-butan-2-ylideneamino]butan-2-imine Chemical compound CC\C(C)=N/N=C(\C)CC LAWAERKRWYQEEN-FKJILZIQSA-N 0.000 description 4
230000003213 activating effect Effects 0.000 description 4
229910052785 arsenic Inorganic materials 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000012535 impurity Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
LVKZSFMYNWRPJX-UHFFFAOYSA-N phenylarsonic acid Chemical compound O[As](O)(=O)C1=CC=CC=C1 LVKZSFMYNWRPJX-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000003556 assay Methods 0.000 description 2
230000000740 bleeding effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
238000012856 packing Methods 0.000 description 2
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
229940080818 propionamide Drugs 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
229940035437 1,3-propanediol Drugs 0.000 description 1
229940043375 1,5-pentanediol Drugs 0.000 description 1
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical group N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
238000004131 Bayer process Methods 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
241001484259 Lacuna Species 0.000 description 1
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229950004243 cacodylic acid Drugs 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
OGGXGZAMXPVRFZ-UHFFFAOYSA-M dimethylarsinate Chemical compound C[As](C)([O-])=O OGGXGZAMXPVRFZ-UHFFFAOYSA-M 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229940047889 isobutyramide Drugs 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
VBYZSBGMSZOOAP-UHFFFAOYSA-N molecular hydrogen hydrate Chemical compound O.[H][H] VBYZSBGMSZOOAP-UHFFFAOYSA-N 0.000 description 1
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/16—Hydrazine; Salts thereof

Landscapes

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

IL13870099A 1998-05-14 1999-05-06 Method for making hydrazine hydrate IL138700A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9806077A FR2778659B1 (fr)	1998-05-14	1998-05-14	Procede de preparation d'hydrate d'hydrazine
PCT/FR1999/001074 WO1999058446A1 (fr)	1998-05-14	1999-05-06	Procede de preparation d'hydrate d'hydrazine

Publications (2)

Publication Number	Publication Date
IL138700A0 IL138700A0 (en)	2001-10-31
IL138700A true IL138700A (en)	2004-09-27

Family

ID=9526341

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13870099A IL138700A (en)	1998-05-14	1999-05-06	Method for making hydrazine hydrate

Country Status (20)

Country	Link
US (1)	US6482383B1 (de)
EP (1)	EP1086045B1 (de)
JP (1)	JP4414091B2 (de)
KR (1)	KR100595950B1 (de)
CN (1)	CN1254434C (de)
AT (1)	ATE234263T1 (de)
AU (1)	AU747335B2 (de)
CA (1)	CA2331058A1 (de)
DE (1)	DE69905880T2 (de)
EA (1)	EA003020B1 (de)
ES (1)	ES2193695T3 (de)
FR (1)	FR2778659B1 (de)
ID (1)	ID27016A (de)
IL (1)	IL138700A (de)
NO (1)	NO20005112L (de)
NZ (1)	NZ508038A (de)
TW (1)	TWI221462B (de)
UA (1)	UA57840C2 (de)
WO (1)	WO1999058446A1 (de)
ZA (1)	ZA200006478B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP6500990B2 (ja) *	2015-08-03	2019-04-17	三菱瓦斯化学株式会社	アジン、ヒドラゾン結合の切断方法
US11225413B2 (en)	2016-10-03	2022-01-18	Council Of Scientific & Industrial Research	Process for production of hydrazine hydrate
FR3096049B1 (fr) *	2019-05-16	2021-12-17	Arkema France	Procede ameliore de preparation d'hydrate d'hydrazine avec recyclage pyrazoline
FR3096048B1 (fr) *	2019-05-16	2021-04-30	Arkema France	Procede ameliore de preparation d'hydrate d'hydrazine avec recyclage oxime

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2120517A5 (de) *	1971-01-07	1972-08-18	Ugine Kuhlmann
US3976756A (en) *	1975-10-28	1976-08-24	Olin Corporation	Preparation of hydrazine and its compounds
JPS5659608A (en) *	1979-10-19	1981-05-23	Otsuka Chem Co Ltd	Hydrazine hydrate purifying method
FR2559472B1 (fr) *	1984-02-14	1986-06-13	Atochem	Procede de purification de solutions aqueuses d'hydrate d'hydrazine
JPS63295408A (ja) *	1987-05-28	1988-12-01	Mitsubishi Gas Chem Co Inc	水加ヒドラジン水溶液の精製方法
FR2647444B1 (de) *	1989-05-24	1991-07-26	Atochem
FR2655336B1 (fr) *	1989-12-04	1993-05-21	Atochem	Procede de vaporisation d'une solution d'hydrate d'hydrazine.
FR2677648B1 (fr) *	1991-06-12	1993-08-27	Atochem	Procede pour reduire la teneur en co2 dans les reacteurs de synthese d'azines.

1998
- 1998-05-14 FR FR9806077A patent/FR2778659B1/fr not_active Expired - Fee Related
1999
- 1999-05-06 EP EP99917001A patent/EP1086045B1/de not_active Expired - Lifetime
- 1999-05-06 CA CA002331058A patent/CA2331058A1/fr not_active Abandoned
- 1999-05-06 JP JP2000548257A patent/JP4414091B2/ja not_active Expired - Fee Related
- 1999-05-06 AU AU35288/99A patent/AU747335B2/en not_active Ceased
- 1999-05-06 NZ NZ508038A patent/NZ508038A/en unknown
- 1999-05-06 ES ES99917001T patent/ES2193695T3/es not_active Expired - Lifetime
- 1999-05-06 AT AT99917001T patent/ATE234263T1/de not_active IP Right Cessation
- 1999-05-06 EA EA200001181A patent/EA003020B1/ru not_active IP Right Cessation
- 1999-05-06 WO PCT/FR1999/001074 patent/WO1999058446A1/fr not_active Ceased
- 1999-05-06 KR KR1020007012764A patent/KR100595950B1/ko not_active Expired - Fee Related
- 1999-05-06 ID IDW20002349A patent/ID27016A/id unknown
- 1999-05-06 DE DE69905880T patent/DE69905880T2/de not_active Expired - Fee Related
- 1999-05-06 IL IL13870099A patent/IL138700A/en not_active IP Right Cessation
- 1999-05-06 US US09/674,574 patent/US6482383B1/en not_active Expired - Fee Related
- 1999-05-14 CN CNB991076621A patent/CN1254434C/zh not_active Expired - Lifetime
- 1999-05-14 TW TW088107881A patent/TWI221462B/zh not_active IP Right Cessation
- 1999-06-05 UA UA2000116384A patent/UA57840C2/uk unknown
2000
- 2000-10-11 NO NO20005112A patent/NO20005112L/no not_active Application Discontinuation
- 2000-11-09 ZA ZA200006478A patent/ZA200006478B/en unknown

Also Published As

Publication number	Publication date
NO20005112D0 (no)	2000-10-11
ID27016A (id)	2001-02-22
DE69905880D1 (de)	2003-04-17
FR2778659A1 (fr)	1999-11-19
JP2002514564A (ja)	2002-05-21
KR100595950B1 (ko)	2006-07-03
AU3528899A (en)	1999-11-29
EP1086045A1 (de)	2001-03-28
NZ508038A (en)	2003-05-30
CA2331058A1 (fr)	1999-11-18
TWI221462B (en)	2004-10-01
FR2778659B1 (fr)	2000-06-23
ES2193695T3 (es)	2003-11-01
WO1999058446A1 (fr)	1999-11-18
US6482383B1 (en)	2002-11-19
NO20005112L (no)	2000-10-11
AU747335B2 (en)	2002-05-16
JP4414091B2 (ja)	2010-02-10
EP1086045B1 (de)	2003-03-12
CN1242339A (zh)	2000-01-26
ZA200006478B (en)	2001-05-07
CN1254434C (zh)	2006-05-03
DE69905880T2 (de)	2003-11-20
ATE234263T1 (de)	2003-03-15
KR20010078714A (ko)	2001-08-21
IL138700A0 (en)	2001-10-31
UA57840C2 (uk)	2003-07-15
EA200001181A1 (ru)	2001-04-23
EA003020B1 (ru)	2002-12-26

Legal Events

Date	Code	Title
2005-02-20	FF	Patent granted
2005-03-20	KB	Patent renewed
2005-07-25	KB	Patent renewed
2010-05-31	MM9K	Patent not in force due to non-payment of renewal fees

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JP3962872B2 (ja)	2007-08-22	ケタジンの合成方法
US3869541A (en)	1975-03-04	Method for manufacturing hydrazine
AU747335B2 (en)	2002-05-16	Method for preparing hydrazine hydrate
US6562311B1 (en)	2003-05-13	Method for preparing hydrazine hydrate
IE914071A1 (en)	1992-06-03	Process for the synthesis of azines
AU747951B2 (en)	2002-05-30	Method for preparing hydrazine hydrate
US12134558B2 (en)	2024-11-05	Process for preparing hydrazine hydrate with pyrazoline recycling
KR20250027267A (ko)	2025-02-25	캐스케이드 반응기를 이용한 아진의 제조 방법
KR20250026856A (ko)	2025-02-25	흡수 컬럼을 이용한 히드라진 수화물의 제조 방법
KR830000207B1 (ko)	1983-02-23	케타진(ketazine)의 제조방법
JPH10130219A (ja)	1998-05-19	ケタジン及び水加ヒドラジンの製造方法
JPH05319811A (ja)	1993-12-03	アジ化ナトリウムの製造方法