CH377842A - Verfahren zur Herstellung neuer Hydrazine - Google Patents

Verfahren zur Herstellung neuer Hydrazine

Info

Publication number: CH377842A
Authority: CH; Switzerland
Prior art keywords: radical; split; hydrazines; dependent; hydrogenolysis
Prior art date: 1959-02-11

Application number

CH1278963A

Other languages

German (de)

English (en)

Inventor

Jean Dr Druey

Paul Dr Schmidt

Max Dr Wilhelm

Kurt Dr Eichenberger

Original Assignee

Ciba Geigy

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.)

1959-02-11

Filing date

1959-02-11

Publication date

1964-05-31

1959-02-11 Application filed by Ciba Geigy filed Critical Ciba Geigy

1959-02-11 Priority to CH1278963A priority Critical patent/CH377842A/de

1964-05-31 Publication of CH377842A publication Critical patent/CH377842A/de

Links

238000000034 method Methods 0.000 title claims description 13
150000002429 hydrazines Chemical class 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title description 2
-1 alkyl radical Chemical class 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 10
238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910052794 bromium Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
125000001309 chloro group Chemical group Cl* 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
BMBQCPJPRYFLNZ-UHFFFAOYSA-N 3-chloro-1-ethoxybutane Chemical compound CCOCCC(C)Cl BMBQCPJPRYFLNZ-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
DFNJWWGSHSQEJX-UHFFFAOYSA-N 4-butoxybutan-2-ylhydrazine Chemical compound CCCCOCCC(C)NN DFNJWWGSHSQEJX-UHFFFAOYSA-N 0.000 description 1
VEFBQCPOTFGNAA-UHFFFAOYSA-N 4-ethoxybutan-2-ylhydrazine Chemical compound CCOCCC(C)NN VEFBQCPOTFGNAA-UHFFFAOYSA-N 0.000 description 1
FCKOSIRJMKNYLH-UHFFFAOYSA-N 4-methoxybutan-2-ylhydrazine Chemical compound COCCC(C)NN FCKOSIRJMKNYLH-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
244000248349 Citrus limon Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
235000011430 Malus pumila Nutrition 0.000 description 1
235000015103 Malus silvestris Nutrition 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 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
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 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
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
235000014101 wine Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines

Landscapes

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

CH1278963A 1959-02-11 1959-02-11 Verfahren zur Herstellung neuer Hydrazine CH377842A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1278963A CH377842A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH6942459A CH377840A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine
CH1278963A CH377842A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine

Publications (1)

Publication Number	Publication Date
CH377842A true CH377842A (de)	1964-05-31

Family

ID=4529499

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH1278963A CH377842A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine
CH1279063A CH377843A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine
CH1278863A CH387649A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine
CH6942459A CH377840A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
CH1279063A CH377843A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine
CH1278863A CH387649A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine
CH6942459A CH377840A (de)	1959-02-11	1959-02-11	Verfahren zur Herstellung neuer Hydrazine

Country Status (3)

Country	Link
BE (1)	BE587448A (fr)
CH (4)	CH377842A (fr)
ES (1)	ES255673A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN109561760B (zh)	2016-03-20	2021-09-17	海德威解决方案有限责任公司	横向折叠台阶单元

1959
- 1959-02-11 CH CH1278963A patent/CH377842A/de unknown
- 1959-02-11 CH CH1279063A patent/CH377843A/de unknown
- 1959-02-11 CH CH1278863A patent/CH387649A/de unknown
- 1959-02-11 CH CH6942459A patent/CH377840A/de unknown
1960
- 1960-02-10 ES ES0255673A patent/ES255673A1/es not_active Expired
- 1960-02-10 BE BE587448A patent/BE587448A/fr unknown

Also Published As

Publication number	Publication date
CH387649A (de)	1965-02-15
BE587448A (fr)	1960-08-10
CH377840A (de)	1964-05-31
ES255673A1 (es)	1960-10-01
CH377843A (de)	1964-05-31

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DE1620392C3 (fr)	1980-11-06
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CH377842A (de)	1964-05-31	Verfahren zur Herstellung neuer Hydrazine
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