Patent US3869541A successfully refreshed from Google Patents.
US3869541A
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Method for manufacturing hydrazine
Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1972-01-03
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Granted: 1975-03-04
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Expires: 1992-01-03
Abstract
Abstract Hydrazine hydrate and hydrazine salts are manufactured by reacting a ketone with ammonia, hydrogen peroxide and a nitrile to produce a ketazine and a carboxylic amide. The ketazine is then reacted with water, a strong acid or both to produce hydrazine hydrate, a hydrazine salt, or both.
Inventors
- 👤 Francis Weiss
- 👤 Jean-Pierre Schirmann
- 👤 Henri Mathais
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:57
CPC Classifications
C; C07; C07C; C07C251/00; C07C251/72; C07C251/88; C01; C01B; C01B21/00; C01B21/082; C01B21/16
Claims Analysis
Total Claims: 52
Claim 1
Independent Claim
88 words
A METHOD FOR THE MANUFACTURE OF HYDRAZINE HYDRATE WHICH COMPRISES: A. REACTING I. A KETONE OF THE FORMULA R1-C0-R2 (1) WHEREIN THE RADICALS R1 AND R2 EACH IS A STRAIGHT OR BRANCHED CHAIN ALKYL RADICAL OR CYCLOALKYL RADICAL CONTAINING UP TO ABOUT 10 CARBON ATOMS, AN UNSUBSTITUTED PHENYL RADICAL OR A PHENYL RADICAL SUBSTITUTED WITH ONE OR MORE RADICALS WHICH ARE STABLE IN THE REACTION MEDIUM OR R1 AND R2 TOGETHER IS A STRAIGHT OR BRANCHED CHAIN ALKYLENE RADICAL CONTAINING FROM 3 TO ABOUT 11 CARBON ATOMS WITH
Claim 2
Independent Claim
88 words
A METHOD FOR THE MANUFACTURE OF HYDRAZINE HYDRATE WHICH COMPRISES: A. REACTING I. A KETONE OF THE FORMULA R1-C0-R2 (1) WHEREIN THE RADICALS R1 AND R2 EACH IS A STRAIGHT OR BRANCHED CHAIN ALKYL RADICAL OR CYCLOALKYL RADICAL CONTAINING UP TO ABOUT 10 CARBON ATOMS, AN UNSUBSTITUTED PHENYL RADICAL OR A PHENYL RADICAL SUBSTITUTED WITH ONE OR MORE RADICALS WHICH ARE STABLE IN THE REACTION MEDIUM OR R1 AND R2 TOGETHER IS A STRAIGHT OR BRANCHED CHAIN ALKYLENE RADICAL CONTAINING FROM 3 TO ABOUT 11 CARBON ATOMS WITH
Claim 3
Dependent Claim
17 words
The process of claim 1 wherein the ketazine is separated from the reaction medium by fractional distillation.
Claim 4
Dependent Claim
15 words
separating the hydrazine hydrate and the ketone produced in (1) from the reaction mixture; and
Claim 5
Dependent Claim
15 words
separating the hydrazine hydrate and the ketone produced in (1) from the reaction mixture; and
Claim 6
Dependent Claim
20 words
treating the remaining unreacted ketrazine (III) with a strong acid in aqueous solution to produce the acid salt of hydrazine.
Claim 7
Dependent Claim
20 words
treating the remaining unreacted ketrazine (III) with a strong acid in aqueous solution to produce the acid salt of hydrazine.
Claim 8
Dependent Claim
15 words
The process of claim 2 wherein the fractional distillation is carried out below about 80*C.
Claim 9
Dependent Claim
23 words
The process of claim 2 wherein the carboxylic amide (IV) is dehydrated to regenerate the starting nitrile (II) and said nitrile is recycled.
Claim 10
Dependent Claim
37 words
The process of claim 4 wherein dehydration of the carboxylic amide (IV) is carried out in the vapor phase in the presence of a catalyst comprising alumina impregnated with from about 5 to 30 percent phosphoric acid.
Claim 11
Dependent Claim
12 words
The process of claim 5 wherein the regenerated ketone (I) is recycled.
Claim 12
Dependent Claim
57 words
The process according to claim 1 wherein 0.01 to 2.0 percent by weight of the total reaction mixture of a catalyst is added thereto, the catalyst selected to be an ammonium or alkali metal salt of a hydracid, mineral oxyacid, aliphatic or aromatic carboxylic acid or an alkyl or arylsulfonic acid having less than 20 carbon atoms.
Claim 13
Dependent Claim
24 words
The process of claim 7 wherein the catalyst is selected to be the ammonium salt of the acid corresponding to the nitrile (II) employed.
Claim 14
Dependent Claim
21 words
The process of claim 1 wherein the radicals R1 and R2 are each alkyl radicals having 1 to 3 carbon atoms.
Claim 15
Dependent Claim
16 words
The process of claim 9 wherein the radicals R1 and R2 are each a methyl radical.
Claim 16
Dependent Claim
11 words
The process of claim 10 wherein R3 is a methyl radical.
Claim 17
Dependent Claim
2 words
AMMONIA (NH3),
Claim 18
Dependent Claim
2 words
AMMONIA (NH3),
Claim 19
Dependent Claim
38 words
The process of claim 1 wherein step (C) is carried out with water at a pressure of from 1 to about 25 bars and at a temperature of from about 100* to about 200*C to produce hydrazine hydrate.
Claim 20
Dependent Claim
24 words
The process of claim 1 wherein the hydrazine hydrate of step (C) is treated by an extractive distillation with ethylene glycol to produce hydrazine.
Claim 21
Independent Claim
151 words
A method for the manufacture of hydrazine salts which comprises: a. reacting i. a ketone of the formula R1-CO-R2 (I) wherein the radicals R1 and R2 each is a straight or branched chain alkyl radical or cycloalkyl radical containing up to about 10 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium or R1 and R2 together is a straight or Branched chain alkylene radical containing from 3 to about 11 carbon atoms with ii. ammonia (NH3) iii. hydrogen peroxide (H2O20). and iv. a nitrile of the formula R3 - CN (II) wherein the radical R3 is an acyclic or cyclic radical containing less than 8 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium to produce v. a ketazine of the formula
Claim 22
Independent Claim
151 words
A method for the manufacture of hydrazine salts which comprises: a. reacting i. a ketone of the formula R1-CO-R2 (I) wherein the radicals R1 and R2 each is a straight or branched chain alkyl radical or cycloalkyl radical containing up to about 10 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium or R1 and R2 together is a straight or Branched chain alkylene radical containing from 3 to about 11 carbon atoms with ii. ammonia (NH3) iii. hydrogen peroxide (H2O20). and iv. a nitrile of the formula R3 - CN (II) wherein the radical R3 is an acyclic or cyclic radical containing less than 8 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium to produce v. a ketazine of the formula
Claim 23
Dependent Claim
21 words
The process of claim 14 wherein step (c) is carried out with sulfuric acid to produce the acid salt of hydrazine.
Claim 24
Dependent Claim
20 words
The process of claim 14 wherein the hydrazine salt of step (c) is treated with anhydrous ammonia to produce hydrazine.
Claim 25
Dependent Claim
17 words
The process of claim 14 wherein the ketazine is separated from the reaction medium by fractional distillation.
Claim 26
Dependent Claim
15 words
The process of claim 17 wherein the fractional distillation is carried out below about 80*C.
Claim 27
Dependent Claim
23 words
The process of claim 17 wherein the carboxylic amide (IV) is dehydrated to regenerate the starting nitrile (II) and said nitrile is recycled.
Claim 28
Dependent Claim
37 words
The process of claim 19 wherein dehydration of the carboxylic amide (IV) is carried out in the vapor phase in the presence of a catalyst comprising alumina impregnated with from about 5 to 30 percent phosphoric acid.
Claim 29
Dependent Claim
12 words
The process of claim 20 wherein the regenerated ketone (I) is recycled.
Claim 30
Dependent Claim
57 words
The process according to claim 14 wherein 0.01 to 2.0 percent by weight of the total reaction mixture of a catalyst is added thereto, the catalyst selected to be an ammonium or alkali metal salt of a hydracid, mineral oxyacid, aliphatic or aromatic carboxylic acid or an alkyl or arylsulfonic acid having less than 20 carbon atoms.
Claim 31
Dependent Claim
24 words
The process of claim 22 wherein the catalyst is selected to be the ammonium salt of the acid corresponding to the nitrile (II) employed.
Claim 32
Dependent Claim
21 words
The process of claim 14 wherein the radicals R1 and R2 are each alkyl racicals having 1 to 3 carbon atoms.
Claim 33
Dependent Claim
16 words
The process of claim 24 wherein the radicals R1 and R2 are each a methyl radical.
Claim 34
Dependent Claim
11 words
The process of claim 25 wherein R3 is a methyl radical.
Claim 35
Dependent Claim
15 words
The process of claim 25 wherein the acid of of step (c) is sulfuric acid.
Claim 36
Independent Claim
155 words
A method for the manufacture of hydrazine hydrate and hydrazine salts which comprises: a. reacting i. a ketone of the formula R1-CO-R2 (I) wherein the radicals R1 and R2 each is a straight or branched chain alkyl radical or cycloalkyl radical containing up to about 10 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium or R1 and R2 together is a straight or branched chain alkylene radical containing from 3 to about 11 carbon atoms with ii. ammonia (NH 3) iii. hydrogen peroxide (H2O2), and iv. a nitrile of the formula R3 - CN (II) wherein the radical R3 is an acyclic or cyclic radical containing less than 8 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium to produce v. a ketazine of the formula
Claim 37
Independent Claim
155 words
A method for the manufacture of hydrazine hydrate and hydrazine salts which comprises: a. reacting i. a ketone of the formula R1-CO-R2 (I) wherein the radicals R1 and R2 each is a straight or branched chain alkyl radical or cycloalkyl radical containing up to about 10 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium or R1 and R2 together is a straight or branched chain alkylene radical containing from 3 to about 11 carbon atoms with ii. ammonia (NH 3) iii. hydrogen peroxide (H2O2), and iv. a nitrile of the formula R3 - CN (II) wherein the radical R3 is an acyclic or cyclic radical containing less than 8 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted with one or more radicals which are stable in the reaction medium to produce v. a ketazine of the formula
Claim 38
Dependent Claim
24 words
The process of claim 28 wherein the hydrazine hydrate of step (c) is treated by an extractive distillation with ehtylene glycol to produce hydrazine.
Claim 39
Dependent Claim
20 words
The process of claim 28 wherein the hydrazine salt of step (c) is treated with anhydrous ammonia to produce hydrazine.
Claim 40
Dependent Claim
17 words
The process of claim 28 wherein the ketazine is separated from the reaction medium by fractional distillation.
Claim 41
Dependent Claim
15 words
The process of claim 31 wherein the fractional distillation is carried out below about 80*C.
Claim 42
Dependent Claim
23 words
The process of claim 31 wherein the carboxylic amide (IV) is dehydrated to regenerate the starting nitrile (II) and said nitrile is recycled.
Claim 43
Dependent Claim
37 words
The process of claim 33 wherein dehydration of the carboxylic amide (IV) is carried out in the vapor phase in the presence of a catalyst comprising alumina impregnated with from about 5 to 30 percent phosphoric acid.
Claim 44
Dependent Claim
12 words
The process of claim 34 wherein the regenerated ketone (I) is recycled.
Claim 45
Dependent Claim
57 words
The process according to claim 28 wherein 0.01 to 2.0 percent by weight of the total reaction mixture of a catalyst is added thereto, the catalyst selected to be an ammonium or alkali metal salt of a hydracid, mineral oxyacid, aliphatic or aromatic carboxylic acid or an alkyl or arylsulfonic acid having less than 20 carbon atoms.
Claim 46
Dependent Claim
24 words
The process of claim 36 wherein the catalyst is selected to be the ammonium salt of the acid corresponding to the nitrile (II) employed.
Claim 47
Dependent Claim
21 words
The process of claim 28 wherein the radicals R1 and R2 are each alkyl radicals having 1 to 3 carbon atoms.
Claim 48
Dependent Claim
16 words
The process of claim 38 wherein the radicals R1 and R2 are each a methyl radical.
Claim 49
Dependent Claim
11 words
The process of claim 39 wherein R3 is a methyl radical.
Claim 50
Dependent Claim
11 words
The process of claim 28 wherein step(c) is carried out by:
Claim 51
Dependent Claim
57 words
HYDROGEN PEROXIDE (H202), AND 1V. A NITRILE OF THE FORMULA R3 - CN (11) WHEREIN THE RADICAL R3 IS AN ACYCLIC OR RADICAL CONTAINING LESS THAN 8 CARBON ATOMS, AN UNSUBSTITUTED PHENYL RADICAL OR A PHENYL RADICAL SUBSTITUTED WITH OR MORE RADICALS WHICH ARE STABLE IN THE REACTION MEDIUM TO PRODUCE V. A KETAZINE OF THE FORMULA
Claim 52
Dependent Claim
57 words
HYDROGEN PEROXIDE (H202), AND 1V. A NITRILE OF THE FORMULA R3 - CN (11) WHEREIN THE RADICAL R3 IS AN ACYCLIC OR RADICAL CONTAINING LESS THAN 8 CARBON ATOMS, AN UNSUBSTITUTED PHENYL RADICAL OR A PHENYL RADICAL SUBSTITUTED WITH OR MORE RADICALS WHICH ARE STABLE IN THE REACTION MEDIUM TO PRODUCE V. A KETAZINE OF THE FORMULA
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-03-03 | 1978-09-02 | 1979-03-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-03-03 | 1982-09-02 | 1983-03-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-03-03 | 1986-09-02 | 1987-03-04 | $7700.00 | Window Closed / Lapsed |