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US3714223A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing aminonitriles

Assignee: WR Grace and Co Conn
•
Filing: 1969-12-15
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Granted: 1973-01-30
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Expires: 1989-12-15
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Abstract

Abstract An aminonitrile having the formula R-N (CH2CN)2, where R is a straight chain non-branched alkyl group having about one to 12 carbon atoms, is prepared by; (a) mixing a primary amine having the formula R-NH2, where R is as defined supra, formaldehyde, and water to form a first mixture; (b) cooling the first mixture to about 0-35*C.; (c) adding sulfuric acid and water in a weight ratio of sulfuric acid, as H2SO4, to water of about 1:0.5-4, to the first mixture while cooling to maintain the temperature of the resulting second mixture within the range of about 0-35*C., the mole ratio of amine to H2SO4 being about 1:0.1-1.5; (d) adding hydrogen cyanide to the second mixture, the mole ratio of amine to hydrogen cyanide being about 1:1.8-2.5 to form a third mixture; and (e) forming the aminonitrile product and a mother liquor by maintaining the third mixture in a closed reaction zone under substantially adiabatic conditions for about 10-300 minutes.

Inventors

  • 👤 J Godfrey
  • 👤 C Morgan

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 04:01
CPC Classifications
C; C07; C07C; C07C255/00

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 263 words
In a process for preparing an aminonitrile having the formula R-N (CH2CN)2 wherein R is a straight chain non-branched alkyl group having about one to 12 carbon atoms, the improvement comprising the following sequential steps: a. forming a first mixture by admixing; (i) a primary amine having the formula R-NH2, wherein R is as defined supra; (ii) formaldehyde; and (iii) water and cooling the resulting first mixture to maintain the temperature thereof within a range of about 0-35*C. by removing heat produced by an exotherm resulting from mixing the primary amine, the formaldehyde, and the waTer, the mole ratio of primary amine to formaldehyde being about 1:2-2.5 and the weight ratio of primary amine to water being about 1:0.4-2; b. forming a second mixture by admixing; (i) sulfuric acid; (ii) water; and (iii) the first mixture from step (a) while cooling the resulting second mixture to maintain the temperature thereof within a range of about 0-35*C., the mole ratio of primary amine to sulfuric acid being about 1:0.1-1.5 and the weight ratio of sulfuric acid, as H2SO4, to water being about 1:0.5-4; c. forming a third mixture by admixing hydrogen cyanide and the second mixture while cooling the resulting third mixture to maintain the temperature thereof within the range of about 0-35*C., the mole ratio of amine to hydrogen cyanide being about 1:1.8-2.5; d. forming the aminonitrile and a mother liquor by maintaining the third mixture under substantially adiabatic conditions in a closed reaction zone for about 10-300 minutes; and e. separating the aminonitrile from the mother liquor, and recovering the separated aminonitrile.
Claim 2
Dependent Claim 263 words
In a process for preparing an aminonitrile having the formula R-N (CH2CN)2 wherein R is a straight chain non-branched alkyl group having about one to 12 carbon atoms, the improvement comprising the following sequential steps: a. forming a first mixture by admixing; (i) a primary amine having the formula R-NH2, wherein R is as defined supra; (ii) formaldehyde; and (iii) water and cooling the resulting first mixture to maintain the temperature thereof within a range of about 0-35*C. by removing heat produced by an exotherm resulting from mixing the primary amine, the formaldehyde, and the waTer, the mole ratio of primary amine to formaldehyde being about 1:2-2.5 and the weight ratio of primary amine to water being about 1:0.4-2; b. forming a second mixture by admixing; (i) sulfuric acid; (ii) water; and (iii) the first mixture from step (a) while cooling the resulting second mixture to maintain the temperature thereof within a range of about 0-35*C., the mole ratio of primary amine to sulfuric acid being about 1:0.1-1.5 and the weight ratio of sulfuric acid, as H2SO4, to water being about 1:0.5-4; c. forming a third mixture by admixing hydrogen cyanide and the second mixture while cooling the resulting third mixture to maintain the temperature thereof within the range of about 0-35*C., the mole ratio of amine to hydrogen cyanide being about 1:1.8-2.5; d. forming the aminonitrile and a mother liquor by maintaining the third mixture under substantially adiabatic conditions in a closed reaction zone for about 10-300 minutes; and e. separating the aminonitrile from the mother liquor, and recovering the separated aminonitrile.
Claim 3
Dependent Claim 20 words
The process of claim 1 in which the weight ratio of sulfuric acid, as H2SO4, to water is about 1:1-3.
Claim 4
Dependent Claim 20 words
The process of claim 1 in which the mole ratio of amine to sulfuric acid, as H2SO4, is about 1:0.12-1.
Claim 5
Dependent Claim 20 words
The process of claim 1 in which the third mixture is maintained under substantially adiabatic conditions for about 30-100 minutes.
Claim 6
Dependent Claim 13 words
The process of claim 1 in which R is methyl, n-butyl, or n-octyl.

References Cited (Backward Citations)

US2504011A Cited
US2855428A Cited
US3424783A Cited
US3463805A Cited
US3515742A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-01-30 1976-07-31 1977-01-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-01-30 1980-07-31 1981-01-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-01-30 1984-07-31 1985-01-30 $7700.00 Window Closed / Lapsed

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