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Process for the production of cyclododecenylacetonitrile

Assignee: Huels AG
•
Filing: 1985-01-10
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Granted: 1988-07-05
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Expires: 2005-01-10
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Abstract

Abstract Cyclododecenylacetonitrile is prepared by reacting cyclododecanone with cyanoacetic acid in the presence of a catalyst. Purified cyclododecenylacetonitrile has a pleasant scent reminiscent of roses and lilies of the valley, containing additionally a musk note, and is suitable as a fragrance and as a fragrance component.

Inventors

  • 👤 Manfred Kaufhold
  • 👤 Slagmulder Andre

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 16:41
CPC Classifications
C; C07; C07C; C07C255/00; C11; C11B; C11B9/00; C11B9/0026; C11B9/0038

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 43 words
A process for the production of cyclododecenylacetonitrile which comprises reacting cyclododecanone with cyanoacetic acid in a molar ratio of 5:1 to 1:5 at temperatures of 100°-170° C. in the presence of 5-1% by weight of a Knoevenagel catalyst, and separating the cyclododecenylacetonitrile produced.
Claim 2
Dependent Claim 43 words
A process for the production of cyclododecenylacetonitrile which comprises reacting cyclododecanone with cyanoacetic acid in a molar ratio of 5:1 to 1:5 at temperatures of 100°-170° C. in the presence of 5-1% by weight of a Knoevenagel catalyst, and separating the cyclododecenylacetonitrile produced.
Claim 3
Dependent Claim 19 words
A process according to claim 1, wherein the molar ratio of cyclododecanone is cyanoacetic acid is 1:2 to 1:1.
Claim 4
Dependent Claim 13 words
A process according to claim 1, wherein the reaction temperature is 120°-140° C.
Claim 5
Dependent Claim 12 words
A process according to claim 1, wherein the catalyst is ammonium acetate.
Claim 6
Dependent Claim 15 words
A process according to claim 4, wherein 3-2% by weight of ammonium acetate is present.
Claim 7
Dependent Claim 15 words
A process according to claim 1, wherein the cyclododecenylacetonitrile is separated by distillation under vacuum.
Claim 8
Dependent Claim 18 words
A process according to claim 1, wherein the cyclododecenylacetonitrile is further purified by passing an inert gas therethrough.
Claim 9
Dependent Claim 23 words
A process according to claim 7, wherein the inert gas is passed through the cyclododecenylacetonitrile at 15°-100° C. for 0.5 to 5 hours.
Claim 10
Dependent Claim 20 words
A process according to claim 1, wherein the reaction is carried out over a period of time of 30 hours.
Claim 11
Dependent Claim 24 words
A process according to claim 1, wherein cyclododecanone is reacted with cyanoacetic acid in the presence of toluene for a period of thirty hours.
Claim 12
Dependent Claim 18 words
A process according to claim 1, wherein cyclododecanone and cyanoacetic acid are reacted in the presence of toluene.
Claim 13
Dependent Claim 80 words
A process for the production of cyclododecenylacetonitrile comprising reacting cyclododecanone with cyanoacetic acid in a molar ratio of 1:2 to 1:1 at a temperature of 120°-140° C. in the presence of 3 to 2% by weight of ammonium acetate, acting as a Knoevenagel catalyst, and in the presence of toluene for a period of thirty hours, separating the resultant cyclododecenylacetonitrile by distillation under vacuum, and passing an inert gas through the cyclododecenylacetonitrile at 15°-100° C. for 0.5 to 5 hours.
Claim 14
Dependent Claim 80 words
A process for the production of cyclododecenylacetonitrile comprising reacting cyclododecanone with cyanoacetic acid in a molar ratio of 1:2 to 1:1 at a temperature of 120°-140° C. in the presence of 3 to 2% by weight of ammonium acetate, acting as a Knoevenagel catalyst, and in the presence of toluene for a period of thirty hours, separating the resultant cyclododecenylacetonitrile by distillation under vacuum, and passing an inert gas through the cyclododecenylacetonitrile at 15°-100° C. for 0.5 to 5 hours.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1991-07-05 1992-01-04 1992-07-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1995-07-05 1996-01-04 1996-07-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1999-07-05 2000-01-04 2000-07-05 $7700.00 Window Closed / Lapsed

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