Patent US4059628A successfully refreshed from Google Patents.
US4059628A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of aromatic amines
Assignee: EIDP Inc
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Filing: 1976-05-17
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Granted: 1977-11-22
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Expires: 1996-05-17
Abstract
Abstract Aniline and alkyl anilines are obtained by the reaction of anhydrous ammonia with cyclohexane or cyclohexane having up to two lower alkyl substituents at elevated temperatures, such as 300-650° C, in the presence of selected catalysts such as zinc oxide alone or with vanadium, molybdenum, or titanium oxides, etc.; metal compounds such as vanadates, molybdates and titanates; and cadmium sulfide, zinc selenide and the like.
Inventors
- 👤 Thomas Wayne Del Pesco
- 👤 Frank Julian Weigert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 17:14
CPC Classifications
C; C07; C07C; C07C209/00; C07C209/02
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
418 words
The process which consists essentially in heating a starting hydrocarbon of the formula ##STR4## wherein R and R 1 are alkyl of 1-4 carbon atoms and m and n are 0 or 1 with anhydrous ammonia at a temperature range of 300°-650° C in the absence of air to produce a compound of the formula ##STR5## where R, R 1 , m and n have the values stated above and where the heating is carried out in the presence of a catalyst selected from the group consisting of: A. one or more oxides of Al, Cd, Ce, Fe, In, Sn, Th, Ti, Zn and Zr; B. vanadium oxide and one or more oxides of Ag, As, Ba, Ca, Cd, Ce, Co, Cu, Eu, Fe, Gd, Hf, In, La, Mg, Mn, Ni, P, Pb, Sb, Sn, Sr, Ti, U and Zn; C. titanium oxide and one or more oxides of Bi, Cr, Cu, Mo, Pb, U and W; D. zinc oxide and one or more oxides of Cr, La, Mg, P, Si, Sb, W and the pair Bi-Mo; E. aluminum oxide and one or more oxides of Cu, Eu, La, Mn, Pb, and U; F. aluminum oxide, molybdeum oxide and one or more oxides of Ca, Cd, Ce, Cu, Er, Fe, In, La, Ni, Pb, Sm, Sr, Ti, U, Y and Zn; G. aluminum oxide, tungsten oxide and one or more oxides of Ca, Ce, Cu, Fe, In, La, Pb, Sm, Ti, U and Zn; H. aluminum oxide, titanium oxide and one or more oxides of Cr, Mg, rare earths, Re, Te and V; I. aluminum oxide, titanium oxide, zinc oxide and one or more oxides of Ag, Bi, Ca, Co, Cr, Cu, Hg, La, Mg, Nb, Ni, Pb, Pr, Ru, Sm, Sr, V, Yb, and Y; J. aluminum oxide, molybdenum oxide, bismuth oxide and one or more oxides of Ca, Cu, Pb, Ti, and Zn; K. aluminum oxide, molybdenum oxide, zirconium oxide and one or more oxides of Ce, Ti, and Zn; L. molybdenum oxide and one or more oxides of Cd, Ce, Cu, Fe, Gd, La, Mg, Mn, Nb, P, Pb, Ti and Zn; M. zinc oxide, titanium oxide and one or more oxides of Cr, La, Mg and Nb; N. cdS; CoS; CdS/aluminum oxide; CdS/titanium oxide/aluminum oxide; chromium sulfide; ZnSe; ZnS; ZnTe; ZnS/aluminum oxide; CdS/ZnS/aluminum oxide and WS 2; and O. aluminum oxide, vanadium oxide and one or more oxides of Ag, Ba, Ca, Cd, Cu, Ga, In, La, Mg, Pb, Sr, Y, Zn, and Zr.
Claim 2
Dependent Claim
418 words
The process which consists essentially in heating a starting hydrocarbon of the formula ##STR4## wherein R and R 1 are alkyl of 1-4 carbon atoms and m and n are 0 or 1 with anhydrous ammonia at a temperature range of 300°-650° C in the absence of air to produce a compound of the formula ##STR5## where R, R 1 , m and n have the values stated above and where the heating is carried out in the presence of a catalyst selected from the group consisting of: A. one or more oxides of Al, Cd, Ce, Fe, In, Sn, Th, Ti, Zn and Zr; B. vanadium oxide and one or more oxides of Ag, As, Ba, Ca, Cd, Ce, Co, Cu, Eu, Fe, Gd, Hf, In, La, Mg, Mn, Ni, P, Pb, Sb, Sn, Sr, Ti, U and Zn; C. titanium oxide and one or more oxides of Bi, Cr, Cu, Mo, Pb, U and W; D. zinc oxide and one or more oxides of Cr, La, Mg, P, Si, Sb, W and the pair Bi-Mo; E. aluminum oxide and one or more oxides of Cu, Eu, La, Mn, Pb, and U; F. aluminum oxide, molybdeum oxide and one or more oxides of Ca, Cd, Ce, Cu, Er, Fe, In, La, Ni, Pb, Sm, Sr, Ti, U, Y and Zn; G. aluminum oxide, tungsten oxide and one or more oxides of Ca, Ce, Cu, Fe, In, La, Pb, Sm, Ti, U and Zn; H. aluminum oxide, titanium oxide and one or more oxides of Cr, Mg, rare earths, Re, Te and V; I. aluminum oxide, titanium oxide, zinc oxide and one or more oxides of Ag, Bi, Ca, Co, Cr, Cu, Hg, La, Mg, Nb, Ni, Pb, Pr, Ru, Sm, Sr, V, Yb, and Y; J. aluminum oxide, molybdenum oxide, bismuth oxide and one or more oxides of Ca, Cu, Pb, Ti, and Zn; K. aluminum oxide, molybdenum oxide, zirconium oxide and one or more oxides of Ce, Ti, and Zn; L. molybdenum oxide and one or more oxides of Cd, Ce, Cu, Fe, Gd, La, Mg, Mn, Nb, P, Pb, Ti and Zn; M. zinc oxide, titanium oxide and one or more oxides of Cr, La, Mg and Nb; N. cdS; CoS; CdS/aluminum oxide; CdS/titanium oxide/aluminum oxide; chromium sulfide; ZnSe; ZnS; ZnTe; ZnS/aluminum oxide; CdS/ZnS/aluminum oxide and WS 2; and O. aluminum oxide, vanadium oxide and one or more oxides of Ag, Ba, Ca, Cd, Cu, Ga, In, La, Mg, Pb, Sr, Y, Zn, and Zr.
Claim 3
Dependent Claim
12 words
The process of claim 1 in which the starting hydrocarbon is cyclohexane.
Claim 4
Dependent Claim
13 words
The process of claim 1 in which the temperature range is 400°-600° C.
Claim 5
Dependent Claim
13 words
The process of claim 1 in which the temperature range is 450°-550° C.
Claim 6
Dependent Claim
27 words
The process of claim 1 in which the reactants are in contact with the catalyst at the reaction temperature for about 0.1 second to about 10 minutes.
Claim 7
Dependent Claim
27 words
The process of claim 1 in which the reactants are in contact with the catalyst at the reaction temperature for about 1 second to about 8 minutes.
Claim 8
Dependent Claim
21 words
The process of claim 1 in which the molar ratio of the starting hydrocarbon to ammonia ranges from 5/1 to 1/10.
Claim 9
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group A.
Claim 10
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group B.
Claim 11
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group C.
Claim 12
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group D.
Claim 13
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group E.
Claim 14
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group F.
Claim 15
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from Group G.
Claim 16
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group H.
Claim 17
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group I.
Claim 18
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group J.
Claim 19
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group K.
Claim 20
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group L.
Claim 21
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group M.
Claim 22
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group N.
Claim 23
Dependent Claim
14 words
The process of claim 1 in which the catalyst is selected from group O.
Claim 24
Dependent Claim
22 words
The process of claim 1 in which a member of group A or vanadium oxide comprises half or more of the catalyst.
Claim 25
Dependent Claim
15 words
The process of claim 1 in which the catalyst contains zinc oxide and titanium oxide.
Claim 26
Dependent Claim
15 words
The process of claim 1 in which the catalyst contain zinc oxide and vanadium oxide.
Claim 27
Dependent Claim
29 words
The process of claim 1 in which the catalyst contains zinc oxide and titanium oxide and one or more oxides of the group aluminum, cadmium, cerium, lanthanum and thorium.
Claim 28
Dependent Claim
15 words
The process of claim 1 in which the catalyst is aluminum oxide/titanium oxide/zinc oxide/cerium oxide.
Claim 29
Dependent Claim
15 words
The process of claim 1 in which the catalyst is aluminum oxide/titanium oxide/zinc oxide/cadmium oxide.
Claim 30
Dependent Claim
14 words
The process of claim 1 in which the catalyst is zinc oxide/titanium oxide/cerium oxide.
Claim 31
Dependent Claim
14 words
The process of claim 1 in which the catalyst is zinc oxide/titanium oxide/lanthanum oxide.
Claim 32
Dependent Claim
16 words
The process of claim 1 in which the catalyst is aluminum oxide/molybdenum oxide/zirconium oxide/cerium oxide/titanium oxide.
Claim 33
Dependent Claim
28 words
The process of claim 1 in which the catalyst is aluminum oxide/molybdenum oxide and one or more oxides of the group consisting of calcium, lead and rare earths.
Claim 34
Dependent Claim
15 words
The process of claim 1 in which the catalyst is aluminum oxide/molybdenum oxide/cerium oxide/lead oxide.
Claim 35
Dependent Claim
14 words
The process of claim 1 in which the catalyst is cadmium sulfide/zinc sulfide/aluminum oxide.
Claim 36
Dependent Claim
17 words
The process of claim 1 in which the catalyst is zinc oxide, vanadium oxide and aluminum oxide.
Claim 37
Dependent Claim
17 words
The process of claim 1 in which the catalyst is zinc oxide, vanadium oxide and cadmium oxide.
Claim 38
Dependent Claim
17 words
The process of claim 1 in which the catalyst is zinc oxide, vanadium oxide and cerium oxide.
Claim 39
Dependent Claim
17 words
The process of claim 1 in which the catalyst is zinc oxide, vanadium oxide and lanthanum oxide.
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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) | 1980-11-21 | 1981-05-23 | 1981-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-21 | 1985-05-23 | 1985-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-21 | 1989-05-23 | 1989-11-22 | $7700.00 | Window Closed / Lapsed |