Patent US4415744A successfully refreshed from Google Patents.
US4415744A
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Vapor phase nitration of aromatic compounds
Assignee: Solutia Inc
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Filing: 1981-10-21
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Granted: 1983-11-15
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Expires: 2001-10-21
Abstract
Abstract Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compound with a nitrating agent in the presence of a nitration promotion catalyst which comprises the adduct of: (a) an alumina-silica-metal oxide combination represented by the formula: (Al2O3)a(SiO2)b(M2/nO)c wherein M is a metal cation selected from the group consisting of the lanthanides or rare earths, Groups 1b, 2b, 5b, 6b, 7b, and 8 of the Periodic Table of the Elements, and mixtures thereof, and a, b, and c represent weight percent of the Al2O3, SiO2, and M2/nO components, respectively, in the alumina-silica-metal oxide combination, with a being 0 to 100, b being 0 to 100, and c being 0 to 50, and n represents an integer from 1 to 7 of the valence of the metal cation, with the proviso that the sum of (a+b) must be greater than 0, and (b) a catalytically effective amount of sulfur trioxide.
Inventors
- 👤 Ignatius Schumacher
- 👤 Kang-bo Wang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:55
CPC Classifications
B; B01; B01J; B01J37/00; B01J37/20; B01J27/00; B01J27/02; B01J29/00; B01J29/04; B01J29/06; C; C07; C07B; C07B43/00; C07B43/02; C07C; C07C201/00; C07C201/06; C07C201/08
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
183 words
In a process for the vapor phase nitration of aromatic compounds where the aromatic compound is contacted with a nitrating agent in the vapor phase to yield the corresponding nitroaromatic compound, the improvement comprising conducting the nitration in the presence of a nitration promoting catalyst which comprises the adduct of: (a) an alumina-silica-metal oxide combination represented by the formula: (Al.sub.2 O.sub.3).sub.a (SiO.sub.2).sub.b (M.sub.2/n O).sub.c wherein M is a metal cation selected from the group consisting of the lanthanides of rare earths, Groups 1b, 2b, 5b, 6b, 7b, and 8 of the Periodic Table of the Elements, and mixtures thereof, and a, b, and c represent weight percent of the Al 2 O 3 , SiO 2 , and M 2/n O components, respectively, in the alumina-silica-metal oxide combination, with a being 0 to 100, b being 0 to 100, and c being 0 to 50, and n represents an integer from 1 to 7 of the valence of the metal cation, with the proviso that the sum of (a+b) must be greater than 0, and (b) a catalytically effective amount of sulfur trioxide.
Claim 2
Dependent Claim
183 words
In a process for the vapor phase nitration of aromatic compounds where the aromatic compound is contacted with a nitrating agent in the vapor phase to yield the corresponding nitroaromatic compound, the improvement comprising conducting the nitration in the presence of a nitration promoting catalyst which comprises the adduct of: (a) an alumina-silica-metal oxide combination represented by the formula: (Al.sub.2 O.sub.3).sub.a (SiO.sub.2).sub.b (M.sub.2/n O).sub.c wherein M is a metal cation selected from the group consisting of the lanthanides of rare earths, Groups 1b, 2b, 5b, 6b, 7b, and 8 of the Periodic Table of the Elements, and mixtures thereof, and a, b, and c represent weight percent of the Al 2 O 3 , SiO 2 , and M 2/n O components, respectively, in the alumina-silica-metal oxide combination, with a being 0 to 100, b being 0 to 100, and c being 0 to 50, and n represents an integer from 1 to 7 of the valence of the metal cation, with the proviso that the sum of (a+b) must be greater than 0, and (b) a catalytically effective amount of sulfur trioxide.
Claim 3
Dependent Claim
35 words
The process improvement in claim 1 wherein the amount of sulfur trioxide is in the range from about 5 weight percent to about 40 weight percent, based on the weight of the alumina-silica-metal oxide combination.
Claim 4
Dependent Claim
25 words
The process improvement of claim 1 wherein the alumina-silica-metal oxide combination is selected from the group consisting of crystalline and noncrystalline phases, and mixtures thereof.
Claim 5
Dependent Claim
17 words
The process improvement of claim 1 wherein a is 100 and b and c each is 0.
Claim 6
Dependent Claim
17 words
The process improvement of claim 1 wherein a and c each is 0 and b is 100.
Claim 7
Dependent Claim
17 words
The process improvement of claim 1 wherein a is 9.4, b is 90.6, and c is 0.
Claim 8
Dependent Claim
17 words
The process improvement of claim 1 wherein a is 12, b is 87, and c is 0.
Claim 9
Dependent Claim
17 words
The process improvement of claim 1 wherein a is 45, b is 53, and c is 0.
Claim 10
Dependent Claim
17 words
The process improvement of claim 1 wherein a is 50, b is 50, and c is 0.
Claim 11
Dependent Claim
14 words
The process improvement of claim 1 wherein M is a mixture of metal cations.
Claim 12
Dependent Claim
22 words
The process improvement of claim 10 wherein M is a mixture of cobalt and molybdenum, with n being, respectively, 2 and 6.
Claim 13
Dependent Claim
17 words
The process improvement of claim 11 wherein a is 86.5, b is 0, and c is 13.5.
Claim 14
Dependent Claim
22 words
The process improvement of claim 12 wherein c comprises 3.5 weight percent cobalt (II) oxide and 10 weight percent molybdenum (VI) oxide.
Claim 15
Dependent Claim
17 words
The process improvement of claim 12 wherein a is 80.5, b is 0, and c is 19.5.
Claim 16
Dependent Claim
22 words
The process improvement of claim 14 wherein c comprises 4.5 weight percent cobalt (II) oxide and 15 weight percent molybdenum (VI) oxide.
Claim 17
Dependent Claim
22 words
The process improvement of claim 10 wherein M is a mixture of nickel and tungsten, with n being, respectively, 2 and 6.
Claim 18
Dependent Claim
16 words
The process improvement of claim 16 wherein a is 17.4, b is 65, c is 17.6.
Claim 19
Dependent Claim
22 words
The process improvement of claim 17 wherein c comprises 3.3 weight percent nickel (II) oxide and 14.3 weight percent tungsten (VI) oxide.
Claim 20
Dependent Claim
16 words
The process improvement of claim 10 wherein M is cobalt, with n being 2 and 3.
Claim 21
Dependent Claim
17 words
The process improvement of claim 19 wherein a is 0, b is 83.7, and c is 16.3.
Claim 22
Dependent Claim
13 words
The process improvement of claim 1 wherein the nitrating agent is nitrogen dioxide.
Claim 23
Dependent Claim
23 words
The process improvement of claim 1 wherein the nitrating agent is admixed with a carrier gas prior to reaction with the aromatic compound.
Claim 24
Dependent Claim
12 words
The process improvement of claim 22 wherein the carrier gas is nitrogen.
Claim 25
Dependent Claim
19 words
The process improvement of claim 1 wherein the nitration promoting catalyst is conditioned by pretreatment with the nitrating agent.
Claim 26
Dependent Claim
20 words
The process improvement of claim 24 wherein the pretreatment is carried out for about 1 minute to about 1 hour.
Claim 27
Dependent Claim
14 words
The process improvement of claim 1 wherein the aromatic compound is an aromatic hydrocarbon.
Claim 28
Dependent Claim
20 words
The process improvement of claim 26 wherein the aromatic hydrocarbon is selected from the group consisting of benzene and toluene.
Claim 29
Dependent Claim
14 words
The process improvement of claim 1 wherein the aromatic compound is a haloaromatic compound.
Claim 30
Dependent Claim
22 words
The process improvement of claim 28 wherein the haloaromatic compound is selected from the group consisting of chlorobenzene, bromobenzene, iodobenzene, and o-dichlorobenzene.
Claim 31
Dependent Claim
14 words
The process improvement of claim 1 wherein the aromatic compound is an aromatic ether.
Claim 32
Dependent Claim
16 words
The process improvement of claim 30 wherein the aromatic ether is selected from anisole and phenetole.
Claim 33
Dependent Claim
14 words
The process improvement of claim 1 wherein the aromatic compound is an aromatic carboxylate.
Claim 34
Dependent Claim
24 words
The process improvement of claim 2 wherein the aromatic carboxylate is selected from the group consisting of benzoic acid, methyl benzoate, and ethyl benzoate.
Claim 35
Dependent Claim
28 words
The process improvement of claim 1 wherein the concentration of the aromatic compound in the feed mixture is between about 1 percent and about 15 percent by volume.
Claim 36
Dependent Claim
23 words
The process improvement of claim 1 wherein about 0.5 to about 5 moles of nitrating agent are used per mole of aromatic compound.
Claim 37
Dependent Claim
23 words
The process improvement of claim 1 wherein the aromatic compound is admixed with a carrier gas prior to reaction with the nitrating agent.
Claim 38
Dependent Claim
14 words
The process improvement of claim 6 wherein the carrier gas is an oxygen-containing gas.
Claim 39
Dependent Claim
12 words
The process improvement of claim 7 wherein the oxygen-containing gas is air.
Claim 40
Dependent Claim
26 words
The process improvement of claim 1 wherein water vapor is admixed with the feed mixture prior to reaction between the aromatic compound and the nitrating agent.
Claim 41
Dependent Claim
30 words
The process improvement of claim 9 wherein the water vapor is present in the feed mixture in a concentration ranging from about 0.1 percent to about 15 percent by volume.
Claim 42
Dependent Claim
25 words
The process improvement of claim 1 wherein the vapor phase reaction is carried out at temperatures ranging from about 80° C. to about 300° C.
Claim 43
Dependent Claim
18 words
The process improvement of claim 41 wherein the temperature ranges from about 150° C. to about 250° C.
Claim 44
Dependent Claim
33 words
The process improvement of claim 1 wherein the aromatic compound is a monosubstituted aromatic compound having an ortho-para orientation substituent and the nitroaromatic compound is a mixture of ortho, meta, and para isomers.
Claim 45
Dependent Claim
25 words
The process improvement of claim 43 wherein the monosubstituted aromatic compound is chlorobenzene and the nitroaromatic compound is a mixture of o-, m-, and p-nitrochlorobenzene.
Claim 46
Dependent Claim
14 words
The process improvement of claim 44 wherein the para/ortho isomer ratio is about 1.8-3.5/1.
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) | 1986-11-14 | 1987-05-16 | 1987-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-14 | 1991-05-16 | 1991-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-14 | 1995-05-16 | 1995-11-15 | $7700.00 | Window Closed / Lapsed |