US4128582A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Chemical process
Assignee: Albemarle Corp
•
Filing: 1974-03-11
•
Granted: 1978-12-05
•
Expires: 1994-03-11
Abstract
Abstract Aromatic amines (e.g., aniline) are selectively alkylated in an ortho nuclear position by reaction with an olefin (e.g., ethylene) in the presence of an aluminum anilide catalyst. Hydrogen halides (e.g., HCl) are added to increase the reaction rate.
Inventors
- 👤 Luke J. Governale
- 👤 John C. Wollensak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:23
CPC Classifications
B; B01; B01J; B01J37/00; B01J37/22; B01J27/00; B01J27/24; B01J31/00; B01J31/02; B01J31/0231; B01J31/0234; B01J31/0235; B01J31/0252; B01J31/12; B01J31/14; B01J31/143; B01J2231/00; B01J2231/30; B01J2231/32; B01J2231/323
Claims Analysis
Total Claims: 67
Claim 1
Independent Claim
103 words
In a process for alkylating an aromatic amine selectively in an ortho nuclear position, said aromatic amine having an unsubstituted ortho nuclear position and at least one hydrogen atom bonded to said amine nitrogen atom, said process comprising reacting said aromatic amine with an olefin at a temperature of about 200°-500°C. in the presence of an aluminum anilide catalyst, the improvement comprising adding a hydrogen halide selected from the group consisting of hydrogen chloride and hydrogen bromide to the alkylation mixture in an amount to provide up to two halogen atoms per aluminum atom in said mixture thereby increasing the rate of alkylation.
Claim 2
Dependent Claim
103 words
In a process for alkylating an aromatic amine selectively in an ortho nuclear position, said aromatic amine having an unsubstituted ortho nuclear position and at least one hydrogen atom bonded to said amine nitrogen atom, said process comprising reacting said aromatic amine with an olefin at a temperature of about 200°-500°C. in the presence of an aluminum anilide catalyst, the improvement comprising adding a hydrogen halide selected from the group consisting of hydrogen chloride and hydrogen bromide to the alkylation mixture in an amount to provide up to two halogen atoms per aluminum atom in said mixture thereby increasing the rate of alkylation.
Claim 3
Dependent Claim
18 words
A process of claim 1 wherein said aromatic amine is aniline and said hydrogen halide is hydrogen chloride.
Claim 4
Dependent Claim
10 words
A process of claim 2 wherein said olefin is ethylene.
Claim 5
Dependent Claim
10 words
A process of claim 2 wherein said olefin is propylene.
Claim 6
Dependent Claim
28 words
A process of claim 1 wherein said aluminum anilide catalyst is formed by adding an alkyl aluminum to said aromatic amine and said hydrogen halide is hydrogen chloride.
Claim 7
Dependent Claim
13 words
A process of claim 5 wherein said alkyl aluminum is a trialkyl aluminum.
Claim 8
Dependent Claim
12 words
A process of claim 6 wherein said trialkyl aluminum is triethyl aluminum.
Claim 9
Dependent Claim
28 words
A process of claim 6 wherein said hydrogen chloride is added to said trialkyl aluminum and the resultant trialkyl aluminum-hydrogen chloride mixture is added to said aromatic amine.
Claim 10
Dependent Claim
12 words
A process of claim 8 wherein said trialkyl aluminum is triethyl aluminum.
Claim 11
Dependent Claim
11 words
A process of claim 9 wherein said aromatic amine is aniline.
Claim 12
Dependent Claim
10 words
A process of claim 10 wherein said olefin is ethylene.
Claim 13
Dependent Claim
10 words
A process of claim 10 wherein said olefin is propylene.
Claim 14
Dependent Claim
25 words
A process of claim 6 wherein said trialkyl aluminum is added to said aromatic amine and said hydrogen chloride is added to said aromatic amine.
Claim 15
Dependent Claim
12 words
A process of claim 13 wherein said trialkyl aluminum is triethyl aluminum.
Claim 16
Dependent Claim
11 words
A process of claim 14 wherein said aromatic amine is aniline.
Claim 17
Dependent Claim
10 words
A process of claim 15 wherein said olefin is ethylene.
Claim 18
Dependent Claim
10 words
A process of claim 15 wherein said olefin is propylene.
Claim 19
Dependent Claim
35 words
A process of claim 5 wherein said alkyl aluminum is the distillation bottoms remaining after distilling alkyl aluminum product from a reaction mixture formed by reacting a C 2-5 alpha-olefin and hydrogen with aluminum metal.
Claim 20
Dependent Claim
18 words
A process of claim 18 wherein said alkyl aluminum product is triethyl aluminum and said alpha-olefin is ethylene.
Claim 21
Dependent Claim
28 words
A process of claim 19 wherein said hydrogen chloride is added to said distillation bottoms and the resultant distillation bottoms-hydrogen chloride mixture is added to said aromatic amine.
Claim 22
Dependent Claim
11 words
A process of claim 20 wherein said aromatic amine is aniline.
Claim 23
Dependent Claim
10 words
A process of claim 21 wherein said olefin is ethylene.
Claim 24
Dependent Claim
25 words
A process of claim 19 wherein said distillation bottoms are added to said aromatic amine and said hydrogen chloride is added to said aromatic amine.
Claim 25
Dependent Claim
11 words
A process of claim 23 wherein said aromatic amine is aniline.
Claim 26
Dependent Claim
10 words
A process of claim 24 wherein said olefin is ethylene.
Claim 27
Dependent Claim
18 words
A process of claim 18 wherein said alkyl aluminum product is triisobutyl aluminum and said alpha-olefin is isobutene.
Claim 28
Dependent Claim
11 words
A process of claim 26 wherein said aromatic amine is aniline.
Claim 29
Dependent Claim
10 words
A process of claim 27 wherein said olefin is ethylene.
Claim 30
Dependent Claim
40 words
A process of claim 1 wherein said aluminum anilide catalyst is formed by reacting aluminum metal with said aromatic amine and hydrogen chloride is thereafter added to said aromatic amine to provide up to 2 chlorine atoms per aluminum atom.
Claim 31
Dependent Claim
11 words
A process of claim 29 wherein said aromatic amine is aniline.
Claim 32
Dependent Claim
10 words
A process of claim 30 wherein said olefin is ethylene.
Claim 33
Dependent Claim
10 words
A process of claim 30 wherein said olefin is propylene.
Claim 34
Dependent Claim
34 words
A process of claim 5 wherein said alkyl aluminum is the distillation residue remaining after distilling alkyl aluminum sesquichloride product from a reaction mixture formed by reacting a lower alkyl chloride with aluminum metal.
Claim 35
Dependent Claim
21 words
A process of claim 33 wherein said alkyl chloride is ethyl chloride and said alkyl aluminum sesquichloride is ethyl aluminum sesquichloride.
Claim 36
Dependent Claim
28 words
A process of claim 34 wherein said hydrogen chloride is added to said distillation residue and the resultant distillation residue-hydrogen chloride mixture is added to said aromatic amine.
Claim 37
Dependent Claim
11 words
A process of claim 35 wherein said aromatic amine is aniline.
Claim 38
Dependent Claim
10 words
A process of claim 36 wherein said olefin is ethylene.
Claim 39
Dependent Claim
10 words
A process of claim 36 wherein said olefin is propylene.
Claim 40
Dependent Claim
25 words
A process of claim 34 wherein said distillation residue is added to said aromatic amine and said hydrogen chloride is added to said aromatic amine.
Claim 41
Dependent Claim
11 words
A process of claim 39 wherein said aromatic amine is aniline.
Claim 42
Dependent Claim
10 words
A process of claim 40 wherein said olefin is ethylene.
Claim 43
Dependent Claim
10 words
A process of claim 40 wherein said olefin is propylene.
Claim 44
Dependent Claim
29 words
A process of claim 1 wherein said hydrogen halide is first added to said aromatic amine and thereafter an aluminum anilide forming composition is added to said aromatic amine.
Claim 45
Dependent Claim
12 words
A process of claim 43 wherein said hydrogen halide is hydrogen chloride.
Claim 46
Dependent Claim
11 words
A process of claim 44 wherein said aromatic amine is aniline.
Claim 47
Dependent Claim
14 words
A process of claim 45 wherein said aluminum anilide forming composition is aluminum metal.
Claim 48
Dependent Claim
10 words
A process of claim 46 wherein said olefin is ethylene.
Claim 49
Dependent Claim
10 words
A process of claim 46 wherein said olefin is propylene.
Claim 50
Dependent Claim
15 words
A process of claim 45 wherein said aluminum anilide forming composition is an alkyl aluminum.
Claim 51
Dependent Claim
12 words
A process of claim 49 wherein said alkyl aluminum is triethyl aluminum.
Claim 52
Dependent Claim
10 words
A process of claim 50 wherein said olefin is ethylene.
Claim 53
Dependent Claim
10 words
A process of claim 50 wherein said olefin is propylene.
Claim 54
Dependent Claim
37 words
A process of claim 45 wherein said aluminum anilide forming composition is the distillation bottoms remaining after distilling trialkyl aluminum product from a reaction mixture formed by reacting a C 2-5 alpha-olefin and hydrogen with aluminum metal.
Claim 55
Dependent Claim
20 words
A process of claim 53 wherein said trialkyl aluminum product is triethyl aluminum anad said C 2-5 alpha-olefin is ethylene.
Claim 56
Dependent Claim
10 words
A process of claim 54 wherein said olefin is ethylene.
Claim 57
Dependent Claim
10 words
A process of claim 54 wherein said olefin is propylene.
Claim 58
Dependent Claim
11 words
A process of claim 1 wherein said aromatic amine is o-toluidine.
Claim 59
Dependent Claim
12 words
A process of claim 57 wherein said hydrogen halide is hydrogen chloride.
Claim 60
Dependent Claim
10 words
A process of claim 58 wherein said olefin is ethylene.
Claim 61
Dependent Claim
20 words
A process of claim 59 wherein said aluminum anilide catalyst is formed by adding an alkyl aluminum to said o-toluidine.
Claim 62
Dependent Claim
12 words
A process of claim 60 wherein said alkyl aluminum is triethyl aluminum.
Claim 63
Dependent Claim
62 words
A process of claim 59 wherein said aluminum anilide catalyst is formed by adding the distillation bottoms remaining after distilling alkyl aluminum product from a reaction mixture formed by reacting a C 2-5 alpha-olefin and hydrogen with aluminum metal, the amount of said distillation bottoms added being adequate to supply about one mole of aluminum per each 5-30 moles of said o-toluidine.
Claim 64
Dependent Claim
18 words
A process of claim 62 wherein said alkyl aluminum product is triethyl aluminum and said alpha-olefin is ethylene.
Claim 65
Dependent Claim
27 words
A process of claim 63 wherein said hydrogen chloride is added to said distillation bottoms and the resultant distillation bottoms-hydrogen chloride mixture is added to said o-toluidine.
Claim 66
Dependent Claim
25 words
A process of claim 63 wherein said distillation bottoms are first added to said o-toluidine and then said hydrogen chloride is added to said o-toluidine.
Claim 67
Dependent Claim
25 words
A process of claim 63 wherein said hydrogen chloride is first added to said o-toluidine and then said distillation bottoms are added to said o-toluidine.
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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) | 1981-12-04 | 1982-06-05 | 1982-12-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-04 | 1986-06-05 | 1986-12-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-04 | 1990-06-05 | 1990-12-05 | $7700.00 | Window Closed / Lapsed |