Patent US3923893A successfully refreshed from Google Patents.
US3923893A
Expired / Lapsed
US
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Production of secondary alkyl primary amines
Assignee: Texaco Inc
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Filing: 1973-12-26
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Granted: 1975-12-02
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Expires: 1993-12-26
Abstract
Abstract A process for producing secondary alkyl primary amines from nparaffins where a portion of the paraffin is nitrated to nitroparaffin along with the formation of nitrated and oxygenated by-products, where the nitroparaffin is essentially completely hydrogenated to the amine, and where the amine is separated from a mixture composed of unreacted paraffin and by products, which comprises catalytically hydrogenating the mixture composed of paraffin and by-products in the presence of a catalyst composed of alumina and a Group VIII metal at a temperature of from about 600* to 750*F. and recycling the hydrogenated product for nitration with the n-paraffin.
Inventors
- 👤 Jr Walter C Gates
- 👤 Robert M Suggitt
- 👤 Jr Ralph B Hudson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 22:01
CPC Classifications
C; C07; C07C; C07C7/00; C07C7/148; C07C7/163
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
137 words
IN A PROCESS FOR PRODUCING SECONDARY ALKYL PRIMARY AMINES FROM N-PARAFFINS HAVING FROM 6 TO 30 CARBON ATOMS WHEREIN A PORTION OF SAID N-PARAFFIN IS NITRATED TO FORM A NITROPARAFFIN ALONG WITH NITRATED AND OXYGENATED BY-PRODUCTS, WHEREIN SAID NITROPARAFFIN IS ESSENTIALLY COMPLETELY HYDROGENATED TO SAID AMINE AND WHERE SAID AMINE IS SEPARATED AND RECOVERED FROM A MIXTURE OF UNREACTED PARAFFIN AND BY-PRODUCTS, THE IMPROVEMENT WHICH COMPRISES: A. CATALYTICALLY HYDROGENATING SAID MIXTURE OF UNREACTED PARAFFIN AND BY-PRODUCTS CONTAINING FROM ABOUT 10 TO 5000 PARTS PER MILLION OF NITROGEN PRESENT AS AMINATED BY-PRODUCTS AT A TEMPERATURE OF FROM ABOUT 650 TO 710*F. UNDER A HYDROGEN PRESSURE OF ABOUT 100 TO 1500 P.S.I.G. IN THE PRESENCE OF A CATALYST COMPOSED OF ALUMINA AND A GROUP VII METAL AND B. RECYCLING SAID HYDROGENATED PRODUCT OF (A) FOR NITRATION WITH SAID N-PARAFFIN.
Claim 2
Dependent Claim
137 words
IN A PROCESS FOR PRODUCING SECONDARY ALKYL PRIMARY AMINES FROM N-PARAFFINS HAVING FROM 6 TO 30 CARBON ATOMS WHEREIN A PORTION OF SAID N-PARAFFIN IS NITRATED TO FORM A NITROPARAFFIN ALONG WITH NITRATED AND OXYGENATED BY-PRODUCTS, WHEREIN SAID NITROPARAFFIN IS ESSENTIALLY COMPLETELY HYDROGENATED TO SAID AMINE AND WHERE SAID AMINE IS SEPARATED AND RECOVERED FROM A MIXTURE OF UNREACTED PARAFFIN AND BY-PRODUCTS, THE IMPROVEMENT WHICH COMPRISES: A. CATALYTICALLY HYDROGENATING SAID MIXTURE OF UNREACTED PARAFFIN AND BY-PRODUCTS CONTAINING FROM ABOUT 10 TO 5000 PARTS PER MILLION OF NITROGEN PRESENT AS AMINATED BY-PRODUCTS AT A TEMPERATURE OF FROM ABOUT 650 TO 710*F. UNDER A HYDROGEN PRESSURE OF ABOUT 100 TO 1500 P.S.I.G. IN THE PRESENCE OF A CATALYST COMPOSED OF ALUMINA AND A GROUP VII METAL AND B. RECYCLING SAID HYDROGENATED PRODUCT OF (A) FOR NITRATION WITH SAID N-PARAFFIN.
Claim 3
Dependent Claim
24 words
A process according to claim 1 wherein said hydrogenating in step (a) is conducted at a liquid hourly space velocity of 0.2 to 10.
Claim 4
Dependent Claim
24 words
A process according to claim 1 wherein said mixture hydrogenated in (a) is additionally hydrogenated at 450* to 650*F. prior to recycling in (b).
Claim 5
Dependent Claim
13 words
A process according to claim 1 wherein said catalyst is platinum on alumina.
Claim 6
Dependent Claim
13 words
A process according to claim 1 wherein said catalyst is nickel-molybdenum on alumina.
Claim 7
Dependent Claim
13 words
A process according to claim 1 wherein said catalyst is cobalt-molybdenum on alumina.
Claim 8
Dependent Claim
38 words
A process according to claim 1 wherein said separated amine is further vacuum distilled to separate an additional by-product stream comprising C6 to C30 diamines, aminoalcohols and aminoketones and introducing said by-product stream to the mixture in (a).
Claim 9
Dependent Claim
34 words
A process according to claim 1 wherein said hydrogenating in step (a) is conducted in the presence of 100 to 3000 parts per million of nitrogen present as aminated by-products basis said paraffin mixture.
Claim 10
Dependent Claim
24 words
A process according to claim 1 wherein said mixture in (a) comprises from about 0.5 to 15 weight per cent oxygenated and aminated by-products.
Claim 11
Dependent Claim
32 words
A process according to claim 9 wherein said oxygenated and aminated by-products comprise a C6 to C30 alcohol, ketone, aminoketone, aminoalcohol, diamine, triamine and a C12 to C60 secondary alkyl secondary amine.
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) | 1978-12-01 | 1979-06-02 | 1979-12-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-01 | 1983-06-02 | 1983-12-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-01 | 1987-06-02 | 1987-12-02 | $7700.00 | Window Closed / Lapsed |