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US3923850A
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US
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Preparation of aromatic isocyanates
Assignee: Olin Corp
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Filing: 1969-03-12
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Granted: 1975-12-02
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Expires: 1989-03-12
Abstract
Abstract In the process for preparing an organic isocyanate by reacting an organic nitro compound with carbon monoxide in the presence of a catalyst, improved recovery of the organic isocyanate is obtained when the reaction is carried out in the presence of a hydroxyl-substituted hydrocarbon. In addition, when a dinitro compound is employed as a reactant, the proportion of ortho isomers in the isocyanate product is markedly reduced.
Inventors
- 👤 Ehrenfried H Kober
- 👤 Wilhelm J Schnabel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:43
CPC Classifications
C; C07; C07C; C07C263/00; C07C263/14
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
7 words
A NOBLE METAL COMPOUND OF IIA, AND
Claim 2
Dependent Claim
7 words
A NOBLE METAL COMPOUND OF IIA, AND
Claim 3
Dependent Claim
150 words
IN THE PROCESS FOR PREPARING AN AROMATIC ISOCYANATE BY REACTING AN AROMATIC NNITRO COMPOUND CONTAINING UP TO ABOUT 20 CARBON ATOMS WITH CARBON MONOXIDE AT AN ELEVATED TEMPERATURE AND AN ELEVATED PRESSURE, THE IMPROVEMENT WHICH COMPRISES CARRYING OUT THE REACTION IN THE PRESENCE OF A MIXTURE OF I. A HYDROXYL-SUBSTITUTED HYDROCARBON SELECTED FROM THE GROUPS CONSISTING OF A. ALIPHATIC ALCOHOLS CONTAINING FROM 1 TO 12 CARBON ATOMS B. PHENOLS CONTAINING FROM 6 TO 10 CARBON ATOMS IN THE RING C. ALKYL-SUBSTITUTED PHENOLS CONTAINING FROM 7 TO 14 CARBON ATOMS AND D. ALIPHATIC DIOLS CONTAINING FROM 1 TO 4 CARBON ATOMS, II. A CATALYST SYSTEM SELECTED FROM THE GROUP CONSISTING OF A. A NOBLE METAL COMPOUND SELECTED FROM THE GROUP CONSISTING OF NOBLE METAL IS SELECTED FROM THE GROUP WHEREIN THE NOBLE METAL IS SELECTED FROM THE GROUP CONSISTING OF PALLADIUM, RHODIUM, IRIDIUM, RUTHENIUM OR MIXTURES THEREOF, B. A MIXTURE OF
Claim 4
Dependent Claim
150 words
IN THE PROCESS FOR PREPARING AN AROMATIC ISOCYANATE BY REACTING AN AROMATIC NNITRO COMPOUND CONTAINING UP TO ABOUT 20 CARBON ATOMS WITH CARBON MONOXIDE AT AN ELEVATED TEMPERATURE AND AN ELEVATED PRESSURE, THE IMPROVEMENT WHICH COMPRISES CARRYING OUT THE REACTION IN THE PRESENCE OF A MIXTURE OF I. A HYDROXYL-SUBSTITUTED HYDROCARBON SELECTED FROM THE GROUPS CONSISTING OF A. ALIPHATIC ALCOHOLS CONTAINING FROM 1 TO 12 CARBON ATOMS B. PHENOLS CONTAINING FROM 6 TO 10 CARBON ATOMS IN THE RING C. ALKYL-SUBSTITUTED PHENOLS CONTAINING FROM 7 TO 14 CARBON ATOMS AND D. ALIPHATIC DIOLS CONTAINING FROM 1 TO 4 CARBON ATOMS, II. A CATALYST SYSTEM SELECTED FROM THE GROUP CONSISTING OF A. A NOBLE METAL COMPOUND SELECTED FROM THE GROUP CONSISTING OF NOBLE METAL IS SELECTED FROM THE GROUP WHEREIN THE NOBLE METAL IS SELECTED FROM THE GROUP CONSISTING OF PALLADIUM, RHODIUM, IRIDIUM, RUTHENIUM OR MIXTURES THEREOF, B. A MIXTURE OF
Claim 5
Dependent Claim
7 words
A NOBLE METAL COMPOUND OF IIA AND
Claim 6
Dependent Claim
7 words
A NOBLE METAL COMPOUND OF IIA AND
Claim 7
Dependent Claim
66 words
A HETEROAROMATIC NNITROGEN COMPOUND HAVING A RING CONTAINING A. 5 OR 6 MEMBERS IN THE RING, B. ONLY NITROGEN AND CARBON IN THE RING, C. ON MORE THAN 2 NITROGEN ATOMS IN THE RING, AND D. AT LEAST 2 DOUBLE BONDS IN THE RING, C. A COMPLEX OF A NOBLE METAL COMPOUND OF IIA WITH A HETEROAROMATIC NITROGEN COMPOUND OF IIB(2) AND D. A MIXTURE OF
Claim 8
Dependent Claim
66 words
A HETEROAROMATIC NNITROGEN COMPOUND HAVING A RING CONTAINING A. 5 OR 6 MEMBERS IN THE RING, B. ONLY NITROGEN AND CARBON IN THE RING, C. ON MORE THAN 2 NITROGEN ATOMS IN THE RING, AND D. AT LEAST 2 DOUBLE BONDS IN THE RING, C. A COMPLEX OF A NOBLE METAL COMPOUND OF IIA WITH A HETEROAROMATIC NITROGEN COMPOUND OF IIB(2) AND D. A MIXTURE OF
Claim 9
Dependent Claim
45 words
AN OXIDE OF AN ELEMENT SELECTED FROM THE GROUP CONSISTING OF A. MOLYBDENUM, B. VANADIUM, C. CHROMIUM AND D. IRON, III. WHEREIN THE PROPORTION OF SAID HYDROXYL SUBSTITUTED HYDROCARBON IS BETWEEN ABOUT 0.001 AND ABOUT 20 MOLE EQUIVALENTS PER MOLE OF SAID AROMATIC NITRO COMPOUND.
Claim 10
Dependent Claim
45 words
AN OXIDE OF AN ELEMENT SELECTED FROM THE GROUP CONSISTING OF A. MOLYBDENUM, B. VANADIUM, C. CHROMIUM AND D. IRON, III. WHEREIN THE PROPORTION OF SAID HYDROXYL SUBSTITUTED HYDROCARBON IS BETWEEN ABOUT 0.001 AND ABOUT 20 MOLE EQUIVALENTS PER MOLE OF SAID AROMATIC NITRO COMPOUND.
Claim 11
Dependent Claim
66 words
a heteroaromatic nitrogen compound having a ring containing a. 5 or 6 members in the ring, b. only nitrogen and carbon in the ring, c. no more than 2 nitrogen atoms in the ring, and d. at least 2 double bonds in the ring, c. a complex of a noble metal compound of IIa with a heteroaromatic nitrogen compound of IIb(2) and d. a mixture of
Claim 12
Dependent Claim
66 words
a heteroaromatic nitrogen compound having a ring containing a. 5 or 6 members in the ring, b. only nitrogen and carbon in the ring, c. no more than 2 nitrogen atoms in the ring, and d. at least 2 double bonds in the ring, c. a complex of a noble metal compound of IIa with a heteroaromatic nitrogen compound of IIb(2) and d. a mixture of
Claim 13
Dependent Claim
45 words
an oxide of an element selected from the group consisting of a. molybdenum, b. vanadium, c. chromium and d. iron, III. wherein the proportion of said hydroxyl substituted hydrocarbon is between about 0.001 and about 20 mole equivalents per mole of said aromatic nitro compound.
Claim 14
Dependent Claim
45 words
an oxide of an element selected from the group consisting of a. molybdenum, b. vanadium, c. chromium and d. iron, III. wherein the proportion of said hydroxyl substituted hydrocarbon is between about 0.001 and about 20 mole equivalents per mole of said aromatic nitro compound.
Claim 15
Dependent Claim
29 words
The process of claim 1 wherein the proportion of said hydroxyl substituted hydrocarbon is between about 0.005 and about 10 mole equivalents per mole of said aromatic nitro compound.
Claim 16
Dependent Claim
26 words
The process of claim 1 wherein the proportion of said catalyst system is between about 0.001 and about 500 weight percent of said aromatic nitro compound.
Claim 17
Dependent Claim
26 words
The process of claim 1 wherein the proportion of said catalyst system is between about 1 and about 100 weight percent of said aromatic nitro compound.
Claim 18
Dependent Claim
21 words
The process of claim 1 wherein said aromatic nitro compound is selected from the group consisting of nitrobenzene, dinitrotoluene and isocyanato-nitrotoluene.
Claim 19
Dependent Claim
30 words
The process of claim 5 wherein said noble metal compound is selected from the group consisting of palladous chloride, rhodium trichloride, iridium trichloride, rhenium trichloride, platinium tetrachloride and mixtures thereof.
Claim 20
Dependent Claim
39 words
The process of claim 6 wherein said oxide of an element is selected from the group consisting of chromic oxide, chromium dioxide, chromic anhydride, chromous oxide, molybdenum sesquioxide, molybdenum dioxide, molybdenum trioxide, ferrous oxide, ferric oxide and vanadium pentoxide.
Claim 21
Dependent Claim
23 words
The process of claim 6 wherein said heteroaromatic nitrogen compound is selected from the group consisting of pyridine, isoquinoline, quinoline and mixtures thereof.
Claim 22
Dependent Claim
21 words
The process of claim 6 wherein said hydroxyl substituted hydrocarbon is selected from the group consisting of phenol and ethylene glycol.
Claim 23
Dependent Claim
25 words
The process of claim 6 wherein said hydroxyl substituted hydrocarbon is phenol and said catalyst system is a mixture of palladous chloride and vanadium pentoxide.
Claim 24
Dependent Claim
21 words
The process of claim 6 wherein said hydroxyl substituted hydrocarbon is phenol and said catalyst system is palladous chloride pyridine complex.
Claim 25
Dependent Claim
21 words
The process of claim 6 wherein said hydroxyl substituted hydrocarbon is phenol and said catalyst system is palladous chloride isoquinoline complex.
Claim 26
Dependent Claim
19 words
The process of claim 6 wherein said hydroxyl substituted hydrocarbon is phenol and said catalyst system is palladous chloride.
Claim 27
Dependent Claim
103 words
The process of claim 6 wherein said catalyst system is selected from the group consisting of I. a mixture of a. a noble metal compound and b. a heteroaromatic nitrogen compound and II. a complex of a. a noble metal compound and b. a heteroaromatic nitrogen compound, III. wherein said noble metal compound is selected from the group consisting of a. palladous chloride, b. rhodium trichloride, c. iridium trichloride, d. rhenium trichloride, e. platinum tetrachloride and f. mixtures thereof and IV. wherein said heteroaromatic nitrogen compound is selected from the group consisting of a. pyridine, b. isoquinoline, c. quinoline and d. mixtures thereof.
Claim 28
Dependent Claim
26 words
The process of claim 9 wherein the proportion of said catalyst system is between about 1 and about 100 weight percent of said aromatic nitro compound.
Claim 29
Dependent Claim
29 words
The process of claim 15 wherein the proportion of said hydroxyl substituted hydrocarbon is between about 0.005 and about 10 mole equivalents per mole of said aromatic nitro compound.
Claim 30
Dependent Claim
61 words
The process of claim 16 wherein said elevated pressure is in the range between about 30 and about 30,000 psig, said elevated temperature is in the range between about 100*C. and about 250*C., and the proportion of carbon monoxide is in the range between about 3 and about 50 moles of carbon monoxide per nitro group in said aromatic nitro compound.
Claim 31
Dependent Claim
46 words
The process of claim 17 wherein said elevated pressure is in the range between about 100*C. and 150*C. and the proportion of carbon monoxide is in the range between about 8 and about 15 moles of carbon monoxide per nitro group in said aromatic nitro compound.
Claim 32
Dependent Claim
127 words
The process of claim 18 wherein said catalyst system is selected from the group consisting of I. a mixture of a. a noble metal compound and b. a heteroaromatic nitrogen compound and II. a complex of a. a noble metal compound and b. a heteroaromatic nitrogen compound, III. wherein said noble metal compound is selected from the group consisting of a. palladous chloride, b. rhodium trichloride, c. iridium trichloride, d. rhenium trichloride, e. platinum tetrachloride and f. mixtures thereof and IV. wherein said heteroaromatic nitrogen compound is selected from the group consisting of a. pyridine, b. isoquinoline, c. quinoline and d. mixtures thereof and V. the molar ratio of said heteroaromatic nitrogen compound to the anion of said noble metal compound is from 0.1:1 to about 10:1.
References Cited (Backward Citations)
GB993704A
Cited
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 |