CA1216853A - Preparation d'isocyanate a l'aide d'un catalyseur perfectionne - Google Patents

Preparation d'isocyanate a l'aide d'un catalyseur perfectionne

Info

Publication number: CA1216853A
Authority: CA; Canada
Prior art keywords: silver; catalyst; reactor; group; oxygen
Prior art date: 1983-03-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000462183A

Other languages

English (en)

Inventor

Peter F. Carcia

George E. Heinsohn

Velliyur N.M. Rao

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-03-14

Filing date

1984-08-30

Publication date

1987-01-20

1983-03-14 Priority claimed from US06/475,032 external-priority patent/US4469640A/en

1984-08-30 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1984-08-30 Priority to CA000462183A priority Critical patent/CA1216853A/fr

1987-01-20 Application granted granted Critical

1987-01-20 Publication of CA1216853A publication Critical patent/CA1216853A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 29
239000012948 isocyanate Substances 0.000 title claims description 8
150000002513 isocyanates Chemical class 0.000 title claims description 8
229910052709 silver Inorganic materials 0.000 claims abstract description 27
239000004332 silver Substances 0.000 claims abstract description 26
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims abstract description 22
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
239000001301 oxygen Substances 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
239000007789 gas Substances 0.000 claims abstract description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
239000000377 silicon dioxide Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 7
239000012159 carrier gas Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
-1 N-monosubstituted formamide Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
229910010293 ceramic material Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
239000011737 fluorine Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
238000005240 physical vapour deposition Methods 0.000 claims description 2
229910001316 Ag alloy Inorganic materials 0.000 claims 1
229910001020 Au alloy Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000003353 gold alloy Substances 0.000 claims 1
239000010453 quartz Substances 0.000 claims 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 abstract description 14
238000006243 chemical reaction Methods 0.000 abstract description 12
239000010931 gold Substances 0.000 abstract description 7
229910052737 gold Inorganic materials 0.000 abstract description 5
239000003701 inert diluent Substances 0.000 abstract 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
229910052681 coesite Inorganic materials 0.000 description 4
229910052906 cristobalite Inorganic materials 0.000 description 4
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
229910052682 stishovite Inorganic materials 0.000 description 4
229910052905 tridymite Inorganic materials 0.000 description 4
210000002268 wool Anatomy 0.000 description 4
239000013078 crystal Substances 0.000 description 3
239000001307 helium Substances 0.000 description 3
229910052734 helium Inorganic materials 0.000 description 3
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
230000001788 irregular Effects 0.000 description 2
229910001092 metal group alloy Inorganic materials 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229940057054 1,3-dimethylurea Drugs 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000005916 Methomyl Substances 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
239000005350 fused silica glass Substances 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000007733 ion plating Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
238000001552 radio frequency sputter deposition Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA000462183A 1983-03-14 1984-08-30 Preparation d'isocyanate a l'aide d'un catalyseur perfectionne Expired CA1216853A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000462183A CA1216853A (fr)	1983-03-14	1984-08-30	Preparation d'isocyanate a l'aide d'un catalyseur perfectionne

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/475,032 US4469640A (en)	1983-03-14	1983-03-14	Catalytic conversion of formamides to isocyanates
CA000462183A CA1216853A (fr)	1983-03-14	1984-08-30	Preparation d'isocyanate a l'aide d'un catalyseur perfectionne

Publications (1)

Publication Number	Publication Date
CA1216853A true CA1216853A (fr)	1987-01-20

Family

ID=25670481

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000462183A Expired CA1216853A (fr)	1983-03-14	1984-08-30	Preparation d'isocyanate a l'aide d'un catalyseur perfectionne

Country Status (1)

Country	Link
CA (1)	CA1216853A (fr)

1984
- 1984-08-30 CA CA000462183A patent/CA1216853A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-08-30	MKEX	Expiry

Publication	Publication Date	Title
US4469640A (en)	1984-09-04	Catalytic conversion of formamides to isocyanates
EP0091027A2 (fr)	1983-10-12	Catalyseur d'hydrogénation à base d'une alliage de nickel de Raney à mailles expansées
JPH01151941A (ja)	1989-06-14	５員飽和窒素含有複素環化合物の製造用触媒組成物
Duan et al.	1995	Novel volatile azatranes of group 4 metals
US4388479A (en)	1983-06-14	Process for producing C4 -C10 ethylene alcohols
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