GB1104917A – Process for preparing organic isocyanates
– Google Patents
GB1104917A – Process for preparing organic isocyanates
– Google Patents
Process for preparing organic isocyanates
Info
Publication number
GB1104917A
GB1104917A
GB6448/65A
GB644865A
GB1104917A
GB 1104917 A
GB1104917 A
GB 1104917A
GB 6448/65 A
GB6448/65 A
GB 6448/65A
GB 644865 A
GB644865 A
GB 644865A
GB 1104917 A
GB1104917 A
GB 1104917A
Authority
GB
United Kingdom
Prior art keywords
radical
aralkyl
solvent
acetic acid
alkyl
Prior art date
1964-02-26
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
GB6448/65A
Inventor
Karl-Friedrich Zenner
Gunter Oertel
Hans Holtschmidt
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.)
Bayer AG
Original Assignee
Bayer AG
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.)
1964-02-26
Filing date
1965-02-15
Publication date
1968-03-06
1965-02-15
Application filed by Bayer AG
filed
Critical
Bayer AG
1968-03-06
Publication of GB1104917A
publication
Critical
patent/GB1104917A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
239000012948
isocyanate
Substances
0.000
title
abstract
2
150000002513
isocyanates
Chemical class
0.000
title
abstract
2
238000004519
manufacturing process
Methods
0.000
title
1
RTZKZFJDLAIYFH-UHFFFAOYSA-N
Diethyl ether
Chemical compound
CCOCC
RTZKZFJDLAIYFH-UHFFFAOYSA-N
0.000
abstract
8
OGCAJUKWNJKZFV-UHFFFAOYSA-N
2-dimethoxyphosphinothioylsulfanylacetic acid
Chemical compound
COP(=S)(OC)SCC(O)=O
OGCAJUKWNJKZFV-UHFFFAOYSA-N
0.000
abstract
3
UHOVQNZJYSORNB-UHFFFAOYSA-N
Benzene
Chemical compound
C1=CC=CC=C1
UHOVQNZJYSORNB-UHFFFAOYSA-N
0.000
abstract
3
YMWUJEATGCHHMB-UHFFFAOYSA-N
Dichloromethane
Chemical compound
ClCCl
YMWUJEATGCHHMB-UHFFFAOYSA-N
0.000
abstract
3
ZMXDDKWLCZADIW-UHFFFAOYSA-N
N,N-Dimethylformamide
Chemical compound
CN(C)C=O
ZMXDDKWLCZADIW-UHFFFAOYSA-N
0.000
abstract
3
YXFVVABEGXRONW-UHFFFAOYSA-N
Toluene
Chemical compound
CC1=CC=CC=C1
YXFVVABEGXRONW-UHFFFAOYSA-N
0.000
abstract
3
125000001931
aliphatic group
Chemical group
0.000
abstract
3
-1
alkaline earth metal cyanate
Chemical class
0.000
abstract
3
239000002798
polar solvent
Substances
0.000
abstract
3
239000002904
solvent
Substances
0.000
abstract
3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N
1,2-diethylbenzene
Chemical compound
CCC1=CC=CC=C1CC
KVNYFPKFSJIPBJ-UHFFFAOYSA-N
0.000
abstract
2
CSCPPACGZOOCGX-UHFFFAOYSA-N
Acetone
Chemical compound
CC(C)=O
CSCPPACGZOOCGX-UHFFFAOYSA-N
0.000
abstract
2
KWOLFJPFCHCOCG-UHFFFAOYSA-N
Acetophenone
Chemical compound
CC(=O)C1=CC=CC=C1
KWOLFJPFCHCOCG-UHFFFAOYSA-N
0.000
abstract
2
230000000895
acaricidal effect
Effects
0.000
abstract
2
125000003710
aryl alkyl group
Chemical group
0.000
abstract
2
RWGFKTVRMDUZSP-UHFFFAOYSA-N
cumene
Chemical compound
CC(C)C1=CC=CC=C1
RWGFKTVRMDUZSP-UHFFFAOYSA-N
0.000
abstract
2
125000004435
hydrogen atom
Chemical class
[H]*
0.000
abstract
2
238000000034
method
Methods
0.000
abstract
2
UAEPNZWRGJTJPN-UHFFFAOYSA-N
methylcyclohexane
Chemical compound
CC1CCCCC1
UAEPNZWRGJTJPN-UHFFFAOYSA-N
0.000
abstract
2
LQNUZADURLCDLV-UHFFFAOYSA-N
nitrobenzene
Chemical compound
[O-][N+](=O)C1=CC=CC=C1
LQNUZADURLCDLV-UHFFFAOYSA-N
0.000
abstract
2
ZMXIYERNXPIYFR-UHFFFAOYSA-N
1-ethylnaphthalene
Chemical compound
C1=CC=C2C(CC)=CC=CC2=C1
ZMXIYERNXPIYFR-UHFFFAOYSA-N
0.000
abstract
1
JSZOAYXJRCEYSX-UHFFFAOYSA-N
1-nitropropane
Chemical compound
CCC[N+]([O-])=O
JSZOAYXJRCEYSX-UHFFFAOYSA-N
0.000
abstract
1
QGZKDVFQNNGYKY-UHFFFAOYSA-O
Ammonium
Chemical compound
[NH4+]
QGZKDVFQNNGYKY-UHFFFAOYSA-O
0.000
abstract
1
239000004215
Carbon black (E152)
Substances
0.000
abstract
1
XDTMQSROBMDMFD-UHFFFAOYSA-N
Cyclohexane
Chemical compound
C1CCCCC1
XDTMQSROBMDMFD-UHFFFAOYSA-N
0.000
abstract
1
CTQNGGLPUBDAKN-UHFFFAOYSA-N
O-Xylene
Chemical compound
CC1=CC=CC=C1C
CTQNGGLPUBDAKN-UHFFFAOYSA-N
0.000
abstract
1
239000000642
acaricide
Substances
0.000
abstract
1
229910052783
alkali metal
Inorganic materials
0.000
abstract
1
150000001340
alkali metals
Chemical class
0.000
abstract
1
229910052784
alkaline earth metal
Inorganic materials
0.000
abstract
1
125000000217
alkyl group
Chemical group
0.000
abstract
1
150000004945
aromatic hydrocarbons
Chemical class
0.000
abstract
1
150000005840
aryl radicals
Chemical group
0.000
abstract
1
RJTJVVYSTUQWNI-UHFFFAOYSA-N
beta-ethyl naphthalene
Natural products
C1=CC=CC2=CC(CC)=CC=C21
RJTJVVYSTUQWNI-UHFFFAOYSA-N
0.000
abstract
1
239000004305
biphenyl
Substances
0.000
abstract
1
235000010290
biphenyl
Nutrition
0.000
abstract
1
150000001875
compounds
Chemical class
0.000
abstract
1
125000004122
cyclic group
Chemical group
0.000
abstract
1
238000007865
diluting
Methods
0.000
abstract
1
239000003995
emulsifying agent
Substances
0.000
abstract
1
229930195733
hydrocarbon
Natural products
0.000
abstract
1
150000002430
hydrocarbons
Chemical class
0.000
abstract
1
229910052739
hydrogen
Inorganic materials
0.000
abstract
1
239000001257
hydrogen
Substances
0.000
abstract
1
230000000749
insecticidal effect
Effects
0.000
abstract
1
239000002917
insecticide
Substances
0.000
abstract
1
125000001261
isocyanato group
Chemical group
*N=C=O
0.000
abstract
1
HTVHSOYSKFBUGY-UHFFFAOYSA-N
isocyanato(methoxy)methane
Chemical compound
COCN=C=O
HTVHSOYSKFBUGY-UHFFFAOYSA-N
0.000
abstract
1
AUHZEENZYGFFBQ-UHFFFAOYSA-N
mesitylene
Substances
CC1=CC(C)=CC(C)=C1
AUHZEENZYGFFBQ-UHFFFAOYSA-N
0.000
abstract
1
125000001827
mesitylenyl group
Chemical group
[H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
0.000
abstract
1
GYNNXHKOJHMOHS-UHFFFAOYSA-N
methyl-cycloheptane
Natural products
CC1CCCCCC1
GYNNXHKOJHMOHS-UHFFFAOYSA-N
0.000
abstract
1
239000000203
mixture
Substances
0.000
abstract
1
MCSAJNNLRCFZED-UHFFFAOYSA-N
nitroethane
Chemical compound
CC[N+]([O-])=O
MCSAJNNLRCFZED-UHFFFAOYSA-N
0.000
abstract
1
VLZLOWPYUQHHCG-UHFFFAOYSA-N
nitromethylbenzene
Chemical compound
[O-][N+](=O)CC1=CC=CC=C1
VLZLOWPYUQHHCG-UHFFFAOYSA-N
0.000
abstract
1
TVMXDCGIABBOFY-UHFFFAOYSA-N
octane
Chemical compound
CCCCCCCC
TVMXDCGIABBOFY-UHFFFAOYSA-N
0.000
abstract
1
239000003208
petroleum
Substances
0.000
abstract
1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N
phenylbenzene
Natural products
C1=CC=CC=C1C1=CC=CC=C1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N
0.000
abstract
1
229920000151
polyglycol
Polymers
0.000
abstract
1
239000010695
polyglycol
Substances
0.000
abstract
1
239000011877
solvent mixture
Substances
0.000
abstract
1
150000003511
tertiary amides
Chemical class
0.000
abstract
1
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
Substances
O
XLYOFNOQVPJJNP-UHFFFAOYSA-N
0.000
abstract
1
239000008096
xylene
Substances
0.000
abstract
1
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C265/00—Derivatives of isocyanic acid
C07C265/02—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms
C07C265/04—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C263/00—Preparation of derivatives of isocyanic acid
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C265/00—Derivatives of isocyanic acid
C07C265/02—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms
C07C265/06—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
C07C265/08—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
Abstract
An organic a -isocyanato alkyl, aralkyl, aralkenyl or cyclic aliphatic ether is obtained by reacting an a -halogeno-alkyl (-aralkyl, -aralkenyl or -cyclic aliphatic ether with an alkali metal, ammonium, or alkaline earth metal cyanate at 0 DEG to 200 DEG C. in a solvent mixture composed of 0.01 to 80 volume per cent of a strongly polar solvent as defined below and 99.99 to 20 volume per cent of an aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon. The term “strongly polar solvent” refers to a solvent which has a dielectric constant greater than 15 and which does not contain Zerewitinoff-type active hydrogen, e.g. a tertiary amide, carboxylic acid nitrile or a dialkyl dicycloalkyl, aralkyl or diaryl sulphone and several such solvents are specified. Other strongly polar solvents specified are nitroethane, nitropropane, nitrobenzene, nitrotoluene, acetone and acetophenone. The hydrocarbon present in the solvent may be e.g. toluene, benzene, xylene, mesitylene, diethyl benzene, isopropyl benzene, ethyl naphthalene, octane, petroleum ether, gasoline, cyclohexane or methyl cyclohexane. Several examples are given and among the isocyanate products obtainable by the process are those of the general formula R-O-CH(R1)-NCO wherein R is an aralkyl radical, an alkylene radical connected to an O-CH2-NCO group, a Cl-CH2-CH2-radical or CH2=CH-CH2-radical and R1 is a hydrogen atom or an alkyl or aryl radical and the invention includes such products per se as well as the compound C6H5CH.(NCO).O.CH3 formed in one of the examples. Methoxymethyl isocyanate obtainable by the above process can be reacted with O,O-dimethyldithiophosphoryl acetic acid in methylene chloride at 40 DEG C. to form O,O-dimethyl dithiophosphoryl acetic acid N-methoxymethylamide which is effective as an insecticide and acaricide.ALSO:A composition having insecticidal and acaricidal properties is obtained by mixing O,O-dimethyl dithiophosphoryl acetic acid N-methoxymethyl amide with the same amount of dimethyl formamide, adding benzyl hydroxy diphenyl polyglycol ether as emulsifier and then diluting with water.
GB6448/65A
1964-02-26
1965-02-15
Process for preparing organic isocyanates
Expired
GB1104917A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
DEF42127A
DE1205087B
(en)
1964-02-26
1964-02-26
Process for the production of organic isocyanates
Publications (1)
Publication Number
Publication Date
GB1104917A
true
GB1104917A
(en)
1968-03-06
Family
ID=7098950
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB6448/65A
Expired
GB1104917A
(en)
1964-02-26
1965-02-15
Process for preparing organic isocyanates
Country Status (4)
Country
Link
US
(1)
US3453310A
(en)
DE
(1)
DE1205087B
(en)
FR
(1)
FR1425137A
(en)
GB
(1)
GB1104917A
(en)
Families Citing this family (4)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
DE1244410C2
(en)
*
1965-02-03
1968-01-18
Bayer Ag
Process for the production of crosslinkable high molecular weight polymerisation, polycondensation and polyaddition products
DE1619235A1
(en)
*
1966-01-15
1969-08-21
Bayer Ag
Process for coating textiles with crosslinkable polymers
DE1644801C3
(en)
*
1966-05-31
1975-08-28
Bayer Ag, 5090 Leverkusen
Stoving enamels based on self-crosslinking alkyd resins
DE2746963A1
(en)
*
1977-10-19
1979-04-26
Bayer Ag
Alkoxy- or allyloxy-methyl isocyanate prodn. – by heating tri:substd. urea with isocyanate, useful as intermediates for paint binders
Family Cites Families (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US2340757A
(en)
*
1935-05-02
1944-02-01
Heberlein Patent Corp
Isocyanates and related substances and process for their manufacture
US3017420A
(en)
*
1957-10-25
1962-01-16
Union Oil Co
Preparation of organic isocyanates
1964
1964-02-26
DE
DEF42127A
patent/DE1205087B/en
active
Pending
1965
1965-02-15
GB
GB6448/65A
patent/GB1104917A/en
not_active
Expired
1965-02-23
FR
FR6611A
patent/FR1425137A/en
not_active
Expired
1965-02-25
US
US435369A
patent/US3453310A/en
not_active
Expired – Lifetime
Also Published As
Publication number
Publication date
DE1205087B
(en)
1965-11-18
US3453310A
(en)
1969-07-01
FR1425137A
(en)
1966-01-14
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