SU567400A3 - Способ получени изоцианатов - Google Patents

Способ получени изоцианатов

Info

Publication number: SU567400A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mol; toluene; reaction; solvent; mixture
Prior art date: 1973-05-04

Application number

SU742024176A

Other languages

English (en)

Russian (ru)

Inventor

Росентал Рудольф

Джордж Заячек Джон

Original Assignee

Атлантик Ричфилд Компани (Фирма)

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.)

1973-05-04

Filing date

1974-04-30

Publication date

1977-07-30

1974-04-30 Application filed by Атлантик Ричфилд Компани (Фирма) filed Critical Атлантик Ричфилд Компани (Фирма)

1977-07-30 Application granted granted Critical

1977-07-30 Publication of SU567400A3 publication Critical patent/SU567400A3/ru

Links

239000012948 isocyanate Substances 0.000 title description 25
150000002513 isocyanates Chemical class 0.000 title description 25
238000000034 method Methods 0.000 title description 20
238000002360 preparation method Methods 0.000 title description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 32
239000002904 solvent Substances 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
239000000203 mixture Substances 0.000 description 22
239000000047 product Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 17
150000001875 compounds Chemical class 0.000 description 15
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 14
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 11
150000002148 esters Chemical class 0.000 description 10
-1 orthoxylol Natural products 0.000 description 9
238000009835 boiling Methods 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
229930195733 hydrocarbon Natural products 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 7
239000012429 reaction media Substances 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000003599 detergent Substances 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
239000004803 Di-2ethylhexylphthalate Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000004996 alkyl benzenes Chemical class 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
229940038384 octadecane Drugs 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
150000005673 monoalkenes Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000005373 porous glass Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 description 1
JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical class C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
DGSAKMIGXBKPTK-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane;toluene Chemical compound CC1=CC=CC=C1.CCOCCOCCOCC DGSAKMIGXBKPTK-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
YHMQRKUXTUROID-UHFFFAOYSA-N 6-(phenylcarbamoyloxy)hexyl N-phenylcarbamate Chemical compound C=1C=CC=CC=1NC(=O)OCCCCCCOC(=O)NC1=CC=CC=C1 YHMQRKUXTUROID-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001454 anthracenes Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
235000012730 carminic acid Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000011437 continuous method Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003759 ester based solvent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002987 phenanthrenes Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
125000005580 triphenylene group Chemical group 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/04—Preparation of derivatives of isocyanic acid from or via carbamates or carbamoyl halides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU742024176A 1973-05-04 1974-04-30 Способ получени изоцианатов SU567400A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US35730173A	1973-05-04	1973-05-04

Publications (1)

Publication Number	Publication Date
SU567400A3 true SU567400A3 (ru)	1977-07-30

Family

ID=23405050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU742024176A SU567400A3 (ru)	1973-05-04	1974-04-30	Способ получени изоцианатов

Country Status (9)

Country	Link
AT (1)	AT334886B (cs)
BE (1)	BE814453A (cs)
BR (1)	BR7403624D0 (cs)
CS (1)	CS186783B2 (cs)
IT (1)	IT1011363B (cs)
PL (1)	PL104085B1 (cs)
SU (1)	SU567400A3 (cs)
TR (1)	TR17862A (cs)
ZA (1)	ZA742569B (cs)

1974
- 1974-04-23 ZA ZA00742569A patent/ZA742569B/xx unknown
- 1974-04-30 SU SU742024176A patent/SU567400A3/ru active
- 1974-04-30 CS CS7400003096A patent/CS186783B2/cs unknown
- 1974-05-02 BE BE1005922A patent/BE814453A/xx not_active IP Right Cessation
- 1974-05-03 AT AT366574A patent/AT334886B/de not_active IP Right Cessation
- 1974-05-03 TR TR17862A patent/TR17862A/xx unknown
- 1974-05-03 BR BR3624/74A patent/BR7403624D0/pt unknown
- 1974-05-03 IT IT50764/74A patent/IT1011363B/it active
- 1974-05-04 PL PL1974170817A patent/PL104085B1/pl unknown

Also Published As

Publication number	Publication date
CS186783B2 (en)	1978-12-29
TR17862A (tr)	1976-09-01
BR7403624D0 (pt)	1974-12-03
AT334886B (de)	1977-02-10
BE814453A (fr)	1974-11-04
IT1011363B (it)	1977-01-20
ZA742569B (en)	1975-04-30
PL104085B1 (pl)	1979-07-31
ATA366574A (de)	1976-06-15

Publication	Publication Date	Title
US3962302A (en)	1976-06-08	Production of isocyanates from esters of carbamic acids (urethanes)
US3919279A (en)	1975-11-11	Catalytic production of isocyanates from esters of carbamic acids
Brown et al.	1966	Selective Reductions. IX. Reaction of Lithium Aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups1
US4692550A (en)	1987-09-08	Continuous process for thermal splitting of carbamic acid esters
CA1178968A (en)	1984-12-04	Process for the preparation of polyisocyanates
Kim et al.	1991	Structure and reactivity of lithium diisopropylamide (LDA) in hydrocarbon solutions. Formation of unsolvated ketone, ester, and carboxamide enolates
England et al.	1966	Fluoroketenes. I. Bis (trifluoromethyl) ketene and its reactions with fluoride ion
US3919280A (en)	1975-11-11	Recovery of solvents employed in the production of isocyanates from esters of carbamic acids
SU567400A3 (ru)	1977-07-30	Способ получени изоцианатов
KR100372141B1 (ko)	2003-02-14	신규한 우레탄화합물 및 다환식 지방족 디이소시아네이트의 제조방법
JPH02295959A (ja)	1990-12-06	ポリイソシアネートの製造方法
DE2421503A1 (de)	1974-11-21	Verfahren zur herstellung von isocyanaten aus carbaminsaeureestern (urethanen)
JP4029225B2 (ja)	2008-01-09	イソシアネート化合物の製造方法
US3925435A (en)	1975-12-09	Production of isocyanates
JPH01121259A (ja)	1989-05-12	ポリイソシアネートの製造方法
US4146550A (en)	1979-03-27	Process for the preparation of an aliphatic monoisocyanate
JPH02212465A (ja)	1990-08-23	ポリイソシアネートの製造方法
Caraculacu et al.	1990	Dibenzyl structuresin a macromolecular chain. III. Dibenzyldiisocyanates reactivity
Dolbier Jr et al.	1995	A kinetic study of the thermal rearrangement of 2-(trifluoromethyl)-1-vinylcyclopropane
Overberger et al.	1981	Syntheses of seven-membered cyclic azo compounds
EP0492594B1 (en)	1995-09-20	Bromination of ortho-xylene
US3133115A (en)	1964-05-12	1, 2-di(fluorohaloalkyl)-1, 2-dicyano-ethylenes and their preparation
US3363012A (en)	1968-01-09	Novel cyclopropane derivatives from 1, 2-bis(3-cyclohexen-1-yl)ethylenes
SU948288A3 (ru)	1982-07-30	Способ получени алкилизоцианатов
JPH02295958A (ja)	1990-12-06	ポリイソシアネートの製造方法