CA1108174A - Methode de preparation de carbamates d'halosilyle et des isocyanates derives - Google Patents

Methode de preparation de carbamates d'halosilyle et des isocyanates derives

Info

Publication number: CA1108174A
Authority: CA; Canada
Prior art keywords: halosilane; carbamate; acid salt; carbamic acid; halogen
Prior art date: 1976-05-17
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

CA359,575A

Other languages

English (en)

Inventor

Eddie Hedaya

Spyros Theodoropulos

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.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

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.)

1976-05-17

Filing date

1980-09-04

Publication date

1981-09-01

1976-05-17 Priority claimed from US05/687,160 external-priority patent/US4064151A/en

1980-09-04 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1980-09-04 Priority to CA359,575A priority Critical patent/CA1108174A/fr

1981-09-01 Application granted granted Critical

1981-09-01 Publication of CA1108174A publication Critical patent/CA1108174A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 59
239000012948 isocyanate Substances 0.000 title claims abstract description 48
150000002513 isocyanates Chemical class 0.000 title claims abstract description 45
150000004657 carbamic acid derivatives Chemical class 0.000 title abstract description 10
238000006243 chemical reaction Methods 0.000 claims abstract description 30
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 22
230000008569 process Effects 0.000 claims abstract description 21
238000010438 heat treatment Methods 0.000 claims abstract description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 53
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 28
239000001569 carbon dioxide Substances 0.000 claims description 24
229910002092 carbon dioxide Inorganic materials 0.000 claims description 24
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 17
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims description 12
239000005049 silicon tetrachloride Substances 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical compound NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000003141 primary amines Chemical class 0.000 claims description 6
125000002877 alkyl aryl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000002723 alicyclic group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
239000005054 phenyltrichlorosilane Substances 0.000 claims description 4
ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 claims description 4
239000005046 Chlorosilane Substances 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims 2
239000007791 liquid phase Substances 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 26
-1 amino, mercapto, nitro, sulfonamido Chemical group 0.000 abstract description 18
150000001875 compounds Chemical class 0.000 abstract description 10
125000003368 amide group Chemical group 0.000 abstract description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
230000015572 biosynthetic process Effects 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 17
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000007789 gas Substances 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
230000009102 absorption Effects 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000005051 trimethylchlorosilane Substances 0.000 description 7
238000005406 washing Methods 0.000 description 7
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
229910052710 silicon Inorganic materials 0.000 description 6
239000002253 acid Substances 0.000 description 5
230000000875 corresponding effect Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000010703 silicon Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
235000011089 carbon dioxide Nutrition 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
229910007161 Si(CH3)3 Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000006884 silylation reaction Methods 0.000 description 3
230000002194 synthesizing effect Effects 0.000 description 3
SOWDBKWCDADBQY-UHFFFAOYSA-N trichlorosilyl carbamate Chemical compound NC(=O)O[Si](Cl)(Cl)Cl SOWDBKWCDADBQY-UHFFFAOYSA-N 0.000 description 3
DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 3
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000011437 continuous method Methods 0.000 description 2
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
229960003732 tyramine Drugs 0.000 description 2
125000005023 xylyl group Chemical group 0.000 description 2
WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
RQMWTTLUOXUKQW-UHFFFAOYSA-N 2-isocyanatoethoxy(trimethyl)silane Chemical compound C[Si](C)(C)OCCN=C=O RQMWTTLUOXUKQW-UHFFFAOYSA-N 0.000 description 1
229940082584 3-(triethoxysilyl)propylamine Drugs 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002101 Chitin Polymers 0.000 description 1
229920001661 Chitosan Polymers 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
101100536931 Escherichia coli (strain K12) thiD gene Proteins 0.000 description 1
101100159279 Escherichia coli (strain K12) yajL gene Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
IHKYSGJNHVOROF-FVGYRXGTSA-N N=C=O.COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 Chemical compound N=C=O.COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 IHKYSGJNHVOROF-FVGYRXGTSA-N 0.000 description 1
241000577218 Phenes Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
241000212342 Sium Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
DORHGRMBOUREIV-UHFFFAOYSA-N [4-(2-isocyanatoethyl)phenoxy]-trimethylsilane Chemical compound C[Si](C)(C)OC1=CC=C(CCN=C=O)C=C1 DORHGRMBOUREIV-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
OATNQHYJXLHTEW-UHFFFAOYSA-N benzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C=C1 OATNQHYJXLHTEW-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
210000001217 buttock Anatomy 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
KQIFRYIYNPGWEK-UHFFFAOYSA-N cyclohexylazanium;n-cyclohexylcarbamate Chemical compound NC1CCCCC1.OC(=O)NC1CCCCC1 KQIFRYIYNPGWEK-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
JIYXHCMRGZVYMA-UHFFFAOYSA-N dimethylcarbamic acid;n-methylmethanamine Chemical compound C[NH2+]C.CN(C)C([O-])=O JIYXHCMRGZVYMA-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
PPNLXDXRZUZRTD-UHFFFAOYSA-N methanamine;methylcarbamic acid Chemical compound NC.CNC(O)=O PPNLXDXRZUZRTD-UHFFFAOYSA-N 0.000 description 1
ZLCYMQQQFBDVFC-UHFFFAOYSA-N methyl 2-isocyanato-3-(4-trimethylsilyloxyphenyl)propanoate Chemical compound COC(=O)C(N=C=O)CC1=CC=C(O[Si](C)(C)C)C=C1 ZLCYMQQQFBDVFC-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
FSWPUPQZFDRXOZ-UHFFFAOYSA-N phenyl N-cyclohexyl-N-dichlorosilylcarbamate Chemical compound C1(=CC=CC=C1)OC(N(C1CCCCC1)[SiH](Cl)Cl)=O FSWPUPQZFDRXOZ-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
PYRLGKOKNUJQQN-UHFFFAOYSA-N silylcarbamic acid Chemical class OC(=O)N[SiH3] PYRLGKOKNUJQQN-UHFFFAOYSA-N 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000013519 translation Methods 0.000 description 1
RDEKHAYBXPYQJQ-UHFFFAOYSA-N trimethylsilyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)O[Si](C)(C)C RDEKHAYBXPYQJQ-UHFFFAOYSA-N 0.000 description 1
GHLWPMXJVBXAGW-UHFFFAOYSA-N trimethylsilyl n-cyclohexylcarbamate Chemical compound C[Si](C)(C)OC(=O)NC1CCCCC1 GHLWPMXJVBXAGW-UHFFFAOYSA-N 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

CA359,575A 1976-05-17 1980-09-04 Methode de preparation de carbamates d'halosilyle et des isocyanates derives Expired CA1108174A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA359,575A CA1108174A (fr)	1976-05-17	1980-09-04	Methode de preparation de carbamates d'halosilyle et des isocyanates derives

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/687,160 US4064151A (en)	1976-05-17	1976-05-17	Halosilyl carbamates
CA278,460A CA1096876A (fr)	1976-05-17	1977-05-16	Procede d'obtention d'holosilyl-carbamates et d'isocyanates qui en derivent
CA359,575A CA1108174A (fr)	1976-05-17	1980-09-04	Methode de preparation de carbamates d'halosilyle et des isocyanates derives
US687,160		1991-04-18

Publications (1)

Publication Number	Publication Date
CA1108174A true CA1108174A (fr)	1981-09-01

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CA359,575A Expired CA1108174A (fr)	1976-05-17	1980-09-04	Methode de preparation de carbamates d'halosilyle et des isocyanates derives

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CA (1)	CA1108174A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9745254B2 (en)	2015-07-17	2017-08-29	Great Eastern Resins Industrial Co., Ltd.	Two-step and one-pot processes for preparation of aliphatic diisocyanates

1980
- 1980-09-04 CA CA359,575A patent/CA1108174A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9745254B2 (en)	2015-07-17	2017-08-29	Great Eastern Resins Industrial Co., Ltd.	Two-step and one-pot processes for preparation of aliphatic diisocyanates

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Date	Code	Title	Description
1998-09-01	MKEX	Expiry

Publication	Publication Date	Title
CA1096876A (fr)	1981-03-03	Procede d'obtention d'holosilyl-carbamates et d'isocyanates qui en derivent
US4697009A (en)	1987-09-29	N-silylpropyl-N'-acyl-ureas and process for their production
US4725660A (en)	1988-02-16	Method for producing polysilazane
JPH0324471B2 (fr)	1991-04-03
AU602057B2 (en)	1990-09-27	Novel aminohydrocarbyl-substituted ketoximosilanes
FR2578256A1 (fr)	1986-09-05	Carbamates de silyle, leur procede de preparation et leur utilisation pour la preparation de bis(aminoalkyl) disiloxanes.
CA1108174A (fr)	1981-09-01	Methode de preparation de carbamates d'halosilyle et des isocyanates derives
US4880927A (en)	1989-11-14	Method for preparing a cyclic isocyanuric ester having organosilicon groups
JPH01502025A (ja)	1989-07-13	オキシモシラン類の製造法
JPH09216860A (ja)	1997-08-19	エーテルイソシアネートの製造方法
US4176131A (en)	1979-11-27	Chemical process
US4886902A (en)	1989-12-12	Process for the preparation of isocyanates and their use for the preparation of polyisocyanates containing ester groups
US5049690A (en)	1991-09-17	N,N'-disubstituted and N,N,N'-/N,N', N'-trisubstituted thioureas and method of their preparation (II)
JP4040731B2 (ja)	2008-01-30	エチレン性不飽和イソシアナートを製造する方法
AU723133B2 (en)	2000-08-17	Process for producing 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof
US4736046A (en)	1988-04-05	β-isocyanato organosilanes
AU597793B2 (en)	1990-06-07	Method for preparing aminohydrocarbyl-substituted ketoximosilanes
SU606863A1 (ru)	1978-05-15	Способ получени полимочевин
US4663471A (en)	1987-05-05	Method for the preparation of N-methyl-N-trimethylsilyl trifluoroacetamide
KR960007530B1 (ko)	1996-06-05	설포닐우레아 유도체의 제조방법
JPS63250391A (ja)	1988-10-18	含ケイ素イソシアン酸エステルの製造方法
KR900006446B1 (ko)	1990-08-31	우레아 유도체의 제조방법
CA2186991C (fr)	2006-01-31	Methode de preparation d'isocyanates acyliques
JPS6391355A (ja)	1988-04-22	ジイソシアネート、その製造法及びその使用
US5227509A (en)	1993-07-13	Process for manufacture of organic esters of strong acids

CA1108174A - Methode de preparation de carbamates d'halosilyle et des isocyanates derives - Google Patents

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Applications Claiming Priority (4)

Publications (1)

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ID=27165078

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Country Status (1)

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