CA1105480A - Process for the preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates by the acid rearrangement of an (alkoxycarbonyl)phenylamino-methylphenyl compound - Google Patents
Process for the preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates by the acid rearrangement of an (alkoxycarbonyl)phenylamino-methylphenyl compoundInfo
- Publication number
- CA1105480A CA1105480A CA306,259A CA306259A CA1105480A CA 1105480 A CA1105480 A CA 1105480A CA 306259 A CA306259 A CA 306259A CA 1105480 A CA1105480 A CA 1105480A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- process according
- per cent
- compound
- alkoxycarbonyl
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 53
- 239000002253 acid Substances 0.000 title claims abstract description 27
- -1 polymethylene Polymers 0.000 title claims abstract description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 229920006389 polyphenyl polymer Polymers 0.000 title claims abstract description 10
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000004657 carbamic acid derivatives Chemical class 0.000 title claims description 10
- 230000008707 rearrangement Effects 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000002841 Lewis acid Substances 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical group CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 claims description 19
- 125000004494 ethyl ester group Chemical group 0.000 claims description 17
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 15
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 14
- 239000003377 acid catalyst Substances 0.000 claims description 13
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- OTSJRHVZRARHBC-UHFFFAOYSA-N benzylbenzene;carbamic acid Chemical compound NC(O)=O.NC(O)=O.C=1C=CC=CC=1CC1=CC=CC=C1 OTSJRHVZRARHBC-UHFFFAOYSA-N 0.000 claims description 9
- 238000006482 condensation reaction Methods 0.000 claims description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- 239000011260 aqueous acid Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 6
- MMWQQTZKNSUIJL-UHFFFAOYSA-N [2-(1-anilino-2-ethoxy-2-oxoethyl)phenyl]carbamic acid Chemical compound C=1C=CC=C(NC(O)=O)C=1C(C(=O)OCC)NC1=CC=CC=C1 MMWQQTZKNSUIJL-UHFFFAOYSA-N 0.000 claims description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 5
- 239000011968 lewis acid catalyst Substances 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- QXPJDCNNOZUMTR-UHFFFAOYSA-N [4-(1-anilino-2-ethoxy-2-oxoethyl)phenyl]carbamic acid Chemical compound C=1C=C(NC(O)=O)C=CC=1C(C(=O)OCC)NC1=CC=CC=C1 QXPJDCNNOZUMTR-UHFFFAOYSA-N 0.000 claims 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 claims 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000007522 mineralic acids Chemical group 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001721 carbon Chemical group 0.000 abstract description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 9
- 229940054025 carbamate anxiolytics Drugs 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000013638 trimer Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 5
- 238000004811 liquid chromatography Methods 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 150000003673 urethanes Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 3
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229960000443 hydrochloric acid Drugs 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 229940116269 uric acid Drugs 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IFTRQJLVEBNKJK-UHFFFAOYSA-N Ethylcyclopentane Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- KGJUAWKSBSUKCA-UHFFFAOYSA-N 2-(anilinomethyl)aniline Chemical compound NC1=CC=CC=C1CNC1=CC=CC=C1 KGJUAWKSBSUKCA-UHFFFAOYSA-N 0.000 description 1
- BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 description 1
- NLONWIQMGNPYEZ-UHFFFAOYSA-N 4-(anilinomethyl)aniline Chemical compound C1=CC(N)=CC=C1CNC1=CC=CC=C1 NLONWIQMGNPYEZ-UHFFFAOYSA-N 0.000 description 1
- HIZRCIJIHBXYMI-UHFFFAOYSA-N C1(=CC=CC=C1)NC(=O)OCC.C(C)N(C(O)=O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)NC(=O)OCC.C(C)N(C(O)=O)C1=CC=CC=C1 HIZRCIJIHBXYMI-UHFFFAOYSA-N 0.000 description 1
- ZKYVDUYVGLQYTR-UHFFFAOYSA-N CCOC(=O)C1=C(C(=CC=C1)N(CN)C(=O)O)C2=CC=CC=C2 Chemical class CCOC(=O)C1=C(C(=CC=C1)N(CN)C(=O)O)C2=CC=CC=C2 ZKYVDUYVGLQYTR-UHFFFAOYSA-N 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- ATIPBKCFGLKIGH-UHFFFAOYSA-N ethyl n-benzyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C(=O)OCC)CC1=CC=CC=C1 ATIPBKCFGLKIGH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83869177A | 1977-10-03 | 1977-10-03 | |
| US838,691 | 1977-10-03 | ||
| US05/905,705 US4146727A (en) | 1977-10-03 | 1978-05-15 | Process for the preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates by the acid rearrangement of an (alkoxycarbonyl) phenylaminomethylphenyl compound |
| US905,705 | 1978-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105480A true CA1105480A (en) | 1981-07-21 |
Family
ID=27126055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA306,259A Expired CA1105480A (en) | 1977-10-03 | 1978-06-27 | Process for the preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates by the acid rearrangement of an (alkoxycarbonyl)phenylamino-methylphenyl compound |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5829943B2 (de) |
| AR (1) | AR222808A1 (de) |
| AU (1) | AU3788478A (de) |
| BR (1) | BR7806538A (de) |
| CA (1) | CA1105480A (de) |
| DD (1) | DD139576A5 (de) |
| DE (1) | DE2832379A1 (de) |
| DK (1) | DK316878A (de) |
| ES (1) | ES473924A1 (de) |
| FR (1) | FR2404631A1 (de) |
| GB (1) | GB2004866B (de) |
| IL (1) | IL55558A0 (de) |
| IT (1) | IT1106036B (de) |
| LU (1) | LU80245A1 (de) |
| NL (1) | NL7807406A (de) |
| NO (1) | NO782288L (de) |
| PL (1) | PL117360B1 (de) |
| PT (1) | PT68605A (de) |
| RO (1) | RO78324A (de) |
| SE (1) | SE7810316L (de) |
| YU (1) | YU231678A (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4202986A (en) * | 1979-02-12 | 1980-05-13 | Atlantic Richfield Company | Preparation of diphenylmethane dicarbamates and polymethylene polyphenyl carbamates with Lewis acid catalysts intercalated in graphite |
| US4230877A (en) * | 1979-03-22 | 1980-10-28 | Atlantic Richfield Company | Method for increasing the 4,4'dicarbamate isomer of the diphenylmethane dicarbamates during preparation thereof |
| JPS55167273A (en) * | 1979-06-18 | 1980-12-26 | Mitsui Toatsu Chem Inc | Novel bis(n-carboalkoxy-anilino)methane and its preparation |
| JPS567749A (en) * | 1979-07-03 | 1981-01-27 | Mitsui Toatsu Chem Inc | Preparation of polymethylenepolyphenylpolycarbamate |
| DE2942137A1 (de) * | 1979-10-18 | 1981-04-30 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von methylen-bis-phenylcarbaminsaeureestern und polymethylen-polyphenylcarbaminsaeureestern |
| JPS5679657A (en) * | 1979-12-04 | 1981-06-30 | Mitsui Toatsu Chem Inc | Novel preparation of polyisocyanate |
| JPS5721356A (en) * | 1980-07-11 | 1982-02-04 | Mitsui Toatsu Chem Inc | Production of aromatic polyisocyanate |
| JPS58194852A (ja) * | 1982-05-10 | 1983-11-12 | Asahi Chem Ind Co Ltd | ジフエニルメタンジカルバメ−ト類の製造法 |
| JPS58198454A (ja) * | 1982-05-12 | 1983-11-18 | Asahi Chem Ind Co Ltd | ジフエニルメタンジカルバメ−ト類の製造方法 |
| JPS58188860U (ja) * | 1982-06-11 | 1983-12-15 | 日本製罐株式会社 | 缶口密封装置 |
| JPS5929651A (ja) * | 1982-08-11 | 1984-02-16 | Asahi Chem Ind Co Ltd | ポリメチレンポリフエニルカルバメ−ト類の製造方法 |
| JPS59106453A (ja) * | 1982-12-09 | 1984-06-20 | Asahi Chem Ind Co Ltd | Ｎ−フエニルカルバメ−ト類の縮合方法 |
| JPS59104354A (ja) * | 1982-12-07 | 1984-06-16 | Asahi Chem Ind Co Ltd | ジフエニルメタンジカルバメ−ト類の製造方法 |
| JPS59172451A (ja) * | 1983-03-18 | 1984-09-29 | Asahi Chem Ind Co Ltd | ポリイソシアナ−ト類の製造方法 |
| JPS59153962U (ja) * | 1983-03-31 | 1984-10-16 | 三菱重工業株式会社 | 折機 |
| FR2649104B1 (de) * | 1989-06-29 | 1991-09-27 | Rhone Poulenc Chimie | |
| FR2649103B1 (de) * | 1989-06-29 | 1991-09-27 | Rhone Poulenc Chimie |
-
1978
- 1978-01-29 PT PT68605A patent/PT68605A/pt unknown
- 1978-06-27 CA CA306,259A patent/CA1105480A/en not_active Expired
- 1978-06-30 NO NO782288A patent/NO782288L/no unknown
- 1978-07-10 NL NL7807406A patent/NL7807406A/xx not_active Application Discontinuation
- 1978-07-10 AU AU37884/78A patent/AU3788478A/en active Pending
- 1978-07-14 DK DK316878A patent/DK316878A/da unknown
- 1978-07-21 GB GB7830628A patent/GB2004866B/en not_active Expired
- 1978-07-24 DE DE19782832379 patent/DE2832379A1/de not_active Withdrawn
- 1978-08-11 JP JP53097420A patent/JPS5829943B2/ja not_active Expired
- 1978-09-12 IL IL7855558A patent/IL55558A0/xx unknown
- 1978-09-15 LU LU80245A patent/LU80245A1/de unknown
- 1978-09-20 DD DD78207956A patent/DD139576A5/de unknown
- 1978-09-27 FR FR7827636A patent/FR2404631A1/fr active Granted
- 1978-09-30 PL PL1978209991A patent/PL117360B1/pl unknown
- 1978-10-02 YU YU02316/78A patent/YU231678A/xx unknown
- 1978-10-02 IT IT51323/78A patent/IT1106036B/it active
- 1978-10-02 SE SE7810316A patent/SE7810316L/xx unknown
- 1978-10-02 RO RO7895314A patent/RO78324A/ro unknown
- 1978-10-02 BR BR7806538A patent/BR7806538A/pt unknown
- 1978-10-03 AR AR273935A patent/AR222808A1/es active
- 1978-10-03 ES ES473924A patent/ES473924A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL55558A0 (en) | 1978-12-17 |
| RO78324A (ro) | 1982-07-06 |
| JPS5829943B2 (ja) | 1983-06-25 |
| IT7851323A0 (it) | 1978-10-02 |
| DD139576A5 (de) | 1980-01-09 |
| DK316878A (da) | 1979-04-04 |
| FR2404631B1 (de) | 1984-06-29 |
| SE7810316L (sv) | 1979-04-04 |
| NL7807406A (nl) | 1979-04-05 |
| GB2004866A (en) | 1979-04-11 |
| AU3788478A (en) | 1980-01-17 |
| IT1106036B (it) | 1985-11-11 |
| BR7806538A (pt) | 1979-05-02 |
| PT68605A (en) | 1978-10-01 |
| PL117360B1 (en) | 1981-07-31 |
| FR2404631A1 (fr) | 1979-04-27 |
| GB2004866B (en) | 1982-05-06 |
| LU80245A1 (de) | 1979-03-07 |
| AR222808A1 (es) | 1981-06-30 |
| PL209991A1 (pl) | 1979-12-17 |
| NO782288L (no) | 1979-04-04 |
| YU231678A (en) | 1982-06-30 |
| JPS5459264A (en) | 1979-05-12 |
| ES473924A1 (es) | 1980-04-16 |
| DE2832379A1 (de) | 1979-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19980721 |