SU363246A1 - - Google Patents
Info
- Publication number
- SU363246A1 SU363246A1 SU52985A SU52985A SU363246A1 SU 363246 A1 SU363246 A1 SU 363246A1 SU 52985 A SU52985 A SU 52985A SU 52985 A SU52985 A SU 52985A SU 363246 A1 SU363246 A1 SU 363246A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- oxide
- epoxypropane
- tetramethyl
- oxy
- hours
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- -1 2-methyl-4-chloroanilino Chemical group 0.000 description 13
- 238000001816 cooling Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- JVGAGAVQROERFI-UHFFFAOYSA-N 2-(2-phenylethyl)oxirane Chemical compound C1OC1CCC1=CC=CC=C1 JVGAGAVQROERFI-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FMRWQLAJBBKXDM-UHFFFAOYSA-N 2,2,5,5-tetramethylpyrrolidine Chemical compound CC1(C)CCC(C)(C)N1 FMRWQLAJBBKXDM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229940117803 phenethylamine Drugs 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- HIOFHWTUAOODBJ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)oxirane Chemical compound C1=C(Cl)C(Cl)=CC=C1C1OC1 HIOFHWTUAOODBJ-UHFFFAOYSA-N 0.000 description 2
- YKIUTLHCSNCTDZ-UHFFFAOYSA-N 2-(4-nitrophenyl)oxirane Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1OC1 YKIUTLHCSNCTDZ-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- JFDMLXYWGLECEY-UHFFFAOYSA-N 2-benzyloxirane Chemical compound C=1C=CC=CC=1CC1CO1 JFDMLXYWGLECEY-UHFFFAOYSA-N 0.000 description 2
- NPRYHWFMGPYJIY-UHFFFAOYSA-N 2-cyclohexyloxirane Chemical compound C1OC1C1CCCCC1 NPRYHWFMGPYJIY-UHFFFAOYSA-N 0.000 description 2
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- ZYDUNXCLPOKBNQ-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1,3-dihydropyridine Chemical compound CC1(C)CC=CC(C)(C)N1 ZYDUNXCLPOKBNQ-UHFFFAOYSA-N 0.000 description 1
- XSCSSBHFRMVAIG-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-(2-phenylethyl)piperidine Chemical compound CC1(C)CCCC(C)(C)N1CCC1=CC=CC=C1 XSCSSBHFRMVAIG-UHFFFAOYSA-N 0.000 description 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- DYXXANFBMYEXAW-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)oxirane Chemical compound C1OC1C1=CC=C(C2CCCCC2)C=C1 DYXXANFBMYEXAW-UHFFFAOYSA-N 0.000 description 1
- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- PGSFTJDYQSZEKZ-UHFFFAOYSA-N 2-[(2,5-dimethylphenoxy)methyl]oxirane Chemical compound CC1=CC=C(C)C(OCC2OC2)=C1 PGSFTJDYQSZEKZ-UHFFFAOYSA-N 0.000 description 1
- VHWHISLSSKROOL-UHFFFAOYSA-N 2-[(2,6-dimethylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC(C)=C1OCC1OC1 VHWHISLSSKROOL-UHFFFAOYSA-N 0.000 description 1
- BJKPANHIWWVGBJ-UHFFFAOYSA-N 2-[(2-methylphenyl)methyl]oxirane Chemical compound CC1=CC=CC=C1CC1OC1 BJKPANHIWWVGBJ-UHFFFAOYSA-N 0.000 description 1
- RTJWCOIBFLXONL-UHFFFAOYSA-N 2-[(2-propan-2-ylphenoxy)methyl]oxirane Chemical compound CC(C)C1=CC=CC=C1OCC1OC1 RTJWCOIBFLXONL-UHFFFAOYSA-N 0.000 description 1
- ZABVHXJGMITPLQ-UHFFFAOYSA-N 2-[(3,4-dimethylphenoxy)methyl]oxirane Chemical compound C1=C(C)C(C)=CC=C1OCC1OC1 ZABVHXJGMITPLQ-UHFFFAOYSA-N 0.000 description 1
- OAVRAFVFWOJGJO-UHFFFAOYSA-N 2-[(4-methylphenyl)methyl]oxirane Chemical compound C1=CC(C)=CC=C1CC1OC1 OAVRAFVFWOJGJO-UHFFFAOYSA-N 0.000 description 1
- YVCOJTATJWDGEU-UHFFFAOYSA-N 2-methyl-3-phenyloxirane Chemical compound CC1OC1C1=CC=CC=C1 YVCOJTATJWDGEU-UHFFFAOYSA-N 0.000 description 1
- VEKOQDMCBFGHBI-UHFFFAOYSA-N 2-naphthalen-1-yloxirane Chemical compound C1OC1C1=CC=CC2=CC=CC=C12 VEKOQDMCBFGHBI-UHFFFAOYSA-N 0.000 description 1
- ZCUPPSGYUUSVHE-UHFFFAOYSA-N 2-nitro-3-phenyloxirane Chemical compound [O-][N+](=O)C1OC1C1=CC=CC=C1 ZCUPPSGYUUSVHE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YCBQFVGGCUDBFW-UHFFFAOYSA-N C(C)N1C(CC=CC1(C)C)(C)C Chemical compound C(C)N1C(CC=CC1(C)C)(C)C YCBQFVGGCUDBFW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Natural products NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000003975 aryl alkyl amines Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical class [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QHUCJYPNJYZEOQ-UHFFFAOYSA-N oxiran-2-yl(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)C1CO1 QHUCJYPNJYZEOQ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NFXCUPVBISCOSF-UHFFFAOYSA-N propan-2-ol;dihydrochloride Chemical compound Cl.Cl.CC(C)O NFXCUPVBISCOSF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU52985A SU19814A1 (ru) | 1929-08-15 | 1929-08-15 | Автоматические весы дл отвешивани обеспыленного при помощи эксгаустере зерна |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU52985A SU19814A1 (ru) | 1929-08-15 | 1929-08-15 | Автоматические весы дл отвешивани обеспыленного при помощи эксгаустере зерна |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU363246A1 true SU363246A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| SU19814A1 SU19814A1 (ru) | 1931-03-31 |
Family
ID=48339311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU52985A SU19814A1 (ru) | 1929-08-15 | 1929-08-15 | Автоматические весы дл отвешивани обеспыленного при помощи эксгаустере зерна |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU19814A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
-
1929
- 1929-08-15 SU SU52985A patent/SU19814A1/ru active
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