SU368739A1 - - Google Patents

Info

Publication number

SU368739A1

SU368739A1 SU21264A SU21264A SU368739A1 SU 368739 A1 SU368739 A1 SU 368739A1 SU 21264 A SU21264 A SU 21264A SU 21264 A SU21264 A SU 21264A SU 368739 A1 SU368739 A1 SU 368739A1

Authority

SU

USSR - Soviet Union

Prior art keywords

reactor

acid

anhydride

amount

yield

Prior art date

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• 239000002253 acid Substances 0.000 claims description 24
• 238000000034 method Methods 0.000 claims description 12
• -1 alicyclic ketenes Chemical class 0.000 claims description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
• 238000004821 distillation Methods 0.000 claims description 6
• 239000000203 mixture Substances 0.000 claims description 5
• 229910021529 ammonia Inorganic materials 0.000 claims description 4
• 239000003054 catalyst Substances 0.000 claims description 4
• 238000001816 cooling Methods 0.000 claims description 4
• 125000002723 alicyclic group Chemical group 0.000 claims description 3
• 238000010438 heat treatment Methods 0.000 claims description 3
• 150000002561 ketenes Chemical class 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
• 238000007086 side reaction Methods 0.000 claims description 2
• 238000000926 separation method Methods 0.000 claims 1
• 150000008064 anhydrides Chemical class 0.000 description 25
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 13
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
• 239000006227 byproduct Substances 0.000 description 8
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
• 229910052802 copper Inorganic materials 0.000 description 7
• 239000010949 copper Substances 0.000 description 7
• CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 7
• 239000007789 gas Substances 0.000 description 6
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 description 3
• FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• QTPJMTACJMLPLL-UHFFFAOYSA-N triethoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OCC QTPJMTACJMLPLL-UHFFFAOYSA-N 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
• 229910000831 Steel Inorganic materials 0.000 description 2
• 239000003990 capacitor Substances 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 229910052759 nickel Inorganic materials 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
• 239000010452 phosphate Substances 0.000 description 2
• 239000011669 selenium Substances 0.000 description 2
• 229910052711 selenium Inorganic materials 0.000 description 2
• 239000010959 steel Substances 0.000 description 2
• DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
• DODNKCRINWUAHH-UHFFFAOYSA-N (diethyl-$l^{3}-selanyl)ethane Chemical compound CC[Se](CC)CC DODNKCRINWUAHH-UHFFFAOYSA-N 0.000 description 1
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 238000010923 batch production Methods 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 229910052804 chromium Inorganic materials 0.000 description 1
• 239000011651 chromium Substances 0.000 description 1
• 239000010724 circulating oil Substances 0.000 description 1
• 238000010924 continuous production Methods 0.000 description 1
• JWIPDQOXAJMVHL-UHFFFAOYSA-N cyclododecanecarboxylic acid Chemical compound OC(=O)C1CCCCCCCCCCC1 JWIPDQOXAJMVHL-UHFFFAOYSA-N 0.000 description 1
• BXQJYIXHTMSDRB-UHFFFAOYSA-N cyclohexane;hydrochloride Chemical compound Cl.C1CCCCC1 BXQJYIXHTMSDRB-UHFFFAOYSA-N 0.000 description 1
• URAXDCBRCGSGAT-UHFFFAOYSA-N cyclooctanecarboxylic acid Chemical compound OC(=O)C1CCCCCCC1 URAXDCBRCGSGAT-UHFFFAOYSA-N 0.000 description 1
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical compound C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1