BE452942A - - Google Patents

Info

Publication number

BE452942A

BE452942A BE452942DA BE452942A BE 452942 A BE452942 A BE 452942A BE 452942D A BE452942D A BE 452942DA BE 452942 A BE452942 A BE 452942A

Authority

BE

Belgium

Prior art keywords

acid

thiourea

calcium

sulfuric acid

aniline

Prior art date

Links

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• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 7
• 239000000243 solution Substances 0.000 claims description 3
• 238000000354 decomposition reaction Methods 0.000 claims description 2
• 238000010790 dilution Methods 0.000 claims description 2
• 239000012895 dilution Substances 0.000 claims description 2
• 238000001816 cooling Methods 0.000 claims 1
• 238000010438 heat treatment Methods 0.000 claims 1
• 238000007738 vacuum evaporation Methods 0.000 claims 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 7
• 238000010521 absorption reaction Methods 0.000 description 6
• 239000000047 product Substances 0.000 description 5
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 3
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
• 235000011130 ammonium sulphate Nutrition 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 238000005057 refrigeration Methods 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• AGVJBLHVMNHENQ-UHFFFAOYSA-N Calcium sulfide Chemical compound [S-2].[Ca+2] AGVJBLHVMNHENQ-UHFFFAOYSA-N 0.000 description 2
• SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 2
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
• 239000007900 aqueous suspension Substances 0.000 description 2
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
• 239000005997 Calcium carbide Substances 0.000 description 1
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000001099 ammonium carbonate Substances 0.000 description 1
• 235000012501 ammonium carbonate Nutrition 0.000 description 1
• 239000001166 ammonium sulphate Substances 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 description 1
• 239000001175 calcium sulphate Substances 0.000 description 1
• 235000011132 calcium sulphate Nutrition 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 239000012295 chemical reaction liquid Substances 0.000 description 1
• 238000006482 condensation reaction Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000001627 detrimental effect Effects 0.000 description 1
• QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000011049 filling Methods 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• NTOLGSSKLPLTDW-UHFFFAOYSA-N hydrogen sulfate;phenylazanium Chemical compound OS(O)(=O)=O.NC1=CC=CC=C1 NTOLGSSKLPLTDW-UHFFFAOYSA-N 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 238000006317 isomerization reaction Methods 0.000 description 1
• 238000013021 overheating Methods 0.000 description 1
• 231100000614 poison Toxicity 0.000 description 1
• 230000007096 poisonous effect Effects 0.000 description 1
• 150000004763 sulfides Chemical class 0.000 description 1
• CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical group CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
• 230000008719 thickening Effects 0.000 description 1