DE1643292A1 - Verbessertes Verfahren zum Nitrosieren von Hexamethylentetramin - Google Patents

Info

Publication number

DE1643292A1

DE1643292A1 DE19671643292 DE1643292A DE1643292A1 DE 1643292 A1 DE1643292 A1 DE 1643292A1 DE 19671643292 DE19671643292 DE 19671643292 DE 1643292 A DE1643292 A DE 1643292A DE 1643292 A1 DE1643292 A1 DE 1643292A1

Authority

DE

Germany

Prior art keywords

hexamethylenetetramine

air

dried

dno

nitrosating

Prior art date

1967-09-07

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.)

Pending

Links

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• VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 title claims description 20
• 239000004312 hexamethylene tetramine Substances 0.000 title claims description 10
• 235000010299 hexamethylene tetramine Nutrition 0.000 title claims description 10
• 238000000034 method Methods 0.000 title claims description 8
• 239000004094 surface-active agent Substances 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 4
• 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 claims description 3
• 239000007864 aqueous solution Substances 0.000 claims description 3
• 150000002832 nitroso derivatives Chemical class 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 239000011734 sodium Substances 0.000 claims description 3
• 238000005406 washing Methods 0.000 claims description 3
• 238000006243 chemical reaction Methods 0.000 claims description 2
• 150000001875 compounds Chemical class 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 239000007858 starting material Substances 0.000 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
• HFWOSHMLDRSIDN-UHFFFAOYSA-N 1,3,5-trinitroso-1,3,5-triazinane Chemical compound O=NN1CN(N=O)CN(N=O)C1 HFWOSHMLDRSIDN-UHFFFAOYSA-N 0.000 claims 1
• IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims 1
• 150000002170 ethers Chemical class 0.000 claims 1
• NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 claims 1
• SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims 1
• 229920000151 polyglycol Polymers 0.000 claims 1
• 239000010695 polyglycol Substances 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 3
• 238000007034 nitrosation reaction Methods 0.000 description 3
• 239000000243 solution Substances 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• -1 methyl palmitylamine Chemical compound 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 230000009935 nitrosation Effects 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 230000004580 weight loss Effects 0.000 description 2
• MJVIZWIQHKRBPI-UHFFFAOYSA-N 1-(aziridin-1-yl)but-3-en-2-ol Chemical compound C=CC(O)CN1CC1 MJVIZWIQHKRBPI-UHFFFAOYSA-N 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 239000004604 Blowing Agent Substances 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 125000000217 alkyl group Chemical group 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 230000000052 comparative effect Effects 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 230000000802 nitrating effect Effects 0.000 description 1
• GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
• 238000012797 qualification Methods 0.000 description 1
• 238000005029 sieve analysis Methods 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 238000010792 warming Methods 0.000 description 1