JPH0465064B2 - - Google Patents

Info

Publication number

JPH0465064B2

JPH0465064B2 JP5776386A JP5776386A JPH0465064B2 JP H0465064 B2 JPH0465064 B2 JP H0465064B2 JP 5776386 A JP5776386 A JP 5776386A JP 5776386 A JP5776386 A JP 5776386A JP H0465064 B2 JPH0465064 B2 JP H0465064B2

Authority

JP

Japan

Prior art keywords

chloromethylthiocyanate

toluene

thiocyanate

reaction

onium salt

Prior art date

1986-03-16

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

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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
• UXUCVNXUWOLPRU-UHFFFAOYSA-N Chloromethyl thiocyanate Chemical compound ClCSC#N UXUCVNXUWOLPRU-UHFFFAOYSA-N 0.000 claims description 16
• JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 8
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
• -1 alkali metal salts Chemical class 0.000 claims description 5
• 150000003863 ammonium salts Chemical class 0.000 claims description 3
• 229910052783 alkali metal Inorganic materials 0.000 claims description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
• 150000004714 phosphonium salts Chemical group 0.000 claims description 2
• 238000006243 chemical reaction Methods 0.000 description 11
• 239000000047 product Substances 0.000 description 9
• 239000003960 organic solvent Substances 0.000 description 7
• 239000012071 phase Substances 0.000 description 6
• 238000000034 method Methods 0.000 description 5
• 230000002194 synthesizing effect Effects 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 238000007796 conventional method Methods 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 3
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 150000001350 alkyl halides Chemical class 0.000 description 2
• SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
• HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 230000000895 acaricidal effect Effects 0.000 description 1
• 239000000642 acaricide Substances 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 238000004891 communication Methods 0.000 description 1
• 230000000052 comparative effect Effects 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000000417 fungicide Substances 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000003444 phase transfer catalyst Substances 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 230000008707 rearrangement Effects 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 150000003613 toluenes Chemical class 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1