NO153101B - Fremgangsmaate til fremstilling av jodmetyltiocyanat - Google Patents
Fremgangsmaate til fremstilling av jodmetyltiocyanat Download PDFInfo
- Publication number
- NO153101B NO153101B NO821596A NO821596A NO153101B NO 153101 B NO153101 B NO 153101B NO 821596 A NO821596 A NO 821596A NO 821596 A NO821596 A NO 821596A NO 153101 B NO153101 B NO 153101B
- Authority
- NO
- Norway
- Prior art keywords
- preparation
- iodmethyltyocyanate
- procedure
- iodomethylthiocyanate
- thiocyanate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 5
- MEZLHPGTFGWNAW-UHFFFAOYSA-N iodomethyl thiocyanate Chemical compound ICSC#N MEZLHPGTFGWNAW-UHFFFAOYSA-N 0.000 claims abstract description 9
- NKZBPOBHIJVVDH-UHFFFAOYSA-N bromomethyl thiocyanate Chemical compound BrCSC#N NKZBPOBHIJVVDH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 229910001505 inorganic iodide Inorganic materials 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UXUCVNXUWOLPRU-UHFFFAOYSA-N Chloromethyl thiocyanate Chemical compound ClCSC#N UXUCVNXUWOLPRU-UHFFFAOYSA-N 0.000 abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 244000005700 microbiome Species 0.000 description 6
- 239000002023 wood Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 241000221832 Amorphotheca resinae Species 0.000 description 1
- 244000221226 Armillaria mellea Species 0.000 description 1
- 235000011569 Armillaria mellea Nutrition 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241001465318 Aspergillus terreus Species 0.000 description 1
- 241000203233 Aspergillus versicolor Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000221955 Chaetomium Species 0.000 description 1
- 241001515917 Chaetomium globosum Species 0.000 description 1
- 241001149956 Cladosporium herbarum Species 0.000 description 1
- 241001600095 Coniophora puteana Species 0.000 description 1
- 241000605739 Desulfovibrio desulfuricans Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001492300 Gloeophyllum trabeum Species 0.000 description 1
- 241000223199 Humicola grisea Species 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000222634 Lenzites Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241001504481 Monticola <Aves> Species 0.000 description 1
- 241001123663 Penicillium expansum Species 0.000 description 1
- 241001193612 Phoma violacea Species 0.000 description 1
- 241001619461 Poria <basidiomycete fungus> Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241001674251 Serpula lacrymans Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000187759 Streptomyces albus Species 0.000 description 1
- 241001136494 Talaromyces funiculosus Species 0.000 description 1
- 241000222355 Trametes versicolor Species 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/04—Thiocyanates having sulfur atoms of thiocyanate groups bound to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/48—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —S—C≡N groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
Den foreliggende oppfinnelse angår en fremgangsmåte til fremstilling av jodmetyltiocyanat, ICH^SCN. Jodmetyltiocyanat kan anvendes for bekjempelse av mikroorganismer, særlig sopper og bakterier. Fremgangsmåten ifølge oppfinnelsen er angitt i kravet, og det vises til dette.
Fra J. Munch-Petersen og G. Østrup, Organisk Kemisk Syntese, Jul. Gjellerups Forlag, København 1964, side 174 er
det kjent klor/jod-ombyttingsreaksjoner når det gjelder enkle organiske forbindelser. Ved disse forbindelser dreier det seg i det vesentlige om monofunksjonelle forbindelser, d.v.s. forbindelser som bare inneholder en halogenrest. I motsetning her-til dreier det seg ved forbindelsen klor- eller brom-metyltiocyanat om en bifunksjonell forbindelse, idet denne forbindelse inneholder både en klor- eller bromrest og en tiocyanat-rest i det samme molekyl, Den glatte omsetning av C1-CH2-SCN med Nal til ICH2-SCN er overraskende da SCN i regelen forholder seg som et halogenid slik at man ved denne omsetning skulle vente som resultat blandinger av CH^ l^, ICH2SCN og C1CH2I. Dette gjelder særlig ved høyt Nal-overskudd.
Det ble nå funnet at jodmetyltiocyanat med formelen ICH2SCN lar seg fremstille meget lett og billig ut fra brom- eller klormetyltiocyanat ved omhalogenering. Omsetter man de nevnte utgangsforbindelser med et metalljodid, fortrinnsvis natriumjodid, i et organisk løsningsmiddel, eksempelvis aceton, metyl-iso-butylketon, metyletylketon, metanol eller etanol, fortrinnsvis aceton, ved temperaturer mellom 10 og 100°C, fortrinnsvis 50-60°C, så oppnår man jodmetyltiocyanat i meget godt utbytte på 80-90 % av det teoretiske.
Eksempel 1
I 1500 ml aceton oppløses natriumjodid (ca. 420 g) til metning ved 35°C. Man tilsetter 215 g (2 mol) klormetyltiocyanat og om-rører i 8 timer ved en temperatur på 50-60°C. Etter avkjøling blir acetonet vidtgående avdestillert, hvoretter residuet opp-løses i 500 ml toluen, uoppløst natriumjodid frafiltreres, og løsningen destilleres i vakuum.
Utbytte: 338 g (85 % av teoretisk) jodmetyltiocyanat Kokepunkt: 53°C/0,3 mbar
Elementaranalyse:
Det aktive stoff egner seg særlig for beskyttelse av for-skjellige materialer mot nedbrytning eller ødeleggelse på
grunn av bakterier og sopper. Materialer som kan konserveres eller gjøres mikrocid ved hjelp av det aktive stoff, er eksempelvis lin og klebestoffer, plastdispersjoner, dispersjonsfarge-stoffer, lær, råhuder og tre. Videre er forbindelsen egnet som mikrocid aktiv tilsetning i rengjørings- og desinfeksjonsmidler og som slim-bekjempelsesmiddel i papirindustrien og ved bekjempelse av uønsket vekst av mikroorganismer ved jordolje-sekundær-utvinning.
Eksempler på mikroorganismer som kan bekjempes med det aktive stoff er: Chaetomium globosum, Chaetomium alba, Aspergillus terreus, Aspergillus niger, Aspergillus versicolor, Penicillium glaucum, Penicillium funiculosum, Trichoderma viride, Pullularia pullulans, Cladosporium herbarum, Cladosporium resinae, Humicola grisea, Glenospora graphii, Phoma violacea, Coniophora puteana, Merulius lacrymans, Poria monticola, Lenzites trabea, Lenzites abietina, Trametes versicolor, Armillaria mellea, Streptomyces albus, Staphylococcus aureus, Escherichia coli, Pseudomonas Aeruginosa, Aerobacter aerogenes, Klebsiella pneumoniae, Desulfovibrio desulfuricans og Serratia marcescens. Midlene som inneholder jodmetyltiocyanat som aktivt stoff, egner seg, generelt sagt, til beskyttelse av mange substrater mot angrep fra mikroorganismer og til bekjempelse av mikroorganismer på eller i de substrater som er angrepet av disse.
Et viktig anvendelsesområde er beskyttelse av tre, dvs. beskyttelse av tre mot angrep fra mikroorganismer. Som mulig-heter nevnes: temporær beskyttelse av frisk-felte tre, beskyttelse av trematerialet under transport eller lagring, og varig beskyttelse av trematerialer i bygninger, etc.
Jodmetyltiocyanatet kan anvendes i hvilken som helst ønsket konsentrasjon, fortrinnsvis i området 0,5 til 90 vekt%,
i et egnet bærer-materiale, i form av en sprøytbar oppløsning, emulsjon, dispersjon eller annen egnet form som letter for-delingen av det aktive stoff, innbefattet pulverform, idet
bruksformen og bærer-materialet retter seg etter anvendelses-formålet .
Claims (1)
- Fremgangsmåte til fremstilling av jodmetyltiocyanat, karakterisert ved at klor-eller brommetyl-tiocyanat omsettes med et uorganisk jodid i et organisk løs-ningsmiddel ved en temperatur på 10 - 10 0°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813119202 DE3119202A1 (de) | 1981-05-14 | 1981-05-14 | Jodmethylthiocyanat und dieses enthaltende mittel zur bekaempfung von mikroorganismen sowie verfahren zu seiner herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO821596L NO821596L (no) | 1982-11-15 |
| NO153101B true NO153101B (no) | 1985-10-07 |
| NO153101C NO153101C (no) | 1986-01-15 |
Family
ID=6132315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821596A NO153101C (no) | 1981-05-14 | 1982-05-13 | Fremgangsmaate til fremstilling av jodmetyltiocyanat |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0065190B1 (no) |
| JP (1) | JPS57193451A (no) |
| AT (1) | ATE9792T1 (no) |
| CA (1) | CA1182466A (no) |
| DE (2) | DE3119202A1 (no) |
| DK (1) | DK170400B1 (no) |
| FI (1) | FI73978C (no) |
| GR (1) | GR75915B (no) |
| IE (1) | IE52550B1 (no) |
| NO (1) | NO153101C (no) |
| ZA (1) | ZA823300B (no) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1188858B (de) * | 1963-05-04 | 1965-03-11 | Schering Ag | Schaedlingsbekaempfungsmittel |
| US3361621A (en) * | 1963-05-31 | 1968-01-02 | Stauffer Chemical Co | Method for controlling microorganisms and nematodes |
| BE679906A (no) * | 1966-04-22 | 1966-10-24 | ||
| FR1545133A (fr) * | 1966-11-21 | 1968-11-08 | American Cyanamid Co | Procédé de préparation de dérivés thiocyaniques |
-
1981
- 1981-05-14 DE DE19813119202 patent/DE3119202A1/de not_active Withdrawn
-
1982
- 1982-04-09 GR GR67877A patent/GR75915B/el unknown
- 1982-04-23 FI FI821414A patent/FI73978C/fi not_active IP Right Cessation
- 1982-04-30 CA CA000402049A patent/CA1182466A/en not_active Expired
- 1982-05-05 AT AT82103834T patent/ATE9792T1/de active
- 1982-05-05 DE DE8282103834T patent/DE3260938D1/de not_active Expired
- 1982-05-05 EP EP82103834A patent/EP0065190B1/de not_active Expired
- 1982-05-07 IE IE1099/82A patent/IE52550B1/en not_active IP Right Cessation
- 1982-05-12 JP JP57078498A patent/JPS57193451A/ja active Granted
- 1982-05-13 DK DK215882A patent/DK170400B1/da not_active IP Right Cessation
- 1982-05-13 ZA ZA823300A patent/ZA823300B/xx unknown
- 1982-05-13 NO NO821596A patent/NO153101C/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI821414A0 (fi) | 1982-04-23 |
| JPS57193451A (en) | 1982-11-27 |
| EP0065190B1 (de) | 1984-10-10 |
| FI73978B (fi) | 1987-08-31 |
| DK170400B1 (da) | 1995-08-21 |
| EP0065190A1 (de) | 1982-11-24 |
| ATE9792T1 (de) | 1984-10-15 |
| DE3119202A1 (de) | 1982-12-09 |
| JPH03381B2 (no) | 1991-01-07 |
| NO153101C (no) | 1986-01-15 |
| DE3260938D1 (en) | 1984-11-15 |
| DK215882A (da) | 1982-11-15 |
| CA1182466A (en) | 1985-02-12 |
| ZA823300B (en) | 1983-04-27 |
| GR75915B (no) | 1984-08-02 |
| IE821099L (en) | 1982-11-11 |
| IE52550B1 (en) | 1987-12-09 |
| FI821414L (fi) | 1982-11-15 |
| NO821596L (no) | 1982-11-15 |
| FI73978C (fi) | 1987-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN NOVEMBER 2001 |