IL97166A - Process for the preparation of 2-methyl-isothiazolin-3-one compounds - Google Patents
Process for the preparation of 2-methyl-isothiazolin-3-one compoundsInfo
- Publication number
- IL97166A IL97166A IL9716691A IL9716691A IL97166A IL 97166 A IL97166 A IL 97166A IL 9716691 A IL9716691 A IL 9716691A IL 9716691 A IL9716691 A IL 9716691A IL 97166 A IL97166 A IL 97166A
- Authority
- IL
- Israel
- Prior art keywords
- mit
- solvent
- process according
- reactor
- mmpa
- Prior art date
Links
- PUSPAPGHKSLKKH-UHFFFAOYSA-N 2-methyl-1,2-thiazolidin-3-one Chemical class CN1SCCC1=O PUSPAPGHKSLKKH-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 46
- 238000002360 preparation method Methods 0.000 title claims description 8
- VYQTZFNKSHBQKY-UHFFFAOYSA-N n-methyl-3-sulfanylpropanamide Chemical compound CNC(=O)CCS VYQTZFNKSHBQKY-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000002904 solvent Substances 0.000 claims abstract description 57
- 239000000203 mixture Substances 0.000 claims abstract description 49
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000460 chlorine Substances 0.000 claims abstract description 18
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 9
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims abstract description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 34
- 239000007787 solid Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 24
- 238000001914 filtration Methods 0.000 claims description 16
- 238000007872 degassing Methods 0.000 claims description 15
- 239000006227 byproduct Substances 0.000 claims description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 8
- 230000008929 regeneration Effects 0.000 claims description 7
- 238000011069 regeneration method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002250 absorbent Substances 0.000 claims description 2
- 230000002745 absorbent Effects 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims 2
- 230000001172 regenerating effect Effects 0.000 claims 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 239000012065 filter cake Substances 0.000 claims 1
- 239000012066 reaction slurry Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000002441 X-ray diffraction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 150000003840 hydrochlorides Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000011324 bead Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000004816 dichlorobenzenes Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical class ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical class C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 2
- -1 2-methylisothiazolin-3-one-HCl salt Chemical compound 0.000 description 2
- UZWXYEHTFDWCIS-UHFFFAOYSA-N 3-chloro-n-methylpropanamide Chemical compound CNC(=O)CCCl UZWXYEHTFDWCIS-UHFFFAOYSA-N 0.000 description 2
- VQXMSONJQUSLMG-UHFFFAOYSA-N 4,5-dichloro-2-methyl-1,2-thiazolidin-3-one Chemical compound CN1SC(Cl)C(Cl)C1=O VQXMSONJQUSLMG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical class O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FKPCCLRWSGMEJU-UHFFFAOYSA-N 1,2-thiazole 1-oxide;hydrochloride Chemical class Cl.O=S1C=CC=N1 FKPCCLRWSGMEJU-UHFFFAOYSA-N 0.000 description 1
- UEFCKYIRXORTFI-UHFFFAOYSA-N 1,2-thiazolidin-3-one Chemical compound O=C1CCSN1 UEFCKYIRXORTFI-UHFFFAOYSA-N 0.000 description 1
- QTPKDDZMDOCKAR-UHFFFAOYSA-N 2,2-dichloropropanamide Chemical compound CC(Cl)(Cl)C(N)=O QTPKDDZMDOCKAR-UHFFFAOYSA-N 0.000 description 1
- PDGOVYBTZIEWRC-UHFFFAOYSA-N 4,4,5,5-tetrachloro-2-methyl-1,2-thiazolidin-3-one Chemical compound CN1SC(Cl)(Cl)C(Cl)(Cl)C1=O PDGOVYBTZIEWRC-UHFFFAOYSA-N 0.000 description 1
- UPJVNXWFKBZLBE-UHFFFAOYSA-N 4,4,5-trichloro-2-methyl-1,2-thiazolidin-3-one Chemical compound CN1SC(Cl)C(Cl)(Cl)C1=O UPJVNXWFKBZLBE-UHFFFAOYSA-N 0.000 description 1
- MZIVASQDXSXHHV-UHFFFAOYSA-N 4,5-dichloro-2-methyl-1-oxo-1,2-thiazolidin-3-one Chemical compound CN1C(=O)C(Cl)C(Cl)S1=O MZIVASQDXSXHHV-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OEZPGUJTMPURAE-UHFFFAOYSA-N Cl.CN1SC(Cl)CC1=O Chemical compound Cl.CN1SC(Cl)CC1=O OEZPGUJTMPURAE-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 206010070835 Skin sensitisation Diseases 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 231100000370 skin sensitisation Toxicity 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL9716691A IL97166A (en) | 1991-02-06 | 1991-02-06 | Process for the preparation of 2-methyl-isothiazolin-3-one compounds |
| AT92101738T ATE197046T1 (de) | 1991-02-06 | 1992-02-03 | Verfahren zur herstellung von isothiazolonderivaten |
| DE69231506T DE69231506T2 (de) | 1991-02-06 | 1992-02-03 | Verfahren zur Herstellung von Isothiazolonderivaten |
| ES92101738T ES2152924T3 (es) | 1991-02-06 | 1992-02-03 | Procedimiento para la preparacion de compuestos de isotiazolona. |
| EP92101738A EP0498347B1 (de) | 1991-02-06 | 1992-02-03 | Verfahren zur Herstellung von Isothiazolonderivaten |
| US07/831,465 US5315008A (en) | 1991-02-06 | 1992-02-05 | Process for the preparation of isothiazolone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL9716691A IL97166A (en) | 1991-02-06 | 1991-02-06 | Process for the preparation of 2-methyl-isothiazolin-3-one compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL97166A0 IL97166A0 (en) | 1992-05-25 |
| IL97166A true IL97166A (en) | 1995-10-31 |
Family
ID=11062082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9716691A IL97166A (en) | 1991-02-06 | 1991-02-06 | Process for the preparation of 2-methyl-isothiazolin-3-one compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5315008A (de) |
| EP (1) | EP0498347B1 (de) |
| AT (1) | ATE197046T1 (de) |
| DE (1) | DE69231506T2 (de) |
| ES (1) | ES2152924T3 (de) |
| IL (1) | IL97166A (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100212963B1 (ko) * | 1995-12-21 | 1999-08-02 | 조민호 | 안정화된 이소티아졸론 조성물과 이소티아졸론 혼합물의 제조방법 |
| JP3732061B2 (ja) * | 1999-12-27 | 2006-01-05 | 株式会社ケミクレア | ２−アルキル−４−イソチアゾリン−３−オン類の製造方法 |
| KR100450692B1 (ko) * | 2002-04-03 | 2004-10-01 | (주)대지화학 | 이소티아졸론 조성물의 제조방법 |
| KR101004368B1 (ko) | 2003-07-29 | 2010-12-27 | 에스케이케미칼주식회사 | Ｎ,ｎ'-디치환-3,3'-디티오디프로피온아미드 제조방법 및그를 이용한 치환된 3-이소티아졸론 제조방법 |
| US7893273B2 (en) * | 2006-04-03 | 2011-02-22 | Beijing Tianqing Chemicals Co. Ltd. | Preparation of N-substituted isothiazolinone derivatives |
| CN101417966A (zh) * | 2007-10-25 | 2009-04-29 | 北京天擎化工有限责任公司 | 3-异噻唑啉酮衍生物的连续式生产方法 |
| JP5581312B2 (ja) * | 2009-03-31 | 2014-08-27 | ナガセケムテックス株式会社 | 殺微生物剤 |
| CN103880773A (zh) * | 2012-12-23 | 2014-06-25 | 北京合创同盛科技有限公司 | 一种异噻唑啉酮衍生物的生产方法 |
| CN104961705B (zh) * | 2015-07-02 | 2017-05-24 | 大连百傲化学股份有限公司 | 一锅法合成4,5‑二氯‑2‑甲基异噻唑啉酮的工艺 |
| CN113651769B (zh) * | 2021-08-31 | 2023-07-28 | 陕西中杰科仪化学科技有限公司 | 2-甲基-4-异噻唑啉-3-酮的连续化生产方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3523121A (en) | 1967-03-09 | 1970-08-04 | Rohm & Haas | Certain 2-carbamoyl-3-isothiazolenes |
| US3849430A (en) | 1967-03-09 | 1974-11-19 | Rohm & Haas | Process for the preparation of 3-isothiazolones and 3-hydroxyisothiazoles |
| CA1189514A (en) | 1982-06-01 | 1985-06-25 | Horst O. Bayer | Nitrosamine-free 3-isothiazolones and process |
| IL87111A (en) | 1987-07-23 | 1994-02-27 | Bromine Compounds Ltd | Method for stabilizing compositions of isothiazolinones |
| US5028620A (en) | 1988-09-15 | 1991-07-02 | Rohm And Haas Company | Biocide composition |
| US5008395A (en) | 1988-12-22 | 1991-04-16 | Rohm And Haas Company | Purification of isothiazolones |
-
1991
- 1991-02-06 IL IL9716691A patent/IL97166A/en not_active IP Right Cessation
-
1992
- 1992-02-03 EP EP92101738A patent/EP0498347B1/de not_active Expired - Lifetime
- 1992-02-03 DE DE69231506T patent/DE69231506T2/de not_active Expired - Fee Related
- 1992-02-03 AT AT92101738T patent/ATE197046T1/de not_active IP Right Cessation
- 1992-02-03 ES ES92101738T patent/ES2152924T3/es not_active Expired - Lifetime
- 1992-02-05 US US07/831,465 patent/US5315008A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2152924T3 (es) | 2001-02-16 |
| EP0498347B1 (de) | 2000-10-18 |
| EP0498347A1 (de) | 1992-08-12 |
| DE69231506T2 (de) | 2001-06-07 |
| IL97166A0 (en) | 1992-05-25 |
| US5315008A (en) | 1994-05-24 |
| DE69231506D1 (de) | 2000-11-23 |
| ATE197046T1 (de) | 2000-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |