JP2002514634A - スルフェンイミドの製造方法 - Google Patents
スルフェンイミドの製造方法Info
- Publication number
- JP2002514634A JP2002514634A JP2000548320A JP2000548320A JP2002514634A JP 2002514634 A JP2002514634 A JP 2002514634A JP 2000548320 A JP2000548320 A JP 2000548320A JP 2000548320 A JP2000548320 A JP 2000548320A JP 2002514634 A JP2002514634 A JP 2002514634A
- Authority
- JP
- Japan
- Prior art keywords
- slurry
- water
- solvent
- product
- heptane
- Prior art date
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 239000002002 slurry Substances 0.000 claims abstract description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000002904 solvent Substances 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 59
- 239000002253 acid Substances 0.000 claims abstract description 28
- 238000001914 filtration Methods 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 18
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims abstract description 17
- 230000008569 process Effects 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 86
- 239000000047 product Substances 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 238000004821 distillation Methods 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 239000012071 phase Substances 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000003863 ammonium salts Chemical class 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 abstract description 3
- 238000007796 conventional method Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- VILGDADBAQFRJE-UHFFFAOYSA-N n,n-bis(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SN(SC=3SC4=CC=CC=C4N=3)C(C)(C)C)=NC2=C1 VILGDADBAQFRJE-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000003809 water extraction Methods 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DZVVLBSDPBGJEM-UHFFFAOYSA-N heptane;hydrate Chemical compound O.CCCCCCC DZVVLBSDPBGJEM-UHFFFAOYSA-N 0.000 description 1
- DLDIDQIZPBIVNQ-UHFFFAOYSA-N hydron;2-methylpropan-2-amine;chloride Chemical compound Cl.CC(C)(C)N DLDIDQIZPBIVNQ-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- -1 t- butyl Chemical group 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8482598P | 1998-05-08 | 1998-05-08 | |
| US60/084,825 | 1998-05-08 | ||
| US09/292,682 | 1999-04-16 | ||
| US09/292,682 US6184385B1 (en) | 1998-05-08 | 1999-04-16 | Process for the manufacture of a sulfenimide |
| PCT/US1999/009876 WO1999058516A1 (en) | 1998-05-08 | 1999-05-06 | Process for the manufacture of a sulfenimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002514634A true JP2002514634A (ja) | 2002-05-21 |
| JP2002514634A5 JP2002514634A5 (enExample) | 2006-06-15 |
Family
ID=26771472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000548320A Pending JP2002514634A (ja) | 1998-05-08 | 1999-05-06 | スルフェンイミドの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6184385B1 (enExample) |
| EP (1) | EP1077961B1 (enExample) |
| JP (1) | JP2002514634A (enExample) |
| KR (1) | KR100582334B1 (enExample) |
| CN (1) | CN100339370C (enExample) |
| AU (1) | AU3884599A (enExample) |
| BR (1) | BR9910304B1 (enExample) |
| CA (1) | CA2331969C (enExample) |
| DE (1) | DE69911004T2 (enExample) |
| ES (1) | ES2207214T3 (enExample) |
| WO (1) | WO1999058516A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101735170B (zh) * | 2008-11-06 | 2012-10-31 | 南化集团研究院 | N-叔丁基双次磺酰亚胺的制备方法 |
| CN106432000A (zh) * | 2016-09-21 | 2017-02-22 | 南开大学 | 由硫醚合成亚磺酰亚胺类化合物的方法 |
| CN106892825A (zh) * | 2017-03-09 | 2017-06-27 | 河北明翔新材料科技有限公司 | 一种回收tbsi生产中副产物的方法 |
| WO2024141927A1 (en) * | 2022-12-28 | 2024-07-04 | Nitrex Chemicals India Limited | A process for the preparation of n, n-disubstituted benzothiazole-2-sulfenamides |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2860142A (en) * | 1957-04-02 | 1958-11-11 | Us Rubber Co | Manufacture of sulfenamides |
| US3151122A (en) * | 1964-09-29 | Preparation of n-alkyl- and n-cyclo | ||
| JPS5862155A (ja) * | 1981-09-17 | 1983-04-13 | バイエル・アクチエンゲゼルシヤフト | Ｎ―スルフエニル化されたベンジルスルホンアミド、その製造法及びそれを用いた殺菌・殺カビ・殺藻または殺粘菌剤 |
| WO1992005218A1 (en) * | 1990-09-21 | 1992-04-02 | Uniroyal Chemical Company, Inc. | Method of manufacturing a nitrosamine-free rubber article |
| JPH05194446A (ja) * | 1991-08-29 | 1993-08-03 | Bayer Ag | ビス−ベンズチアゾリルアルキルスルフエンイミドの製造方法 |
| JPH069587A (ja) * | 1992-06-08 | 1994-01-18 | Monsanto Co | スルフェンイミドの製造方法 |
-
1999
- 1999-04-16 US US09/292,682 patent/US6184385B1/en not_active Expired - Lifetime
- 1999-05-06 AU AU38845/99A patent/AU3884599A/en not_active Abandoned
- 1999-05-06 WO PCT/US1999/009876 patent/WO1999058516A1/en not_active Ceased
- 1999-05-06 DE DE69911004T patent/DE69911004T2/de not_active Expired - Fee Related
- 1999-05-06 KR KR1020007012408A patent/KR100582334B1/ko not_active Expired - Fee Related
- 1999-05-06 CN CNB998071684A patent/CN100339370C/zh not_active Expired - Fee Related
- 1999-05-06 ES ES99921709T patent/ES2207214T3/es not_active Expired - Lifetime
- 1999-05-06 BR BRPI9910304-4A patent/BR9910304B1/pt not_active IP Right Cessation
- 1999-05-06 EP EP99921709A patent/EP1077961B1/en not_active Expired - Lifetime
- 1999-05-06 JP JP2000548320A patent/JP2002514634A/ja active Pending
- 1999-05-06 CA CA002331969A patent/CA2331969C/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3151122A (en) * | 1964-09-29 | Preparation of n-alkyl- and n-cyclo | ||
| US2860142A (en) * | 1957-04-02 | 1958-11-11 | Us Rubber Co | Manufacture of sulfenamides |
| JPS5862155A (ja) * | 1981-09-17 | 1983-04-13 | バイエル・アクチエンゲゼルシヤフト | Ｎ―スルフエニル化されたベンジルスルホンアミド、その製造法及びそれを用いた殺菌・殺カビ・殺藻または殺粘菌剤 |
| WO1992005218A1 (en) * | 1990-09-21 | 1992-04-02 | Uniroyal Chemical Company, Inc. | Method of manufacturing a nitrosamine-free rubber article |
| JPH05194446A (ja) * | 1991-08-29 | 1993-08-03 | Bayer Ag | ビス−ベンズチアゾリルアルキルスルフエンイミドの製造方法 |
| JPH069587A (ja) * | 1992-06-08 | 1994-01-18 | Monsanto Co | スルフェンイミドの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999058516A1 (en) | 1999-11-18 |
| CA2331969A1 (en) | 1999-11-18 |
| US6184385B1 (en) | 2001-02-06 |
| CN1305468A (zh) | 2001-07-25 |
| EP1077961B1 (en) | 2003-09-03 |
| AU3884599A (en) | 1999-11-29 |
| CA2331969C (en) | 2009-12-08 |
| EP1077961A1 (en) | 2001-02-28 |
| KR20010034846A (ko) | 2001-04-25 |
| ES2207214T3 (es) | 2004-05-16 |
| CN100339370C (zh) | 2007-09-26 |
| DE69911004T2 (de) | 2004-06-03 |
| BR9910304A (pt) | 2001-01-09 |
| BR9910304B1 (pt) | 2010-07-13 |
| KR100582334B1 (ko) | 2006-05-23 |
| DE69911004D1 (de) | 2003-10-09 |
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