ES2207214T3 - Procedimiento para la fabricacion de una sulfenimida. - Google Patents
Procedimiento para la fabricacion de una sulfenimida.Info
- Publication number
- ES2207214T3 ES2207214T3 ES99921709T ES99921709T ES2207214T3 ES 2207214 T3 ES2207214 T3 ES 2207214T3 ES 99921709 T ES99921709 T ES 99921709T ES 99921709 T ES99921709 T ES 99921709T ES 2207214 T3 ES2207214 T3 ES 2207214T3
- Authority
- ES
- Spain
- Prior art keywords
- suspension
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 71
- 239000002904 solvent Substances 0.000 claims abstract description 62
- 239000000725 suspension Substances 0.000 claims abstract description 50
- 238000001914 filtration Methods 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000007900 aqueous suspension 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 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract 3
- 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 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 90
- 239000000047 product Substances 0.000 claims description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000006227 byproduct Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 5
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 claims description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 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
- 239000000126 substance Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 238000009413 insulation Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 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 3
- 239000012467 final product Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 238000003809 water extraction Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000012360 testing method Methods 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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling 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
- 238000007689 inspection Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- SDNJNDFHCODQDQ-UHFFFAOYSA-N n-(2-ethylphenyl)-2-[[2-[(2-ethylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=CC=C1CC SDNJNDFHCODQDQ-UHFFFAOYSA-N 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time 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
- 239000007921 spray Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005406 washing 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8482598P | 1998-05-08 | 1998-05-08 | |
| US84825P | 1998-05-08 | ||
| US09/292,682 US6184385B1 (en) | 1998-05-08 | 1999-04-16 | Process for the manufacture of a sulfenimide |
| US292682 | 1999-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2207214T3 true ES2207214T3 (es) | 2004-05-16 |
Family
ID=26771472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99921709T Expired - Lifetime ES2207214T3 (es) | 1998-05-08 | 1999-05-06 | Procedimiento para la fabricacion de una sulfenimida. |
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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3151122A (en) * | 1964-09-29 | Preparation of n-alkyl- and n-cyclo | ||
| NL98032C (enExample) * | 1957-04-02 | |||
| DE3137061A1 (de) * | 1981-09-17 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | N-sulfenylierte benzylsulfonamide, ein verfahren undihre verwendung als mikrobizide |
| WO1992005218A1 (en) * | 1990-09-21 | 1992-04-02 | Uniroyal Chemical Company, Inc. | Method of manufacturing a nitrosamine-free rubber article |
| DE4128682A1 (de) * | 1991-08-29 | 1993-03-04 | Bayer Ag | Verfahren zur herstellung von bis-benzthiazolyl-alkyl-sulfenimiden |
| US5204481A (en) * | 1992-06-08 | 1993-04-20 | Monsanto Company | Process for preparing benzothiazole sulfenimides using an aliphatic hydrocarbon solvent |
-
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
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 |
| CN100339370C (zh) | 2007-09-26 |
| JP2002514634A (ja) | 2002-05-21 |
| 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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