DD142879A5 - Verfahren zur herstellung von 2-mercaptobenzthiazol - Google Patents

Verfahren zur herstellung von 2-mercaptobenzthiazol Download PDF

Info

Publication number: DD142879A5
Authority: DD; German Democratic Republic
Prior art keywords: reaction; nitrobenzene; hydrogen sulfide; temperatures; carbon disulfide
Prior art date: 1978-04-15

Application number

DD79212194A

Other languages

German (de)

English (en)

Inventor

Manfred Bergfeld

Hans-Georg Zengel

Heinz Praetorius

Original Assignee

Akzo Nv

Priority date (The priority date 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 date listed.)

1978-04-15

Filing date

1979-04-12

Publication date

1980-07-16

1978-04-15 Priority claimed from DE19782816503 external-priority patent/DE2816503C3/de

1978-04-15 Priority claimed from DE2816407A external-priority patent/DE2816407C3/de

1979-04-12 Application filed by Akzo Nv filed Critical Akzo Nv

1980-07-16 Publication of DD142879A5 publication Critical patent/DD142879A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 57
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 title claims description 96
238000002360 preparation method Methods 0.000 title claims description 11
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 111
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 90
238000006243 chemical reaction Methods 0.000 claims abstract description 88
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 44
229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 36
NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 claims abstract description 35
XDAHMMVFVQFOIY-UHFFFAOYSA-N methanedithione;sulfane Chemical compound S.S=C=S XDAHMMVFVQFOIY-UHFFFAOYSA-N 0.000 claims abstract description 17
239000000376 reactant Substances 0.000 claims abstract description 7
239000011541 reaction mixture Substances 0.000 claims description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
150000003738 xylenes Chemical class 0.000 claims description 3
230000035484 reaction time Effects 0.000 abstract description 13
150000001875 compounds Chemical class 0.000 abstract description 5
239000003054 catalyst Substances 0.000 abstract description 4
238000004073 vulcanization Methods 0.000 abstract description 2
229940054266 2-mercaptobenzothiazole Drugs 0.000 description 41
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 36
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 15
229910052717 sulfur Inorganic materials 0.000 description 14
239000011593 sulfur Substances 0.000 description 14
238000007363 ring formation reaction Methods 0.000 description 13
239000000047 product Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 6
239000007789 gas Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
239000007858 starting material Substances 0.000 description 4
230000007306 turnover Effects 0.000 description 4
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
-1 aliphatic alcohols Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000000155 melt Substances 0.000 description 3
QDTDFSFRIDFTCF-UHFFFAOYSA-N n-phenyl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC1=CC=CC=C1 QDTDFSFRIDFTCF-UHFFFAOYSA-N 0.000 description 3
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
238000001632 acidimetric titration Methods 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
238000001461 argentometric titration Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229910017464 nitrogen compound Inorganic materials 0.000 description 2
150000002830 nitrogen compounds Chemical class 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
231100000989 no adverse effect Toxicity 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000006276 transfer reaction Methods 0.000 description 2
239000002699 waste material Substances 0.000 description 2
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-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
230000010777 Disulfide Reduction Effects 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
CTRSTUUBBQTFST-UHFFFAOYSA-N [S].NC1=CC=CC=C1 Chemical compound [S].NC1=CC=CC=C1 CTRSTUUBBQTFST-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
NLRKCXQQSUWLCH-IDEBNGHGSA-N nitrosobenzene Chemical group O=N[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 NLRKCXQQSUWLCH-IDEBNGHGSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000009790 rate-determining step (RDS) Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000010626 work up procedure 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
- C07D277/72—2-Mercaptobenzothiazole

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)

DD79212194A 1978-04-15 1979-04-12 Verfahren zur herstellung von 2-mercaptobenzthiazol DD142879A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19782816503 DE2816503C3 (de)	1978-04-15	1978-04-15	Verfahren zur Herstellung von 2-Mercaptobenzthiazol
DE2816407A DE2816407C3 (de)	1978-04-15	1978-04-15	Verfahren zur Herstellung von 2-Mercaptobenzthiazol

Publications (1)

Publication Number	Publication Date
DD142879A5 true DD142879A5 (de)	1980-07-16

Family

ID=25774251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79212194A DD142879A5 (de)	1978-04-15	1979-04-12	Verfahren zur herstellung von 2-mercaptobenzthiazol

Country Status (13)

Country	Link
JP (1)	JPS54138555A (fr)
BR (1)	BR7902252A (fr)
CS (1)	CS209920B2 (fr)
DD (1)	DD142879A5 (fr)
ES (1)	ES479380A1 (fr)
FR (1)	FR2432514A1 (fr)
GB (1)	GB2018774B (fr)
HU (1)	HU179918B (fr)
IT (1)	IT1117172B (fr)
NL (1)	NL7902705A (fr)
PL (1)	PL119658B1 (fr)
RO (1)	RO77250A (fr)
SU (1)	SU1005661A3 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997046544A1 (fr) *	1996-06-03	1997-12-11	Akzo Nobel N.V.	Procede a catalyse acide, destine a la preparation de 2-mercaptobenzothiazole et de derives de celui-ci
US6222041B1 (en) *	2000-02-24	2001-04-24	Uniroyal Chemical Company, Inc.	Method for the production of 2-mercaptobenzothiazole

1979
- 1979-04-06 NL NL7902705A patent/NL7902705A/xx not_active Application Discontinuation
- 1979-04-06 ES ES479380A patent/ES479380A1/es not_active Expired
- 1979-04-11 BR BR7902252A patent/BR7902252A/pt unknown
- 1979-04-11 CS CS792479A patent/CS209920B2/cs unknown
- 1979-04-11 IT IT48697/79A patent/IT1117172B/it active
- 1979-04-11 PL PL1979214829A patent/PL119658B1/pl unknown
- 1979-04-12 DD DD79212194A patent/DD142879A5/de unknown
- 1979-04-12 GB GB7913139A patent/GB2018774B/en not_active Expired
- 1979-04-12 FR FR7909358A patent/FR2432514A1/fr active Granted
- 1979-04-13 SU SU792753405A patent/SU1005661A3/ru active
- 1979-04-13 HU HU79AO478A patent/HU179918B/hu unknown
- 1979-04-13 RO RO7997222A patent/RO77250A/fr unknown
- 1979-04-13 JP JP4441279A patent/JPS54138555A/ja active Pending

Also Published As

Publication number	Publication date
IT1117172B (it)	1986-02-17
BR7902252A (pt)	1979-12-04
GB2018774B (en)	1982-12-01
FR2432514B1 (fr)	1983-07-29
PL214829A1 (fr)	1980-01-14
SU1005661A3 (ru)	1983-03-15
IT7948697A0 (it)	1979-04-11
HU179918B (en)	1983-01-28
CS209920B2 (en)	1981-12-31
PL119658B1 (en)	1982-01-30
JPS54138555A (en)	1979-10-27
NL7902705A (nl)	1979-10-17
ES479380A1 (es)	1979-07-16
GB2018774A (en)	1979-10-24
RO77250A (fr)	1981-08-17
FR2432514A1 (fr)	1980-02-29

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