SK72294A3 - Method of desulfurizating of organic mercapto-compounds and/or disulfidic compounds - Google Patents

Method of desulfurizating of organic mercapto-compounds and/or disulfidic compounds Download PDF

Info

Publication number: SK72294A3
Authority: SK; Slovakia
Prior art keywords: compounds; zinc; organic; nickel; mercapto
Prior art date: 1993-06-14

Application number

SK722-94A

Other languages

English (en)

Slovak (sk)

Inventor

Ferdinand Hagedorn

Helmut Fiege

Hans-Joachim Traenckner

Original Assignee

Bayer Ag

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.)

1993-06-14

Filing date

1994-06-13

Publication date

1995-02-08

1994-06-13 Application filed by Bayer Ag filed Critical Bayer Ag

1995-02-08 Publication of SK72294A3 publication Critical patent/SK72294A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract 4
238000000034 method Methods 0.000 title claims description 37
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 53
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 36
229910052742 iron Inorganic materials 0.000 claims abstract description 25
-1 mercapto compounds Chemical class 0.000 claims abstract description 24
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 18
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 17
229910052782 aluminium Inorganic materials 0.000 claims abstract description 17
229910017052 cobalt Inorganic materials 0.000 claims abstract description 17
239000010941 cobalt Substances 0.000 claims abstract description 17
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 17
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052725 zinc Inorganic materials 0.000 claims abstract description 16
239000011701 zinc Substances 0.000 claims abstract description 16
229910052759 nickel Inorganic materials 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 11
230000003197 catalytic effect Effects 0.000 claims abstract description 6
239000003960 organic solvent Substances 0.000 claims abstract description 6
150000002894 organic compounds Chemical class 0.000 claims abstract description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
150000002019 disulfides Chemical class 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
230000001590 oxidative effect Effects 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002228 disulfide group Chemical group 0.000 claims description 3
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims 1
150000007524 organic acids Chemical class 0.000 claims 1
235000005985 organic acids Nutrition 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 abstract 2
230000007017 scission Effects 0.000 abstract 2
239000005864 Sulphur Substances 0.000 abstract 1
239000004411 aluminium Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 18
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
229910000564 Raney nickel Inorganic materials 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
229940054266 2-mercaptobenzothiazole Drugs 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 5
238000009835 boiling Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
150000001556 benzimidazoles Chemical class 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
235000019441 ethanol Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000006477 desulfuration reaction Methods 0.000 description 2
230000023556 desulfurization Effects 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
238000005406 washing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
VAVFJHFIZXVICW-UHFFFAOYSA-N S=[Co](=S)=S Chemical compound S=[Co](=S)=S VAVFJHFIZXVICW-UHFFFAOYSA-N 0.000 description 1
QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical compound [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
DZRJLJPPUJADOO-UHFFFAOYSA-N chaetomin Natural products CN1C(=O)C2(Cc3cn(C)c4ccccc34)SSC1(CO)C(=O)N2C56CC78SSC(CO)(N(C)C7=O)C(=O)N8C5Nc9ccccc69 DZRJLJPPUJADOO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
UGKDIUIOSMUOAW-UHFFFAOYSA-N iron nickel Chemical compound [Fe].[Ni] UGKDIUIOSMUOAW-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical class [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods

Landscapes

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

SK722-94A 1993-06-14 1994-06-13 Method of desulfurizating of organic mercapto-compounds and/or disulfidic compounds SK72294A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4319574A DE4319574A1 (de)	1993-06-14	1993-06-14	Verfahren zur Entschwefelung organischer Mercapto- und/oder Disulfid-Verbindungen

Publications (1)

Publication Number	Publication Date
SK72294A3 true SK72294A3 (en)	1995-02-08

Family

ID=6490248

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK722-94A SK72294A3 (en)	1993-06-14	1994-06-13	Method of desulfurizating of organic mercapto-compounds and/or disulfidic compounds

Country Status (6)

Country	Link
US (1)	US5463068A (ja)
EP (1)	EP0629618A1 (ja)
JP (1)	JPH0797376A (ja)
KR (1)	KR950000682A (ja)
DE (1)	DE4319574A1 (ja)
SK (1)	SK72294A3 (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20040063576A1 (en) *	2002-09-30	2004-04-01	Sud-Chemie Inc.	Catalyst adsorbent for removal of sulfur compounds for fuel cells
JP5244604B2 (ja) *	2006-10-13	2013-07-24	あすか製薬株式会社	ベンゾチアゾール化合物の製造方法
CN106380432B (zh) *	2016-08-23	2018-06-01	山东阳谷华泰化工股份有限公司	一种由促进剂m制备二苯氨基二硫化物的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2402642A (en) *	1942-09-24	1946-06-25	Du Pont	Chemical processes
US2610190A (en) *	1949-03-12	1952-09-09	American Cyanamid Co	Preparation of benzothiazole through pyrolysis
US4977174A (en) *	1989-06-12	1990-12-11	E. R. Squibb & Sons, Inc.	7-oxabicycloheptane imidazole prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease

1993
- 1993-06-14 DE DE4319574A patent/DE4319574A1/de not_active Withdrawn
1994
- 1994-06-01 EP EP94108444A patent/EP0629618A1/de not_active Withdrawn
- 1994-06-07 US US08/255,024 patent/US5463068A/en not_active Expired - Fee Related
- 1994-06-09 JP JP6150633A patent/JPH0797376A/ja active Pending
- 1994-06-13 SK SK722-94A patent/SK72294A3/sk unknown
- 1994-06-13 KR KR1019940013217A patent/KR950000682A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
JPH0797376A (ja)	1995-04-11
DE4319574A1 (de)	1994-12-15
EP0629618A1 (de)	1994-12-21
KR950000682A (ko)	1995-01-03
US5463068A (en)	1995-10-31

Publication	Publication Date	Title
KR102300703B1 (ko)	2021-09-09	무용매(Solvent-free) 알칸 설폰화
EP0108149B1 (en)	1986-04-09	Process for preparing dialkyl trisulfides
CA1230880A (en)	1987-12-29	Process for the production of thiazolyl-2- sulphenamides
US11718524B2 (en)	2023-08-08	Method for manufacturing sulfur tetrafluoride
JP4812840B2 (ja)	2011-11-09	硫化ジアルキルジチオカルバミン酸モリブデンの調製方法
WO2015082519A1 (fr)	2015-06-11	Procede de preparation d'un compose fluore et soufre et de ses sels en milieu aqueux
FR2499984A1 (fr)	1982-08-20	Procede pour la preparation de disulfures de thiurame
SK72294A3 (en)	1995-02-08	Method of desulfurizating of organic mercapto-compounds and/or disulfidic compounds
CN1240433A (zh)	2000-01-05	N－取代3－羟基吡唑类的制备方法
JP3223586B2 (ja)	2001-10-29	２，５−ビス（メルカプトメチル）−１，４−ジチアンの製造法
EP2024330B1 (en)	2012-04-25	Production method of heterocyclic mercapto compound
CA1173461A (en)	1984-08-28	Process for producing 2-mercaptoethylamine hydrohalides
AU674558B2 (en)	1997-01-02	Catalytic oxidation process
EP0700901B1 (en)	2000-06-28	Processes for producing thioaryl compound
EP0002148B1 (fr)	1980-12-10	Compositions à base d'aminoalcoxyamines et procédés pour leur préparation
EP1978008B1 (en)	2011-07-20	Method for producing halogen-substituted benzenedimethanol
JPS5850233B2 (ja)	1983-11-09	含モリプデン化合物の製造方法
JP4640997B2 (ja)	2011-03-02	還元型グルタチオンの製造法
US2402641A (en)	1946-06-25	Production of aryl thiols
CA2310985C (en)	2008-08-12	Process for manufacture of n-alkoxy (or aryloxy)carbonyl isothiocyanate derivatives in the presence of n,n-dialkylarylamine catalyst and aqueous solvent
CA2135792A1 (en)	1993-11-25	Process for preparation of aromatic thiols
JPH0369514A (ja)	1991-03-25	固体モリブデン化合物の回収方法
JP4640996B2 (ja)	2011-03-02	還元型グルタチオンの製造方法
CN120020125A (zh)	2025-05-20	一种含联苯硫醚化合物的制备方法
US2176593A (en)	1939-10-17	Manufacture of mercapto-aryl