JPS6215071B2 - - Google Patents

Info

Publication number: JPS6215071B2
Authority: JP; Japan
Prior art keywords: sulfuric acid; organic solvent; parts; acid; water
Prior art date: 1981-09-09
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

Application number

JP56142673A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5843947A (ja

Inventor

Akira Takeshita

Makoto Hatsutori

Akihiro Taguma

Tetsuya Myamoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sumitomo Chemical Co Ltd

Original Assignee

Sumitomo Chemical Co Ltd

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.)

1981-09-09

Filing date

1981-09-09

Publication date

1987-04-06

1981-09-09 Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd

1981-09-09 Priority to JP14267381A priority Critical patent/JPS5843947A/ja

1983-03-14 Publication of JPS5843947A publication Critical patent/JPS5843947A/ja

1987-04-06 Publication of JPS6215071B2 publication Critical patent/JPS6215071B2/ja

Status Granted legal-status Critical Current

Links

QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 99
239000003960 organic solvent Substances 0.000 claims description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
238000005893 bromination reaction Methods 0.000 claims description 15
PZSHANOBYYVNEX-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(S(O)(=O)=O)=C2N PZSHANOBYYVNEX-UHFFFAOYSA-N 0.000 claims description 14
239000011541 reaction mixture Substances 0.000 claims description 13
230000031709 bromination Effects 0.000 claims description 11
QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 claims description 9
230000005484 gravity Effects 0.000 claims description 8
KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
239000012535 impurity Substances 0.000 claims description 3
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 33
238000000034 method Methods 0.000 description 25
239000006227 byproduct Substances 0.000 description 22
239000002253 acid Substances 0.000 description 17
239000000203 mixture Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
-1 alkali metal salts Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
238000000926 separation method Methods 0.000 description 5
230000007423 decrease Effects 0.000 description 4
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910017053 inorganic salt Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
238000005192 partition Methods 0.000 description 2
238000005185 salting out Methods 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000006277 sulfonation reaction Methods 0.000 description 2
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
JOVRIPGYHSRFFR-UHFFFAOYSA-N 1-amino-4-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2N JOVRIPGYHSRFFR-UHFFFAOYSA-N 0.000 description 1
YPHVAUHAOHVMND-UHFFFAOYSA-N 1-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 YPHVAUHAOHVMND-UHFFFAOYSA-N 0.000 description 1
CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000001000 anthraquinone dye Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP14267381A 1981-09-09 1981-09-09 １−アミノ−４−ブロムアントラキノン−２−スルホン酸の製造方法 Granted JPS5843947A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP14267381A JPS5843947A (ja)	1981-09-09	1981-09-09	１−アミノ−４−ブロムアントラキノン−２−スルホン酸の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP14267381A JPS5843947A (ja)	1981-09-09	1981-09-09	１−アミノ−４−ブロムアントラキノン−２−スルホン酸の製造方法

Publications (2)

Publication Number	Publication Date
JPS5843947A JPS5843947A (ja)	1983-03-14
JPS6215071B2 true JPS6215071B2 (de)	1987-04-06

Family

ID=15320840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14267381A Granted JPS5843947A (ja)	1981-09-09	1981-09-09	１−アミノ−４−ブロムアントラキノン−２−スルホン酸の製造方法

Country Status (1)

Country	Link
JP (1)	JPS5843947A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105330573A (zh) *	2015-11-19	2016-02-17	江南大学	一种异丙苯磺酸钠溶液及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5530510A (en) *	1978-08-21	1980-03-04	Iritsuchi Gorukofu Peetoru	Planetary crank gear device

1981
- 1981-09-09 JP JP14267381A patent/JPS5843947A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5530510A (en) *	1978-08-21	1980-03-04	Iritsuchi Gorukofu Peetoru	Planetary crank gear device

Also Published As

Publication number	Publication date
JPS5843947A (ja)	1983-03-14

Publication	Publication Date	Title
JPH0482142B2 (de)	1992-12-25
JPS6215071B2 (de)	1987-04-06
US4042604A (en)	1977-08-16	Isolation of dinitroanthraquinone having a high content of α,α-d
EP0396458A1 (de)	1990-11-07	Verfahren zur Reinigung von Natriumtrifluormethansulfinat und -sulfonat
US4324742A (en)	1982-04-13	Process for separation of naphthalenedisulfonic acids
US4076734A (en)	1978-02-28	Process for preparing dinitroanthraquinones
US4246180A (en)	1981-01-20	Process for separating off 1-amino-4-bromoanthraquinone-2-sulphonic acid
JPS60231647A (ja)	1985-11-18	パラフインのスルホ酸化で生じた反応混合物から残留硫酸を除く方法
DE2517437A1 (de)	1976-10-28	Dinitronaphthaline
US4538007A (en)	1985-08-27	Process for the simultaneous recovery of 4-hydroxy-diphenyl and 4,4'-dihydroxydiphenyl
JPS6058229B2 (ja)	1985-12-19	１−アミノ−４−ブロムアントラキノン−２−スルホン酸の製法
US3994963A (en)	1976-11-30	Schaeffer salt purification
JPH0558987A (ja)	1993-03-09	４，４′−ジニトロスチルベン−２，２′−ジスルホン酸の製造方法
US2465952A (en)	1949-03-29	Manufacture of para-nitrobenzene sulfonyl chloride
JPH0665511A (ja)	1994-03-08	ジアントラキノン−ｎ，ｎ’−ジヒドロアジン及びその塩素化生成物の製法
CN110950809B (zh)	2021-07-27	一种芳基***啉酮化合物的合成后处理方法
US3933929A (en)	1976-01-20	Process for the purification of p-nitrophenol
US4540525A (en)	1985-09-10	Method for producing 1-naphthol-4-sulphonic acid
JPH0853406A (ja)	1996-02-27	１−アミノ−４−ブロムアントラキノン−２−スルホン酸塩の製造方法
US2001063A (en)	1935-05-14	Manufacture of bz1, bz1'-dibenzanthronyl
JP2629044B2 (ja)	1997-07-09	メタクリルアミドの取得方法
JPH0512344B2 (de)	1993-02-17
US2033363A (en)	1936-03-10	Separation of isomeric chloromethyl-anthraquinones
JP2770512B2 (ja)	1998-07-02	アミノエチルスルホン酸アルカリ金属塩類の精製方法
US2745840A (en)	1956-05-15	Recovery and purification of saccharin