JPH0143737B2 - - Google Patents

Info

Publication number: JPH0143737B2
Authority: JP; Japan
Prior art keywords: sulfonic acid; aminoanthraquinone; amino; sulfuric acid; parts
Prior art date: 1981-06-17
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

JP9433781A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57209264A (en

Inventor

Akira Takeshita

Makoto Hatsutori

Akihiro Taguma

Kenji Yoshinaga

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.)

1981-06-17

Filing date

1981-06-17

Publication date

1989-09-22

1981-06-17 Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd

1981-06-17 Priority to JP9433781A priority Critical patent/JPS57209264A/ja

1982-12-22 Publication of JPS57209264A publication Critical patent/JPS57209264A/ja

1989-09-22 Publication of JPH0143737B2 publication Critical patent/JPH0143737B2/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 36
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 21
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 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 7
238000004519 manufacturing process Methods 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
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 3
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 24
238000000034 method Methods 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 11
239000013078 crystal Substances 0.000 description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
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 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000005893 bromination reaction Methods 0.000 description 6
230000031709 bromination Effects 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ZINRVIQBCHAZMM-UHFFFAOYSA-N 1-Amino-2,4-dibromoanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2N ZINRVIQBCHAZMM-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
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 3
-1 alkali metal salt Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture 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
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910001513 alkali metal bromide Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 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
KXEWYGIZIZYGDL-UHFFFAOYSA-N 1,3-dibromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC(Br)=C3C(=O)C2=C1 KXEWYGIZIZYGDL-UHFFFAOYSA-N 0.000 description 1
MVRDXWVWKOUPDO-UHFFFAOYSA-N 1-amino-2-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Br)=C2N MVRDXWVWKOUPDO-UHFFFAOYSA-N 0.000 description 1
MMKNBFSDCOALQO-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(O)=O)=C2N MMKNBFSDCOALQO-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000001000 anthraquinone dye Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1

Landscapes

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

JP9433781A 1981-06-17 1981-06-17 Preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid Granted JPS57209264A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP9433781A JPS57209264A (en)	1981-06-17	1981-06-17	Preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP9433781A JPS57209264A (en)	1981-06-17	1981-06-17	Preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid

Publications (2)

Publication Number	Publication Date
JPS57209264A JPS57209264A (en)	1982-12-22
JPH0143737B2 true JPH0143737B2 (ko)	1989-09-22

Family

ID=14107464

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9433781A Granted JPS57209264A (en)	1981-06-17	1981-06-17	Preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid

Country Status (1)

Country	Link
JP (1)	JPS57209264A (ko)

1981
- 1981-06-17 JP JP9433781A patent/JPS57209264A/ja active Granted

Also Published As

Publication number	Publication date
JPS57209264A (en)	1982-12-22

Publication	Publication Date	Title
JPH0143737B2 (ko)	1989-09-22
US4213909A (en)	1980-07-22	Process for the preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid II
JP3806962B2 (ja)	2006-08-09	３，５−ビス（トリフルオロメチル）ブロムベンゼンの製造法
EP0105762B1 (en)	1988-03-09	Process for producing anthraquinone compounds
EP0146923B1 (en)	1991-07-10	Preparation of halogenated phenols
JPH0649675B2 (ja)	1994-06-29	４，４′−ジニトロスチルベン−２，２′−ジスルホン酸の製造方法
JPS627895B2 (ko)	1987-02-19
JPS61183254A (ja)	1986-08-15	１‐アミノ‐２‐ブロモ‐４‐ヒドロキシアントラキノンの製造方法
KR940007747B1 (ko)	1994-08-24	할로페닐 하이드록시에틸 설파이드 및 이의 산화물의 제조방법
JPS5925773B2 (ja)	1984-06-21	１．５−ジフエノキシ−アンスラキノンの製造方法
JP2730991B2 (ja)	1998-03-25	１―アミノ―２―クロル―４―ヒドロキシ―アントラキノンの製造方法
US1965818A (en)	1934-07-10	Manufacture of nitro-anthraquinone-sulphonic acid
JPH05500813A (ja)	1993-02-18	アルキル―〔３クロロフェニル〕―スルホンの製造方法
JPH01228943A (ja)	1989-09-12	２，４―ジクロロ―３―アルキル―６―ニトロフェノールの製造方法
JPS6233137A (ja)	1987-02-13	３，３’−ジニトロベンゾフエノンの精製方法
JP2003321438A (ja)	2003-11-11	ハロスルホニル基含有キノンジアジド化合物の製造法
JPH0413657A (ja)	1992-01-17	２，４―ジアミノベンゼンスルホン酸の製造方法
JPS6011986B2 (ja)	1985-03-29	ジオキサジン系化合物の製造方法
JPS58131965A (ja)	1983-08-06	１−アミノ−４−ブロムアントラキノン−２−スルホン酸の製法
JPS6215072B2 (ko)	1987-04-06
EP0093490B1 (en)	1988-04-27	Process for preparing 3,5-disubstituted 2-pyridylalkyl amines
JPS62298564A (ja)	1987-12-25	１−アミノ−２−クロル−４−ヒドロキシアントラキノンと１−アミノ−２−ブロム−４−ヒドロキシアントラキノンとの混合物の製造方法
JPS6046108B2 (ja)	1985-10-14	１，４−ジアミノアントラキノン−２，３−ジスルホン酸の製造方法
JPS6215071B2 (ko)	1987-04-06
JPS5869855A (ja)	1983-04-26	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