CH401953A - Verfahren zur Herstellung reiner Natriumsalze der 5-Sulfoisophthalsäure und 2-Sulfoterephthalsäure - Google Patents

Verfahren zur Herstellung reiner Natriumsalze der 5-Sulfoisophthalsäure und 2-Sulfoterephthalsäure

Info

Publication number: CH401953A
Authority: CH; Switzerland
Prior art keywords: acid; sodium; acids; sulfonation; salts
Prior art date: 1960-10-22

Application number

CH783661A

Other languages

German (de)

English (en)

Inventor

Nat Burkhardt Rudolf Dr Rer

Original Assignee

Chemische Werke Witten Gmbh

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.)

1960-10-22

Filing date

1961-07-05

Publication date

1965-11-15

1961-07-05 Application filed by Chemische Werke Witten Gmbh filed Critical Chemische Werke Witten Gmbh

1965-11-15 Publication of CH401953A publication Critical patent/CH401953A/de

Links

159000000000 sodium salts Chemical class 0.000 title claims description 21
238000000034 method Methods 0.000 title claims description 14
RAADBCJYJHQQBI-UHFFFAOYSA-N 2-sulfoterephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(S(O)(=O)=O)=C1 RAADBCJYJHQQBI-UHFFFAOYSA-N 0.000 title claims description 10
CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical class OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 20
238000006277 sulfonation reaction Methods 0.000 claims description 18
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 17
SDGNNLQZAPXALR-UHFFFAOYSA-N 3-sulfophthalic acid Chemical class OC(=O)C1=CC=CC(S(O)(=O)=O)=C1C(O)=O SDGNNLQZAPXALR-UHFFFAOYSA-N 0.000 claims description 16
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 11
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 10
229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
238000006386 neutralization reaction Methods 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
150000002731 mercury compounds Chemical class 0.000 claims description 3
229910052753 mercury Inorganic materials 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 16
150000003839 salts Chemical group 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
239000002253 acid Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 8
YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
238000001035 drying Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
150000003460 sulfonic acids Chemical class 0.000 description 4
DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
229910006069 SO3H Inorganic materials 0.000 description 2
-1 aromatic sulfonic acids Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229910000474 mercury oxide Inorganic materials 0.000 description 2
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000001226 reprecipitation Methods 0.000 description 2
238000005185 salting out Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
XWOKSGKAPGSACB-UHFFFAOYSA-N 2-methyl-6-sulfobenzoic acid Chemical class CC1=CC=CC(S(O)(=O)=O)=C1C(O)=O XWOKSGKAPGSACB-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000001838 alkalimetric titration Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000003879 lubricant additive Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940008718 metallic mercury Drugs 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical class OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH783661A 1960-10-22 1961-07-05 Verfahren zur Herstellung reiner Natriumsalze der 5-Sulfoisophthalsäure und 2-Sulfoterephthalsäure CH401953A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEC22604A DE1127891B (de)	1960-10-22	1960-10-22	Verfahren zur Herstellung reiner Mono- und Dinatriumsalze der 5-Sulfoisophthalsaeureund Sulfoterephthalsaeure

Publications (1)

Publication Number	Publication Date
CH401953A true CH401953A (de)	1965-11-15

Family

ID=7017251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH783661A CH401953A (de)	1960-10-22	1961-07-05	Verfahren zur Herstellung reiner Natriumsalze der 5-Sulfoisophthalsäure und 2-Sulfoterephthalsäure

Country Status (4)

Country	Link
BE (1)	BE609424A (fr)
CH (1)	CH401953A (fr)
DE (1)	DE1127891B (fr)
GB (1)	GB934427A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8809565B2 (en)	2011-08-29	2014-08-19	Futurefuel Chemical Company	5-sulfoisophthalic acid salts and process for the preparation thereof
CN102633693B (zh) *	2012-03-22	2013-11-13	潍坊沃尔特化学有限公司	一种间苯二甲酸二甲酯-5-磺酸钠的合成方法
CN109180538B (zh) *	2018-09-19	2021-04-16	山东第一医科大学(山东省医学科学院)	一种提高三单体合成用间苯二甲酸-5-磺酸收率的生产方法
CN109020840A (zh) *	2018-09-19	2018-12-18	青岛中科荣达新材料有限公司	一种提高间苯二甲酸-5-磺酸收率的生产方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1089375B (de) *	1957-10-21	1960-09-22	Du Pont	Verfahren zur Herstellung von m-Sulfoisophthalsaeure

1960
- 1960-10-22 DE DEC22604A patent/DE1127891B/de active Pending
1961
- 1961-07-05 CH CH783661A patent/CH401953A/de unknown
- 1961-10-20 BE BE609424A patent/BE609424A/fr unknown
- 1961-10-23 GB GB3793361A patent/GB934427A/en not_active Expired

Also Published As

Publication number	Publication date
DE1127891B (de)	1962-04-19
BE609424A (fr)	1962-02-15
GB934427A (en)	1963-08-21

Publication	Publication Date	Title
CH401953A (de)	1965-11-15	Verfahren zur Herstellung reiner Natriumsalze der 5-Sulfoisophthalsäure und 2-Sulfoterephthalsäure
DE2154943C2 (de)	1983-12-08	1-Aminobenzol-4-(&beta;-sulfatoxyäthylsulfon)-2-sulfonsäure, die entsprechende 4-Vinylsulfon-Verbindung, Verfahren zur Herstellung dieser Verbindungen und ihre Verwendung als Diazokomponente
DE2156648C3 (de)	1981-07-30	Verfahren zur Herstellung von 2-[4,4'-Bis-(dimethylaamino)-benzohydryl]-5-dimethylamino-benzoesäure
AT224107B (de)	1962-11-12	Verfahren zur Herstellung reiner Natriumsalze der 5-Sulfoisophthalsäure und 2-Sulfoterephthalsäure
DE963332C (de)	1957-05-09	Verfahren zur Reinigung von Terephthalsaeure-bis-aethylenglykolester
EP0064651B1 (fr)	1984-06-20	Procédé pour l'isolation de l'acide H et de l'acide K
DE2758397C2 (de)	1983-08-04	Verfahren zur Herstellung von Chinizarin (1,4-Dihydroxyanthrachinon)
DE2259074C3 (de)	1982-04-22	Verfahren zur Herstellung von praktisch 1,5-Dinitro-anthrachinon-freiem 1-Nitro-anthrachinon
EP0037510B1 (fr)	1983-03-09	Procédé pour la préparation de l'acide 1-naphtylamine-4,6-disulfonique et de l'acide 1-naphtylamine-2,4,6-trisulfonique
DE507210C (de)	1930-09-13	Verfahren zur Herstellung von Oxyanthrachinonen, insbesondere Alizarin
EP0014366B1 (fr)	1981-09-16	Procédé de préparation du sel de magnésium de l'acide 2-nitro-naphtalène-4,8-disulfonique
AT94833B (de)	1923-11-10	Verfahren zur Herstellung von Gerbmitteln.
CH640216A5 (de)	1983-12-30	Verfahren zur herstellung von 4-acylamido-2-nitro-1-alkoxybenzol-verbindungen.
EP0751115B1 (fr)	1998-09-09	Procédé pour la préparation de l'acide 5-fluoro-2-nitrobenzoique
DE953701C (de)	1956-12-06	Verfahren zur Herstellung von Sulfobenzoesaeure oder ihren Salzen
EP0015486B1 (fr)	1984-01-04	Procédé de préparation de 4,5-dinitro-1,8 dihydroxyanthraquinone
DE530737C (de)	1931-07-31	Verfahren zur Herstellung von 6-Arylamino-2-oxynaphthalin
DE2346459A1 (de)	1974-04-11	Verfahren zur isolierung von r-salz und einem zwischenprodukt
AT159321B (de)	1940-08-10	Verfahren zur Herstellung von Salzen der Äthensulfonsäure.
DE626788C (de)	1936-03-03	Verfahren zur Herstellung von reinem 2-Acetylamino-3-chloranthrachinon
DE607535C (de)	1934-12-29	Verfahren zur Herstellung von Sulfonsaeuren der Diaminodiphenylreihe
DE1543636A1 (de)	1969-07-31	Verfahren zur Herstellung von Cleve-Saeure
DE3937342A1 (de)	1991-05-16	Verfahren zur herstellung von 2-aminobenzol-disulfonsaeuren-(1,4) und die neue verbindung 6-chlor-2-aminobenzol-disulfonsaeure-(1,4)
EP0052307A1 (fr)	1982-05-26	Procédé de préparation de l'acide amino-1-naphtalène disulfonique-4,6 et de l'acide amino-1-naphtalène trisulfonique-2,4,6
DE1668494B1 (de)	1971-07-08	Verfahren zur Herstellung von Methylen-bis-thiocyanat