CH441283A - Procédé de préparation d'allyloxybenzène-sulfonates alcalins - Google Patents

Procédé de préparation d'allyloxybenzène-sulfonates alcalins

Info

Publication number: CH441283A
Authority: CH; Switzerland
Prior art keywords: sodium; sulfonate; preparation; potassium; allyl
Prior art date: 1962-08-27

Application number

CH1052563A

Other languages

English (en)

French (fr)

Original Assignee

Monsanto Chemicals

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.)

1962-08-27

Filing date

1963-08-26

Publication date

1967-08-15

1963-08-26 Application filed by Monsanto Chemicals filed Critical Monsanto Chemicals

1967-08-15 Publication of CH441283A publication Critical patent/CH441283A/fr

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 9
150000003871 sulfonates Chemical class 0.000 title claims 2
239000003513 alkali Substances 0.000 title description 2
229910052708 sodium Inorganic materials 0.000 claims description 16
239000011734 sodium Substances 0.000 claims description 16
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 15
-1 allyl halide Chemical class 0.000 claims description 15
239000000243 solution Substances 0.000 claims description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
238000010992 reflux Methods 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 8
150000001340 alkali metals Chemical class 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 6
229940044652 phenolsulfonate Drugs 0.000 claims description 6
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
VMNZSPZHEZLXCQ-UHFFFAOYSA-M potassium;4-hydroxybenzenesulfonate Chemical compound [K+].OC1=CC=C(S([O-])(=O)=O)C=C1 VMNZSPZHEZLXCQ-UHFFFAOYSA-M 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
BYMHXIQVEAYSJD-UHFFFAOYSA-M sodium;4-sulfophenolate Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1 BYMHXIQVEAYSJD-UHFFFAOYSA-M 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000002585 base Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
238000013019 agitation Methods 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
JDRMAAWYNHZPQV-UHFFFAOYSA-M C(C1=CC=CC=C1)S[U] Chemical compound C(C1=CC=CC=C1)S[U] JDRMAAWYNHZPQV-UHFFFAOYSA-M 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000000981 basic dye Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
229940044654 phenolsulfonic acid Drugs 0.000 description 2
229920002239 polyacrylonitrile Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
229940087596 sodium phenolsulfonate Drugs 0.000 description 1
BLXAGSNYHSQSRC-UHFFFAOYSA-M sodium;2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=CC=CC=C1S([O-])(=O)=O BLXAGSNYHSQSRC-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F246/00—Copolymers in which the nature of only the monomers in minority is defined

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Artificial Filaments (AREA)

CH1052563A 1962-08-27 1963-08-26 Procédé de préparation d'allyloxybenzène-sulfonates alcalins CH441283A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US21976062A	1962-08-27	1962-08-27

Publications (1)

Publication Number	Publication Date
CH441283A true CH441283A (fr)	1967-08-15

Family

ID=22820661

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1052563A CH441283A (fr)	1962-08-27	1963-08-26	Procédé de préparation d'allyloxybenzène-sulfonates alcalins

Country Status (4)

Country	Link
CH (1)	CH441283A (de)
DE (1)	DE1267424B (de)
GB (1)	GB974408A (de)
NL (2)	NL297182A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108067102B (zh) *	2017-12-30	2020-08-04	山东天维膜技术有限公司	一种阳离子交换膜及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB816841A (en) *	1955-10-07	1959-07-22	Dow Chemical Co	Method for preparing acrylonitrile containing fibres
BE554995A (de) *	1956-02-15

0
- NL NL127231D patent/NL127231C/xx active
- NL NL297182D patent/NL297182A/xx unknown
1963
- 1963-08-26 CH CH1052563A patent/CH441283A/fr unknown
- 1963-08-26 DE DE19631267424 patent/DE1267424B/de active Pending
- 1963-08-26 GB GB3365063A patent/GB974408A/en not_active Expired

Also Published As

Publication number	Publication date
NL297182A (de)
GB974408A (en)	1964-11-04
NL127231C (de)
DE1267424B (de)	1968-05-02

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Noller et al.	1926	Synthesis of a Homolog of Chaulmoogric Acid.▵ 2-CYCLOPENTENYLACETIC Acid. VII
EP0032275B1 (de)	1984-07-25	Verfahren zur Herstellung substituierter 2-Hydroxybenzophenone
FR2510578A1 (fr)	1983-02-04	Acides 1-phenyl-1-phosphoniques substitues et leur utilisation
JPH0676347B2 (ja)	1994-09-28	アルカリ金属アルコラートの製造法
FR3109150A1 (fr)	2021-10-15	Procédé de synthèse de composés triarylméthane sulfonés
EP0231257A1 (de)	1987-08-12	Chemische verbindungen mit substituierten phenylringen
US2354013A (en)	1944-07-18	Dihydroxy halogenated diphenyl methanes and process for making same
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FR2583040A1 (fr)	1986-12-12	Procede pour la production de 2,6-naphtalenediol et de 2,6-diacetoxynaphtalene
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FR2489317A1 (de)	1982-03-05
US2338569A (en)	1944-01-04	Preparation of coumarin-3-carboxylic acid
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CA1111447A (fr)	1981-10-27	Composes halogenes, procede de preparation et application a la preparation du metaphenoxy benzaldehyde
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