DE2426401A1 - 2,2-bis-hydroxymethyl-alkansulfonate - Google Patents
2,2-bis-hydroxymethyl-alkansulfonateInfo
- Publication number
- DE2426401A1 DE2426401A1 DE19742426401 DE2426401A DE2426401A1 DE 2426401 A1 DE2426401 A1 DE 2426401A1 DE 19742426401 DE19742426401 DE 19742426401 DE 2426401 A DE2426401 A DE 2426401A DE 2426401 A1 DE2426401 A1 DE 2426401A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- hydroxymethyl
- alkanesulfonates
- water
- product
- Prior art date
- 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.)
- Withdrawn
Links
- 150000001335 aliphatic alkanes Chemical class 0.000 title description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title description 2
- -1 alkaline earth metal sulfite Chemical class 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- KZPMDGJBWCEYFG-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butane-1-sulfonic acid Chemical compound OCC(CS(=O)(=O)O)(CC)CO KZPMDGJBWCEYFG-UHFFFAOYSA-N 0.000 claims description 5
- JSTVTNWIAJJBSM-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)-2-methylpropane-1-sulfonic acid Chemical compound OCC(C)(CO)CS(O)(=O)=O JSTVTNWIAJJBSM-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- YPFUJZAAZJXMIP-UHFFFAOYSA-N 3-sulfopropanediol Chemical compound OCC(O)CS(O)(=O)=O YPFUJZAAZJXMIP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742426401 DE2426401A1 (de) | 1974-05-31 | 1974-05-31 | 2,2-bis-hydroxymethyl-alkansulfonate |
| GB2121775A GB1455554A (en) | 1974-05-31 | 1975-05-19 | 2,2-bis-hydroxymethyl alkane sulphonates |
| IT4982075A IT1035866B (it) | 1974-05-31 | 1975-05-28 | 2.2 bis idrossimetil alcan solfonati e procedimento per produrit |
| LU72607A LU72607A1 (enExample) | 1974-05-31 | 1975-05-29 | |
| BE156842A BE829652A (fr) | 1974-05-31 | 1975-05-29 | 2,2-bis-hydroxymethyl-alcane sulfonates, leur preparatio et leur utilisatyion |
| IE121275A IE41250B1 (en) | 1974-05-31 | 1975-05-30 | 2,2-bis-hydroxymethylalkanesulphonates |
| FR7516897A FR2275447A1 (fr) | 1974-05-31 | 1975-05-30 | 2,2-bis - hydroxymethyl - alcane sulfonates, leur preparation et leurs utilisations notamment pour l'amelioration de l'aptitude a la teinture de polymeres |
| JP6443075A JPS5111717A (en) | 1974-05-31 | 1975-05-30 | 2 22 bisuhidorokishimechiruarukansuruhoneetonoseiho |
| NL7506468A NL7506468A (nl) | 1974-05-31 | 1975-05-30 | Werkwijze voor de bereiding van 2,2-bis-hydroxy- methylalkaansulfonaten. |
| DK243875A DK243875A (da) | 1974-05-31 | 1975-05-30 | 2,2-bis-hydroxymethyl-alkansulfonater, deres fremstilling og anvendelse |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742426401 DE2426401A1 (de) | 1974-05-31 | 1974-05-31 | 2,2-bis-hydroxymethyl-alkansulfonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2426401A1 true DE2426401A1 (de) | 1975-12-11 |
Family
ID=5916982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742426401 Withdrawn DE2426401A1 (de) | 1974-05-31 | 1974-05-31 | 2,2-bis-hydroxymethyl-alkansulfonate |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5111717A (enExample) |
| BE (1) | BE829652A (enExample) |
| DE (1) | DE2426401A1 (enExample) |
| DK (1) | DK243875A (enExample) |
| FR (1) | FR2275447A1 (enExample) |
| GB (1) | GB1455554A (enExample) |
| IE (1) | IE41250B1 (enExample) |
| IT (1) | IT1035866B (enExample) |
| LU (1) | LU72607A1 (enExample) |
| NL (1) | NL7506468A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3643791A1 (de) * | 1986-12-20 | 1988-06-23 | Basf Ag | Waessrige polyurethan-klebstoff-dispersion |
| US8431748B2 (en) | 2006-01-16 | 2013-04-30 | Bwe I Malmo Ab | Low protonation constant hydroxy acids |
-
1974
- 1974-05-31 DE DE19742426401 patent/DE2426401A1/de not_active Withdrawn
-
1975
- 1975-05-19 GB GB2121775A patent/GB1455554A/en not_active Expired
- 1975-05-28 IT IT4982075A patent/IT1035866B/it active
- 1975-05-29 LU LU72607A patent/LU72607A1/xx unknown
- 1975-05-29 BE BE156842A patent/BE829652A/xx unknown
- 1975-05-30 DK DK243875A patent/DK243875A/da unknown
- 1975-05-30 IE IE121275A patent/IE41250B1/xx unknown
- 1975-05-30 FR FR7516897A patent/FR2275447A1/fr active Granted
- 1975-05-30 JP JP6443075A patent/JPS5111717A/ja active Pending
- 1975-05-30 NL NL7506468A patent/NL7506468A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IE41250B1 (en) | 1979-11-21 |
| LU72607A1 (enExample) | 1976-03-17 |
| IE41250L (en) | 1975-11-30 |
| NL7506468A (nl) | 1975-12-02 |
| FR2275447B1 (enExample) | 1978-09-22 |
| FR2275447A1 (fr) | 1976-01-16 |
| IT1035866B (it) | 1979-10-20 |
| JPS5111717A (en) | 1976-01-30 |
| BE829652A (fr) | 1975-12-01 |
| DK243875A (da) | 1975-12-01 |
| GB1455554A (en) | 1976-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |