DE10259403A1 - Verfahren zur Herstellung von Alkyl- und/oder Alkenyloliglykosidcarbonsäure-Salzen - Google Patents
Verfahren zur Herstellung von Alkyl- und/oder Alkenyloliglykosidcarbonsäure-Salzen Download PDFInfo
- Publication number
- DE10259403A1 DE10259403A1 DE10259403A DE10259403A DE10259403A1 DE 10259403 A1 DE10259403 A1 DE 10259403A1 DE 10259403 A DE10259403 A DE 10259403A DE 10259403 A DE10259403 A DE 10259403A DE 10259403 A1 DE10259403 A1 DE 10259403A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- alkenyl
- salts
- ppm
- compounds
- 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- Withdrawn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
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 28
- 125000003342 alkenyl group Chemical group 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 17
- 150000001734 carboxylic acid salts Chemical class 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000004045 organic chlorine compounds Chemical class 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 150000003977 halocarboxylic acids Chemical class 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 halogen carboxylic acids Chemical class 0.000 claims description 5
- 229910052783 alkali metal Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229930182478 glucoside Natural products 0.000 claims 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940120124 dichloroacetate Drugs 0.000 description 3
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- HPBFSDXZIQIDSL-UHFFFAOYSA-N 2-chloroacetic acid;2,2-dichloroacetic acid Chemical compound OC(=O)CCl.OC(=O)C(Cl)Cl HPBFSDXZIQIDSL-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 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 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 238000006473 carboxylation reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 2
- CFOQKXQWGLAKSK-KTKRTIGZSA-N (13Z)-docosen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCO CFOQKXQWGLAKSK-KTKRTIGZSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- DJYWKXYRGAMLRE-QXMHVHEDSA-N (z)-icos-9-en-1-ol Chemical compound CCCCCCCCCC\C=C/CCCCCCCCO DJYWKXYRGAMLRE-QXMHVHEDSA-N 0.000 description 1
- TVPWKOCQOFBNML-SEYXRHQNSA-N (z)-octadec-6-en-1-ol Chemical compound CCCCCCCCCCC\C=C/CCCCCO TVPWKOCQOFBNML-SEYXRHQNSA-N 0.000 description 1
- CFOQKXQWGLAKSK-UHFFFAOYSA-N 13-docosen-1-ol Natural products CCCCCCCCC=CCCCCCCCCCCCCO CFOQKXQWGLAKSK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229940096386 coconut alcohol Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- ALSTYHKOOCGGFT-MDZDMXLPSA-N oleyl alcohol Chemical compound CCCCCCCC\C=C\CCCCCCCCO ALSTYHKOOCGGFT-MDZDMXLPSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10259403A DE10259403A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur Herstellung von Alkyl- und/oder Alkenyloliglykosidcarbonsäure-Salzen |
| US10/539,668 US7384904B2 (en) | 2002-12-19 | 2003-12-09 | Method for producing alkyl oligoglucoside and alkenyl oligoglucoside carboxylic acid salts with reduced organochloride compounds |
| EP03785775A EP1572706B1 (de) | 2002-12-19 | 2003-12-09 | Verfahren zur herstellung von alkyl- und/oder alkenyloliglykosidcarbons ure-salzen |
| DE50302682T DE50302682D1 (de) | 2002-12-19 | 2003-12-09 | Verfahren zur herstellung von alkyl- und/oder alkenyloliglykosidcarbons ure-salzen |
| PCT/EP2003/013920 WO2004056842A1 (de) | 2002-12-19 | 2003-12-09 | Verfahren zur herstellung von alkyl- und/oder alkenyloliglykosidcarbonsäure-salzen |
| JP2004561246A JP2006516125A (ja) | 2002-12-19 | 2003-12-09 | アルキルオリゴグリコシド−及び／又はアルケニルオリゴグリコシドカルボン酸塩の製造方法 |
| ES03785775T ES2258739T3 (es) | 2002-12-19 | 2003-12-09 | Procedimiento para la obtencion de sales de los acidos alquil- y/o de alqueniloligoglicosidoscarboxilicos. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10259403A DE10259403A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur Herstellung von Alkyl- und/oder Alkenyloliglykosidcarbonsäure-Salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10259403A1 true DE10259403A1 (de) | 2004-07-01 |
Family
ID=32403930
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10259403A Withdrawn DE10259403A1 (de) | 2002-12-19 | 2002-12-19 | Verfahren zur Herstellung von Alkyl- und/oder Alkenyloliglykosidcarbonsäure-Salzen |
| DE50302682T Expired - Lifetime DE50302682D1 (de) | 2002-12-19 | 2003-12-09 | Verfahren zur herstellung von alkyl- und/oder alkenyloliglykosidcarbons ure-salzen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50302682T Expired - Lifetime DE50302682D1 (de) | 2002-12-19 | 2003-12-09 | Verfahren zur herstellung von alkyl- und/oder alkenyloliglykosidcarbons ure-salzen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7384904B2 (enExample) |
| EP (1) | EP1572706B1 (enExample) |
| JP (1) | JP2006516125A (enExample) |
| DE (2) | DE10259403A1 (enExample) |
| ES (1) | ES2258739T3 (enExample) |
| WO (1) | WO2004056842A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110176872A1 (en) | 2010-01-15 | 2011-07-21 | Lamberti Usa, Inc. | Process for wetting a water repellent soil |
| EP4438031A1 (en) * | 2023-03-27 | 2024-10-02 | KAO CHEMICALS GmbH | A process for preparing a composition comprising a carboxyalkylated alkyl- and/or alkenylglycoside, and the composition obtainable by this process |
| EP4438032A1 (en) * | 2023-03-27 | 2024-10-02 | Kao Corporation, S.A. | Composition comprising an alkyl- and/or alkenylglycoside |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0768262B2 (ja) * | 1986-08-22 | 1995-07-26 | 川研ファインケミカル株式会社 | 新規なメチルα−Ｄ−グルコピラノシド化合物、該化合物の製造方法および該化合物を含む金属イオン封鎖剤 |
| JPH03287595A (ja) * | 1990-04-04 | 1991-12-18 | Kao Corp | カルボキシアルキル化グリコシド及びその製造方法 |
| DE4015655A1 (de) * | 1990-05-16 | 1991-11-21 | Basf Ag | Alkylmono- und alkylpolyglucosidethercarboxylate, verfahren zu ihrer herstellung und ihre verwendung |
| JP2633174B2 (ja) * | 1993-06-04 | 1997-07-23 | ダイセル化学工業株式会社 | α−アシルオキシ脂肪酸の製造法 |
| JP3299862B2 (ja) * | 1995-06-26 | 2002-07-08 | 花王株式会社 | 淡色化ベタインの製造法 |
| DE19600620C1 (de) * | 1996-01-10 | 1997-04-17 | Hoechst Ag | Verfahren zur Darstellung einer besonders reinen Glykolsäure |
| JP2000509713A (ja) * | 1996-05-08 | 2000-08-02 | ヘンケル コーポレーション | アルキルポリグリコシドエーテルカルボン酸 |
| JPH10167953A (ja) * | 1996-12-06 | 1998-06-23 | Daicel Chem Ind Ltd | 化粧品組成物 |
| DE10122255C1 (de) * | 2001-05-08 | 2002-11-07 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von Tensidgemischen |
-
2002
- 2002-12-19 DE DE10259403A patent/DE10259403A1/de not_active Withdrawn
-
2003
- 2003-12-09 ES ES03785775T patent/ES2258739T3/es not_active Expired - Lifetime
- 2003-12-09 DE DE50302682T patent/DE50302682D1/de not_active Expired - Lifetime
- 2003-12-09 EP EP03785775A patent/EP1572706B1/de not_active Expired - Lifetime
- 2003-12-09 JP JP2004561246A patent/JP2006516125A/ja active Pending
- 2003-12-09 US US10/539,668 patent/US7384904B2/en not_active Expired - Lifetime
- 2003-12-09 WO PCT/EP2003/013920 patent/WO2004056842A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1572706B1 (de) | 2006-03-15 |
| US7384904B2 (en) | 2008-06-10 |
| US20060172915A1 (en) | 2006-08-03 |
| DE50302682D1 (de) | 2006-05-11 |
| ES2258739T3 (es) | 2006-09-01 |
| EP1572706A1 (de) | 2005-09-14 |
| JP2006516125A (ja) | 2006-06-22 |
| WO2004056842A1 (de) | 2004-07-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: COGNIS IP MANAGEMENT GMBH, 40589 DUESSELDORF, DE |
|
| 8139 | Disposal/non-payment of the annual fee |