JP3597873B2 - ニトロソアミンの生成抑制法 - Google Patents
ニトロソアミンの生成抑制法 Download PDFInfo
- Publication number
- JP3597873B2 JP3597873B2 JP1471693A JP1471693A JP3597873B2 JP 3597873 B2 JP3597873 B2 JP 3597873B2 JP 1471693 A JP1471693 A JP 1471693A JP 1471693 A JP1471693 A JP 1471693A JP 3597873 B2 JP3597873 B2 JP 3597873B2
- Authority
- JP
- Japan
- Prior art keywords
- amine
- weight
- amine oxide
- phosphonate
- composition
- 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.)
- Expired - Fee Related
Links
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims description 34
- 230000015572 biosynthetic process Effects 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims abstract description 34
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 26
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 22
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 18
- 230000002195 synergetic effect Effects 0.000 claims abstract description 14
- TTZMPOZCBFTTPR-UHFFFAOYSA-N O=P1OCO1 Chemical compound O=P1OCO1 TTZMPOZCBFTTPR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000003860 storage Methods 0.000 claims abstract description 12
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 238000011109 contamination Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims description 98
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 35
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 27
- -1 alkaline earth metal carbonate Chemical class 0.000 claims description 19
- 150000004005 nitrosamines Chemical class 0.000 claims description 19
- 239000003381 stabilizer Substances 0.000 claims description 17
- 150000003512 tertiary amines Chemical class 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- 150000002826 nitrites Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-L phosphonate(2-) Chemical compound [O-]P([O-])=O ABLZXFCXXLZCGV-UHFFFAOYSA-L 0.000 claims description 4
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000003352 sequestering agent Substances 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000001099 ammonium carbonate Substances 0.000 claims description 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 229910001428 transition metal ion Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 15
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 230000027311 M phase Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- GWASTCVCPXFIQT-UHFFFAOYSA-N NC1OP(=O)O1 Chemical class NC1OP(=O)O1 GWASTCVCPXFIQT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000003752 hydrotrope Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 230000005070 ripening Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- MZKSBYBYCXBNGA-UHFFFAOYSA-N n-dodecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNCCCCCCCCCCCC MZKSBYBYCXBNGA-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012070 reactive reagent Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- RCUMDGGJOOTRBS-UHFFFAOYSA-M sodium;[bis(phosphonomethyl)amino]methyl-hydroxyphosphinate Chemical compound [Na+].OP(O)(=O)CN(CP(O)(O)=O)CP(O)([O-])=O RCUMDGGJOOTRBS-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/32—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal
- C09K15/322—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal containing only phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/32—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929202057A GB9202057D0 (en) | 1992-01-31 | 1992-01-31 | Synergistic inhibition of nitrosamines and nitrites |
| GB9202057.7 | 1992-01-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06107621A JPH06107621A (ja) | 1994-04-19 |
| JP3597873B2 true JP3597873B2 (ja) | 2004-12-08 |
Family
ID=10709589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1471693A Expired - Fee Related JP3597873B2 (ja) | 1992-01-31 | 1993-02-01 | ニトロソアミンの生成抑制法 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5442113A (OSRAM) |
| EP (1) | EP0553800B1 (OSRAM) |
| JP (1) | JP3597873B2 (OSRAM) |
| CN (1) | CN1084508A (OSRAM) |
| AT (1) | ATE127448T1 (OSRAM) |
| AU (1) | AU665794B2 (OSRAM) |
| CA (1) | CA2088386C (OSRAM) |
| DE (1) | DE69300420T2 (OSRAM) |
| DK (1) | DK0553800T3 (OSRAM) |
| ES (1) | ES2089596T3 (OSRAM) |
| GB (2) | GB9202057D0 (OSRAM) |
| GR (1) | GR3018291T3 (OSRAM) |
| HK (1) | HK159496A (OSRAM) |
| IN (1) | IN185978B (OSRAM) |
| MY (1) | MY108950A (OSRAM) |
| NZ (1) | NZ245815A (OSRAM) |
| PH (1) | PH30450A (OSRAM) |
| ZA (1) | ZA93625B (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9301836D0 (en) * | 1993-01-29 | 1993-03-17 | Albright & Wilson | Nitrosamine inhibition |
| EP0730439A1 (en) * | 1993-11-27 | 1996-09-11 | Knoll AG | Compositions comprising iminium ion scavengers and/or nitrite scavengers |
| US5583258A (en) * | 1995-02-15 | 1996-12-10 | The Procter & Gamble Company | Process for preparing mono-long chain amine oxide surfactants |
| US6849588B2 (en) | 1996-02-08 | 2005-02-01 | Huntsman Petrochemical Corporation | Structured liquids made using LAB sulfonates of varied 2-isomer content |
| US5693796A (en) * | 1996-08-14 | 1997-12-02 | Basf Corporation | Method for reducing the nitrosamine content of N-methylmorpholine-N-oxide |
| US5866718A (en) * | 1997-03-20 | 1999-02-02 | General Electric Company | Synthesis of tertiary amine oxides |
| US6166255A (en) * | 1998-04-01 | 2000-12-26 | Albemarle Corporation | Production of tertiary amine oxides |
| US6080889A (en) * | 1998-04-01 | 2000-06-27 | Albemarle Corporation | Production of tertiary amine oxides |
| US6037497A (en) * | 1998-09-29 | 2000-03-14 | Albemarle Corporation | Process for producing amine oxides |
| US6294514B1 (en) * | 1998-11-24 | 2001-09-25 | The Procter & Gamble Company | Process for preparing mono-long chain amine oxide surfactants with low nitrite, nitrosamine and low residual peroxide |
| US6121490A (en) * | 1999-04-14 | 2000-09-19 | Albemarle Corporation | Production of solid tertiary amine oxides |
| DE10207924A1 (de) * | 2002-02-23 | 2003-09-04 | Clariant Gmbh | Hochkonzentrierte wässrige Lösungen von Betainen oder Aminoxiden |
| US7650891B1 (en) | 2004-09-03 | 2010-01-26 | Rosswil Llc Ltd. | Tobacco precursor product |
| EP2481466A1 (de) * | 2011-01-31 | 2012-08-01 | Siemens Aktiengesellschaft | Vorrichtung und Verfahren zum Aufreinigen eines mit Nitrosamin verunreinigten Produktes einer Prozessanlage |
| CN102229619A (zh) * | 2011-04-26 | 2011-11-02 | 河南清水源科技股份有限公司 | 四乙烯五胺七亚甲基膦酸及其生产工艺 |
| BE1021535B1 (nl) * | 2014-01-08 | 2015-12-09 | Eoc Surfactants Nv | Nitrosamine inhibitie in tertiair alkylamine oxide samenstellingen |
| CN106390853B (zh) * | 2016-08-30 | 2018-10-23 | 四川花语精细化工有限公司 | 一种制备低亚硝酸盐、高活性烷基氧化胺的方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL128580C (OSRAM) * | 1964-05-25 | |||
| US3463817A (en) * | 1967-04-18 | 1969-08-26 | Millmaster Onyx Corp | Process for producing amine oxides |
| US3450637A (en) * | 1968-05-03 | 1969-06-17 | Procter & Gamble | Detergent containing hydroxy alkyl amine oxide |
| GB1255102A (en) * | 1968-05-09 | 1971-11-24 | Armour Ind Chem Co | Spray drying amine oxides |
| GB1379024A (en) * | 1971-04-02 | 1975-01-02 | Unilever Ltd | Detergent compositions |
| JPS5528968A (en) * | 1978-08-24 | 1980-02-29 | Nissan Chem Ind Ltd | Production of amine oxide |
| US4273937A (en) * | 1979-12-19 | 1981-06-16 | Union Carbide Corporation | Organic amine compositions |
| US4359413A (en) * | 1981-03-17 | 1982-11-16 | The Procter & Gamble Company | Solid detergent compositions containing alpha-amine oxide surfactants |
| US4581072A (en) * | 1982-06-08 | 1986-04-08 | Courtaulds Plc | Polymer solutions |
| EP0105556A1 (en) * | 1982-09-30 | 1984-04-18 | THE PROCTER & GAMBLE COMPANY | Liquid detergent composition containing nonionic and ionic surfactants |
| AU615471B2 (en) * | 1987-09-08 | 1991-10-03 | Ethyl Corporation | Amine oxide process |
| FR2632638B1 (fr) * | 1988-06-10 | 1991-04-19 | Atochem | Procede de fabrication d'oxydes d'amines |
| US5023376A (en) * | 1989-07-17 | 1991-06-11 | Interox America | Reduction of nitrosamine formation |
| US4960934A (en) * | 1989-10-27 | 1990-10-02 | Ethyl Corporation | Amine oxide process |
| US5077329A (en) * | 1990-04-06 | 1991-12-31 | Ciba-Geigy Corporation | Hydroxyaminomethylphosphonates and stabilized compositions |
| GB9102311D0 (en) * | 1991-02-02 | 1991-03-20 | Albright & Wilson | Nitrosamine inhibition |
-
1992
- 1992-01-31 GB GB929202057A patent/GB9202057D0/en active Pending
-
1993
- 1993-01-28 ES ES93101234T patent/ES2089596T3/es not_active Expired - Lifetime
- 1993-01-28 AT AT93101234T patent/ATE127448T1/de not_active IP Right Cessation
- 1993-01-28 EP EP93101234A patent/EP0553800B1/en not_active Expired - Lifetime
- 1993-01-28 ZA ZA93625A patent/ZA93625B/xx unknown
- 1993-01-28 DK DK93101234.8T patent/DK0553800T3/da active
- 1993-01-28 DE DE69300420T patent/DE69300420T2/de not_active Expired - Lifetime
- 1993-01-28 PH PH45631A patent/PH30450A/en unknown
- 1993-01-29 IN IN81DE1993 patent/IN185978B/en unknown
- 1993-01-29 CA CA002088386A patent/CA2088386C/en not_active Expired - Fee Related
- 1993-01-29 AU AU32082/93A patent/AU665794B2/en not_active Ceased
- 1993-01-29 GB GB9301761A patent/GB2263698A/en not_active Withdrawn
- 1993-01-30 MY MYPI93000150A patent/MY108950A/en unknown
- 1993-01-30 CN CN93102395A patent/CN1084508A/zh active Pending
- 1993-02-01 US US08/011,976 patent/US5442113A/en not_active Expired - Lifetime
- 1993-02-01 JP JP1471693A patent/JP3597873B2/ja not_active Expired - Fee Related
- 1993-02-01 NZ NZ245815A patent/NZ245815A/en not_active IP Right Cessation
-
1995
- 1995-01-20 US US08/376,040 patent/US5498791A/en not_active Expired - Fee Related
- 1995-12-05 GR GR950403409T patent/GR3018291T3/el unknown
-
1996
- 1996-08-22 HK HK159496A patent/HK159496A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0553800A3 (en) | 1993-10-20 |
| GB9301761D0 (en) | 1993-03-17 |
| ZA93625B (en) | 1994-06-13 |
| HK159496A (en) | 1996-08-30 |
| ES2089596T3 (es) | 1996-10-01 |
| GB9202057D0 (en) | 1992-03-18 |
| AU665794B2 (en) | 1996-01-18 |
| DE69300420T2 (de) | 1996-03-07 |
| DK0553800T3 (da) | 1995-10-16 |
| US5442113A (en) | 1995-08-15 |
| CA2088386C (en) | 2004-07-06 |
| DE69300420D1 (de) | 1995-10-12 |
| EP0553800B1 (en) | 1995-09-06 |
| NZ245815A (en) | 1995-10-26 |
| GB2263698A (en) | 1993-08-04 |
| IN185978B (OSRAM) | 2001-05-26 |
| CN1084508A (zh) | 1994-03-30 |
| EP0553800A2 (en) | 1993-08-04 |
| AU3208293A (en) | 1993-08-05 |
| CA2088386A1 (en) | 1993-08-01 |
| MY108950A (en) | 1996-11-30 |
| JPH06107621A (ja) | 1994-04-19 |
| PH30450A (en) | 1997-05-28 |
| GR3018291T3 (en) | 1996-03-31 |
| ATE127448T1 (de) | 1995-09-15 |
| US5498791A (en) | 1996-03-12 |
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