CA1048028A - Method for preparing a complex of a phenolic compound and hexamethylenetetramine - Google Patents
Method for preparing a complex of a phenolic compound and hexamethylenetetramineInfo
- Publication number
- CA1048028A CA1048028A CA232,262A CA232262A CA1048028A CA 1048028 A CA1048028 A CA 1048028A CA 232262 A CA232262 A CA 232262A CA 1048028 A CA1048028 A CA 1048028A
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- parts
- hexamethylenetetramine
- product
- mixer
- 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
Links
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 239000004312 hexamethylene tetramine Substances 0.000 title claims abstract description 32
- 235000010299 hexamethylene tetramine Nutrition 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 21
- 150000002989 phenols Chemical class 0.000 title claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 238000002156 mixing Methods 0.000 claims abstract description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000001035 drying Methods 0.000 claims abstract description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 229960004592 isopropanol Drugs 0.000 claims description 5
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 claims 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 claims 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims 1
- 235000010292 orthophenyl phenol Nutrition 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000004615 ingredient Substances 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 40
- 229960004011 methenamine Drugs 0.000 description 28
- 239000000463 material Substances 0.000 description 14
- 239000005060 rubber Substances 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002226 simultaneous effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/18—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50090674A | 1974-08-27 | 1974-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048028A true CA1048028A (en) | 1979-02-06 |
Family
ID=23991419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,262A Expired CA1048028A (en) | 1974-08-27 | 1975-07-25 | Method for preparing a complex of a phenolic compound and hexamethylenetetramine |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4069220A (online.php) |
| CA (1) | CA1048028A (online.php) |
| DE (1) | DE2535509A1 (online.php) |
| FR (1) | FR2283137A1 (online.php) |
| GB (1) | GB1483570A (online.php) |
| IT (1) | IT1041293B (online.php) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4338442A (en) * | 1981-04-15 | 1982-07-06 | The United States Of America As Represented By The Secretary Of The Army | Preparation of 1,5-methylene-3,7-dinitro-1,3,5,7-tetraazacyclooctane |
| AU580682B2 (en) * | 1985-07-31 | 1989-01-27 | Indspec Chemical Corporation | Process for resotropin |
| US4588760A (en) * | 1985-08-09 | 1986-05-13 | Clairol Incorporated | Hair treatment composition |
| JPH1088028A (ja) * | 1996-09-02 | 1998-04-07 | J M Huber Corp | シラン処理クレー製品、その製法及びその組成物 |
| CA2264722A1 (en) * | 1996-09-02 | 1998-03-12 | Sanyo Trading Co., Ltd. | Silane-treated clay production method, silane-treated clay and composition containing same |
| US5840795A (en) * | 1997-04-30 | 1998-11-24 | J. M. Huber Corporation | Treated clay product, methods of making and using and products therefrom |
| WO2007127065A2 (en) * | 2006-04-21 | 2007-11-08 | Living Proof, Inc. | In situ polymerization for hair treatment |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618664A (en) * | 1950-07-29 | 1952-11-18 | Texas Co | Process for isolating phenolic compounds from mixtures thereof |
| US2697122A (en) * | 1951-05-16 | 1954-12-14 | Texas Co | Process for isolating phenolic compounds from mixtures thereof |
| IT951612B (it) * | 1971-12-27 | 1973-07-10 | Sir Soc Italiana Resine Spa | Procedimento per il recupero della formaldeide e del fenolo contenuti in acque di scarico |
-
1975
- 1975-07-22 GB GB30671/75A patent/GB1483570A/en not_active Expired
- 1975-07-25 CA CA232,262A patent/CA1048028A/en not_active Expired
- 1975-08-06 DE DE19752535509 patent/DE2535509A1/de not_active Withdrawn
- 1975-08-21 IT IT51022/75A patent/IT1041293B/it active
- 1975-08-25 FR FR7526185A patent/FR2283137A1/fr active Granted
-
1976
- 1976-09-21 US US05/725,240 patent/US4069220A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1483570A (en) | 1977-08-24 |
| FR2283137B1 (online.php) | 1979-05-18 |
| FR2283137A1 (fr) | 1976-03-26 |
| IT1041293B (it) | 1980-01-10 |
| US4069220A (en) | 1978-01-17 |
| DE2535509A1 (de) | 1976-03-11 |
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