JPH02240035A - 環境的に安全なジコホールの製造方法とその組成物 - Google Patents
環境的に安全なジコホールの製造方法とその組成物Info
- Publication number
- JPH02240035A JPH02240035A JP2031306A JP3130690A JPH02240035A JP H02240035 A JPH02240035 A JP H02240035A JP 2031306 A JP2031306 A JP 2031306A JP 3130690 A JP3130690 A JP 3130690A JP H02240035 A JPH02240035 A JP H02240035A
- Authority
- JP
- Japan
- Prior art keywords
- dicofol
- ddt
- solvent
- ddtr
- acetic acid
- 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.)
- Pending
Links
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000002904 solvent Substances 0.000 claims abstract description 26
- JOQCINXYMZALAZ-UHFFFAOYSA-N 1-chloro-4-[1,2,2,2-tetrachloro-1-(4-chlorophenyl)ethyl]benzene Chemical compound C1=CC(Cl)=CC=C1C(Cl)(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 JOQCINXYMZALAZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 7
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 229960000583 acetic acid Drugs 0.000 claims description 16
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- LUXSISXJGNCOKN-UHFFFAOYSA-N 2,2,2-trichloro-1-(2-chlorophenyl)-1-(4-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 LUXSISXJGNCOKN-UHFFFAOYSA-N 0.000 claims description 11
- 241000238876 Acari Species 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004563 wettable powder Substances 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims 8
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 claims 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 4
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 2
- 150000001924 cycloalkanes Chemical class 0.000 claims 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- NIBKDWIGIKUFKL-UHFFFAOYSA-N 1,2,2-trichloroethanol Chemical compound OC(Cl)C(Cl)Cl NIBKDWIGIKUFKL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 235000021374 legumes Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- OKLCLELNELHMEB-UHFFFAOYSA-N 1-chloro-2-[1,2,2,2-tetrachloro-1-(4-chlorophenyl)ethyl]benzene Chemical compound C1=CC(Cl)=CC=C1C(Cl)(C(Cl)(Cl)Cl)C1=CC=CC=C1Cl OKLCLELNELHMEB-UHFFFAOYSA-N 0.000 description 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
- ZDYJWDIWLRZXDB-UHFFFAOYSA-N 2,2-(2-Chlorophenyl-4'-chlorophenyl)-1,1-dichloroethene Chemical group C=1C=CC=C(Cl)C=1C(=C(Cl)Cl)C1=CC=C(Cl)C=C1 ZDYJWDIWLRZXDB-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- -1 inoctane Chemical compound 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- NEMFQSKAPLGFIP-UHFFFAOYSA-N magnesiosodium Chemical compound [Na].[Mg] NEMFQSKAPLGFIP-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/78—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by condensation or crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL89274 | 1989-02-13 | ||
| IL8927489A IL89274A (en) | 1989-02-13 | 1989-02-13 | Process for preparing environmentally safe dicofol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02240035A true JPH02240035A (ja) | 1990-09-25 |
Family
ID=11059684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2031306A Pending JPH02240035A (ja) | 1989-02-13 | 1990-02-09 | 環境的に安全なジコホールの製造方法とその組成物 |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009093487A1 (ja) * | 2008-01-25 | 2009-07-30 | Daikin Industries, Ltd. | オレフィン－アルコール共沸混合物の分離方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL89274A (en) * | 1989-02-13 | 1994-04-12 | Agan Chemical Manufacturers | Process for preparing environmentally safe dicofol |
| DE69017965T2 (de) * | 1989-07-18 | 1995-11-16 | Elf Atochem S.A., Puteaux, Hauts-De-Seine | Verfahren zur Reinigung von 1,1-bis(4-chlorphenyl)-2,2,2-trichlorethanol. |
| JP2931096B2 (ja) * | 1990-06-22 | 1999-08-09 | エルフ アトケム ソシエテ アノニム | １，１―ビス（クロロフェニル）―２，２，２―トリクロロエタノールの合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2812362A (en) * | 1955-10-12 | 1957-11-05 | Rohm & Haas | Preparation of bis (chlorophenyl)-trichloroethanol |
| EP0065354B1 (en) * | 1981-05-12 | 1985-07-03 | Imperial Chemical Industries Plc | Process for the preparation of 1,1-bis phenyl-2-haloalkan-1-ols |
| US4705902A (en) * | 1985-10-03 | 1987-11-10 | Rohm And Haas Company | DDTR-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol |
| IL89274A (en) * | 1989-02-13 | 1994-04-12 | Agan Chemical Manufacturers | Process for preparing environmentally safe dicofol |
-
1989
- 1989-02-13 IL IL8927489A patent/IL89274A/en not_active IP Right Cessation
-
1990
- 1990-01-22 EP EP90101212A patent/EP0383054B1/en not_active Expired - Lifetime
- 1990-01-22 DE DE69020377T patent/DE69020377T2/de not_active Expired - Fee Related
- 1990-01-22 ES ES90101212T patent/ES2073461T3/es not_active Expired - Lifetime
- 1990-01-22 AT AT90101212T patent/ATE124384T1/de not_active IP Right Cessation
- 1990-01-30 IN IN90/CAL/90A patent/IN170240B/en unknown
- 1990-02-09 JP JP2031306A patent/JPH02240035A/ja active Pending
- 1990-02-13 BR BR909000709A patent/BR9000709A/pt not_active IP Right Cessation
- 1990-11-08 US US07/611,396 patent/US5118881A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009093487A1 (ja) * | 2008-01-25 | 2009-07-30 | Daikin Industries, Ltd. | オレフィン－アルコール共沸混合物の分離方法 |
| JP2009173588A (ja) * | 2008-01-25 | 2009-08-06 | Daikin Ind Ltd | オレフィン−アルコール共沸混合物の分離方法 |
| US8143440B2 (en) | 2008-01-25 | 2012-03-27 | Daikin Industries, Ltd. | Method for separation of olefin-alcohol azeotropic mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2073461T3 (es) | 1995-08-16 |
| IN170240B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-02-29 |
| BR9000709A (pt) | 1991-01-22 |
| DE69020377D1 (de) | 1995-08-03 |
| IL89274A (en) | 1994-04-12 |
| IL89274A0 (en) | 1989-09-10 |
| EP0383054A3 (en) | 1992-01-29 |
| US5118881A (en) | 1992-06-02 |
| EP0383054A2 (en) | 1990-08-22 |
| ATE124384T1 (de) | 1995-07-15 |
| EP0383054B1 (en) | 1995-06-28 |
| DE69020377T2 (de) | 1995-12-21 |
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