DE2802292C3 - Bis-Tetrahalophthalate und Verfahren zu deren Herstellung - Google Patents
Bis-Tetrahalophthalate und Verfahren zu deren HerstellungInfo
- Publication number
- DE2802292C3 DE2802292C3 DE2802292A DE2802292A DE2802292C3 DE 2802292 C3 DE2802292 C3 DE 2802292C3 DE 2802292 A DE2802292 A DE 2802292A DE 2802292 A DE2802292 A DE 2802292A DE 2802292 C3 DE2802292 C3 DE 2802292C3
- Authority
- DE
- Germany
- Prior art keywords
- bis
- carbon atoms
- reaction
- tetrahalophthalates
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000003063 flame retardant Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- -1 N-Substituted Tetrabromophthalimide Chemical class 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZLJNHKUVTZKFRC-UHFFFAOYSA-N NCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC Chemical compound NCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC ZLJNHKUVTZKFRC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical group CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- PQPDJEKDXRVUCH-UHFFFAOYSA-N 2-azaniumylethylazanium 2,3,4,5-tetrabromo-6-[2-(2,3,4,5-tetrabromo-6-carboxylatobenzoyl)oxyethoxycarbonyl]benzoate Chemical compound [NH3+]CC[NH3+].[O-]C(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OCCOC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C([O-])=O PQPDJEKDXRVUCH-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- AOFARNWWIBEOCC-UHFFFAOYSA-N CC(N)CN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC Chemical compound CC(N)CN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC AOFARNWWIBEOCC-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- BLEOWQIGEPJXHW-UHFFFAOYSA-N NCCCCCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC Chemical compound NCCCCCCN.COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OC BLEOWQIGEPJXHW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical group OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical group CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/759,949 US4140862A (en) | 1977-01-17 | 1977-01-17 | Salts of diamines and tetrahalophthalates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2802292A1 DE2802292A1 (de) | 1978-07-20 |
| DE2802292B2 DE2802292B2 (de) | 1980-06-04 |
| DE2802292C3 true DE2802292C3 (de) | 1981-02-05 |
Family
ID=25057562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2802292A Expired DE2802292C3 (de) | 1977-01-17 | 1978-01-17 | Bis-Tetrahalophthalate und Verfahren zu deren Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4140862A (en, 2012) |
| BE (1) | BE862992A (en, 2012) |
| CA (1) | CA1115712A (en, 2012) |
| DE (1) | DE2802292C3 (en, 2012) |
| FR (1) | FR2377371A1 (en, 2012) |
| GB (1) | GB1565791A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666958A (en) * | 1982-01-07 | 1987-05-19 | Ppg Industries, Inc. | Polymeric compositions containing polyhalophthalimidoalkyl-functional carbonates |
| US4515964A (en) * | 1982-01-07 | 1985-05-07 | Ppg Industries, Inc. | Polyhalophthalimidoalkyl-functional carbonates |
| US4414396A (en) * | 1982-01-07 | 1983-11-08 | Ppg Industries, Inc. | Polyhalophthalimidoalkyl-functional carbonates and haloformates |
| US4467062A (en) * | 1983-08-18 | 1984-08-21 | Ethyl Corporation | Flame retarded polyethylene terephthalate blends |
| CN1041718C (zh) * | 1994-11-14 | 1999-01-20 | 山东建筑材料工业学院 | 白色n,n'－烷撑双(四溴邻苯二甲酰胺)系列化合物的制备方法 |
| US6180560B1 (en) | 1997-08-14 | 2001-01-30 | Ricoh Company, Ltd. | Thermosensitive recording material and color developer compound therefor |
| FR2767283B1 (fr) * | 1997-08-14 | 2001-11-23 | Ricoh Kk | Materiau d'enregistrement thermosensible, developpateur de couleur pour celui-ci, et procede de preparation de ce developpateur de couleur |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS536857B2 (en, 2012) * | 1972-08-16 | 1978-03-11 | ||
| US4092345A (en) * | 1976-07-30 | 1978-05-30 | Cities Service Company | (Cyclo)alkylenediammonium-bis-tetrahalophthalates |
-
1977
- 1977-01-17 US US05/759,949 patent/US4140862A/en not_active Expired - Lifetime
-
1978
- 1978-01-13 CA CA294,951A patent/CA1115712A/en not_active Expired
- 1978-01-17 GB GB1778/78A patent/GB1565791A/en not_active Expired
- 1978-01-17 FR FR7801271A patent/FR2377371A1/fr active Granted
- 1978-01-17 BE BE184390A patent/BE862992A/xx not_active IP Right Cessation
- 1978-01-17 DE DE2802292A patent/DE2802292C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1565791A (en) | 1980-04-23 |
| FR2377371A1 (fr) | 1978-08-11 |
| FR2377371B1 (en, 2012) | 1981-08-07 |
| US4140862A (en) | 1979-02-20 |
| DE2802292A1 (de) | 1978-07-20 |
| CA1115712A (en) | 1982-01-05 |
| DE2802292B2 (de) | 1980-06-04 |
| BE862992A (fr) | 1978-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ETHYL CORP., 23219 RICHMOND, VA., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: BOEHMERT, A., DIPL.-ING. HOORMANN, W., DIPL.-ING. DR.-ING. GODDAR, H., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW. STAHLBERG, W. KUNTZE, W., RECHTSANW., 2800 BREMEN |
|
| 8339 | Ceased/non-payment of the annual fee |