CA1042011A - Tetrachloroethyl esters of unsaturated organic acids, their homopolymers, mixed polymers and the method for their preparation - Google Patents
Tetrachloroethyl esters of unsaturated organic acids, their homopolymers, mixed polymers and the method for their preparationInfo
- Publication number
- CA1042011A CA1042011A CA189,040A CA189040A CA1042011A CA 1042011 A CA1042011 A CA 1042011A CA 189040 A CA189040 A CA 189040A CA 1042011 A CA1042011 A CA 1042011A
- Authority
- CA
- Canada
- Prior art keywords
- general formula
- tetrachloroethyl
- cocl
- organic acids
- esters
- 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
- -1 Tetrachloroethyl esters Chemical class 0.000 title claims abstract description 17
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 8
- 235000005985 organic acids Nutrition 0.000 title claims abstract description 8
- 229920001519 homopolymer Polymers 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 8
- 229920000642 polymer Polymers 0.000 title abstract description 15
- 238000002360 preparation method Methods 0.000 title abstract description 8
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 6
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 4
- 150000007513 acids Chemical class 0.000 abstract description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract description 2
- 230000036647 reaction Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 2
- 229920002554 vinyl polymer Polymers 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 14
- 239000003708 ampul Substances 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229960001701 chloroform Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 230000009850 completed effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- AQGMJUDZABJUBH-OWOJBTEDSA-N (e)-4-chloro-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(Cl)=O AQGMJUDZABJUBH-OWOJBTEDSA-N 0.000 description 1
- ICBZSKCTKKUQSY-YUWZRIFDSA-N 4-[(1r,2s)-1-hydroxy-2-(methylamino)propyl]phenol;hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 ICBZSKCTKKUQSY-YUWZRIFDSA-N 0.000 description 1
- 101150094734 CCDC89 gene Proteins 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- VJSNXWFGYZTLAQ-TYYBGVCCSA-N Cl.OC(=O)\C=C\C(=O)OC(Cl)C(Cl)(Cl)Cl Chemical compound Cl.OC(=O)\C=C\C(=O)OC(Cl)C(Cl)(Cl)Cl VJSNXWFGYZTLAQ-TYYBGVCCSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HTLLFPHFIQBRPJ-OWOJBTEDSA-N bis(1,2,2,2-tetrachloroethyl) (e)-but-2-enedioate Chemical compound ClC(Cl)(Cl)C(Cl)OC(=O)\C=C\C(=O)OC(Cl)C(Cl)(Cl)Cl HTLLFPHFIQBRPJ-OWOJBTEDSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- FITUNPSTVBUGAH-UHFFFAOYSA-N chloroform;heptane Chemical compound ClC(Cl)Cl.CCCCCCC FITUNPSTVBUGAH-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA302,505A CA1044843A (en) | 1972-12-28 | 1978-05-03 | Method for producing mixed polymers of tetrachloroethyl esters of unsaturated organic acids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS903072A CS165291B1 (enrdf_load_html_response) | 1972-12-28 | 1972-12-28 | |
| CS903172A CS162192B1 (enrdf_load_html_response) | 1972-12-29 | 1972-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042011A true CA1042011A (en) | 1978-11-07 |
Family
ID=25746621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA189,040A Expired CA1042011A (en) | 1972-12-28 | 1973-12-27 | Tetrachloroethyl esters of unsaturated organic acids, their homopolymers, mixed polymers and the method for their preparation |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4994628A (enrdf_load_html_response) |
| CA (1) | CA1042011A (enrdf_load_html_response) |
| DE (1) | DE2363778A1 (enrdf_load_html_response) |
| FR (1) | FR2212322B1 (enrdf_load_html_response) |
| GB (1) | GB1400910A (enrdf_load_html_response) |
| IT (1) | IT1010530B (enrdf_load_html_response) |
-
1973
- 1973-12-19 GB GB5879073A patent/GB1400910A/en not_active Expired
- 1973-12-21 DE DE19732363778 patent/DE2363778A1/de active Pending
- 1973-12-24 IT IT842673A patent/IT1010530B/it active
- 1973-12-25 JP JP14387473A patent/JPS4994628A/ja active Pending
- 1973-12-27 FR FR7346465A patent/FR2212322B1/fr not_active Expired
- 1973-12-27 CA CA189,040A patent/CA1042011A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1400910A (en) | 1975-07-16 |
| IT1010530B (it) | 1977-01-20 |
| FR2212322B1 (enrdf_load_html_response) | 1977-08-12 |
| FR2212322A1 (enrdf_load_html_response) | 1974-07-26 |
| JPS4994628A (enrdf_load_html_response) | 1974-09-09 |
| DE2363778A1 (de) | 1974-10-03 |
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