CN1096510A - 甲基丙烯酸烷基氨基烷酯的制造方法 - Google Patents
甲基丙烯酸烷基氨基烷酯的制造方法 Download PDFInfo
- Publication number
- CN1096510A CN1096510A CN 93111314 CN93111314A CN1096510A CN 1096510 A CN1096510 A CN 1096510A CN 93111314 CN93111314 CN 93111314 CN 93111314 A CN93111314 A CN 93111314A CN 1096510 A CN1096510 A CN 1096510A
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- CN
- China
- Prior art keywords
- catalyzer
- reaction
- stopper
- zinc
- product
- 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.)
- Granted
Links
- -1 alkylaminoalkyl methacrylate Chemical compound 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 8
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims abstract description 5
- 239000011667 zinc carbonate Substances 0.000 claims abstract description 5
- 235000004416 zinc carbonate Nutrition 0.000 claims abstract description 5
- 229910000010 zinc carbonate Inorganic materials 0.000 claims abstract description 5
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004246 zinc acetate Substances 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- WNHHYBRJPHLYGD-UHFFFAOYSA-N N=O.N1(CCCCC1)O Chemical group N=O.N1(CCCCC1)O WNHHYBRJPHLYGD-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 239000011787 zinc oxide Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 11
- 238000006116 polymerization reaction Methods 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 6
- 230000005764 inhibitory process Effects 0.000 abstract description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract description 6
- 239000011592 zinc chloride Substances 0.000 abstract description 3
- 235000005074 zinc chloride Nutrition 0.000 abstract description 3
- 150000002148 esters Chemical group 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 150000003751 zinc Chemical class 0.000 abstract 1
- 235000013904 zinc acetate Nutrition 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical group C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- GDEBSAWXIHEMNF-UHFFFAOYSA-O cupferron Chemical compound [NH4+].O=NN([O-])C1=CC=CC=C1 GDEBSAWXIHEMNF-UHFFFAOYSA-O 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZMVHTLOQSTVDFE-UHFFFAOYSA-N methanol;methyl 2-methylprop-2-enoate Chemical compound OC.COC(=O)C(C)=C ZMVHTLOQSTVDFE-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
回用次数 | 1 | 2 | 3 | 4 | 5 |
收率(%) | 92.8 | 91.6 | 92.3 | 92.0 | 92.1 |
纯度(%) | 99.4 | 99.6 | 99.4 | 98.9 | 99.2 |
阻聚剂名称 | 高聚物生成量(g) |
对苯二酚 | 9.1 |
苯基-α-萘胺 | 13.1 |
对苯二酚单甲醚 | 7.1 |
铜铁试剂 | 13.1 |
吩噻嗪 | 6.6 |
哌啶醇氮氧自由基(本发明) | 4.1 |
哌啶氮氧自由基亚磷酸酯(本发明) | 3.7 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN93111314A CN1039410C (zh) | 1993-06-18 | 1993-06-18 | 甲基丙燃酸烷基氨基烷酯的制造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN93111314A CN1039410C (zh) | 1993-06-18 | 1993-06-18 | 甲基丙燃酸烷基氨基烷酯的制造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1096510A true CN1096510A (zh) | 1994-12-21 |
CN1039410C CN1039410C (zh) | 1998-08-05 |
Family
ID=4989111
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN93111314A Expired - Lifetime CN1039410C (zh) | 1993-06-18 | 1993-06-18 | 甲基丙燃酸烷基氨基烷酯的制造方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1039410C (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102372644A (zh) * | 2010-08-23 | 2012-03-14 | 歙县元一科技有限公司 | 一种甲基丙烯酸二甲基氨基乙酯生产工艺 |
CN103221381A (zh) * | 2010-09-23 | 2013-07-24 | 巴斯夫欧洲公司 | N,n-取代氨基醇的(甲基)丙烯酸酯的制备方法 |
JP2017048172A (ja) * | 2015-09-03 | 2017-03-09 | 東亞合成株式会社 | 単官能(メタ)アクリレートの製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3642877A (en) * | 1968-12-27 | 1972-02-15 | Du Pont | Process for the preparation of dimethylaminoethyl methacrylate |
JPS5760331B2 (zh) * | 1972-03-06 | 1982-12-18 | Nippon Shokubai Kagaku Kogyo Kk | |
US4059617A (en) * | 1976-04-29 | 1977-11-22 | American Cyanamid Company | Synthesis of dimethylaminoethyl methylmethacrylate |
-
1993
- 1993-06-18 CN CN93111314A patent/CN1039410C/zh not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102372644A (zh) * | 2010-08-23 | 2012-03-14 | 歙县元一科技有限公司 | 一种甲基丙烯酸二甲基氨基乙酯生产工艺 |
CN103221381A (zh) * | 2010-09-23 | 2013-07-24 | 巴斯夫欧洲公司 | N,n-取代氨基醇的(甲基)丙烯酸酯的制备方法 |
CN103221381B (zh) * | 2010-09-23 | 2015-08-05 | 巴斯夫欧洲公司 | N,n-取代氨基醇的(甲基)丙烯酸酯的制备方法 |
JP2017048172A (ja) * | 2015-09-03 | 2017-03-09 | 東亞合成株式会社 | 単官能(メタ)アクリレートの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
CN1039410C (zh) | 1998-08-05 |
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Owner name: CHINA PETROCHEMICAL CORPORATION Free format text: FORMER OWNER: SINOPEC QILU PETRO-CHEMICAL CORP.; INST. OF QILU PETRO-CHEMICAL INDUSTRY CO. Effective date: 20071228 |
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Effective date of registration: 20071228 Address after: Linzi Zibo District, Shandong province Sinopec Qilu Branch of science and technology Patentee after: China Petrochemical Group Corp. Address before: Zibo City, Shandong Province, 124 mailbox Zip code: 255436 Patentee before: Qilu Petrochemical Company of China Petrochemical Corp. Patentee before: Qilu Petrochemical Company Research Institute |
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C17 | Cessation of patent right | ||
CX01 | Expiry of patent term |
Expiration termination date: 20130618 Granted publication date: 19980805 |