DE3149652A1 - Verfahren zur herstellung von chloracetaldehyddimethylacetal - Google Patents
Verfahren zur herstellung von chloracetaldehyddimethylacetalInfo
- Publication number
- DE3149652A1 DE3149652A1 DE19813149652 DE3149652A DE3149652A1 DE 3149652 A1 DE3149652 A1 DE 3149652A1 DE 19813149652 DE19813149652 DE 19813149652 DE 3149652 A DE3149652 A DE 3149652A DE 3149652 A1 DE3149652 A1 DE 3149652A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- chloroacetaldehyde
- reaction mixture
- distilled
- vinyl acetate
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 13
- CRZJPEIBPQWDGJ-UHFFFAOYSA-N 2-chloro-1,1-dimethoxyethane Chemical compound COC(CCl)OC CRZJPEIBPQWDGJ-UHFFFAOYSA-N 0.000 claims description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- 238000005191 phase separation Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- -1 chloroacetaldehyde acetals Chemical class 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/54—Preparation of compounds having groups by reactions producing groups by addition of compounds to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/58—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813149652 DE3149652A1 (de) | 1981-12-15 | 1981-12-15 | Verfahren zur herstellung von chloracetaldehyddimethylacetal |
| US06/437,909 US4440959A (en) | 1981-12-15 | 1982-11-01 | Process for the manufacture of chloroacetaldehyde dimethyl acetal |
| CA000415055A CA1181101A (en) | 1981-12-15 | 1982-11-08 | Process for the manufacture of chloroacetaldehyde dimethyl acetal |
| JP57217900A JPS58105933A (ja) | 1981-12-15 | 1982-12-14 | クロルアセトアルデヒドジメチルアセタ−ルの製法 |
| DE8282111648T DE3262573D1 (en) | 1981-12-15 | 1982-12-15 | Process for the preparation of chloroacetaldehyde-dimethyl acetal |
| EP82111648A EP0081856B1 (de) | 1981-12-15 | 1982-12-15 | Verfahren zur Herstellung von Chloracetaldehyddimethylacetal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813149652 DE3149652A1 (de) | 1981-12-15 | 1981-12-15 | Verfahren zur herstellung von chloracetaldehyddimethylacetal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3149652A1 true DE3149652A1 (de) | 1983-06-23 |
Family
ID=6148790
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813149652 Withdrawn DE3149652A1 (de) | 1981-12-15 | 1981-12-15 | Verfahren zur herstellung von chloracetaldehyddimethylacetal |
| DE8282111648T Expired DE3262573D1 (en) | 1981-12-15 | 1982-12-15 | Process for the preparation of chloroacetaldehyde-dimethyl acetal |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282111648T Expired DE3262573D1 (en) | 1981-12-15 | 1982-12-15 | Process for the preparation of chloroacetaldehyde-dimethyl acetal |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4440959A (en, 2012) |
| EP (1) | EP0081856B1 (en, 2012) |
| JP (1) | JPS58105933A (en, 2012) |
| CA (1) | CA1181101A (en, 2012) |
| DE (2) | DE3149652A1 (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4642389A (en) * | 1986-05-30 | 1987-02-10 | National Starch And Chemical Corporation | Process for the manufacture of chloroacetaldehyde dialkyl acetals |
| US4642390A (en) * | 1986-05-30 | 1987-02-10 | National Starch And Chemical Corporation | Process for the manufacture of acetals of chloroacetaldehyde |
| JPH02109467U (en, 2012) * | 1989-02-20 | 1990-08-31 | ||
| JPH02124082U (en, 2012) * | 1989-03-27 | 1990-10-12 | ||
| JPH0413643A (ja) * | 1990-05-07 | 1992-01-17 | Kureha Chem Ind Co Ltd | クロロアセタール類の製造方法 |
| JP2003073322A (ja) * | 2001-08-31 | 2003-03-12 | Kuraray Co Ltd | ハロゲノアセトアルデヒドジアルキルアセタールの製造方法 |
| DE102015204901A1 (de) | 2015-03-18 | 2016-09-22 | Wacker Chemie Ag | Verfahren zur Herstellung von Chloracetaldehydacetalen |
| CN107954869A (zh) * | 2017-11-22 | 2018-04-24 | 临沂优盛新材料科技有限公司 | 一种氯乙醛缩二甲醇的制备方法 |
| CN112010740A (zh) * | 2019-05-29 | 2020-12-01 | 石家庄欧特佳化工有限公司 | 一种由氯乙烯制备氯乙醛缩二甲醇的绿色工艺技术 |
| CN112047818A (zh) * | 2019-06-06 | 2020-12-08 | 石家庄欧特佳化工有限公司 | 一种由乙酸乙烯酯制备氯乙醛缩二烷基醇的绿色方法 |
| CN111875510B (zh) * | 2020-08-20 | 2022-12-06 | 厦门优孚利生物医药科技有限公司 | 一种制备氨基乙醛缩二甲醇的方法 |
| CN119569586A (zh) * | 2024-12-16 | 2025-03-07 | 新沂市永诚化工有限公司 | 一种氨基乙醛缩二甲醇的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2330570A (en) * | 1943-09-28 | Halo acetal | ||
| US2411826A (en) * | 1946-11-26 | Haloacetals | ||
| US3379772A (en) * | 1965-11-10 | 1968-04-23 | Gen Aniline & Film Corp | Process for the production of dimethyl chloroacetal |
| US4130592A (en) * | 1967-11-11 | 1978-12-19 | Dynamit Nobel Aktiengesellschaft | Method for the preparation of chloroacetaldehydedimethyl acetal |
-
1981
- 1981-12-15 DE DE19813149652 patent/DE3149652A1/de not_active Withdrawn
-
1982
- 1982-11-01 US US06/437,909 patent/US4440959A/en not_active Expired - Lifetime
- 1982-11-08 CA CA000415055A patent/CA1181101A/en not_active Expired
- 1982-12-14 JP JP57217900A patent/JPS58105933A/ja active Granted
- 1982-12-15 EP EP82111648A patent/EP0081856B1/de not_active Expired
- 1982-12-15 DE DE8282111648T patent/DE3262573D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6217982B2 (en, 2012) | 1987-04-21 |
| CA1181101A (en) | 1985-01-15 |
| JPS58105933A (ja) | 1983-06-24 |
| EP0081856A1 (de) | 1983-06-22 |
| EP0081856B1 (de) | 1985-03-13 |
| US4440959A (en) | 1984-04-03 |
| DE3262573D1 (en) | 1985-04-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |