DE1593588C3 - Verfahren zur Herstellung von m- und p-Xylylendiisocyanat - Google Patents
Verfahren zur Herstellung von m- und p-XylylendiisocyanatInfo
- Publication number
- DE1593588C3 DE1593588C3 DE1593588A DE1593588A DE1593588C3 DE 1593588 C3 DE1593588 C3 DE 1593588C3 DE 1593588 A DE1593588 A DE 1593588A DE 1593588 A DE1593588 A DE 1593588A DE 1593588 C3 DE1593588 C3 DE 1593588C3
- Authority
- DE
- Germany
- Prior art keywords
- phosgenation
- phosgene
- xylylenediamine
- temperature
- products
- 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 12
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 title claims description 6
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 28
- 239000006227 byproduct Substances 0.000 claims description 23
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- -1 Aromatic isocyanates Chemical class 0.000 claims description 8
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 6
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 6
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 6
- 239000012948 isocyanate Substances 0.000 claims 6
- 150000004985 diamines Chemical class 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- 150000002513 isocyanates Chemical class 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 230000009615 deamination Effects 0.000 claims 1
- 238000006481 deamination reaction Methods 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 229940117389 dichlorobenzene Drugs 0.000 claims 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 239000011347 resin Chemical class 0.000 claims 1
- 229920005989 resin Chemical class 0.000 claims 1
- 239000012261 resinous substance Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5482365 | 1965-09-06 | ||
| JP5490966A JPS4947736B1 (en:Method) | 1966-08-20 | 1966-08-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1593588A1 DE1593588A1 (de) | 1971-12-23 |
| DE1593588B2 DE1593588B2 (de) | 1973-10-25 |
| DE1593588C3 true DE1593588C3 (de) | 1974-05-22 |
Family
ID=26395635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1593588A Expired DE1593588C3 (de) | 1965-09-06 | 1966-09-01 | Verfahren zur Herstellung von m- und p-Xylylendiisocyanat |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3470227A (en:Method) |
| DE (1) | DE1593588C3 (en:Method) |
| GB (1) | GB1162155A (en:Method) |
| NL (1) | NL6612511A (en:Method) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4422976A (en) * | 1981-04-07 | 1983-12-27 | Mitsui Toatsu Chemicals, Incorporated | Continuous preparation of organic isocyanates |
| JP2790513B2 (ja) * | 1989-02-23 | 1998-08-27 | 三井化学株式会社 | キシリレンジイソシアネートの製造方法 |
| DE102004032871A1 (de) * | 2004-07-07 | 2006-02-09 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyisocyanaten durch adiabate Phosgenierung von primären Aminen |
| CN105218422B (zh) * | 2015-10-16 | 2017-03-22 | 万华化学集团股份有限公司 | 一种异氰酸酯的制备方法 |
| FR3049950B1 (fr) | 2016-04-07 | 2020-09-25 | Vencorex France | Procede de preparation des xylylene diisocyanates xdi |
| KR102370108B1 (ko) * | 2017-09-11 | 2022-03-04 | 한화솔루션 주식회사 | 지방족 이소시아네이트의 제조방법 |
| CN108101810A (zh) * | 2017-12-18 | 2018-06-01 | 甘肃银光聚银化工有限公司 | 一种直接光气化法制备苯二亚甲基二异氰酸酯的方法 |
| CN108484447A (zh) * | 2018-05-28 | 2018-09-04 | 江阴市万丰化工物资有限公司 | 间苯二亚甲基二异氰酸酯的合成方法 |
| EP3750868A1 (de) | 2019-06-11 | 2020-12-16 | Covestro Deutschland AG | Verfahren zur herstellung einer amin-hydrochlorid-suspension |
| CN111718282B (zh) * | 2020-06-30 | 2022-08-05 | 万华化学集团股份有限公司 | 一种基于成盐光气化制备低氯代杂质含量异氰酸酯的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2642449A (en) * | 1953-06-16 | Preparation of polyisocyanates | ||
| US2953590A (en) * | 1953-04-11 | 1960-09-20 | Mobay Chemical Corp | Production of alkylene diisocyanates |
| US3381025A (en) * | 1964-06-29 | 1968-04-30 | Hodogaya Chemical Co Ltd | Process for preparing isocyanates |
-
1966
- 1966-09-01 DE DE1593588A patent/DE1593588C3/de not_active Expired
- 1966-09-02 GB GB39403/66A patent/GB1162155A/en not_active Expired
- 1966-09-06 US US577170A patent/US3470227A/en not_active Expired - Lifetime
- 1966-09-06 NL NL6612511A patent/NL6612511A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1162155A (en) | 1969-08-20 |
| DE1593588A1 (de) | 1971-12-23 |
| NL6612511A (en:Method) | 1967-03-07 |
| US3470227A (en) | 1969-09-30 |
| DE1593588B2 (de) | 1973-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |