CN103319372B - 一种制备浅色二环己基甲烷二异氰酸酯的方法 - Google Patents
一种制备浅色二环己基甲烷二异氰酸酯的方法 Download PDFInfo
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- CN103319372B CN103319372B CN201210084152.5A CN201210084152A CN103319372B CN 103319372 B CN103319372 B CN 103319372B CN 201210084152 A CN201210084152 A CN 201210084152A CN 103319372 B CN103319372 B CN 103319372B
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- methyl hydride
- dicyclohexyl methyl
- sulfydryl
- cyclohexyl
- reaction
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- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- -1 alcohol compound Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 43
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 43
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 26
- 238000004821 distillation Methods 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 21
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000012071 phase Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- DZHXXLDTPQDLRD-UHFFFAOYSA-N 4-[(4-sulfanylcyclohexyl)methyl]cyclohexan-1-ol Chemical compound OC1CCC(CC1)CC1CCC(CC1)S DZHXXLDTPQDLRD-UHFFFAOYSA-N 0.000 claims description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims description 3
- JYGRMXYSBUHFOS-UHFFFAOYSA-N 4-methylcyclohexane-1-thiol Chemical compound CC1CCC(S)CC1 JYGRMXYSBUHFOS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 4
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229940117389 dichlorobenzene Drugs 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 239000007792 gaseous phase Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FMAHOAYYHYQVID-UHFFFAOYSA-N 2-sulfanyl-5-[(4-sulfanylcyclohexyl)methyl]cyclohexan-1-ol Chemical compound OC1CC(CCC1S)CC1CCC(CC1)S FMAHOAYYHYQVID-UHFFFAOYSA-N 0.000 description 1
- NSOVWPQJUXRVNM-UHFFFAOYSA-N 4-[(4-hydroxycyclohexyl)methyl]-3-sulfanylcyclohexan-1-ol Chemical compound SC1C(CCC(C1)O)CC1CCC(CC1)O NSOVWPQJUXRVNM-UHFFFAOYSA-N 0.000 description 1
- GAASGTOOMWIDNB-UHFFFAOYSA-N 4-methylcyclohexane-1,2-diol Chemical compound CC1CCC(O)C(O)C1 GAASGTOOMWIDNB-UHFFFAOYSA-N 0.000 description 1
- REWFYZJFPHSHRW-UHFFFAOYSA-N 4-methylcyclohexane-1,2-dithiol Chemical compound CC1CCC(S)C(S)C1 REWFYZJFPHSHRW-UHFFFAOYSA-N 0.000 description 1
- HHQLOVPQADAUDW-UHFFFAOYSA-N 4-methylcyclohexane-1,3-diol Chemical compound CC1CCC(O)CC1O HHQLOVPQADAUDW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-AKLPVKDBSA-N Ammonia-N17 Chemical compound [17NH3] QGZKDVFQNNGYKY-AKLPVKDBSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QZQGLEDPDWGLIX-UHFFFAOYSA-N OC1C(CCC(C1)S)CC1CCC(CC1)O Chemical compound OC1C(CCC(C1)S)CC1CCC(CC1)O QZQGLEDPDWGLIX-UHFFFAOYSA-N 0.000 description 1
- MDRZXTXDGRYINZ-UHFFFAOYSA-N OC1C(CCC(C1)S)CC1CCC(CC1)S Chemical compound OC1C(CCC(C1)S)CC1CCC(CC1)S MDRZXTXDGRYINZ-UHFFFAOYSA-N 0.000 description 1
- UWXWZTQVWWMRNW-UHFFFAOYSA-N OC1CC(CCC1S)CC1CCC(CC1)O Chemical compound OC1CC(CCC1S)CC1CCC(CC1)O UWXWZTQVWWMRNW-UHFFFAOYSA-N 0.000 description 1
- ZRKGKQNJYQFCJV-UHFFFAOYSA-N SC1C(CCC(C1)O)CC1CCC(CC1)S Chemical compound SC1C(CCC(C1)O)CC1CCC(CC1)S ZRKGKQNJYQFCJV-UHFFFAOYSA-N 0.000 description 1
- FGBIVMCIJBSLSI-UHFFFAOYSA-N SC1C(CCC(C1)S)C Chemical compound SC1C(CCC(C1)S)C FGBIVMCIJBSLSI-UHFFFAOYSA-N 0.000 description 1
- FCABTGXVXAZGLO-UHFFFAOYSA-N SC1CC(CCC1O)CC1CCC(CC1)O Chemical compound SC1CC(CCC1O)CC1CCC(CC1)O FCABTGXVXAZGLO-UHFFFAOYSA-N 0.000 description 1
- DGOBQDOPSOOTQH-UHFFFAOYSA-N SC1CC(CCC1O)CC1CCC(CC1)S Chemical compound SC1CC(CCC1O)CC1CCC(CC1)S DGOBQDOPSOOTQH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
醇类化合物含量(wt%) | NCO(%) | 色号 | |
实施例1 | 0.05 | 32.01 | 5# |
实施例2 | 0.10 | 32.00 | 7.5# |
实施例3 | 0.20 | 31.98 | 10# |
实施例4 | 0.50 | 31.95 | 25# |
Claims (9)
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CN201210084152.5A CN103319372B (zh) | 2012-03-19 | 2012-03-19 | 一种制备浅色二环己基甲烷二异氰酸酯的方法 |
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CN201210084152.5A CN103319372B (zh) | 2012-03-19 | 2012-03-19 | 一种制备浅色二环己基甲烷二异氰酸酯的方法 |
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CN103319372B true CN103319372B (zh) | 2014-11-05 |
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CN106554293B (zh) * | 2015-09-24 | 2018-04-20 | 万华化学集团股份有限公司 | 一种制备无色或浅色多异氰酸酯的方法 |
CN106946741B (zh) * | 2017-04-26 | 2018-12-07 | 万华化学集团股份有限公司 | 一种二环己基甲烷二异氰酸酯的制备方法 |
CN109761855B (zh) * | 2018-12-20 | 2020-07-28 | 万华化学集团股份有限公司 | 一种制备异佛尔酮二异氰酸酯的方法 |
KR20230079440A (ko) | 2020-12-01 | 2023-06-07 | 완후아 케미컬 그룹 코., 엘티디 | 폴리이소시아네이트 조성물, 이의 제조 방법 및 응용 |
CN112592457B (zh) * | 2020-12-01 | 2023-04-07 | 万华化学集团股份有限公司 | 一种多异氰酸酯组合物及其制备方法和应用 |
WO2024103323A1 (zh) * | 2022-11-17 | 2024-05-23 | 万华化学集团股份有限公司 | 一种异氰酸酯组合物及其制备方法和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0581100B1 (en) * | 1992-07-23 | 1996-09-04 | Bayer Corporation | Color reduction of polymethylene polyphenyl polyisocyanates |
CN101429139A (zh) * | 2008-12-18 | 2009-05-13 | 宁波万华聚氨酯有限公司 | 二环己基甲烷二异氰酸酯及其中间体的制备方法 |
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WO2011130907A1 (zh) * | 2010-04-21 | 2011-10-27 | 烟台万华聚氨酯股份有限公司 | 一种通过界面光气化反应制备异氰酸酯的方法 |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0581100B1 (en) * | 1992-07-23 | 1996-09-04 | Bayer Corporation | Color reduction of polymethylene polyphenyl polyisocyanates |
CN101429139A (zh) * | 2008-12-18 | 2009-05-13 | 宁波万华聚氨酯有限公司 | 二环己基甲烷二异氰酸酯及其中间体的制备方法 |
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