KR100995840B1 - 시클로알킬 알킬 에테르 화합물의 제조방법 - Google Patents
시클로알킬 알킬 에테르 화합물의 제조방법 Download PDFInfo
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- KR100995840B1 KR100995840B1 KR1020087012008A KR20087012008A KR100995840B1 KR 100995840 B1 KR100995840 B1 KR 100995840B1 KR 1020087012008 A KR1020087012008 A KR 1020087012008A KR 20087012008 A KR20087012008 A KR 20087012008A KR 100995840 B1 KR100995840 B1 KR 100995840B1
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- Prior art keywords
- solvent
- group
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- extraction
- ion exchange
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 41
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- 230000008569 process Effects 0.000 title description 5
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 13
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
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- 238000012360 testing method Methods 0.000 description 13
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 9
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- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 8
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
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Abstract
Description
분획(유출온도) | 수득량(부) | 기체크로마토그래피의 분석결과(%) |
Fr.1(100℃미만) | 77.1 | 요오드화메틸(88.3), CPME(3.3) |
Fr.2(100∼106℃) | 3.40 | 요오드화메틸(58.7), CPME(40.9) |
Fr.3(106℃) | 70.0 | CPME(99.8) |
잔분(106℃초과) | 53.5 | CPME(64.4), CPL(19.6) |
유지류 | 실시예1 |
니혼코우사쿠유 프레스오일 No.660 | 신속하게 용해 |
이데미츠 마그플러스 LA-15 절삭유 | 신속하게 용해 |
로진 | 신속하게 용해 |
스카이왁스 415 | 50℃ 20분에서 용해 |
스테아린산 | 실온에서 서서히 용해 |
라우린산 | 신속하게 용해 |
도코산산 | 50℃ 20분에서 용해 |
유지류 | 비교예1 | 비교예2 |
니혼코우사쿠유 프레스오일 No.660 | 신속하게 용해 | 신속하게 용해 |
이데미츠 마그플러스 LA-15 절삭유 | 신속하게 용해 | 신속하게 용해 |
로진 | 교반에 의한 백탁 | 신속하게 용해 |
스카이왁스 415 | 가열하여도 백탁 그대로임 | 50℃80분에서 용해 |
스테아린산 | 50℃40분에서 용해 | 실온에서 부분적으로 용해, 가열하여 완전히 용해 |
라우린산 | 실온에서 부분적으로 용해, 가열하여 완전히 용해 | 신속하게 용해 |
도코산산 | 50℃60분에서 용해 | 50℃30분에서 용해 |
실시예11 | 실시예12 | 비교예10 | 비교예11 | |
박리제 | CPME | CPME | i-PrOH | BnOH |
침지온도(℃) | 70 | 70 | 70 | 70 |
초음파처리 | 없음 | 있음 | 있음 | 있음 |
박리시간 | 48분 | 24분 | 60분 이상 | 60분 이상 |
산성이온교환수지 | 수분 함유량 (중량%) |
CPME의 단리 수율(%) | MeOH의 전환율 (%) |
반응선택율 (%) |
|
실시예14 | A2 | 1.5 | 75.5 | 83.6 | 94.9 |
실시예15 | B2 | 1.5 | 68.9 | 76.2 | 96.2 |
실시예16 | C2 | 1.5 | 39.9 | 62.2 | 67.5 |
실시예17 | D2 | 1.5 | 39.4 | 51.9 | 80.9 |
실시예18 | E2 | 1.5 | 50.1 | 64.1 | 82.4 |
실시예19 | F2 | 1.5 | 60.0 | 68.3 | 92.5 |
실시예20 | G2 | 1.5 | 56.2 | 62.7 | 95.3 |
비교예14 | A1 | 45∼50 | - | 0.7 | 82.3 |
비교예15 | B1 | 55∼60 | - | 0.6 | 86.5 |
비교예16 | C1 | 58∼68 | - | 0.5 | 80.2 |
비교예17 | D1 | 46∼52 | - | 0.3 | 64.3 |
비교예18 | E1 | 37∼43 | - | 0.4 | 74.3 |
비교예19 | F1 | 50 | - | 0.6 | 79.6 |
비교예20 | G1 | 46 | - | 0.5 | 75.5 |
경과시간(hr) | 수분 함유량(ppm) | |
CPME | THF | |
0 | 962 | 1024 |
0.5 | 391 | 532 |
1.0 | 249 | 412 |
1.5 | 151 | 310 |
2.0 | 98 | 278 |
2.5 | 76 | 265 |
3.0 | 54 | 258 |
4.0 | 44 | 242 |
경과시간 | 실시예16 |
과산화물(ppm) | |
28 | 1 |
56 | 5 |
84 | 5 |
Claims (3)
- 식(1): R1-O-R2[식(1)에서, R1은 치환기를 가지고 있어도 좋은 시클로펜틸기 또는 치환기를 가지고 있어도 좋은 시클로헥실기를 표시하고, R2는 치환기를 가지고 있어도 좋은 탄소수 1~10의 알킬기 또는 치환기를 가지고 있어도 좋은 탄소수 3~8의 시클로알킬기를 표시한다. 상기 치환기는 탄소수 1~4의 알킬기, 탄소수 1~4의 알콕시기, 탄소수 1~4의 알킬티오기, 할로겐원자 중 1종 이상이다.]으로 표시되는 시클로알킬 알킬 에테르 화합물의 제조방법으로서,수분 함유량이 5중량% 이하인 산성 이온교환수지의 존재하에, 지환식 올레핀과 알콜류를 기체상태에서 반응시키는 것을 특징으로 하는 시클로알킬 알킬 에테르 화합물의 제조방법.
- 식(2): R1-O-R3[식(2)에서, R1은 치환기를 가지고 있어도 좋은 시클로펜틸기 또는 치환기를 가지고 있어도 좋은 시클로헥실기를 표시하고, R3은 탄소수 1~10의 알킬기 또는 탄소수 3~8의 시클로알킬기를 표시한다. 상기 치환기는 탄소수 1~4의 알킬기, 탄소수 1~4의 알콕시기, 탄소수 1~4의 알킬티오기, 할로겐원자 중 1종 이상이다.]으로 표시되는 시클로알킬 알킬 에테르 화합물의 제조방법으로서,수분 함유량이 5중량% 이하인 산성 이온교환수지의 존재하에, 지환식 올레핀과 알콜류를 기체상태에서 반응시키는 것을 특징으로 하는 시클로알킬 알킬 에테르 화합물의 제조방법.
- 식(3): R4-O-R3[식(3)에서, R3은 탄소수 1~10의 알킬기 또는 탄소수 3~8의 시클로알킬기를 표시하고, R4는 시클로펜틸기를 표시한다.]으로 표시되는 시클로알킬 알킬 에테르 화합물의 제조방법으로서,수분 함유량이 5중량% 이하인 산성 이온교환수지의 존재하에, 지환식 올레핀과 알콜류를 기체상태에서 반응시키는 것을 특징으로 하는 시클로알킬 알킬 에테르 화합물의 제조방법.
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JPJP-P-2001-00196766 | 2001-06-28 | ||
JP2001196766 | 2001-06-28 | ||
JP2001332009 | 2001-10-30 | ||
JPJP-P-2001-00332009 | 2001-10-30 | ||
JPJP-P-2001-00377483 | 2001-12-11 | ||
JP2001377483 | 2001-12-11 | ||
JP2002094269 | 2002-03-29 | ||
JPJP-P-2002-00094269 | 2002-03-29 | ||
JPJP-P-2002-00123832 | 2002-04-25 | ||
JP2002123832 | 2002-04-25 | ||
PCT/JP2002/006501 WO2003002500A1 (fr) | 2001-06-28 | 2002-06-27 | Solvants contenant des cycloalkyl alkyl ethers et procede de production de ces ethers |
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KR1020097015801A KR100970133B1 (ko) | 2001-06-28 | 2002-06-27 | 시클로알킬 알킬 에테르 화합물의 제조방법 |
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KR20037017037A KR20040012990A (ko) | 2001-06-28 | 2002-06-27 | 시클로알킬 알킬 에테르 화합물을 함유하여 이루어지는용제 및 시클로알킬 알킬 에테르 화합물의 제조방법 |
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KR1020087012008A KR20080049149A (ko) | 2001-06-28 | 2002-06-27 | 시클로알킬 알킬 에테르 화합물의 제조방법 |
KR20037017037A KR20040012990A (ko) | 2001-06-28 | 2002-06-27 | 시클로알킬 알킬 에테르 화합물을 함유하여 이루어지는용제 및 시클로알킬 알킬 에테르 화합물의 제조방법 |
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EP (2) | EP2279995B1 (ko) |
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CN (1) | CN100509734C (ko) |
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JPWO2003002500A1 (ja) | 2004-10-14 |
EP1405840A4 (en) | 2006-05-17 |
JP2008156367A (ja) | 2008-07-10 |
KR20090085711A (ko) | 2009-08-07 |
US20080312125A1 (en) | 2008-12-18 |
KR100970133B1 (ko) | 2010-07-14 |
IN2003KO01661A (ko) | 2006-03-17 |
US7494962B2 (en) | 2009-02-24 |
JP4140523B2 (ja) | 2008-08-27 |
KR20040012990A (ko) | 2004-02-11 |
US8017813B2 (en) | 2011-09-13 |
WO2003002500A1 (fr) | 2003-01-09 |
EP1405840A1 (en) | 2004-04-07 |
CN100509734C (zh) | 2009-07-08 |
JP4178483B2 (ja) | 2008-11-12 |
EP2279995A3 (en) | 2012-01-11 |
EP2279995A2 (en) | 2011-02-02 |
JP2008179638A (ja) | 2008-08-07 |
EP1405840B1 (en) | 2014-08-20 |
EP2279995B1 (en) | 2013-09-18 |
KR20080049149A (ko) | 2008-06-03 |
CN1543449A (zh) | 2004-11-03 |
US20050065060A1 (en) | 2005-03-24 |
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