isoprenen.

/ˈʌɪsəʊpriːn/

Etymology: < iso- comb. form, perhaps + pr- + -ene (in propylene n.).

2-Methyl-1, 3-butadiene, CH₂:C(CH₃)CH:CH₂, a colourless liquid obtained by the destructive distillation of rubber and from petroleum and used in the manufacture of certain synthetic rubbers.

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the world > matter > chemistry > organic chemistry > organic compounds > [noun] > isoprenes

isoprene1860

1860 C. G. Williams in Philos. Trans. (Royal Soc.) 150 244 I have given the substance thus examined the name of isoprene.

1860 C. G. Williams in Philos. Trans. (Royal Soc.) 150 249 Isoprene combines explosively with bromine.

1860 C. G. Williams in Philos. Trans. (Royal Soc.) 150 255 The isolation of isoprene, C¹⁰H⁸.

1862 W. A. Miller Elem. Chem., Org. (ed. 2) 591 To the most volatile of these [hydrocarbons] Williams has given the name of Isoprene.

1867 C. L. Bloxam Chemistry 481 Heated in a retort, caoutchouc is decomposed into several hydrocarbons, one of which, called isoprene, boils at about 100°F.

1900 S. P. Sadtler Handbk. Industr. Org. Chem. (ed. 3) 99 On submitting it [sc. caoutchouc] to destructive distillation it yields..isoprene.

1906 Westm. Gaz. 8 Sept. 10/2 In forming caoutchouc from isoprene, the great problem is already practically solved.

1957 Technology July 176/3 By the use of Ziegler catalysts..Goodrich-Gulf were able to synthesize from isoprene a polymer almost identical with natural rubber.

1972 P. Wiseman Introd. Industr. Org. Chem. vii. 253 More important than high molecular weight homopolymers of isobutene are copolymers with 1·5 to 4·5% of isoprene, known as butyl rubber.

Compounds

isoprene rule n. the rule that the carbon skeleton of a terpene is made up of isoprene units linked together.

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the world > matter > chemistry > organic chemistry > organic compounds > [noun] > isoprenes > isoprene rule

isoprene rule1931

1931 J. L. Simonsen Terpenes I. p. xii An apparent exception to the ‘isoprene rule’, the hydrocarbon, sylvestrene, has been shown not to be a plant product.

1971 J. D. Roberts et al. Org. Chem. xxix. 779 The empirical isoprene rule resulted from Ruzicka's observation that the majority of the terpene families could be considered as arising from head-to-tail combinations of isoprene units.

isoprene unit n. the arrangement of five carbon atoms found in the isoprene molecule (the single or double nature of the bonds between them being disregarded).

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the world > matter > chemistry > organic chemistry > organic compounds > [noun] > isoprenes > isoprene unit

isoprene unit1926

1926 C. K. Ingold in Proc. Leeds Philos. & Lit. Soc. (Sci. Sect.) I. 11 It is known..that the carbon skeletons of all terpenes of established constitution can empirically be built up from the skeleton of isoprene, the common product of thermal degradation of almost all terpenes. Divisibility into isoprene units may therefore be regarded as a necessary condition to be satisfied by the structure of any plant-synthesised terpene product.

1942 R. C. Fuson & H. R. Snyder Org. Chem. xxvii. 358 Caoutchouc is composed of the isoprene unit repeated over and over.

1942 R. C. Fuson & H. R. Snyder Org. Chem. xxvii. 358 The occurrence of isoprene units is so general that investigators of the structures of natural products generally consider the most probable formula of an unknown compound to be that which contains the maximum number of isoprene units.

1959 L. Ruzicka in Proc. Chem. Soc. 343/2 Up to 1921, the idea that the higher terpenes are structurally composed of isoprene units was not used as an accepted working hypothesis.

1967 Nature 18 Nov. 642/2 The occurrence of a series of hydrocarbons, with structures based on the C₅H₈ isoprene unit, has been invoked as evidence for life-forms in Pre-Cambrian times.

This entry has not yet been fully updated (first published 1933; most recently modified version published online March 2020).

单词	isoprene
释义	isoprenen. /ˈʌɪsəʊpriːn/ Etymology: < iso- comb. form, perhaps + pr- + -ene (in propylene n.). 2-Methyl-1, 3-butadiene, CH₂:C(CH₃)CH:CH₂, a colourless liquid obtained by the destructive distillation of rubber and from petroleum and used in the manufacture of certain synthetic rubbers. ΘΚΠ the world > matter > chemistry > organic chemistry > organic compounds > [noun] > isoprenes isoprene1860 1860 C. G. Williams in Philos. Trans. (Royal Soc.) 150 244 I have given the substance thus examined the name of isoprene. 1860 C. G. Williams in Philos. Trans. (Royal Soc.) 150 249 Isoprene combines explosively with bromine. 1860 C. G. Williams in Philos. Trans. (Royal Soc.) 150 255 The isolation of isoprene, C¹⁰H⁸. 1862 W. A. Miller Elem. Chem., Org. (ed. 2) 591 To the most volatile of these [hydrocarbons] Williams has given the name of Isoprene. 1867 C. L. Bloxam Chemistry 481 Heated in a retort, caoutchouc is decomposed into several hydrocarbons, one of which, called isoprene, boils at about 100°F. 1900 S. P. Sadtler Handbk. Industr. Org. Chem. (ed. 3) 99 On submitting it [sc. caoutchouc] to destructive distillation it yields..isoprene. 1906 Westm. Gaz. 8 Sept. 10/2 In forming caoutchouc from isoprene, the great problem is already practically solved. 1957 Technology July 176/3 By the use of Ziegler catalysts..Goodrich-Gulf were able to synthesize from isoprene a polymer almost identical with natural rubber. 1972 P. Wiseman Introd. Industr. Org. Chem. vii. 253 More important than high molecular weight homopolymers of isobutene are copolymers with 1·5 to 4·5% of isoprene, known as butyl rubber. Compounds isoprene rule n. the rule that the carbon skeleton of a terpene is made up of isoprene units linked together. ΘΚΠ the world > matter > chemistry > organic chemistry > organic compounds > [noun] > isoprenes > isoprene rule isoprene rule1931 1931 J. L. Simonsen Terpenes I. p. xii An apparent exception to the ‘isoprene rule’, the hydrocarbon, sylvestrene, has been shown not to be a plant product. 1971 J. D. Roberts et al. Org. Chem. xxix. 779 The empirical isoprene rule resulted from Ruzicka's observation that the majority of the terpene families could be considered as arising from head-to-tail combinations of isoprene units. isoprene unit n. the arrangement of five carbon atoms found in the isoprene molecule (the single or double nature of the bonds between them being disregarded). ΘΚΠ the world > matter > chemistry > organic chemistry > organic compounds > [noun] > isoprenes > isoprene unit isoprene unit1926 1926 C. K. Ingold in Proc. Leeds Philos. & Lit. Soc. (Sci. Sect.) I. 11 It is known..that the carbon skeletons of all terpenes of established constitution can empirically be built up from the skeleton of isoprene, the common product of thermal degradation of almost all terpenes. Divisibility into isoprene units may therefore be regarded as a necessary condition to be satisfied by the structure of any plant-synthesised terpene product. 1942 R. C. Fuson & H. R. Snyder Org. Chem. xxvii. 358 Caoutchouc is composed of the isoprene unit repeated over and over. 1942 R. C. Fuson & H. R. Snyder Org. Chem. xxvii. 358 The occurrence of isoprene units is so general that investigators of the structures of natural products generally consider the most probable formula of an unknown compound to be that which contains the maximum number of isoprene units. 1959 L. Ruzicka in Proc. Chem. Soc. 343/2 Up to 1921, the idea that the higher terpenes are structurally composed of isoprene units was not used as an accepted working hypothesis. 1967 Nature 18 Nov. 642/2 The occurrence of a series of hydrocarbons, with structures based on the C₅H₈ isoprene unit, has been invoked as evidence for life-forms in Pre-Cambrian times. This entry has not yet been fully updated (first published 1933; most recently modified version published online March 2020). < n.1860
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